Ai uth FH BAR EH RR BE FRE FRR BB UEC EME ZS & FER RR DR RBH FRE FRE RH F BRM F H FRA RAK REL HER He REF HR RELBREE REHAB + — DORA AAA A HIRE ER, CAME EIR EMO RHEE RAR ED TMT RM it B —MC2001 HF) = RR C2O04 4) RHE BY DE a RE AA ST Re Om ob 2 a fH RZ a a BSH. MSRP RA RRR BSR REE MARAT BERR RA ER PRG ARHAMCERROT EMOTE RAED ESP MAME SRE TY BARR, ABH ELA TAH AGEN BRA ESA MASH RRAT BER eB AHL A Ee HME OR = BO OLA OL Me OB fe A EL CE ER aE a aR fo CSRAPKEW LEP MPEP TESA Re BRERA TRE, PL EM te TPF Aa ih HAR IS wh OT ROT AR EH 2 th th Ce a PRADH RRA TERR T ORAS ESE ARMA K, PIRKHRMAMARM, BO EHKPSHANMS tH RMT EORTAR IK, LTRAHKR GT OE HT OE a YEG HY oh A th 5 A EB ER MP 2 RT CS A Ao ak RRR GHAR, S~WHELEA RHR HA AER DESH RE —— 4 oy MRCS MAHER HM SRANR A ARPEKELALE SHE R- PRE ARMY MRR BY OR AR OR ae eT AC oH ae SE ARM CT ED), KEAMHACDA LEE ALAR SHE REHAR AAMER TOR AP RRA GH #. ARB I~ 1 ERE KANE RED) SHRP REF URE OAH ETM Sa wR, CAPE ICE EKO S SAREE ROS TALES ee RAL RERRRAREOR UMRELE TAME HAM ERKENH EM. SWARMS HERA ONAF RRRER CRERAY MS EEKE ARE HA MRF I Ee Ee ME Om TE. APMSARFAAT SRP APR SAA HRAAERAS ARH ACRES ARE BRAD R RAM AROS RE BM FR tk TAERAABA LE A-FKRAERC HR HTRMNMOUSAFAR PPR RRBRLR MRM K MP AWARE, UE Wat oy E. & F 2008 4 5 AFARR-REAES ABROMRAESRAR RB TH — BAM ING fF RZ He AE ah HB AAO hy ELE TS, OK ET Oh ae Rt — EAR GH” SBIRGRA CEORD RMSE He RAM KOR, RAKE Ta RB RE PAR SA A IR RO OY Bal oR, BORMAN CS hE kA ALR AMLERARS RHO RORABEO KAM LOKP CMR TRATHAME ARR. BRKT BA, BRM wT AL RAKE. AFA LAER NR ANTARO SPMD BEN ER. ARDS HAR HP Re Sh ee OB a io RD HRT PE eB RAR, BL REAMALSHHRRA BHA RERPESR CREKRSH, HOT eam CER M—H ELT MRARANCESERAEMES THEATRE LARA PRR. ATA RRB BEM RL IT RE a HE IR OY YA A Ht ok Bl SR TT BA ERK LS — EPA TARA HHH AR, STSMHARARR AE HE OY RM LEMHAGA SE EST RAAHN OAL ERMA, SwWAKBREHERA DAF RARER ORERAY MX RFR RE R 1 DE Ao EB AGREREPRA TEMP NARSHAHREMSRASHRH UREAHRER RYPCHHS URF MOEA SAA REE LHRH AR RMT A HRR BY wR. HTRMALEKPAR BPREAPHLR REGR BASH EUR Met AE. te 2004 4 5 AHR-BAS ACE RADE GRREF LESEUALERA HEH SHRSERME A PoE TRAN a SAAR LAT ESF RAH RES th. RRS RRR SRO SR AR EE BAAS, CARHRA. BRR GEERAASHE POKER AREA EHC EHA REESE LAS HAAR Fe BE tg AE a AR, AMCERR-MEMEGR. LR-NSASHEREMANSE RAR. CHROE, SABO. Bk CARA ORT BME AML Ste AEE eS ER RO AE MECE RR EMRE EGE ED RHK AR EA RITE eR OY KM. HLAMABRAK LARA RARE 2B. KEVANK SHEED DER AMES AOR KAD OEAMRE EEO REM IL SE SLHEAPTS AS HRRBAA MEGA RRMA PAREKH SKS HEE, ETROTHAERSE LAMA MRA SE RAT SMES RAE ORR AB ME TB FB — R.A ah aw HL Ae hE a HR ER. ARMARRHGADRARA, RBG SPA REA A AOR, RHA RE REARS PA MY Ol A TREES HEAT REET CEASA OPEC HPSRTMMAREWL., HSER H-EEHARASS MH FLBM PAH. SwWKBRS HERA ONAFX CREAAES GEAAF BAKER MEER FN a ER. APMSARS MAANHSRAYEREASRERARRENH SOR BHAA WAR RS eH A ET AY ART PE HERMERAKPARORZMBSE BPRRARMA YZ RAT IEE fo RMP HE. te & 2001 4 4 5we 1 FA AAC 1 HARD EP wt seh FE Hh SH RCE A eT EASE SERIE one 5 5 SREP HE RE AACE RA th RA BLA A Cie RE NG > BZ 8.2 RPI eres 41 MP MIE 2 mr me - oa AMR NDR mrrrrrnerenene I Hea ERD 1.5.2 HRB Cit] RO am HI RE 21 RAHA RNR Le eRe aH 1s. 1 2 Rie Rik HEHE HE 2.3.1 RRS RHE DIE 2.8. 2 BBO He Ce] ee AR R SIR WS Re He - + 30 3.1 BR PA .- SL 1 REAR ROE « 30 B12 AAR A A 33 B18 AR AIG OM EE 35 3.14 ME ARE ON HH 3.2 Site 3.2.1 SEDI AR eee 3.2.2 See BRE, 45 (Mk) ##ok AB. 4 Rie BL FPR I reese 38 Lo RRERREOY SEMA B wore 88 RRM HE DE = BR GEE 0 AB He 3 1 1 4. 16 FRREREIN HR seers HBB ceeceece eee sesesee 62 1 FARA SERRA orev eeeeoee 62 2 RAN HY ree 3 Wea E AO wom Me 1 5 SANE RH HE 4.2.6 RAVI HE srs Cake) wee “ 7 es BSH TR STOR 1 ate FEE He 2 RRR HERDER HE : AY BR eA BY BR IE Th ee 84 5.21 PTAA5.2.2 MEK HE AUDEN we 8 5.2.3 BONA MEIEBE wrens 86: 3 AEH ER BY HIE on 87 5.3.1 RIB SE HY HR A A AR Oi ar 5.8.2 APR EAHA 0 Be 89 S.A FARR TS at OR EY Ok a Sh THEM FECA ones 91 SA CATER EADIE A oon 92. SAS AFH ORIE 09 16-9 + 93, 5.5 Sb TH BR AR BRB A Re TR OY A AP 98 5.5.1 SbF BENS of 5.5.2 SATB AP wre reeee 96 5.5.3 AA EER c 97 5.6 ABR AK Oy AE Ai ER 98 (Akt) FRR 99 ae 100 Mom wR 103 6.1 BR KE By a aR A oh 4 so 108 BLL RARER SS ~~ 103 B12 AREA i low 2 ATE ON HE 105, 6.21 LACE HE BE 108 6.2.2 ACRE HA HE oem 106 3 RH A A RR R m4 5.3.1 CAUCE AD RICA it Cae] DBL esse S78 BG tb 83.2 RT EAU ALA RRE AS RAED corer 115) Be 3.3 MIST ACRE poe 1S: DERE GPR IG OR 6 6 hig e hi 19 121 2 122 128 128 LiL MEA SDR AH Le mast 1 1 HEH on - 129 OE 129 Tk MEE TE 7 130 7.3 133 731 REO SER A = 138 7.3.2 REA Hy 7.3.3 EAD BBTE DE a REMC EHE - oe 134 7.3.5 REE ~ secensmsess 136 7.4 HARB BREE on 137 711 I we 2% 137 74. 2 A 88 HS 138 Take 3 RRL RE 7 LE 138, a (ARH) AMHRRS MAT t# - 139, FE sosessee S8R eae M3 8.1 8A 143 8.1.1 RE MEYER HS SP A 143 81. 2 RE ARE SE 5 513 eH 8.2 155 8.2.1 REA He, ~ F 8.2.2 RUE ME 156 (HHA) #2 K 5 en co SOR Ren 16h 91 RR 161 8. Le RR A iL 9.12 eA oR 9.1.3 RRR ONE A 9.2 RARER 1 aR 2.2 RA a COR te H]AA A A EER 178 am 8 10e RnaHaniad - see 181a OR ll 10.1 Be 181 115.5. CoS REBR 27 LOL 1 REASSEIE -~ 18 aE sescesniee 217 10, 1.2 WEA A 4% 12 SIR RRA E 220 10.1.3 REAM ~ 183 121 RK AH on 220 1014 RAMA EH HE TRA BERR AHN SEE ve vrereneee 220 Wo. 5 Met Ae te 184 121.2 AERA NEN AR one onee 22 10. 16 Feed ne ei eH 190 12.2 FRR 1017 5 BRB AMEE N ) 19 12.2.1 WEB 10.2 ERAGE Hn IS 193 12.2.2 ERE BEAT 227 10.2.1 SADA 193 12.3 #REDRH 228 10. 2.2 AAR HED 193 12.3.1 mb 228 10.3 AHL RED 195 12. 3, 2 RO em A a 10.3.1 MRSA 196 124 RH 233 10.2 RAR 196 1241 TE 233 10. 3.3 ALA AF OL A 197 12.4.2 RO BIA 234 Ca] RR Oe 198, 12.5 + ae FHL wrseseene Iss LA AB Sue MwA 201 12. 5. 2A aR — i LL 1 RR AT Oh Ot 8 201 5.3 HAE aR 12 RTE S 201 Ca] RE 1121 A 202 a8 12.2 MMP A 202 SIR MAMA 12 8 iA 202 13.1 240 2.4 Et 203 13.1.1 NM 240 11.3 mE He 204 13.1.2 RAPA 244 11.4 Heme AE A AO AG AP 204 13.2 Bo at 27 DR ee Bea A 13.2.1 BAe Ant AAR A A Lat sesceeneaensens 204 4% 248 142 REI 13.2.2 (Me Aine HAD ATH 29 143 UATE BEE ~ 13.2.3 ERA HORA A ee 4 209 1144 REINER ~ 13.2.4 Cae ~ Cie at] pnnrees 13.3 BAKE MAS RELIMRZ 13.3.1 HAM 1.5 £EARR ETE 13.3.2 BAA Me 15.1 SAGA RAE 13.3.3 SU 11.5.2 ROR) au 13.3.4 RRO a CREB) RBA EH oe 258 13.4 Bm 216 AgW BR Rise RA - wT 11 Be 16.2.2 BOHEME + Li LR Fa 260 16.3 BERR ANSE A 306 141.2 SUR SEAR ER Hy 261 16.3.1 eRLEO— OLEH - 308 113 A I 265 16.3.2 eNO ake 309 LL mi Hee HE Ae 285 16.4 BeBe AY HE 312 M1 5 RCE RTA 268 16.41 NEO 312 14.2 16 an 16.4.2 BERBIIRRORYE Be A 312 ewe 2 16.4.3 BRR HE BE He A 312 4 i 9 sesso 278 Cl tH] DNA a aF de RR SE VA, 3 BP cseeesernccnerneensennennies 27 aml 313 M31 BH 24 AR so 813 143.2 RE 277 IT tk ONCE SEH) 315 1.3.3 SPH ar 11 RRA 315 13.4 BER 217 VTL NEHER eee “ 278 17.12 REA FE PH OA 8 kHA] Pere 7 1718 RRR ALR V4 MEAGHER ise nee, shaman 1715 WEN Sh At % 15.1 Rae 116 MARR RALE LE 1S. LL RUMRAR AY YAP CAH] Sam 15.1.2 REAR He 17.2 Ak iy eo 3B Mt 15.2 ik + 17.2.1 ARE RIIBEEAE - oo 3 15.2.1 AR AOsH AN AB 17.2.2 HALPER ABAD PR HE ces 921 15.2.2 WRAREEE BM ON Fr ARB AE — He BE 822 15.2.3 ERR za EO Bn oy ARAL 8 15.3 FOR 292 ah 32 15.3.1 BRAUN TE ARAL FUME cesses 2 15.3.2 BEA ERY SPS S188 SHH eT 328 15.3.3 ARMS FeM 18.1 AFB ER sree 828 15.3.4 Be BAH 181 BAP a AMS 328 CAAA] SRR ERA a0 18.1.2 THe ett RAI 329 FRE vec 400 18.103 REA AER NTE eat Hise we - 302, 18.2 2b iy BE AE EN AE EGE Oh 332, 16.1 HRA eM R 1 AOA RHE READE 352 161 PRR + 18.2.2 ea EHR or 333 16.12 RRA Ae REA Ae 162.5 SRE OS aR BIE 333 16.2 at Em 18.3 HAF KS MER BE LHALA oe 18.3.1 18.3.2 18.3.3 CO) A Ae A aR S19 Rie Ay LR RAR 19.2 Hab IE 19.3 HIB 19.1 19.3.1 19.3.2 19. - 334 iS Pee TE bth a Sb Te 5%: AL 2 0B FILE + 384 338 340 aun 3a + 343 343 34 345, Lb HY A IE Lb Hit 8 mR OUR EES HK a 345, 346 347 19.3.4 SSR HEART SE 19.4 Heat ze aR CNMR) 19.4.1 BRS AE A 19.42 Hee 19.4.3 BUSPAR Ss SUR 19.4.4 FU A EE 6 19.4.5 HNMR iB aR BE 19.4.6 SC Be RSE a 1 St Cie Ht A] AR AR 19.5 Rit AR SEAM - SEARS) CEP CAL A He) wieeee ae AG BLAC AE FLEE BEAL Fe LSAT LAL ED EE. BR CE TG HE PI et ZL Ab BAG Co 900 fe WE Oy — Tah Se 09% GRE J RE D5 GE DS I th aE SE HAGE TS HE ARAYA Go IR & «LAY AT AEE 2.000 Fa HP AY Ce He HAH DS +) CH HEL FAY A RS PAD) BBN BH BE) Se A) Ft «RR ACES AN WS FAB IE AT LAG Pe. AL ACE ST) OTE EAL REE EDR AR BEE ESE I a BE HE. BR PE CL REL A IE aE PE RE 9 FO HE ABE RS A eR AE J GET ts URE CE. AS EEL AL SP A LA A eH Le FHL AL LAE AF: 12 NE AS A AEB Te ALA AE AR WA FE 1.1 Ae A Fo A te MUR LFA BW Corganic compound) fh & A RICK » HE & MEA AL FW (carbon com- pound). BRE BRIG Sh , BRAT TCH SLU HE AL RL PG BR ETH «PT LL SEAL Me Pe Or FE A BRA AL A D BE IE A 4 49 (compound of hydrocarbon and its derivatives). SEA FEAT UAL Eo 109 AAD AE Ad FL LB a A) A « FU DLACE TY LETT — aS A AHL 89 BBR. 19 EER a Bh AT AGF ME ah Fh Ba SN | AAT ARAB BR RHO AST) A I FEL A, FD A PR CLD MA HE 5 Ai BA HD A 5 19 BP WAT LAG 2 «ATR AT LD 0 3 FR BLA Fe LD AME LD IR Sb TH «SO BEER A aL AS iB I «A A Bh) AUN RAR AG» ARE A Se EP HTS. 1828 AF 28 YE EE OF. Wobler 2908 FP HM i ek A A FL 9 9 4H DR AE 1845 ETD H. Kolber 4 it 7 AMAR. 1854 47 32: FRAY M. Berthelot 2s Fi F30h HH (499 He «ERE TAT. Ge RAL OL HOE AR. BATT ETF A DA A LER HAE PLAT LEK OL A A A ES 19 EEE AAT BAT FR RR AT LA Eo OAL A 6 AE BIL A I — HB 1858 4748 LF HK A. Kekulé ASEH LER A. S. Couper SPS) 88 Hi A ALAC A SPF Be FEV Bt AR DF 0) AT A PR BD RES «TBE AL A 2 FY HIE. 20 HEE 30 AFAR HEF JF RANT 2 S| A Hee SUBS EE TR HG EEE PAAR AS TT) A «AG 2 Aha BA — FB) I A a SL | ET HE DE T Aa BLA I CA FC HAR ED HAY BCR. 20 EEE FRE AiR OY aA SL eo 2 OE Pl2 ik @ it SL Bb HE ABE XD AY iE FH BD PAT 5 RE BR FG FA AM EAR IO SR Aa J FER PASE ARR HP EL 1 98 PF ES Ud A BE BABA FSR Es AR BAL RAS HBR Pa eh PUB A BE EA i EJ 0 TDi ABRFEL) SE ISE DR SAS HE i Sk EAT WR AT BL A Ca PA AS TB > BHT BULENT FE TI. 2002 AEE I AS He EAE SP HAT EF fy A FT A A) FN PB RE HG i ARAM PER BLD KA A Ba AAT ft ER RA ie EE 4 a 2 A) ew TB A iE NT BE MG HE" HE BES BL BE AE BTL A Ff) AS BG 7 5 Pt LAT HAS AY BA AS A A AR ATT TE BHO EAE DRA RO MATTE TAA 4 I AES AE a PUMA RAS FF IE TL BE A: i HE ET SE ARAN TELE SEF AGE FM Ba ARF PR HE TBF AA GA SE A HE hr BR, 2000 AF 6 26 EL Bd as A 2S i th 20 AAS STF dS Sa A SS Ke BASS 4 ER M.S AAS DL i 8) 7 6 AE AAT BAA Bt A TE 6 TT A EL 2 in Le ER FR C0 RE AE «AAT AG SA) Fk — SE RE i OY Be FIA YAEL PE. 2003 46 4 14 FG EA SE 8 FETE BE Collins (HE CEE POURB HCE 5 = AS AR TAL AL PRD hl A «AIS ALS 9 STAT i BB SR A OR 11 FL Fd I A) 96 AL AK ABT AR (post genome era) AY) TERK MM. TE Ja AIT AR AEE 31 89 FE ALL HE AB as DNA. 55 $6 BS PE Pk Ee a 9 BE 9 SE TE i ON UA) 4 CE Kee AS RA, PAR HE ANT ES A DA PRA AB LB BO ES A AR EE BMAEKEL. APMC ESD RTE OH MIS SE AMR IM BE FR LBD YB a EE ARG TIL SEAN RE 5 A A RE ARE AES 1.2 AP RUG Ba > FP A 1 Fk — 3 PE FM DTD FF BY Ce RE BE HE 3K HY BH (covalent bond ) » die 2 AY St ft HE BIG HE He FN AT Was » IEG RHE Ah BE) DR 69 aA EW PAT HE 9 os A BSF LXE Ft. BRAC HE Dt BR Uy «4 SLATE Ta) AAD I OB FO A |B — Be LDL FPS A EL BE AF Tl FE AY A i AO IE WE Sk Fr ARIE SE tS AS HE EH LSE A a BB he BR a SCA FE BE Bt REED A> Lo He — aE Ar) « A A RE FE eA EH ES fp LAS OH te. PRN AEA A RE TAA wD FE — ee AR EH TT AR IE AT AR EBAY AC HIN LS MATAR AS ILA Go OA He At A HS1.2 AMEDD F hee — stor 3 1.2.1 PEM AA SE Pt ae ELT o BA x © BAT DAF HS BAF A ae OY A DD HT I A EK o BEC bond). HEATH BERL AK «Sth Fs MF WS TS a I A AE — FO BE Int 5 BAR hE a A a a «Ate oT EE”. AL ABE 0 Ft, BPTI AY p it HOF FT AAA tt HE RE BG x EC bond), HF ADA PER EY BF CD A FO PE HT eI ee A ie A BE MMe BAF ve SR BE AT AA PE GW SRE DF Le A HE HOE | oe ARTERY HL ED HEL Ze AS TH HBS SPM) SEER Dy ly Sh SE hI wT AB A» Ce BBL BEHE HEH o BER. 1.2.2 RAF MRC SE SOSH A SAR AO AL BRR Et BR DF MSC EE a A SG EW PS «RU A YD BEA HE A BY OL AM GK ht AY FHL (hybridization) . #6 ARAN Bi MLPA HAL Mi (hybrid orbital) , AeA Sith (A) 3 Ei HF 5 Ate my DF I SEES is OU EL A HE «A PFE 2. RF WAKA PSH 1. sp ate AF 09 ths FH 1s'2s' 2p! 2p) EAS). EIS TRUE 2s) A — PHL FRB) 2p, UE be HE WM 1s*2s' 2p! 2p! 2p: MAAS) HELI LAN 2s Al 2p SiH RA A TEAR 4 A AT AY sp’ ARCHIE. ES sp’ ARAL MI A 1/4 AY s MLA SP AM 3/4 AY p MRD, HIB ARB— KS LBM LC), PERF BIE US 4 sp’ He 4 EE BAY tH ZEB A A EW A A 2 oC A) BAT Pd HE 9) eA BD A Te 109. 5°, SUPA 1-10). SAF spt Ae fe MiB Z Ii 69 AT FR 2 die ]s REBAR AR HAR SEE. A HLH sp' Ate. 2. sp art RIT MRE PM 2s SPD 2p HIN WER = PREREATIAL AY sp* Axe. KS Ay sp? Ae eA ih 6 x ean FE DF] — 9 tt 5 eA SEL ARH] 1 Sp 120° RR = 9 OF M12), RRP ERE TASS AEM 2p Mill EHO A BE ELT spi ate itt MF TAT PL 1. 20). GRAAL EAR sp’ Arte. © & & %° (a) MPP spt RACAAAEAR Cb) DAY sp! ALLIEN ANAL Ca) spt eA Cb) spf eA p Mill P11 BUR AY sp deAeeh tt P12 BRIE AY sp ete ah3. sp Att EFA AS HY 2s PBT — 4 2p IA FE MAE ME ALTAL EY sp Ae te LAR. Bee Ae SUES PL FE Hy AY A Ae ARE As AT fe 180°, LFA 1. 36a), RETA BREA 2p Cc) GAS sp 48 4e Mi ME A. WLP 1.30). ) BEAR CL PRN sp Fett. 12.3 SFetBE eo ‘EG AAU A iE A ie Ae a BE TSE At SEB HEE A} sl HY Ff] BE fA pt at Ei] a ot, FR a Zl) BEATE SD PG EE — PR TALE» PI Ai — ERE TRE AEP AY a eA HY AST AR TE HAG, 1932 4 Mulliken, Hund il Slater PEGE FANE MIG RIE TOY. SPB HP AIRE OR PF Des He (delocalization) » PS ste «85 FE HR HF sy Ht F te Sb FH 38 fi] 9 iz AR AS HK DP F MLE (molecular or- bitab. BY Fil MIE A: PF HBL EH A HE 9 DR FF LB (atom orbital) HEM F iM 5 FEL BAY SRC Ak A a 0) BB ART) HAS PN A> RH AR 9 DR A SE a Fs AR AS 9 OE SP SUI Bs obo BRA « BAS UGA FILA 10 WB A PACA AL A VUE « fH, 5s BR SY DE BE Ab = Bt By EAR «BOG ACA a « 455 9 Sb FAI A a DG AE A a 5 A HL 9 Pe ALAA 2 5 ARASH TE RBA b= 9, — b, R R OH T RGTAL« B e ee AV DBE A AR EAS Hd SI A SB AR JL SP AG PEAR ASIN Aa PAG LF HH SAH BS AE A Ht DR A «i a JF iB A WL OY FO iB AL 4 SPAR CLD fe ANE $1 RG) PAE A FA a ETE AEA Et, A TF AY 1s HLF He BUF AY Ls Al 2s FRE BEES. ASE ARE. TS RE AY 2p FRE RAE WEE A (2) LF 25 Hie HR SE AB ARR AS DN a EL Ag — sk 9 ews Sk Re HE EA He. ALN AF AY s Bie BUF AY 2p, MUL RHE x RATT Ha a SEK TE URGE BC. (3) TF Ba RY PRE VER A WR PF ABE DKF aR OY hs He BED, BA Le 0 ALAR AB TAL » AE A TE A eH AM 1, 3—T HPF IU 1.3- TOM Fay oo A RF PRIMA AR 4 Pt FOUL BD gh oe ys A OA PBL) AM 1.4 RAR JAP 1. 4 FBT LEE AS 4 AS pF AOU EE A AE IE 9 « ys ofr -—s Ld 18- Poam AVF ® = & lecular orbital, LUMO). AAC itt BH i A HE HR 3 TC, Cy a9 EK A fe He SHA. Lt. BAP SAG AT LE OW Hh 3 1.2.4 Stteie 1813 TAR ELA AF BRU AS OS AER EF 8 kB FE Re EAL 2 SU fe RHE AL. PAWN Kelcule 2 9% «BU AS RE RE A 2A HS Hy HE DE PB BNE. BAMA ERK MY TT 1 ALE FE 1931-1932 4F, LER L. G. Pauling Ze ft AIC Ay A #2 1h SEMRIE (resonance theory) M5 WER. HAH Hi — AP AG A yas FA Ma eH AT D4 SR BAY SNE SoBe 2 Hy fil SL ak HL FE ae ALR BE HR BR AL HE (resonance hy: ride) 5 Hi PSEA as EAA Re 2s SbF TAY FF He. Ste Zi AR OB 2B Ry 3 HR A HY C reso~ mance structure) . HH FS is eis HY AL StF OBR AAD Ea Fie a aE HR A FZ «AS BE He Aa An eB HE TR, SEAR AA aS TRE HR hh eH Be SRA 2a HY A A BW HE A. ARN EAT LA Hh EP SERA HITE EAT I SER RES <> "RAR O-0-0-8-9 FE RSE DEAR ER AE FOB Ss CL) 4 Fe the SATE 9 DR BO 2 UB) AE «PH A A6 Bim # (2) SERRATE A Lewis FHM. (3) LA SPER ERR IEE SEG Fb Bim x FAY p PIAA TARA Fig ah PS AC AR A AF SEHR AP AE CL) A FEAR LA FAT SEAR AY BEAR A 5 FEE AY HE» EERIE SET WR CS A AY FE SE PITCH LAL UAE AN HEME AL, EAT AS SER Ae He HAY TE WR EY i 80%, ARCH ETF « ESO AN NE A SR AH A ES a RE HL. AA. 1.3 TO SER (CH)»=CH—CH=CH, +—* CH:=CH—-CH—CH, ++ CH,—CH—CH—CH, ++ 1 q a CH:—CH—CH—CH, “> CH.—CH—CH—CH, ++ CH —CH—CH—CH, wv y u cn. —cH—cr—Cn, u 163 ~ TW 4 Sean SR PT Bit EE PAL SER ie 1 BY OK SEH FE UAL AEF ARS) 25 EE A AA gS a IS 152 7AL 4 — UA A A= ys 9 AR BS C—O RFE BES 1.2.5 See AY ER 1. BRK FRE KK Chond length) 42:4 48 BY BR 4S RF 0) 0 BE SB ARE OY WA HE AO | Fa 5 OH AAR BSF a os BG SV SRS St FT CA ROX BEER AT TH CRO TU. BER AY ALL FH pm Be nm Fea, — ERAN LZ 11, Ril ER DSEMFS Fh eK ANE tK/pm $f /CleJemol-') 109 439 154 376 134 612 108 460 120 836 106 cH 178 355 CH,OH 143 389 CH,OH 96 360 CH,Br 194 297 cH au 238 co 122 7501.2 BMS MSF hi — ste 7 al — 8 EA TL A So EK 8 2 Ab 9. A C—C RE PEW 154 pm. FER EHH 153 pr, BEAR ARK 4 RSD SEI} FE a A OT A A INT AR SY KC A HT MBE. 2. SA $898 (bond angle) 24% BH PFE ff fat Z Ue Ee Fs ARR HE AS TRL Sh FP a AR AAT) A eh My A OA) KF HOH BAH 104. 5°, i EP RRS} C—O—C BB A 112°, BRA REF ESE A LA Po 9d StF PH A BH REM SX. 3. BEBE tf (bond energy) 248 HIE 19 101.3 kPa. HEY 298.15 KF. ABRP ARTA iL mol SPF CAST BF CH 89 Ae BE. BEG 1 mol LAREF AB PRS ALB BEA ASE FFAG OY AE Hk. ALM 1 mol UAL 5} A AL FG BEE 436) PE EF fe» BNE ERE (dissociation energy), (HIEX F & MF St F He TR BE RES RP AE JE AN Tr. AO BR Se Sb Ef Dd Be RB A TL BSC RE A: AST] CH, -H— cH, + He D=485.1 kJemol +CH, = -CH, + He D=443.5 kJ+mol sa eb + He D=445.6 kleml CH Get D=338.9 kJ-mol Ui i Se PE PT HR A) PHBE 1 661.0 Jemol? yA ATI A (8 SHG HEF Hf 415.5 kJ > mol ' #9 C—H Sab RAE. TEN be C—O A A) a8 Be te SE Ht & Fb FILA Aa DS aS a 2 a de 1.1, ‘SR A Ee HE tO BE — AS RR A ARR TT A WET RL BK. A. RMB HE ey BS A DF RS TR, EH Et OD A HE PR ZU TE A A PES AA BRE TEA HEY 5 PAE AR HE SE aE a HE A DD ES FEED RF ZA Hp ID A 6 TE HH AF Le AB BE BG BEL AT AR HE» Bs HE SE (polarity of bond) Sail HCl 5} 5 UR FH ts Hh HE TE ARF HE Za i) I AH RUSE 89 — SAF A AF AD OR AR 5 SU) — i a TE FL 8 + RR HY cH 5 HR EA rh A ER LE DA Oe HE SE. — A «fhe HE AE E17 DAE 3 TG FE Hs SEAL DE TE 0. 6~ 1. 7 FE RR ESE PE, HE 1. 2 A BB he A tte.8 Rie e ® H12 BAT RM Mt H 2.20 Li Be B c N ° F 0.98 1.57 2.04 2.55 3.04 a44 3.98 Na Mg Al Si P a 0.93 1.31 161 1.90 2.19 3.16 K Ca Br 0.82 1.00 2.96 7 2.66 RE BE A SRE 8 EE AC ls Ae tL GA He 9 SC A ‘font CH, CH2CH, #l CH, CH, NO, S>-F 4" iA AR BE EIL PE BR HE J BE HE BE He WL AL AD Ht ULE 3 R13 eR REMAN cH, cr, cel cN COOH NO, on 2.5 34 3.0 3.3 2.9 34 a0 RY GAAS FB BRE Spe Re AR a RG IEE A ot ES GE HT A Ht g RAR. wagXd MI CemUR OK) Ai LAG AS A Sh FH — SE SL SO HB IN BE — ABI C1. 33~ 1. 16) X10 Com, BEAL ATTEN RAR EK AE BLA — 8h. SP OI RI RAS 5 ELI WF 3) 9 AS AS «EAT. 1.5. y f 7 ofa yo w= 5. 2810" Com 3. 83X10 "Com, REL. 5 TL A 1 AVR (polarization of bond) MEAIB AL AL AN TE Sh A HELI PE AD By SE OP Ze Sh hE BCE» RUSE A HB EAR AS EA, A SR a SR HO BS ORB AE: 5 AF Zeb EL Bi AO BR Om SE Af LL BS} FB HE AR SE HAR AS SE AE Fe FL, 2p BRP ABR RFE 3s BSE A: AS] «kA 3) EY A A13 MARR wea 9 SR Af a A BAPE A TBE AR A RE eB BL «5 YS A a OY HK. 1.3 APPR RHRAKA ALLE FED FE SE IT ARE A 2 9 MG BES RLY « RL ER he a 2 REVI FEE a 5 MAD HG ART AR AI IN A A AS VR) « Sa 2B = Ty IS 1.3.1 Bae (RE) RE SE PERRET RLY 5 $61 SR BACHE A) — HL ot BRB AS 9D PD SR — SE a NB hy 4) 8 (homol, HY Re A te HB sy HB Cree radical), HH A HH Je 5 9 12 ON BB Be AB BRAY CEree radical reaction), f/f: RCH, 1A —+ RCH, + Ae iP HA A aR EE edt AE] BL ek MCA DP A AER 5 SA a 20 — AB A A EE AE 7 oP AS TS IB 1.3.2 BFORR SHAT ERT LIDS BRE BY FR A FS EAL ATE TE FF Cation) A FCanion) 5X A BL MOB BI A AW RB Cheterolysis) . hy Se 7 7E AYE FR BS FE RH ‘Ye rie TaD (AS «8h 55 tk AE A Ay BF IZ BZ onic type reaction), fi) Atl; RCH, fA—* RCH, +A ERT A—+ RCH +A OR AD Uo BAR AH AT LAG ES IRS LL SG LA RY BS OI AE HAS A ALA TM — AL Je PE A WL) Fe HE Sh GT EF BA AOL ESF A) I Oa SCY A A a GL LAST) 4} A A FBR M (nucleophilic reaction) FE di BF Aa 4 Mt He F HY 5} F CN NH, , HO) i BR NLD Fo wa 2 BE A A RP FE Ra AY A Se DD 5 A PA MT FRR BR 483A (nucleophilic reagent) , RB RM (electrophilic reaction) Ak HH TE PS F ah fie He 3 — XY Hs F OY PF Ch FeCl, » AICI, ) it CIR INL) SS FF eB DE AY RF FE A Ae Pa «A I TR FRA MA (clectrophilic reagent)10 Rie * ®t 1.4 ALA EP ay wR dE AS AE BS BE ES — 6 PEA LAE FE BA TR SLT LE ARBRE BL HAY $9 AS TdT SP AS TAD PD aE SF Be a OI FRG AA GPR HF TR LF BW Aa FB A BE 1.4.1 KRFBE Bronsted ~Lowry(J. N. Bronsted~T. M. Lowry) Ai H9 92 3 : ALRE #2 EEF CH") AY 46 PAR » BUTI RF BS TA, PLR ARE SE OL OS 4 Ae RB J OR HH HOP AR Bt EKA He FAL BH SE Js A CH,COOH + CHLNHe—= CHLCOO.-+CH,NH, % “ sesiok seme I a EF EJ TS eR I ECS «TS a FE ORE ERS. LINZ AEE ZO RZ HEM FUER TH. Me 0 OR RE SEAT A 9 «GH Eb RE Ag ATK A ZS HH HH BER 5 25S SPS a A a 2H,O + 2Na—* 2NaOH + He ® sem 2CH,CH,OH + 2Ns—+ 2CH,CH,ONa + H, 4 stem HO + H,SQ.—= H,0° + HSO; * & sefume ea CH,CH,OH + H,SO,=—= CH,CH,OH, + HSO, a ® sen se at AEE A BY HE aR BE A HK, RRA 4 AG Po KS PSP A ok PLMSF pK, + pKy = pK. «AE AK EF MU AR a FKP ALI HK, ZEA pK, SPH 15.7 15.9. 1.4.2 BFR Lewis ABBR A 382 X - FLARE BE ert, Ft 8 Fe 2 My BR I HR FO ASS AL A EF COC EAR PUA ERE, AT DTT LES OLA tA LE HAG ALCL BR Hy C58 OF BE AS TE ACL 4 9 Sb ee A 2 BY Sb RT DH AH rh RC. DSF PHY RF 2 HE AY — Ot Alcl, + RCL Lewis Lewist AIL] +R1.5 BUMS MD u DRA Aa Be BY A AL PT LE J Lewis A. tu] NH. .X” SH”, RNH:.ROH, C1 As AS a TH RL AY a EE Lewis MR, tH’. BF,, AIC, ZnCly +SnCh +R! VRyC! «C—O, CHEN HAE BREA BAT TBE — RE AF Oe HA BEA OT Sb Oy BIL Hts FHA BEAR AAS NT oe RY oe RL ER HE ON oe Bis A A MZ, Ms A HH) oe ST REE oh OO AR. Lewis MIRC HEE SS AA LAC ES DS BOR BAH SIR FEAL A HE AE Ph) ZU AY BT DE 9 F SE HZ Tl 4 1 Wh Ae Es HT VA SL SL HF AMHR ote FH a «a eH A LB MY US sb SO Lewis ARBRE X GAA Sk AE «BES OY TRE 5 UP RSF A AB YA $A Te Foi se HE Lewis MRA BRIS. BI) Lewis ORY TRIE UE 5 OTF AIPA. 1.5 Ape DK KES CUAL LAG PA AY 2 000 FF HP, CATT HY He HH A SR SB TO HE EE OPS EE FUG FE Hae AHR BE, ELT FA AE LA BRS AGL A BY SPS BOR Be FO SR FENG DF OY REO BE AB) PK 1.5.1 RBEABRDA (RA TE OT AAG LAR Co SPR 1. BUR A) {82846 M0 Cchain compound) 5}-F + BAF ANE 28 > HR AEAR A HY. hh KA Ae PI) BED Be BR EAS «JE EA REAR A 2 3 Ps OY BR HBR AL BM (aliphaticecompound) . fH Mil: cu, cH,—CH,—CH, CH, CH, cH,—CH—cH.—cH, we Front 2. BURA En BIR AM (carbocyclic compound) AP AE Hy We WK FH. AGE EHR AY RAR A 2 AR BR EM RPA ER: CD) BRACE BERL BM (alicyclic compound) M44 EPR 2 LE ES AG DA YE A AN MR As. cH, H.C—CH, “oN ZN HC cH. HC cH, A Z H,C—CH, H.C—CH, ee wor (2) HRBA MD HMA AM (aromatic compound) fH) 45 HIF HEY F BAL — SAE YE EL Sa RAT BEACH. fAH ne~ SCH HO, CH HEA OG ACH A HOOK * m 3. AMC A RRL BW (heterocyclic compound) 4+F "Hy APA He BER FAM FL EH BY IF Cn OLN, S) Ua. pala: HC—cH He~ SCH nd tu tL No ne, cH a a 1.5.2 BREA SH ‘AEB functional group) Jt 24 2 BEE HA DH FCA AL. — RBC AA TAL AR ET VAY Ae yee ASAT «PAG A ADT EA A a HANA HI Ae 1 aod Rid —SR RO wR ee eH Pe ft at HME H Be Heme m ae c—C”~*COR RL Zi Zh C)H,CL MCE GHOH Zam Cy H, OH a “ 0-c- atte CHOC Ht Za = ~CH.CHO 2m ~ CH,CCH, eA Load 1 vi 6 ee Wik CH,COOH, Ze aA ° fi Lit ite LMR Z oO cn,-ocat ie NE 2 _GHGNEL RR aim 5 GHSH Zam = “ es cH. SH RAB ame ‘SO, H wee H.SO;H Blea 13 AS Hh SE BER FLA Br fi FO RG «IES eR A PEE TT IE AMMEHRRELS SHEA RAMS MEBMRURAR, 200 RE Fob, A FRARET — i EH NEE thE MACE MERGE PREKES, FHMRO ME tT RA, REE RS ORR ELUM RRAR HA RH ES MBM T AWA, ap HBR MC TSR REE SRD AL AEA MLA HO SR Ah RT A eR ho aR AAA 09 it A fo RH THR, ROR EH RAR ARES RR E TE POG WAM. IG REE ANCE RAE ALE EE Ob RIT he RAL HL TRAP RIG, Hy Be Bi Ae LR SH Sk EY 1 Oe fo th ak A REIS RF RE RE LAE HS fo TH Ait ik 47 09 1) FRB AR RO IE (2) RRB HE HERA MARE 4 FAH) FAT ER RMA) FP RH HH AMS) RS Mia) 3h HME I AE Kes Se AE An Ty EE 0 th 4 wx 1. AUT BLUE YELM CA A J)? 2. SEAN 9 A SF A () CH,CH,OH (2) CHO (3) CHENH: (4) CH, —CH—COOH 3.5 Fe 2 a A I Me BC, (DG H.O CHO ) CHO, 8. PUM FU A 9 Sb AAS eA EAE t= A I, «) CH,CL (CCl () CH,OCH, () CHLOH 5. WAR FF 4 HLM Meh CH XLO.N BRIBE KAS, (D CHCl CHF CH,Br (2) CH,CH,OH — CH.CH, NH, 5. HAN FEC DD TP UR AOS. () CH,CH—CH: (2 Hy HG) Hi CH,—CH—CH, 7. FAG MMe PM TAL Lewis He? B— TH Lewis () NH-H (2) CH.SCH,-BH, (3) HCHO-NH, (4) AIC-RCIiM sie * 8. RR IRE AT AE A? () HCl + CH,COO- —+ CH,COOH + CI (2) CH\OH + CH,COO” —* CH,COOH + CH.O * % % 9. FAA EL HY sh HE RSE AR eth Ek? cH. cH, i oO (2) CH,» —C—CH, — CH,C=CH (9) CH, =CH—CH—CH, — GH,—CH—CH—CH, CH, —-CH—CH—cH, 10, FFA 2 SE BR aA HA I — OT SE Be AL TAR cp cr. —bne—eH,—- OH ° 2) CHy (3) 2CH 8 Co AE FMRI)H2e & He EER A Rc FA 1G KK Chydrocarbon) , Ae 4 ALA fA RAIA LAE OD I th, Ai BAG FE DAT BL KE 89 67 AE MH (derivatives), TET HLL A WAY F PRE 4 tt RE AU ELEE ES HE IRA LAC AY A 3A RA Sb Fe BRIAR HE WT 5 8 $8 HB (chain hydrocar bon, PRB RH (aliphatic hydrocarbon) } MER # (cyclic hydrocarbon) , HEE AAPAE L WT BE — He SYA FS fWAIRE ERE I CHLCH,( ZH) fre ME CH CH, (2.48) “eke fg CH=CH (2.8) \ tH { 8 ~ paste mC) GER “RES C wae (op IIB (alkene)! VEAELET APIS» BER IRE Fa IM AIR «AE BEB AT. RA Be. ARE ACT A OYA FALSE SEH BER Oe 2 HE ELA Deo AE OL 2.1 BERR aD 28 44 Fo FR 21.1 Bea FP toe MY PAA EAE CAL 2.1. SPE PIR W sp Ae 4 SAA AREY ‘Oui AE @ CH o ft, AF STG oe oh FTE DU Ta Gag RY we DF 0 FE Bm AH Ls 4 SCH fat 5) SHH 1 TE PU AAD 4 TL fa Af 109°28", o> ua. UE cb) Ra W201 HSA16 aoe me OB LEE PRE UAE sp* Ate IRE A — 1 sp? Ae AC ie Bs BE Me CC o BE BEE Hy 154 pm, HERE 376 kJ+mol' AF HY Let 4} 45 SURF s Gill HIE C—H o BE, MNP 2.2 Bra, FUER WF tt EVA IR) PE a Dy CHE ML C—C RE A C—H AR, AR TA ARE BEA ELA i) ES BSF AAD AG AA ALA 5 DD) — 4° iS ne AR os «SL BB ate BA BEE 4 CH: at n 4 CH, i) 5 4G 4 9 BEN Bl HF (homologous series). [i] AW) tH 4 16 & 9 Hy FW (homolog). CH: WK IE. BEREAN AY C,Havs2 Ve) R20 AB AOL hs A «AB Ok FM a 4 OE BAT ZEB HT AEE tA AE 2.2 Ciera re SMA OAR? FAME 2.2 PGES eS ha EE — PE Lm FAM LAH CM A 2.1.2 REO RMR eke Ae Te aie Ra FP A At CC o BE He EO HP HS 1. mee PED & 1~3 TRIE BENE BEE AA — ISR EA AR MR A NE RF ERE « FRU ZI EAR OY Ty INGLE AR: — FEE BC RE 7 eB PHA NF SK IT Cy Ho Cs He ESAT 2 AA 3 AP SEAT 33 I SO ABBE F449 (carbon chain isomer) ,’E FL 5}-F 3k FF HAY — AF can cH,—cH—cH. cH cu—cH—cn, ou, 1 1 om cH, CH.CHLCH.CH.CH, cuter, én, 1 1 1 BL Re a 3D SS PY A Bea SA I PF EW Cy Cy Hic s Cho Hae PS 59 ACAI 75 RE SPH SB Coo Hee BEE OU SES B) 366 319 BH, BEKEBR RT OT 5) 4 AS A eG he EA HE AY I) CH, .—CH, PR 1°(481) RRR F (primary carbon) 545 2 VoD F AME HE A BIRT CH — A 2° 4) BE I I (secondary carbon) ; iii —CH— #l a Br 3 APA 4 RF A He I SP BO 3°( AR) BUR F (tertiary carbon) Al 4° (3) BUR F (quaternary carbon), {A fil:2.1 eI ts HAO HH 7 HEAEAA C1") A C2°) ALCS") BRI Ae 0 RD AS AFA Rk CED) AR, 2° HD) CHD. Be SF AI ZT] 99 ie SR TD SS LR FB AN He A MF AS 2. HRP HY (GEE C— CAA aR Be a Bie Nt 5 BR RE AD HAND ie ER EE TT AST 2 HST BEN HAR (conformation) «ik ARE Fo ESE HEA Be mE 2 OR +H 3 SO HHCY $ FRAG (conformation isomerism) , HIE MLA) FH APR 2s #9 FEN HE (conformation isomers), CD) CREAR BME ZEEE BY — PD BLE 9 «HE ‘SAE 8 Ae 5 BAR FA 9 FA BAS AF BA BARA LAH. HIS. AMAL (perspective formula) #1 Newman #4 5t (Newman projection formula) # Fis «BBE SAA LAR Ab 4 a PY, 5 DR AA A SC Ae ET ACF TT Pt a 5 AB Re a8 a SOT Fs RE FG Re ok HY Ze A A Be SB ANIN 2.9 FR. Newman ARES IT RAR IS IRE Sh Pa A CD) ae AE IR Am. (>) Ae a FPL P28 SRA A ft) Newman #3. \ : wy wSn ohn ) MRK ) BK @ Rat () RRA 23 Zien ae P24 Ziseft) Newman $i BAIR 2.5 Se SOF 4 Ew PY a a rh A Rk « BE Sh ee AH SSE TAL Ay AR SR DF 8) Cat FH HU KAR RS, RRA ER. SRA RIT & OY ARE He fide SHEDS: 60°F. EAC ATE FRG JR 7 Re ly, A RAR ER AE OH RN KBR. SPT RAE KZ li HY HS EEK HE HE HZ US HAC ANIE KK OT Mt CC EH TT APE AE, EE 60" ak HA — HY RR EO 3 GRAPH EAR We Be TE AY aR UL GR AN AR oe OS 4 AE Rt — 09 EH «KE PROTA HE. He ACHE MM 12.6 Kemol | ABA LZ Hetote. or siete fe PR 2. 5 Zasie A e WC 12.6 kJemol ‘AAEM. ik AE BEAR. 9 RF Zeb F BY Ae wh wT P/E 83. 8 kJemol | AY MEHL, LUA SEURIK PE «PIG A 9 Se Ui) AE A HTP DS TPE SEHD RS RES A BP (2) ET REAR BEE Ae PP EAS AR WIE TB Ba, ETE T Co Cy BE GERI TIES «IAT 4 FE Bb ah Rd 150 9 CL th 5 BEE 60" 5 A 4 A By 2 HE AE I A A A Be HCA Eh 2K PA 2. 6 BT fle Ta Te sete Ae P26 TET EC, Cy Bee ME ir Me 82.2 IB e 19 PA 2.6 CTD CMD CV RESERVE MRR, SEM CLR BR AF Eh FF ANE A A RY HAR A MR ALL BEM PMA BBR A I I A Ha BOA ALPE A AR ABA RE ERM. CID) ACV RE EAE] SA BBE K AE AF AB AE AY Se HB AB AL BER SK Hs A MOT ER HE 4 FT M2 id BPS BU «FV HR Be he eR A EE, a Beeb CV) VP aE oe A A, A A HY SH AL D> FP A BE SUT HLF Ja Sak ACT GA iE FY CTL) AN CV a Ha LT a SO PRA ME MAGIK HR HN RA ERS EB HU ABE BLISS. HL AT, ThE AT 4 AP AS Wel 2.7 Se TR aH) BUR AL SEB Ale eA oy BR Ae TZ se ADL 4 UE TEBE Be Fa SAA DY AS A SP SAE DL HAF ETB RH BOSE THE Ce 0 TE A PAR Ae BOWE, FE AEE MOR MAF IE Te BELL, LE IE I RE ST EAR A 2.7 AR BEF IAI BG PF Oy BF HE BAT BT AH BP HA BR SR AE DP oC BT aL « BAT ASB i 0H HH AAS SO Be 2 EE RSM RN KRW EY) RH A RII LG SM PEE A HH HER SK (AME 2.3 Fs Cy Hy AY wT A a SPH. (ABE 2.4 SPI 1.2~ IZ REARS HRY Newman BEM SK AEWA. 2.2 were ERE AY Or HH RAE Mt 1d: AR GE th HH 2.2.1 Siw eie TRY FA te ORF Lin 44 i «SC AS IS 1. Ebb GEE BET E RIF ERE RAKE OBZ PT REE RARER, PAP RUF LE BOISE AE FAD SOBRE Be a BRP ABNER HABE HT KS SE EH 46% PsA iF] “TE (normal a n—)” Gif cH. CHLCH, Whe (methane Zit (ethane) CH,CH.CH,CH, CH, (CH,),CH, CE) THR Cabutane) GEYF A BDRE (or -hexadecane)20 Roe Re OB 2. AR Si AEB eS SUE HCC SAAD ERE AS APF iso MR FD Hea cH Hyc—cH-cH H,C—CH—CH.—CH, on, cu, TR Coo~buano FR opens) ch, FAECAL A RI — EEF Teo Bef cH, CH, . CH, cH. —t-cn, cH, —C-cH,cn, én, én, 5108 (eo pene) Bee (wo -hoxne) BR CBE Ai BEAR AR Bet BK 2.2.2 RABE HRB ie HW FE LAE OA AC $5 I HY 4K Ze CInternational Union of Pure and Applied Chemistry 44% TUPAC) bil 17 Bot 4 BRM) » 5 FDA OC SFE 5 eH A Se FT LA, Fr 1 hs UAW AH Bs BE OHH 1. GER AR HESS FE BA AF AA 9 AE A AE I A tH R-H he CH, HUE CHCH, Ze R~BEAECalky) CH Wak Gmethy!) CH.CH.— ZagCethyl) OE 3 VA BRI AGERE» SAR AS TAL FY SE EA Te KE Bl Se AH cl CH.CH.— CHACHCH, GEDPEM Gr—propyl A propyl) SPI (iso ~propyd) BEE RAT Cy Hin IT Be 41 BSE BS TA BAST EI CH,CH,CH,CH,— CH,CH,CHCH, GEYT AE (n—butyd 2 TA Cee bury) cH, CH,CHCH,— CH,—C— I cH, CH, FT H Cso-boryd SUR) TR (ere botyRIAN HB a1 2. UFR RLM RAS LA Cs TR Ha AA LA FH A 5 ASD A DR AD) J A BU” (rules of priorities) MOM FLUE FEU FF +" OC ALIN” BEA AF CL) PADRE BAC As Ba FP SABLE A 6 OE AB A ae PT) A St FTE «DAM. FFA DRE BR A 1 Be ECE I>Br>Cl>C>N>D>H SH>—OH>—NH, 2) 5 FOR Ee Be BP SC TD DB BD BA SE OR PC RS PAF YAIR) Seb BO BEEF OOF A AB wR se HE BOE ik. Bil a, —CH, #l—CH, CH; MA RAF S = HME. HG AZ RRIF RS H.C Ht iD en (i) cue (-< PRLL. —CH.CH, fE9EF—CH,. HARE NIE EN (3) EAP A OUR SE SRS A. BN CH,—CH— = Fife eee HOS Rte ie H i Fite H i Ne=C— Bite 3. BEEN RR HA Bike RG % HM ME C1) a SEE EAS AR Py HE AD ER I IA A PR SE. AT A] Ot PEL ARE KR GEMY , WT AE A BR ES AOE HE EE. A on, cm, cn ten—cn, Gc, csc, —tcr—ccH.—c, cHon, Gi) oH—cn, on, (2) Ea ER AR eet SRT ET eS eH BAD RU AE DA SR AE AR 09) — Sa TP CD 14243 eda OLS ae a ha AR BE» SU SSE SA A SS AHO RO — a 5 ET Aa BAR i RC AS OA — 4B TO FELT J ME SAA BE AS 6 9 — i et22 Be Re OB cH, fad orb babe, bu, —én, en —En, én bn én, Gn cH, cH, C3) FEA SAR A ARBOR Se 2 FAT J 3H 9 DI CB He SE TI) A AR a TR Oa FRR RE (iE BE CL 4 i 5 (RE IO fd FD 2 ee Re AS AE OZ RS 3 A AR. fA (CH,—CH—CH,—CH, CH.—CH, CH, C,H: CH, cH.—CH "CH, a ee SPM —3— 2, Ae (3-methylpentane) (S-ethyl=2,2,5-~trimethyl—4—propylheptane) (AMES HY RHE A Re he FN FE oF A, CHLCH—CH—CHyCH—CH CH, —CH,—CH—CH—CH, CH, CH, cH, CH,—CH CH, I cH, (9M 2.6 ee 2.3- <4 ako eH E, 2.3 Be 2.3.1 Se te AHS TIER Cy ~ Cy 9 TEE RE AE SUR Cy ~ Cie 9 TE BE RAK Cy DA 89 TE A BB ‘SE AE BA) SL Sa SO SS 8 Ag I AE DEAS TESS RE AY BB ABD LZ DS HO FS EL EAA — SCH, BF aS RAIA] (BRIE A BALA Sb HR 3 FG «TRE SF RR A AC EA TH cd +s ~ Cg BAY TE SEE BEA RS SF OE A HF « Lp RR SH Le A F BY BE be 5 BRE a ALG FI 9 AE HT AEE BG FE PE AH — RBI FARIS A «LE ABE HAE BR A HR A GX ATS EN 2 UF SB SEE FA ODI A S5EKE Cus BE TE SEAS BADE Sh A FG LAS HB BET GE AE IS KE A TAA LA A AN RL EAB 12.3 eA NE 23 FRESE IME EAE AR AE ARE SDF ARE ok EEE PS A LPR MR SA A eS He 2.1 UM TRF HK 1 ~ 10: BY TE Se A) — 2 i SB R21 Emenee er % DER 8, xt EECA”) te meth cH 0.466 ZR ethane C:He 183.3 ~88.6 0.572 Woe propane CoH 189.7 42.1 0. 5005 vow butane CH = 138.4 =0.5 0. 6012 Re pentane CH =128.7 36.1 0. 6262 ek hexane GHu 95.0 68.9 0. 6603 Bee heptane GH. = 90.6 98.4 0. 6838 ew octane Gy —56.8 125.7 0. 7025 = he nonane CHa -51 150.8 0.7176 he decane CHa =29.7 174 0.7298 2.3.2 BIBRA DERE Fe C—C 1 C—H EAB AE 4 EADY oo BE RAE AC RYT A HE EL i TDR SERS AE 5 SR SR SIR AACA FA) GR DICH ee BME AE — EE BH dH SRA FAL FE te F 6 C—C $88 A CH Sat th A LA 2, ee — 8 ee Be . Le RUE IE FETE TT FE EI AR 5 A A TL BN ELT 2 HR RAI So HH COTA IT DLE HE A aE A) EZ CH, +20, co, +2H,0 AH=—881 kJemol PE Th Be AE AF RR) ARLE BE i ET FD AA BH AAS TM) PLA A Se HE EAE BAY IME DFE BE TRL. GO «eT A A, A PE | 460% 20 kPa Hy CH,OH+ HC cH Sat CHLOH+ HCHO Fee ths AT A AR — 9 Re A TR Sa RR PO A Tk aE a 2. PARR AE ADF PAIRS We WAR AY 12 OT RN BR BR AW Chalogenation reaction). eke 7E WB Ht FE BM HEA TF AE Be Ae AB 4 AS WB ABR A HP PE — BB 8 RAH. EAE PT AR I BAYT LE a SAR SAR AR BAR CARR IRL TD PE I Hd» RAR TAL Bi BN A HEE» AE A AR LTR CL) FR Boe RA Be A BL DFR ASE FS A RM FRA AN Bt A A EDF» ie FR24 Boe & ow FREAD ARLA, CH. +Cly — CHCl + HCl a cHro+e, #8 cH.c1, +Her ra CH Ch + Ch: eax CHC), + HCl SR eH) cue, tc, BH cc, + Hel PURUIP Bec oU a He D Hse RAR NEALE. BR ALHLEB (reaction mechanism) # HRV BRE RT SE BL IL « RA A SL, Eh «SA i AE AH. FASE OY SC Rs CE He BG RLF ET 6 BS RAR I PET MD AAT HH TE AR EL a. ENG 2 (chain initiating step) ; 4} F WR We AE Hi. Ae He Se Ot A AY HE AE AO FO JF A — 4 HE TA. C1 C+ fig it + Cle+Cl+ AH= +242, 5 kJomol wo SA ML FO DF a AY BE CKree radical), fr AGE MIG AR — RB A TE 5 fT b. BEAYIEC (chain propagating step) 4 Ht E55 Fst SbF CREAM C—H BR IF SG RRP EAA FE BRAG ASF DINE Oh I a SALT OY A AY hE A AF C2) « (3) BR I 4 PT MB Ba (FEAL READS RE A «A A aD. (Cl HiCH, —+ HCI+CH,+ AH= +401 kJemol o CH 1—+ CH CL+ Cl AH = ~109. 3 KJemol* @ c. fEAV#E IE (chain terminating step ) : BA 2 Fe Hk 69 Wh > 5 S.A ea AE AS FF Ge aR AA BL 2D WD, ATL 3 4 IT AR PE ES Fal ABS Oe He RC 9 a AB RZ PA 5 LS A BSE AE AUER EOS Cle+Cle — Ch, @ Cle-+CH,+ —+ CHCl oo) CH,++CH,+ —+ CH,CH, <6) Ha A ABI SLL), (SAR MEME TTF de» BR TB FASE AY SRA IE LH « SR BF EES A Cl) 283] BE TEER — 7 BE. — A — FR ih ETF 2S. FLL Pe) Bo BE AE AY (free radical chain reaction), 52S: A958 — Br BLA Pe A ri ME Je BRM Oe OP REA S| ETB. 3B BP BE2.3 ERASE AR 25 SRE (PYSEL EG BC) 5 C3) RIE BS aE A 5 AS AR TY A A fo WTB ARE KR Be ASLEEP RR 9 a ob RE A TT» OE BUT EAL LA D KRIBHA, EEE ON HA OE SL WE AS «LE AS EAH Sh I WR ST, ASBHC mt [ABC] SA IR IRE) Lik WES A AR AS HOF « GAS a ON SG PAT A A RR {NG 5 JE iP «NS BAS ZU A ED PAE FE, eas PA 2. 8 des Be AEG DA E, RAE RMA REA. E, By READER TRO A+B-C Pant PH 2. 8 IRE RE fe Ws He A SRC FF Ws» SR HC wR LEA) — a CS RO, 5 RG AVA EF a Tw A AH TS 2 AL AS DR De A IRL FA aL RF bs RG 0 J A PS REAR» D2. 9 SB — PB BR A BK A DRM A AR AE A, A ee EE TO RSP PRE» SOG LE AS EO I WEF PA 2. 9 BHR 98 he — a BERN I PLACA. 1 kJ emol”'). BIA REHEAT. mai We 2. 9 Bf eH26 eee SEE BF Dy BAR I AB AC AE RASA He SS i Fo eG A Ry 4 A A FPA ET] A) eA = AER SE BS — Ae be a A A A Ro HR) — a 5 Ha Be BR SI a CH, +c H, + HCI 17 kJemol* sorte ® cHcr+-c1 Ligemol! ThA 6 MEH FR A A A RA 5 AR AFLAC SE ‘LSAT T(E a FTE FA 5 PGT HA « PAL A He cf br oe (CH) HBr) > CHy++ HBr E,=75 kl+mol cu Leth CH HCl) CH +HCL — E,=17 Kjemot ! (BE 2. 7 YR LE A 5 HGR eR — RA A A BEBE LR HS — A RA ZH C2) ALARA A A A LI AOL Le. 51 — LT LA BL. CH.CH,CH, SE. CHCHCH CL + CHICHCH, cl IRINA a mRECST BARE SE FP 1° TCG 4) A 2° C2 1) HBC SRE A SF yo — SC 15% «2 — TIE Hs 25.26 5 TSE AG YS AY SP Sy 43.9% 7% 5 BD 2° RAE ON ER A 1° HOR, BAO 2° BORE HE 1 HR BO ERT HE HO 2° Hilt H=57/2243/6=421 SET et) — RAR AT 18 Bi) 36% OY 2 — FA 2 — USE AN 64.96 HY 2-H —1 — ERE (CH, ))CH+Ch —+ (CH,),C—Cl+ (CH, ),CHCH; —Cl 36% 64% BATE HE 3 Hl H=36/1264/9=5:1 FRE L URSA TR OT eA HE A = AP LY BH EEO S H>2 HDI H oe SA LS FS AL ADL «Sk RA AS BS,Cone] ene 27 (CH,CH.CH,—H+ Cl+ —+ [CHsCH,CH,--H--Cl] —+ CH,CH,CH, ++ HCI ams 1m a CHLGH H+ G+ —= [CH GHe-Ho-CI] —r CHLEH + FHCI cH, cH, cH, Mme 2° aK A SABES C1) HUH Sh Te AD PG A AE ZO) TRL AS (2) ASAE Fi AA ZT), SIE GE WE AS 2) 0 A Heat WE ASC) dy 4. 2 kJemol |, lute 2° PAR A aA EAE He 1° FUSE A eH aR BR SEA SR 2° He 1° RRR, Ac Hat SK BHA AD FDS A A a HT te A LAB A a A 19 8 AE aH ot RE «SLOP HE He LH (CH, ),C>(CH, ), CH>CH, CH, >CH, AA HALE LT He 3 H>2 H>1°H AL ADF ZTE OTE EE SPR RRA Kb ES BU RAR, a EE BURT A 1d by, CHLCHLCH, +Br gee CHCHCHBr+ CHyCHCH, Br 3% 97% BERS AY— RAR BL =P RF HE 3° Hi 2° HE 1° Hy 1600: 82:1 AFH ASR IME AS S24 21, SCR PY AS TA EG ly AE eS RTE) 9 A BROS REPRE TE AT BLIGH IM PE HE DS FAM 2.8 BW CCHO.CCH(CHO, AFCA SF HIE, + ® fe PIEAART ZAM OH TS — REAR HARRY. WTERAD HMR KARA ALARMS th RRL MEER ORT RRR HR, RARE HERB thy THR 39 RRATHR 60 F METAR 221 H MHA S BR PRA Rh ARR th OE RAR AT IRD, Bk AE TAA RR RD Bh RRA. PREM B HERR A KT HERR A il RA LMURALTUMARGKER LAAT TASHA, SHHABESES HAY HEE LGR AE ty I OL a8 PA Bh HAL oe hy, VR RAK A Ey hE fe Rat AA , REDREBA EMSA, CLHER GE RKREBE A KH EE EST28 aoe me oR 1400~ 1800 1208 3K #2 HEE FS PSUR GH EH 10 RAR RM ERS 2% AA BABAK FR, 2th BAL ACH ERR Blt RIE Ae ED), RA RAR ke 5 A ha BBR EA AB AT BOR PEA EIR Rab aK AL te 0 Fh eA Be AN ERR LEB ARILLAMR I Rik F, DEA DRA MAT AA BE BR ih fo MH OME, 1 MRD BM FMEA (DCH, —CH~CH.—CH.—CH—CH.—CH, cH, cr, CH.—CH,—CH, @ CH, —cH-CH cH, bn, GHcH, ee ect CH, CH.—CH, eH, cH G-cH, cr, cb FS He 00 BH « CD 2-8 TBE (2) 2,3- HF ae Re (3) 2,2,5- SAE 4-2 BE 3. MAF IEH Cy Hye FRE FUER OE ) BTR E41 BRE (2) RP ARE A EE 4. HAG A MO ARE SPF ME Wy 1A TER SP OTA A C84. 2% 5 HS. 8%6 GS ULE Oat Se ATH 4 BL EDRF 18 He 0 A ik HB A Ht 5. SSF a AEH FE FABER WY C,H, AO Mae a CD) ARR EAE 1 RCD 2) BURR HES 3 RCD 3) ACR CA RCD 6. APSF FUER Fo MER SE HEE «> GH, @) CHCHCH, == (3) CH,——CH, =) CH) —CH—CH, cH, cH,29 wi @ Te BP ERH Cy Hoe FEM OOS SPE oH" Ha Hh? 8. FF fe a RR SC HR Af nua ca w . : H cn, cH, Hn, fe oH, Chi, CH, Wf CH, fi, A ch, Ch, # cH, ni Hcl F 9. CHCH, + Cle 2. CHCH CL HCI 652 BLLs URAL BL RT HS HE O99] I Ee SeRm, 10. af oC AR A EA 2 OR ER KF)$32 BRAS ww HAE RH AM 4) Fl FAR $9 A HB Cunsaturated hydrocarbon), #8 4BKE AE AR IA]. 7B Ma ALAS. MD Hy AS Hl FARE AS GA) ANAS AR SH A A OE BFE. 3.1 Hp tS fo th ks SHB (alkene) Jd % CoC TUB IKE SbF & — > CC RU BRE LIAS RS GE), PE BBE CHC AB BY PR SHE (diene) SPF PUL CHC RUBE AY He BME, BIB (alkyne) ee C: SAR IOS » SAE AL RIEL Sb ON PBR ON RE), BEE BE ACH SE aE DT iG AUR Ke AL Be ke. 11 9 i CPW C,H ALC. 2. 3.11 BMRB A 1. RAY CAB AER AT POURED EP A Com RUBE. nF TRE ALE SP ES GE ZS SSF BA BF Fe Fl — 9 i 8 A HE Ly 120°, CC RRC 134 pm,C—H 8K % 109 pmCR AH 3.1). Mi BIEU A, TLE DRI FH sp? Ae tk. C=C RUE — 4 o BRR BD We CRBS F PB BU Ee A — 4 sp* 28 Ae EO A FEE Cu Cys o HE SEAR A 9p? ARLES 4 HE 9 1s Hi HAR TERR 4 Cy Ho RS to Ite eg, CAB EA BIRT LAA 2p OL AELET 9. sp ee it BF He YF Om ee ALL Om EAL it IAT LT C—C BE CILIE 3.2 U P32 ZMH we x EAT EY p OLIN OTE AE SE AE eh ERE.3.1 RIB FORIE 31 PREMIER Is HA oe SR AR a Fs A OT A, oe FR A He E SP TRL GS Le Fa AVF i» BS ARGEE «BE CSR Hh 1s RARER «LT EAS» BF LL CC 8 EE C—C FUE SS Bet BEE. RES o SRD THe EAS TAL IT AE FP, OAR 3.1 BRA R31 oR RHEE ARR ott x tt THe yD Ah te HEME TE NES 0 BESTE PO RR =a Hem RC LHS Hw a ARAL AA TTP A TERK Bol WEE HL ao SE REAR HE BM DAE Tt OF BAR, ALM ee Ot i Ce BO ERE PH] FT IF ‘a fe BK ERB HE Bs RRA GE a Mee Bs BK ‘aa ne i a OR FT a FH” SC DAFA eH 2. BRA AY SA HY PIES Fe CHC SHE, AV HIM aE. Z. Be RIB ob BA 180°, 14 120 pm,C~ H #8 108 pmC WL 3.3). HIRAM: TK LF sp Ate HEHE — 1 o BEAN xe BRR. Zo aE SC fal WEF HL 4 sp Ae HG MELT BEA 7 RIE Cy Cy BF ioe fit SEAR AY sp 28 He PS URE 09 1s SLi IE 180° BPC, A, o HEAP o RMIT RARE. BEC WRF EAA PA p Pit ae AE BL EOE AEG AS LR,» AT EL OM AF 5 A I WAS oe ES HT C= DATED F o Mb FAN BAR CLL 3. 4), oo. ofa-0- MSA ZR PONTE A PAS.3 | CRF ie fh ARC St. FAR PR ay TEP AY CF sp Ate WEAR AREAL EY s MRD spt sp’ AAEM «a F BCAA. ee RS, A BE. AT C=C = tA EKC120 pm) 8 C—C RUHR AY BIC (134 pm) C—C MARA BRK 154 pm) 4h. 3. RAKE ALE A SRD ‘HAG KE FAL HES OY) SP HAD BR IGE KS he WRT LA Pa Sb AEB RS32 Bom Mie I CL) BEIGE AUR AS 0 FADE ASHE ATE HS A ESA HF C=C AT =i 9 457 BE AS Vd JA 4B $449 (positional isomerism) {AA C=C = Bt ny BR il, BEF BAe Fal ER AS Ma EE BE f cath cu,—cnef cu.cH—cuen, weve] cu.—crcth>, __ wn Guth cuscciich, cucmccn, C2) PKS AMOI EA LA 9 DB AL Ui 9 HE Dy SR BY (con figuration) . 5} -F $41 3 48 FA] TAT #8 99 7 Fel) BE SPR 9 #49 BY SF WR (configurational isomerism), 19 1 SP Hg 47 MR SRAW (cis —trans isomerism) ALRY RFA (enantiomerism) FHA , SBE IDE C=C AURRIA oe BAS AE HE HEE 5 EC CL RR BE eB Dk aE ALD 69 25 TD HE Fy XAG BA — AR AAT) DR aE HAL) bP ED» PS MR SA HE cis isomer) 5 55 — A HE AFA JRF CR ADD bP CR FAM» BR BSR RAE Corans isomer) . fF ML 2—T eh BS A Hy USF AD cic, ch wey won, 2-7 m2 (eis-2-butene) Cirans=2=butene) SAA EE SPE FF BBE ON ECR BAS HL Ep FL Ag AS Th 2 AY BB TS FAYE «ASTD SbF RIL LSPA St FEL AS BR Wk ba I A) De EAH BAC — At. SMUT HS (CH, CH=CH, ) Ail 2— FH —2 — Tf ( (CH, ) CCHCH, } + BSE HABE DBR i BE 9 DN FE LED AE,» ELSE CC RE 8) — RP be Be A] 9 FCG AD AB ELA — ir A AS FF CE II A SR NB SH TI A BB 4D SPF Hy BR i 8 09 TC RE EBD PELE sD AR AE REE RE bh i FHF RIED. HEB MERE SE Fh ALE C= C UE CEL 9 $8 NO AK HIB El eS HA, AN 2 Be =i (CH, CH=CHCH=CHCH, CH, ) 4 4 AHURA He SH He NH nea ee ee wee ane I cer, " wo NCH.CH, es ee (cisstrans~hepta~2.4~diene) Coransstrans~hepta=2.4—diene)3.1 ARBORS 33 FARES. Fe nt OT IL SEH? AT a IC HH a -2— 18 (2) 34-1 CHCH;CH, (@ (CH,),C=CHCHO, MA ER SHY FEAT SH ICH. AU CoN BLEE NN UBB SH 1K By ORE FH He 8 DF CORRE PAL) AS A BH. BRL th FASE LE ELE TR C—C BRAY rh eRe AT A UL NA 19 bf wh DF oR AL I 7 DOH HS ALAC ME SE 5 PA AM 5 2 — TB SA 2 HE SE A A PE 2 Ti A/C BAIT M200 /Cgrem?) ——BHHRIEE/(C+m) Hk 139.3 35 one2i3 67x10 Bist 105.5 0.9 0.6042 0.0 ARCHAEOL RAN He OLR ARE 5 Ta TJs 9 A Sth AS TO BEES BE ARC RE TR EER RS ER. TR Te A MLE IEF HER Ha Bes He BBR HE HOT RK 3.12 RR ARR A e HOKE AURKE 1 tt A RI RG B&W « EP A NOT A PHL ZH Le HAE AUB AE O1S FRE tt % te HB KE TIS IE OA FB Bt 2 HAE AS 5 HEAL ADL HEE C—C RUB AL C. SARE KK Re EO SEBEL BE BRU FBC “EAS eR ARE ta = BR — Bt EU a a PU = AE BR TEE RES PAT. BA. cH, CH,CH,C—CH; HC=CCH,CH, 2-1-7 1-TR (2=methyl bur—1 ene) (but-1-yne) cH, AK, I CH,—C—C=CCHCH, \cu, CH.CH.CHLCCH,CH cH, 4H 2— 1 (4 methyl-2~ propyl pent~I-ene) (2.2,5~tvimethyl hex-8—yne) TESh. AF HLS AL CC RRA CSC = RA, MB A ee a A SO BG BRE FE IA ER AB” OS SE RE BRU F aS AAR LE CC RE C=C = BBY — OFF Rs La 5 SBR FS LOS , eS AEE C—C RRS. Ban,34 Mom Me he me CH,C—CHC=CH AP 3 ~~ He (4=methyl=3~penten=1=yne) (4~methyl-2—hepten-5—yne) 2, MR LSP CL) NORRIE ATIF CARE ADD Ab OE TALIM SE Fa cis RI. FF CRE AD) Sb FE SRR FF aR crans" bie. BILAN: CH Ath HCH, H/”NCH.CH, cH” \CH.CH, Wi 3—tB ae 2 3-H Me -2- Ra (cis-3~methylpen~2—tene) (trans—3—methylpen—2~tene) NOL / BR THA: He BE LR EL A i a DD OR FAD AY Hk #9 CA) abC—=Cab a abi dU AG A) 4 SARE HT RF HE ASAT CR JRE ALD, FELINE / 52 3 1 NOU SF PA Be LE FLA AE 1980 2B HE AE BL AL 2 i % DURAN BR RICE RIA Z/E RICE AEE Fy EO — AR A EG OR BL / 1 I (2) Z/E PRict& —Z/E BRACE AL VA UIE BLU” Dy A ae ERE Le TH A A AST FAR BAL) ee 25 TB AT SD BD Aa 9 DD Ca DD FR UC FE LN EH TE FEAR Fe IRE CARE VAL) Ab PR A SP RI Z HH AY AR FER CAR PAL) tb CE A EAP Ab i EAR. Z,E 9p SR AF fA “zusammen” (Hei) “emtgegen” AIR). i) M0 CH,CBr=-CHCI Gs H Crt -Br>~CH, CH CH At Bre Nc BY MH (D1 8-2 (2-1-2 ((Z)=2-bromo~ 1 ~chloropropene (£)~2—bromo~1 ~chloropropene) RELIED Ft SB aR LAI SPY CC BLABY A} CC 1 FY AY 2A th RA A ZEST TERT PK ES. a Chee Hi cH, cue uNCH.CH, QB AD) 2-5-2 ME (28,42) ~5~bromo~2-chlorohepta~2.4 diene HERO Z/E RAKES O/ LK MBAA MR. ALARA LRMKR, A A MB —2— THB SL BY HZ) —2— Te 5 M1, 2— 1 AZ HB AR BE 6 (Z) —1,2- 2 - 1 — Wo.3 RIB ROR AE 35 HL Al © C! co Nor M-a.2- 12-1 RIS (cis~1—bromo~1.2—dichloro—ethene? (erans~1—bromo~1,2~dichloro~ethene) (EV-1.2- 21H (D712 MARL ((E)~1—bromo=1,2~dichloro~ethene) (2)~1—bromo~1 ,2-dichloro~ethene} GLB 3.3 5A} TS Ba CH A AE A TLD HEAD «FS er Hae AS L/D ak Z/E mit Oe % MLE HO. OOS AS A SA AA th FARA BS iS ATE HE HS BLL I TERR LITRE 7~ 10 4, CO I RG FA (eR 0) a OR HE = AS «FE AG C—C RR AY HU AB JETS, TEE EAL PE pM 6 A) C—C TR AIH UH OE cH, on GH “ Ryo s™ Sc Ho Non H0< Xo -on LL 4 ss akeeM sukerean Cirans~estradiod (cie-estadid i » AWA i HNC ww NN Nae x on (CH; ), COOH, | cme Nhe ° - wae ALKA, linoleic acid) vitamin AD 3.1.3 IB FOR EE Le BRE A A Ey SA Ok «ISERIES ADE BANE RY FL HRSA I FAS A OA EMI. A Cy BI REIE II AUR Cs ~ Cis BY HB RE BI Cas, WA AEE Os FG. BEY F 1 gee HEA RLASE EIR HA ME Pk TT PE AT FP)» ELS PE PA BEAR. EB. 2 PT Hy — BA AO BS £32 ALR ORR 4% Hest w/c E200) /geem) “2 i CH=CH: — 103.7 0.8790 om CH,CH—CH; —aTd 0.51 Te CH,CH,CH—CH, = 185.4 —6.3 0.5951 1a CH\(CH,);CH=CH; —165.2 30.0 0. 6405, 1-e a CHCH.) CH: 139.8 63.4 0.673136 S38 82 he ee he a itt eC KC IE C20U)/(grem Bee CHC =e 93.6 0.6970 1 (CH, (CH; ); CH=CH; 101.7 121.3 0.7419 1-6 (CH, (CH, 6 CH» He 46 0.7300 1-346 = 66.3 172.6 0.7400 2, BEE BY Sy HE BEE SGEKE JAKE ATADL SCR ABE EAB ROA RE SE EE OS TT ES AFC. ~ Ca BE 1s AY BR AEE HOR AS 5 Cs LAE Jo A Ay TAS OH A BE CEE Ta A He CSC SBR TEA MAY I FEA ABES BRAUER ABNF 1 gecm™* ALEGRE AIMEE, BIS SSBB HE A 2p « oH BH EE ABR ly ELS PE GLE HAL. PE. 3H Hy — ae Be sO He Be R33 MAREE a ft w/e BAIT IE /(erem 1) a ot =82 = mote 101.5 —23 17a 122 9 2- Ti -24 ar 0. 694 1-1 —98 40 0. 695 late 2=CCHCH, CH, CH, 128 n 0.791 Soh CH.CH, -51 81 0.725 1 Bese ~80 oo 0.738 1 -70 126 0.747 Ee S(CH.),CH, 65 15 0. 763 1 se HC=C(CH.),CH, =36 182 0.770 3.1.4 BOMRBN LEER Sb Re Be th 1% HE Ht SEE EA CC EAN C=C = BRE. C—C MRR C=C St FIN BIE BY o REA EAY w BEL F o OY F e E) HFae E FUT TE AP TADS LFF « SBR EA) RCE 0 8 ly 9 BEE ]y 5 AB AL, ETE WOT BS DT HS BBE RE TE WR « 5h Be He J AG EAS AE BR Le HR OE IMAL BBL Caddition reaction) S24 BE MEAT 5 5} AY a SDT, BO AB — tt OE Ca a AL) 2 i Bik: AS Ae AB) AS «A 2 a A A eee Nb vy Deacg + A-B— Yo-eK B3.1 BB ROE 37 C1) REAGAN, HE RIE AE ARAL FAL Pt Pd Ni BY FE CE Fo 5 SH A RT HEE BRIE IRA IE BY A AS ARSE AP IGE CH,—CH. +H. 1 CH.CH, CH.CH, hr RE A EF EE OA) « FL AR A TB A BH Bb AS A eA. “AR A I PD ATL he 5 A A kA a LA AAAS 8 ATM ALE C=C RBH) oe READ Ho RBS RS +H 5 A A A VV o88ok B.A A I A PB A 5 A A ET. (2) SRL IR I, ABI, RR I GS Ee AC A Ha A A AR 6 RT CHS BRIN, HC RAS IE PASE. D Am ARE. AE IE aT RCE RRB Be HR «A A LB eR ART) IAEA HAG UR «ME id PL IE EM 5 TT I 15S BEA I ASN 5 A RI AP A EL YE 2 SRT «FL A) FAL bt a Be A SAT LAG 2a — BRAS tA FE. BH: CH=CH, + Br, —* BrCH, CH, Br ER) RED D WPA A FARES RA AIM A RARE 5 Et A FA TEE FH A «ET RAB UAE. AST AY Pe HENLE 9 I> HBr > HCL> HF. iit: CH; —CH. + HBr —+ CH,CH: Br acecu "8 cH, —crpr MS cH, CHB, © HMR, BES oh ERR Me BA i I WR I RR AS 8S cH. —cH, +11,0 2 cH,CH.OH BRAS TE A ROR CA A BE AF I» WR BECHER FLAT ZBOK PAE RE BEAR BE OK Pt 7 BB fe on 4 cucacn Of | JB crscoce, He WS0./11680." L cH,38 Mom tis tis 080. H AV) 24 #8 BAA» BNL AE Sy AS) AR AS Td #0, CH, =CH, + HeSO, (98%) —» CH,CH.O80,H “=°. CH,CH,OH 1.0. CH,CH=CH, + H;S0, (80%) —* CH,CHCH, “2°. cH,CHCH, 080, H OH cH, cH, | HO. I PH: + H:80, (63%) —» CHCCH, SS CH,CCH, O80, H OH Hs Re SUK TAR COX jai 5 AE ACB LYRE BR. fa an RU aM 5 SL KH Se CH.—CH, + Cl. +H,0 + CICH:CH,OH CH,CH=CH, +Cl, +H,0 —* CH,CHCH,CI On DBAS AN «MAS SF HO 9 A 5 0-44 38) BP A TRAE AT AS Oy, Gade a p-SCk CH,CHCH, CL CH,CH—CH. + Cl: thO_. CH,CHCH.CL OH C3) ARH AR OME LES BRE WH HE I RI SB HE 5 SB A Fi oe BE BGT BES C1) A ABLE SF (carbonium ion) + fil fh 3X — Se AG AY HS AE AE DA REE BRET RAR HBR A RO SEE Bate ASCII AE RUBE RAE HOS — I FAH AE A LARSEN LX I ARR fl SAA (i>3.1 RARE 39 H ft H ce (zeus « | i x J x sta SH BR MEP AG AB a A BS TE BD a, zs RE HH C=C a TI EP TE FAR AU SF. ARI PR AR A LIAL Celectrophile) , ely 7 4 ia 7H) ME Cin Ss 9 Dm AI a mi BL BE(clectrophilic addition reaction) 5 PX J HAA (4) hm i BRIM Hy 2 48, WR BR LNA 5 TN AR IB Ae EA RD HSE OTT BE BR AL CB Bel) BAG A BASF TESS oe FE SL oe ED EAT HAE Br — Br ESE BL A AE He AF BO) = 7 fl {DEF (bromonium ion), =e —C-C— +x — Br—Br + CH.-CH, —+ CH.—CH: —+ CH:—CH, + Br BeBe Br aR aT PARAS TE ET A TE RR EB CBr BE RUS» UO SO a FS ke FY NAF 09 p BLE A TT BH J UAT A A) Be PAS A ME 2 At HOH Bet) Pye GB BC H/ SH HSH ‘Hg SALAH HBR AB eR wa PRE ET dy TE HH BE, ea SH «RHA TE BA FE WA AR Oe PT \ eg ae \oue% Demet + ch —+ Ye— te eK IES BE) J I IML ILS AL IA A 1 AB ES, RR» HE DAL AE BY he th A TES ih Bae te. A) FR Hes On RE BB A HE De He I AR ER ARR RIAL CTX, HO ARE A ANE SAM RRA C H—X ARI) AT RT A ARE.40 Rom ie ee CH,CH=CH, +HCI—» CH,CHCH, + CH,CHCH,CI a 2 iN 1 me C1) 90% aD 10% CH,CH;CH—CH, + HBr —+ CH\CH,CHCH, + CH,CH, CH. CH. Br Br 2- MT HRC80%) 1-MTH20%) 1866 4F FRR #E°# 3E-V. M. Markovnikow #848 4M AR 1 P56 X85 FOX jin LAYS OE De 4S 8 BI AEs ABS ARIA AEG AB A RIA A «A PT MPS J Ae RE 1 REDE be 1H i 8 FSP WI PE AR RR ROR Eb RS LIU PT EAI, AR PRR KES ARE Ms aR FAL TR tS EI. Ba: CH,C=CH+ HBr —» CH,CBr.CH, D HS I Be FY LI OR Fb TAL I AL A 23 BE SL FETE 9 HL «BPH AT AE Dh Fk IN, GP Fs IE RY | SE > AD AIR A FB A PH A HAS. FRET (electric effect) Ay 5) 29 BRUM (inductive effect) AF SERA (conjugative effect) HAI AL. a AEE ICI, = HES RE SbF 5 — A OY BR Bo BS Eh a FB IEP A Bee — EPR EO COME 5 BATT Bh FB HE SA HE EEE HC CL BR He tH A TT i, CC SA HE» CC) HE 9 BO Lo HE A BB) CC, AUC. BRUNE TSP FO HL ae IE BRT A SBE AS PR AY TE Het. SA ea IRR Dk Fv PAE AST] (UE AR HF Th] — a a A A gL HEE Ff HEE BH HOHE 5 BUR SDF 09 HF i EP AG EH REIT KT BE. ES BU BY Ty TALE LA, C— Ht 9 EO ER ES SA CR ADD XY BR CH BRE AY BR a « BARRE HF a Ih A — EE CAL X ot HEX F AMF CX RL FH thal] FX, AA HG SX FAR FE EES HR HF 28 | BE ESM PS RO TR RZ AE READY Hh fe PEA URE CY HRY HLF 2 i UE AY ARF HE OR PR, HF HS FE 5] A IG SR FR Os TSP HEL RR Cx —C-H “HY ~ 1 0 Heth +1 es BUTE KE BFR ie LA A 9 HE Ac3.1 BE ARIE 41 OH>—NH—CO—CH, >—C, Hy; >~—CH=CH; > —CH,>—CH, CH, >~CH(CH, ),>—C(CH,), fe NF RAE AD NR FOE HF RE Dy FR EE HS Rie ELAS TO AAV «FLD HEE SF SSL oe HLF Ah wl Te He 5 A ES J A ACN Ze I DT EAR, MUA Sh 8B ET 2 AS a SR AG EBL”. the Ry ER LU FA AE «SI ACL A RE 5 AEF 1 a ES oT CH,CH—CH, + H* —+ CH,CHCH, +CH,CH,CH, Hee ABE HF CH,CH.CH, 38 1°RRIE RF .CH,CHCH, Ji 2°R8 iE WSF. 2° TE BSF 08 TE 1B LL FECA AP REM ARE AE AC Sh PIG aL. OF SE HE A TE Dk A a Tt ABR ALTE AGA AD AB 5 A A AB A A, TE SAR EAS D9 Ho TE HE FR [MS oO E> a rE OEE ai me EMF AEE ° e r cH, SMM IAF 1.11- SR AMS HC HRM. EERE ES EASA IDR AFH AE CC RE BY oe BF a Sh A AR) «HT Poa APT BA EY GBB CS Bh AF a BI AR > RR DR LS FE Wt a OY TE BS FCCICC! CHL EB 18 A WE 1 9 A A BE 1 LF LY 11,152 — DU RETR BE ON aN mw a , ciec=CH Ch, ciccr.cH, + check. cH.cl a’ Smite SRPIREF 11s NRE BEAR BRB TA Dy « TB AR 9 Se BAS ae a AS AB FR ATE BS (a) Be a BL BY EE BH A I HA 5 — BOAR BEE A DR Ca A PAT) AS A OD YH, RI RS A) NL HAGA: EE RL J AH BEB i] AHS AB a BO SR SE Sis FG ae HT AS EP BGA BERR OTS ZZ 5 RR HI A AY BET PE UC a (CH, ), CCH, >CH; CH; CH=CH, > CH, CH, >CH, =CHCI FAM 3.4 GARG es HBr Re ER eM IE RE (CH, ),C—CHCCCH,);42 B38 8 we Ae FA 3.S MRR NI, 1 () CH=CH, +B /H,0 27 cy cH, + CH—cH, + CHL—CH, | | boob On be (2) SET HT AA BLT MB Ha RE BR AE FAS. 6 RR FN TE aS FH (D (CH),CCH, (CH), CCH. (2) CRCHCH, —CF\CH,CH, 2. PUA hi HIKE BIKE BOISE KE 5 A ERE AAR AEP Le RL ARES ZT Gt ll AL 05 FA Fy BAL ALA HL I IM A A BR PF 2 A AST CD) SPER AR ER EFDA KEG BRIE IKMnO, 7 2 FE LE ATID. AS A A oe BL TARE AE CB BE AE ME A LB A. CHy=CH; + KMaQ, + 120 = (CH, —CH, + KOH + MnO, | OH OH 00 \ CH, + KMnO, + H,0 ‘ASAE BR 5 OR PE a PP EH PE FD 4 ZS RAH 9) LA OE 2S 4 AA AC WRF LGR AO AEA ANT TB AAR De. BA —CH, +KOH+Ma0, 4 RH HR, c=cC + KMad, HS Sco + Cort Rem RA R R He R R Se + kav, 1 “Sco + o-c% Rr Rr” Nou * wa RC=CR'+KMn0, “ RCOOH + R'COOH em wane HF BRAC es KM, 9 A LT 8, A a A A. (2) SARE IR MN BRACE HR 66 ~ 8.6 ) PE AIR LF AE 5 MS AS Sa A SE AR A ACD GEA LAG DAE 6, Zo 8/10 Semeg 2 YK Se-0+ 006 6-6 et SEAL BL ABE (—O—O—) FRA EASE» BE RR AE AL — AAG BE DS HAR PE ABC RE TAA AR» 4B PRE BR — SEE oO DH BE dt — 9 TA IE A kA TY SAC 2 FA) CCB AL «JL A BEF SB HE hs ab Kee 9 2H.3.1 ARRAN 43 RARE Ab FE A AE,» A A FAP RARE POT AS HT eB I cha a FAM .7 Sb FSR Cy Hye AME AD ASB. A SE CAA FG ESET ER Bb Mb 1h hy A ZEB A eR 1 1 A A 2— RP AE. RR IT AB AB HIE KMa0/# FUME 3.8 CH)—CHCH,O=CH, cH, 1983.9 CHp—CH—CH.—C—C(CH, >, CH, 3. KE AY AY Hi AE Be LY Sam RII Lak AE ES A SR BB RII SB BR AE PHS ATA aah AL 19 FF AE IT SL AB AS BMG HR A A WR AS SB HS AL MAM (peroxide effect), HF it MAL A St Ff) O—O BEAR PS HE 1s » 5 38) BE HE FAURE Be AL eh AE POL LE FT. fA an: fP312 — R-O-O-R + 2RO+ RO++ HBr —* ROH + Bee SEI Bre HCH\CH—CH, —+ CH,CHCH, Br THE) CH,CHCH, Br-+ HBr —> | CH, CH, Br+ Bee wei Bret Bre Bre Br Br Bre +CH,CHCH, Br —* CH,CHCH, SEE RA DR FA He FAB IG HG A A J A HE BFL UE AE. (2) oH APARNA HE REA RU URE A Bi Hy BL IH SY FH BY a BDF SE TRE A BO 5 ED AR 5 GH RE A SBME YH EHDA» Ae RAB aT AES BB A 500% CH,CH—CH, + Ch + CICH.CH—=CH, 2079 3-9 (DE 3, 10 Ye AR A LR EF CH,CH,CH = CH, +Bn “+ CH,CHCH—CH, I Br44 3 MIE I Se 4. PME AY BETTE SAR RU YA SUF RIE A ASH REF HE sp Fee HEH HA PE BE spt FM sp? AAG BDF EBA {EAS AR Si RA Oe SL AT CAR «SG — BE I RB He ARTE BAG «MULE A St Be A 5 RAL) SL aR A A EHR A OA Be Ae a we ET A Ae BE Ae we R-C=CH+[Ag(NH, ); JNO, —+ R-C=C—Ag 4 +NH, +NH,NO, sete R~C=CH+[Cu(NH,); JCL—* R-C=C—Cuy + NH, +NH,CI Sift cab er Ei IR LA Dy RAB BB, FS ACS CH SAE OY RE IE AT IG HE, CTP SD RS HO ‘SLAB Be 9 eB TE 5 PE A te aR TARR EM at Sc 9 HE ee ‘TL, BDF POR a ae EI SA A Se eH FS 5. RAR TE 5 A AEP A RE AE eb BR FA eB Ss ie ATTY CRA) Ud SE HR JE ANY SF MAB FRE AD» ES BT <— ft Gin ZH te 160~280°C ,101. 325 kPa LAE AY FE INF HA fick at 4 0 Hy 5 BR A BE FT) 8) A INE 5 UA PR TS ZZ _160~ 260 101.925 kPa ELLA EE A n CHy-=CH, POOR £CH.CH.3y ZAM 500~2000) BRE BATES LF. 3.2 = th MIE ARA TD Fd BS Comm C a A A AS HH RG MANDO Cy Hes 3.2.1 SRS Ae Anz 1, SME BY SPS RX BB (diene) Fh 4 C—C SLE OAL RYE BE 5 KE AT Sb DR QQ) @ A= HK (cumulative diene) B+ C—C MH AM HET RT Le * SCRCHCO "AMR A IRE A RBIS, MCHC ACH, C1 2-5 He RLSWRE A.3.2 mB 45 CLARE A > eB A Se (6) ACO "ORS DERE IE, PS ATS RE, GAN.CHy=CHCH, CH, CH CH: (2) FAR SHAE isolated diene) BIC C165 LIA) 2A A A AG RA FB «AT Td A A TA te ES OL A (3) SEHE = MEE (conjugated diene) FH 4+ C=C 3 68 Fa] BA — > RR AFR» BDL BLE 3 HE i." Sc CH 8) I A MG» CH; CH CH=CH, C13 TRB). HEIR ta I A A RC LAB Pe BLS AS PR Fs BE A AS AA i DCS 5 A A i eI JG AN OR fala CH,CH—C—CH, (CH,),C=CH—CI Le-T = Hae Chota=1,2-diene) =methylpenta~ CH.-CH—CH=CH, ICHCCH, CH, cH, BoM 2-Z a1 MM (2-ethyl~3~methylpenta~1 SF AT UF HD 9 — Ha Ke WL / RZ RH AR, ~ Pan cae CH Ce eet HW HOH M26 Re FRI 2.4— Be =36 (cisscishepta~2,4~diene) (22ND) ~ 2A REE ((22,42) ~hepta-2.4 diene) 3.2.2 ROIS 1. SEE KE HS AE, C1) Se IHL 18 Tn Oe SEE ME. FE 1,3-T at Fd PRUE EB spt HAG RUF ZAHER 3 Cyr Cyt o BE IL FBR IEA spi FACE SY HS AOR OY 1s PUI RA HE IER 6 PS Cyt Hi, 0 REE EY o EAB OF. ERIE RRC p PREAH MFT ARC SOC SCS (i) AY TB AH a oe RE TAL Co AY Ca BAD pa AS a REAR FEO AE TES » ETE TUL 4 SR FP as LA A Ap TEAK oe BE, SR RM $B (conjugated x bond). HAE 3.5 ATLA x LF ANDRE C)— Ce MC, —C, 21) ABI46 Bie Be he oe DEBT EP BY x ttf 84 BHM (delocalization) . m HLF i BRA AY FP th F 2 EAD AF PMG BEN TE BEA HA» RE AR AG SP I PE ER AR ESI, — ARE A SE 0 oe SRE CAI A FR ak Hy 38 AE HE HH (conjugation system). 1,3— J ASP FFE RT WE We ae EL HR. FERIA Rp SMILE x HLIG AY AB AY Ms Hy SE BE | (2) SESE CME RUNIE SCRE MRE rh PEE SEE 0 RO BY TD OES KE AE SE FEAST HE | D BR FEE. 1,3- TOMS FH C.F CoC. 5 Cy TAD AU RE I 135. pm He Za C=C FER C134 pn) RAG Cy 55 Cy (BDAY BK 147 pm, LEZEN C—C BE C154 pm) BFL SB JRE CRID 3.6), HBA 1.3 — TRF iP ASF Ae eB PE ARE AE Co Cy ee Hm geo FLA RBS) OE A HE 4 H f. \ ison. 7 ou, A on ivan Sa We) ee", 108” H PA S.5 13 TARA r ASME FIS.6 1.3 TASER Bt D DY FAY AR EME. AE SAL IL DBE IE— 4 oe Bt FS Ao RB A FR a SO BL, Bee BRK RD FAR HERES PRR HE Dy RZ NS PE HE A. SRM EH — KEI ACHR MF CH,CH,CH—CH, CH—CH—CH, teh 126.9 kJ+mol 19 kJemol CH,CH,CH, CH=CH, CH, =CHCH, CH=CH, CH,CH=CHCH—CH, Beth 125.9 kJ+mol 254.4 kJemol ! 226 kJ+mol SCARE ZEN] HE HA IS) SA A BT SI — Be SAA A EA 1) SPI RACHA Is BEAN SE PENI KE BTR Ha EAR,» HERE EL ACHE AT FE Ee BD PP AE (M311 3-15 ROM ye Re BAL tI Ae 2. Se AR ASE CD SEI FERIA RA AME x MAR, UBD FMM ERTS. RHE TE SEE BE AY Ph BY AN Ie He RA FL As OD row HG, xn EAE RA TR Ee BY p AER RM ROA, SORE APLAR SC Me iE He AO A AB PR AY, CH,CH—CH—CH—CHCH, 24-232 2% B 47 @ pow el. pom SEW p PIAA « BRAM RMR. BYE p MIM ab Fay ASMA] pa FES HT 5 LAF = Bet a SWF px SEG. GON WZ CCH, —CHBr) FP REF o A ER ALE TRE A TUS p LF ES we EM A RU C.C.Br SRF WAL Le 4 pt FASE ve BRE Se A FI FA TE I» ISK BF p— ae SEN BB es FR A HL pa SE PEC WLA 3. 7(a)d]. b. SRL pn FES BN ET AE BRIE BE FC CH, CH=CH.) Hk RY 3 ARF HA sp’ AR AG Hf TE HO RF 9 p AURORE. p MINTS AY ow EAE AE ON TT EI LL ABD Hs Paks ADA 2 AY p ALF A SE oe HBR i A FRET A DS BY pa Fea Ret ty FY pax FEEL ULE 3. 7b), ce SEAL Ppa FA «AAO 5 SAL PB A SF PH TAPE YH A CCH CH=CH, ) , 9 0 BEATE EW BOR TAY p Pi 1 PTR p Mi oe RON IER 3 OO a 3D pF fy He oe AB, a oa FP AE AG AP poe SEA MR BY pm SEMEL WLR 3. 700d]. vey PS. 7 pow SESE DA A 7 AE OD MBF. BSE HE A C—T o ES HABE x OR p PLM AT HAE MAR. WAY AT DAE Ba RR 3.8 MIRAE a. om RA SEAG ON , PI AS CCH, CH=CH, ) , 5 XX SE Be UF AE BY A UR 8 Co Ho fit, HF ARF A) RR HE C Ho BP 4 At C—H o BELA Lt HF 4 C—C Abie ee Fe ET 6 C—H oo GRA BL ee AA — 0 Fo SE (LA 3. 8¢a)), b. amp a See «AAA, Z, AMIE BS (CH, CH, ) . FE He AY CRE sp? Hee IFA — 2 p48 Mom we hee om SU .C—C Pay 8 rae EAE Fi) CH oo RAMASSKS pMiRE- REM HR, JEW op BIEL MLPA 3. 8b). BRAT AE RR TE SF Sb te eae TE PS — A AB AT AS 2 LEE SERCH ANTE A — ARAB I LE hs CG) FB RSE we HE VRP os LSE «BL AFT p Mil. GD ARERR CARD F 3) A PERE AY p * (2) FESERON HR AERLAL Cconjugative effect) BANFF FE F SEMEL A HY AY HLF « BD oe Ht SBE SF YS NL pW SS A BI AS A BO WB AS SH a CML SI A ART oe RRR EB ED 0 BAIR RIC F 1. PARSE A FS Aa Ow SHR A AD. SO RET FPL RL Fe 5 RE AA ERA A He a PY TY neon -8 LS ub hu-8 2 én, én, miter Tm a FOL SEBO OR ARSE hE CH RTA HD PE HR RR. BM 13 BB a FFA AS BAG EF RAE BR HE FM SE ae a Ba CECI SP RA a ‘EAE tL Be PA we ads Sead, DEI PR Fi, Si — RS BE Sw SRI «EAT SR A AD RD 2 AR ATIAD — #F HE BE SL #2 3. A R34 FSRKAARRAHTESA Hw 3 OW PA Fb ERA FESR BIE Rm FR tent SALAD o HL FH SP FE I NCL Lm HS ici ae eH ASE Se a KH PSE Bh FEM BN SE AER I ACE TY TZ a EK RT A “ K RE. LON wl RE PH DATE AN eS BN, ET eR «AR ER FSB, Se A I SE PE OR HF SA th 5 Se — a ESR tg «TT RB 5 $y HL] AS — ANY iS SO Hd 7° I] SY A 5 RZ, CCH, CHB) St FP Deny FF TES SF Cia ANSE EG Br A AY 5 Be EAE BD HB Ze 5 BB SE A I Fa SS HC-SenBr Hea CuBr a eee 3. Hei ASB ae FNPARTE BAGH 0 A Ae RS SAS A AS ANTAL Zh ew BRP] Be Ae ew AA J HOR. MEL FH MA SE og Soe FRR ALB SR RL A A J «a SR ES FEB) 1.22 1.4 — PRR A A fo. HeC—CH—CH—CH, + CH, —CH=CH—CH, RO=CH-CH= CHL Bro Be Be Be CHB Hc—cH—Ch—CH, + Ci —cH—CH—CH, Be br H 12m 1 io 1,2 — fA He RIAL BA BY OP AE Cy AD Co es — AR a He RFA AY EB SP SP Jane SEA fae AY Cy A Cy ND oe BRIERE TT TE Ce AT Cy TDF RT AY oe BE AL 388 5 HY FE HE HM. (9M 3.12 CH,CH—CHCCHCH(CH,), + HCI—+ cH FEA AE OA Hs RL SP AS AAT) BF EA. WT RL BAe SB Ab RAH OH SEI a fay Ee AR A A AY 3 Tl Pa TEE TE BF 2 we + ide Gad bn, —> crn SH -cH—cH, +EH.cH CHU, a aD BRE PS CT) Hy HAS AR AU TE SF AP TE Bp LSE ET oe RI RR Don FEMA A «SOAPS ATA I 3 4S C—H or $REFE BR o — p AY SEE « SA TT AE FR 9 TE HH HB LL BUG. BRIER FC AL VRE FFG poe FM aE EEE AL a EI BE MRESF CI). Sas AR Ta BF CBr UEC PER TE SE CP BR, ha PE ERE BE DAS Hy SG LA Fe HL RS LE TE, AT A BSR HT A IO OA, (A TA) AB Sd Aa CE Co AD CoE PUA Br BE CH TE A TH Oy Co ALC » ATG Sb AB) 1 .2— He PEMD ADL A — Jo ORG) «RTE PE Hf i) ey SI AS BR oe HLF SLC TE A Br CH,—CH—CH—CH, + bea 12— fn) CH,CH—CH—CH,; + CH,CH+CH=CH, BD (CH,CH—CH—CH, Br 1d na SRG MB AE MB OT Be He 1, 2— FLD A — SL a RE ELA WR 2 — J AD kf50 Bs MIE is oS COATS LE A RAK. M13 — TOMS HBr fy fo AE 80°C AER YE PAE RL 9 BZ WAT 6 12 — Fd RF PE 80% «TT HE 40°C aR HE PRE A ZI 5 1 A — SU a 80% 5 BWA T AG Mek AF AA) S15 2 — Fo I, 5 Py) lA a I a» a a CE BEG MN PSE A 1h — ft Hy SE Fe AE HE «I HE AF FEM MRE OY 1.2 — DR Ld RARE AR AEE 1,2 1 eA Le AAR TD REA Be He SEA SE A BL 0 YO % th & Hic # (lycopene) RAAF b HH — 4, 4c Wh Harlsen AH HP BAM Re AE. RPK GH HA A iG HARA A 1959 HF, Ernster MIR fe hi AE OY os MRE PENSAR SCMAFPRE HM Re ORR, LLP R AM, GAH BRAG PEL M RE AHACAHEKALAFT MAR MRAM REARE ERD HABA, SHOES EPH T SAAD? RAO CEMMREP SERS. oh oe. BK Ha GSH GHRPSERS APS PHERAASERE BABRRH SHARKS EAS, RAMEE APAPAMS 20 me SHAH. AMALEHGE EAR, EEDHE AM fie I BR IPR EAP. AR AB HE BL A a a ae REAR a PR SRLEOTFRA CoHs, CLRABHH KAD FEH. SH 11 PRAMAS SEM RR RA HE do F ae oe Oe Ay | SHOERARRHLHEUL AAR OHRPRAKEM, CER OBREPAA DNA.K 8 JR RACE Ah Fo Be RF EL KD FR AIRE A Hh HE» 31 Re A OH BR CHER REF, HLSRAA GSROKABRIRS A HAART AR HAREGLAVY DH ARREARS B-Ab HH 2S. AMAHE H 100 F, HH SEARAKRE GRRE MRS ERA RP RRR EE IM A RRA HF EAM, WH BS ARIE. GLA T MRA CMR SE RRR SRA BRET. HARSHA TRGEPARARL AREF,a 51 Le ARR AH tee FA. () (CH,),CCH—CHCH(CH, (2) (CH,),CHCH,C cH I (3) CH\CH:—C—CHCH)e ) HO=C—C=C(CH)): CH(CH, >»: (6) CH,CH;O=CHCH=CHC(CH; )s CH-CH, CH, 2. 5a Fo Ae es HSK CD W342 — (2) 4,5 IR a2 Rese () 02,38) - 1-4 -1,3- Ro (A) (GE) ~2— FPP 1,5- Be 3. LAS ACIS SEE RC 7 MERE AT 4. FOR FAC Be. wy petace, +a, HO. (2) CH,CH.C=CH, + Cl. CH, Ho (3) (CH,),C—CHCH(CH,), + H.S0, — (CH) C CHCH, C=CHCH, + KMn0, I CH, os H.0/20 (5) (CH)),CCH=C(CH,); 5 = a ROOR (6) CH,CH,C=CH, + HBr —“~*—+ cH, o oO +o, Same HgsO./ Ht «8) CH, H,+H.O. 5. AE FSA Be ts BER A AV. 1) BRIE FR EHE © CH.—CHCHCH, @ CH,CH.CH.CH, @ CH,CHCH.CH, @ CH.CH.C(CH)): cn, (2) 5 HeSO, LA HE: © CH—CH, Q(CH),C=CHCH, = @ HC=CHCHCCH 8. NaH Fe SEE A SE () CH,=CHCHCH, (3) CH,CH =CHCH=CH,52 Rim i i SR 7 RARE ty ES ° CL) AR a4 HE ABER FUE IG 8 CH, COOH A (CH, ).CHCH, CCH, (2) RE NRE RENE LAE I 18 Hb FZ. BEI — 4} FZ —ACHOOC COOH) ° ° I IL (3) #6 BE 0 $8 BLA FLIE 8 CH)COOH. CH,CCH,COOH fl (CH,);CHCCH, ° (4) SLAG EDK MUR #4(CH,), CHCHO #1 CHLECH, BF Ae MF HA C1882 THB Tae (2) CH=CCH(CH, ); ,CH,C@CCH,CH, #1(CH, )s CHCH,CH, 8. Met) ACC, Ho BR BCC: He) RE 1 A 5 a ERE HE AL BAT CO, AHH A 2 5k 9 fezR SEG #8 HCHO #1(CH, ), CHCHO,B 460 Re AF-4E FS 8 LA HE FH MN — Be AG CE A ALB.C aT HEH. 10. DUANE A) ALBeC.D AB AAT SP Fak Cy His. EAT HE ER 0) DU LIE AE HEHE. A HESS AgNO, (98 HEEL MRCRE B.C. MARAE. 4 FA OO IR ae ARP PLA. 4 CO, FIPRLAR(CH, CH,CH. CH, COOH) «B #4Z,.AEAI 2~ HAE DUAR (CH, CHCOOH) sC 518 FAR: D #4 2— 11M AW CHOOCCHCOOH) AI COs. 8 cH, A.BAC.D 0880044) (RARER FRE)RAE Mm 4 ERIB (cyclic hydrocarbon) FE AAi MARE HY HY RB ACO) RARER, HUE E (109 2 HY PED FY Sb Hs A SPE ANH FAS DH AWE HiT ONT EAE EG EE RA SA, HY FAR KEY SRP BBA I I, ODL, we HR YE AMET, Hticlcel SLI ASF AE HE 5 4.1 9 BR I AS LAT AR SA A Eb 4g ERE ALL % BEBE (alicyclic hydrocarbon). HR AKER IE GER MDT TZ DP A RE Ea 8 A AL BOD ER IE A 0 A A Fi (VDE IS A FO)» YO FS SE 411 BRERA SS Ae 1. PR ARLAAEBE RC J7 AL AE } AB G A A S A O BUR ADS RARE. BRA ST AA ARLE RED BOY ARCs ~ Co) HBB CC, ~ CoP (Cys DLE) BRE. TE DLR aR Ae HR A KE 4 RSE FAD — BR FR DR TB HJ A> RE A> PPR» SA ES PMB RAS AK 2. eH CL) FRR PUR ARES A 5 FE RE REAL ADL FR PE A OE KE He PTI TE eH, Ce HA BE KE 4% HS HN da] Ke “‘cyclo” EHR LAT IRAE AE aR MARE ES A AS ALE lS. PAA A O om Ceyclopropane) (eyclobutane) (iethy!—eyclopentane) a, wy cy 1-P MARR SAF MF A 1- PM -1,3-FHF MO -metigl-t-icpropyysohesse) ——G-mehyeyopenten)——_I=methylgelopent-12oe) (2) BIR AE D BHR. MII (spiro hydrocarbon) fi) Mr % MEARE MAE BER FY PR BEE» IF HER54 wie wR OB (spiro) FJ AY 48 A FA BATE BC bah a MR DEE Sh A Bb RR Hb CHE, SCF TELA 2a $A FOL SS TP BR A A Se A EF i Fh WA RO BA GAT BEAR REAR CC 4S MITC, BE fae CXS 5-H AML 4 Ne 2- CMM. 5-5 aR (methyl 2. ¢Theptane (2-eahylpiro S]dee~8 ened @ PERE.‘ HUREHPERIG (bridged hydrocarbon) (8 ABH IK. = HK HR ik CAT LAGE PRET LBA BR Ze C—C HRB ES AHL FRE SE RB SR) RD ROMER «RARER SL JE 5 4 DBS A CF He a KS hy OC EBD PR BFR EC TA LE 4G fs FL BP 27 8S BE ROU IA “AF SRE GSH BE DE FEA ER BEES — AK FE CK BU A I I Bh a SLE ELE C—C RICA. AA J H6L3. 2, ODER 2.0)-2-4 1-2-2 KL. 2.17 Chieyclol 3. 2. 0Theptaned (bieyclol 4. 2.0]oct~2-ene) 2 ethyl=1-methylbicyeloL3, 2. 1Joctane) FRA HAPS CH JAIN SBIR OY = RET RE OE M42 WEEE, o> «AY 4.1.2 FRAO 1. PRE ‘IG 0B ES BREE LDL Zn IR OS BR ACR TB RAGGA AY, EA I AB LAL PE ES G4 BK ADA MER RR AG — a A HY DRC 4.1), FRA UR 5 18 IRIE A A & & aC 8 1E/(geom) Pie 2 “0. 5808 RB —33 0. 689 The 0.5 0. 579% RY be 13 0. 689%0.746 0.659 0.778 0. 684 0.810 nyo + Omi Kw. 2. feet i ARH AUG RE A 4 HE IL SES RE A AL 4 5b Be AH A EE ER EH (cyclo aalleame) B49 tA ASE IEE (5 1 29 AE A ALL» FE eT A A « PR HR ANAS Td, AE RH ERED JE SE AAC SI TE OY EE HEL DEI AS RE «EL AG J 8 AE SS SU 8 CL) Fa EME RT a A AA A HEE IES 5H PB YA 7] AS UB HE A, AST 24 BRE RE Fe) 5 BO °C At A BS eT RE A A: WC Be 5 120° CNS IT So TE HF ET Es RR ERG BE 300 CA HB BEN. Ni,a00°C Oo +H => CH,CH.C (2) SHE i eB IN SR He Ba AT AE TE HP TG XX BE TNL RT 8 i SE TE ER A A eH HE A +o 28 crmicrcriae + HBr CH,CH.CH,CH,Br 1s CH: CHs SAR A te 5 SL RT 9 a I FT ‘i TE SF ee a EP, FEMS FEAL. A as ) A crcHcni.ch, Br DAE BY ACE BEE RL Ts EA Sh FPA 9 A TD» FE SY BRT I PRA HE AR AR SEE. NRG IR PR AS ADL HB A HI» HF 8 SE AL HS (3) BARR LIC ANA TO EE He BEAR AE «HE a A, EAA ‘fain: Cre 28 CFA ener36 aie RB 4.1.3 TRB AE 1885 4F.A. von Baeyer $81 3k 1° BE (strain theory) 3 MEREAR RAEN GE HE. Bacyer DOK PLA BR DR FE FA] — PTT DWE aT «EE 0 5 YF YR BE AH L109. 5° 5 Ah Ae «RT BR HET PAIK Cangle strain) AY Ky. FPR BE ATER T ef) C—C ETB AY Se Ah. Hh FY 28 8 A FH 10 Sy TESA 60° aR 90°, fe HE SP SR AG 24. 7° 9. 7 LG REE = fe TE Fa FEE 9 JL Ao HEE FH A SAO» DAL A BR A Fa «FRAT ts BE ALA 5 D5 OO TA Dk Es SER a a OE PE RE. Te SUA BRT ie UE AY TR a» SBS AS EY AS AR BH 109. 5° Sy" FER I HR” JE EE OY NTS Baeyer 9K 11°F BEAR A = DIES BY AB He PE A Te AE EL AR HE a A PRR RERE AYERS TE. TIM .Bacyer AY 9K 17H BLE YDB UA BUR A SEF TR HE. SCRE BR REE HE 3 ASR DRE SEE TES «HEA PR EA 08 BB DF BASF] SE Le TIT AR RI WHE BIE IK A I. SUCHE A BR BREE TA Wy «PIA DE HE ARSE «SP CLE Ze) HE IE RTE SE 5 ARE AH EL a EO BL sph BUT AIDE RCE A449 109. 5° 5 SR SRE Wk Fs ATH a UE A A A EA RY BRE, eke HY C- HE FAs LZR 109. 5°, ASH A BE ARO A RARE XP ER TH BT BALE AEH RTS BE C—C Ti] EA 105. 5°, WR RE BN DR FO he He aE OF ty BUR AE BB HE A HEE AY «Ba eB TE A REE. 41 BAR. go> ies Nico. Co) SSPE IA Cb) FRE S-F Mt ASF He P41 BSE ATSR EAA SPF MA SBE KE TY FA Ha 0 AR AE A] MR HER ARPA HH 1 mol #7 UL SE SENABE HE HB CO, AH, O i BT RHC HH SR. AL He BRAS CH, ATEN SE BR Beh a Ay Le HEA HRT AR Se HE — ARLE. CH, SR WEA 658. 6 kJ+mol | WARMED. AeA. 2 TEAR PRG Be BUR SE RE CH, HR BEM ELSE IT BRAG 5 BE PF A BEAT RE MEARE. ERDWSE CH, MR REARME RTPI SPEAR J EES EE HE. ATER UAE RISERS HP CH 2 ORR EFA PL AB BEAR «APL AE BS BH EH. SRE RAY Ha HE 5 AY DD ALPE ON BO AIK. GLH TAO ER HE AA (ring strain) BTM See.1 ROR 57 RAD RAISON MRMETA (AH) (149,480, + HCO ALO ab FR SH./CsS+mol"!) (aH, 2 GH «20918 CH, 686.0 CH 564.0 CH 658, 6 Hy 662.4 CH 664.2 CHa 658.8 CoH 659.0 CHose 658.6 FAN I Ay REE A AE BT] eC RR EL OY PSE ARLGEE «sp 8 HE RU BY 109. 5° FE fal $5 UE A HE A 8 Os eR PK ELBE Ja « UA ADS 6) DR WSL «A FHT EF Se aE EM HS EAT BEM SK 65 Sak 2B oF LG ST GLI Jy PBT A] ) A BR AS WF a PAN ZA 9 2 FBS APE ATV AY van der Waals EZ AUS. SEAT ALR ZL. FF van der Waals EE AUN. RLU HEAR JA TPE van der Waals SKA). BU FOF Jy BS RS A) «Ae A. 3S EDF RAE AA GY van der Waals “P48. 4.3 FAY van der Waals ¥48(r) TR PGORED rom | REFORM r/pm | GCECRIEAD —r/pm | MF GRIED — r/pm H 120 N 150 oO 140 F 135 cn 200 P 190 s 185, a 180 cH, 200 Br 195 \ I 1 215 1-0-1 nm =100 pm. 41.4 TRE ATR 1. BRE HH RIBERA BSE (envelope form) 4 4 Be a F kb te l— Fb RR HPS R29 50 pm Bb Jt C—Co SEAN MTEL TCE FASE. FR RE SL FE A HK I) ELAR SEE 9 5 BR DF A SR EL AR BSL HK 70 A TS SINE 5 AASB BR FB] 9 Swe) 3 SR A AS A IK AR I A HL 3K A178 Aah ee CR 4. 2). 2. RO en wR CL) REISE RG RU A AA eRe A OP A AR 9K LE CC BE WL FH OY RS —— 89 BAY (chair conformation) Al At 249 K (boat con58 Big R OK formation) , M4 JE 11 °F RE JRE OY IMO. “— iE ee Hib Re, CHa (RAW) a2 BRM CE RS AAD Se BU FE AF BES PRE TPT. LE MBO RE” OBIE AS AOL FT He BY A Ai 36 RH HL ey TRA CRD 4. 3). RS TD AY 8 4 CH Bit Ef RF ide LE ATT 3S CHa 9 a 2 3 230 pm 4. 3¢a)] 45 AUF AY van der Waals F482 #1240 pméHliE TIE van der Waals JF Fis BOUBLAT STN IK AD © EE Z EAD BBE FE A HK DD « SUP AIK Ja ADE TI DL ARP TELE ARR SER me __183pm__ co tat (m8 4.3 Ree HRC eH AA RAE AH dE ER 4 RU Cs AC, RC, GC FAG6 1 ROR Fy RAR CPE 4. 4 BY Newman Bat), FA RE UTE IK. BO ob AK APE BR FLA 4. 3b) FY Cy 5 Co] 9 EF ADE 183 pm, sh FE 7A van der Waals RZ A MNS IH. SURLY A OP AT» HB HRA PE. 29.7 kJemol "5 ROA HLF i F SbF 0 tick a 5 ABA A 9 A A 2 LANE PALME AR BE SP SH 3 A BN OD ESE IE SCTE MF 99. 9% AY EE UY SRF TE AG Ft AG HE » AS PH Pe He co) mem HE 4.4 SRCLBEEY Newman fest (2) ADHD Se OES RRR PE HP UA PC, Cy Cs SESE Te CeCe ATE AF tii LASS Bi AB 90 pr, LAT ELF. Pa HH HE RL “NP BE 50 pm AYE TAT.11 me OR 59 2A CHH ES RS WS BARE NE AT AY 86 CH BRA a eo (axia bond) SE = 4 AL 32 8 4 [Bl 5D 18 Fd FF i 5 =P a A DF SEA 6 CH BRS RFRA 109. SICA SEBS OM RABE o $ECequatorial bond) AP 4. 5 Ram. PR RE — RF BI EAE EAT 1S a SEA ea 5 atk 230 pm, H yy a AE CCCs He HF RL CeCe 6 a RE CEE CarCa Ce 6 EEL HEAUROURH ase H FO 4.5 HRB BMY a OI BE RCA A HAS AH Be A A FY RE YB A RT DG SE C—C a a EH $e He, «WUE ath AY ( — AG A AY Ca) St CC 9 Gah EW — BP CD fe}HGring reversal), 2:3 BARE «HEA a BEBE AR e FAR TITS AY © AE ME ak a HEL SL 2S FH HARARCTAL 4.6). [esi { ah £ = — : = = ne feamcos0% or tem ar50% P46 RL NEMS OORT TEA HALA RAE A I FG BES 46 kJ mol | (HES AG A EB A A FO TT ETT FER — PAP BAR 3. HARIRC Beh C) BURA BE ERE REA a — BCA e — BUC AER Ce A BP Ge ELBE Ee A. FP AY OR Be yD A AK S205 7 AL Sr SURF (3,5 (ONAL r PAE AY van der Waals Fe 133 (a3 7) AN BRE. Te ~ FFE FRE Bo FEE AY Ar 1 AT 5 5 A SR AV SB Ee ED RO PRR PALS HE ROR BATE 95 7 LAM 4.7),60 sig KR ® 4 H(a.a) a ME ERS%) eB REE HCO) Laat AOTE OR a 5 A A I BR FEAT WT ee TH ET — ASE HAS BE A A EE HE A LS LDR, Bt New man O50 200 Se FALSE Ge C\—C. HE AE AE a — RC Be CH, PR Cy AYRE SALE RACH ye — FER CL BE! CH, 5K Cy AA BEE RE eS. RAL T EB BEM HYG REE AE RHR EH «AI SA LA — I IK AY — UP FRO BEAR BAY He Js TEAL He SK AD 18) e — HEIR ECHR) 4. 8), ¥ cH, PHA LH BI EL AR P48 HUE BE Newman #5 EGR ve FRR OB» BEG IK 0 RAILS IK J — A ne a — BHR, (2) BURG he RO eRe PR ee 4 RAIA B11 212 13 14 CE SEH Ly 1 BRIBE RELA RAF BY 3 OR OAT HP YA SP, Fn VAL, 2- ARC BEN PEAT HI. 162 A HER EL AWOL DE HH EHO SN YA FN oH AMF o SEE ATH He Ht AA CEE OTR A DH oy 50% LP 4. 9, Lr. CH, : ae OR a woe 2 Y eva HR P49 ME-1,2- sae eA RARE TEAR AT PAE ae BAR AR eve MAR RAS OAs SL IE HE A i 8h OF (CHR 4. 10). eve BUCH Se BEREAN.41 BOR ae 61 1 ay = VCH, ee a CH, cH, 2a he Foe RRM BD W410 2 -1,.2-— aE He W-1,2- BRR RA 1 Be. AMR a .e WY, R-1,2- RRR ee Mla, ce FSB RATA, NGL SP HY HD YA 5 PL SP BP eos. — eS OP ST SE HOR HOHE EEL o GRAF BY EAT VL th — BP Re EO — AR ETS EE, +H BAN AU BL. — EA ET. (AB 4.3 Sih 1-3 ~ ZEKE HEATH MK Newman BELL). (AMAA Th 11 AR —3— Za EMA SRT. Tea NL ICU AB A EAR 5H SERH RADITHE «D LE A FRCL ISH FY POLS Ry AR EB OT A BA OY IE SA RETR OH Bi KRALL F ¢ PHT ARB. 1 PRR +3 (decahydronaphthalene) 8] Ff 1k SE th BY HG 2 Ae BAS TA A BRR AL CA 4, 0) SR KE. BAA HR BT LISTS we Ie SC By SA ASE SS RS OS UAH At FT] Oe Fa ESR ML A A FSC Rie He 6 SE HU 09 PF SEM ES PIL AGS 5 TEER Be BEE HP BRP UH SO Re Oe ALE AS SER FAL 2d HY Se EL 4. 11, H q Hu wtf _2 7 3 G ; H H H NEF REA Cea BI) FF Nea Cee BAD FAT) fe a RR RY FE HE FMR LAT LA FP CD) BA ARAA RR BAL cc BAA BDL — SR EE BAR RH CC BED BAC AE » SELL SELF ce HARI Ta SRS PR CE ASS I AR TA RB BS UC RR ca AR A Fa RBM ES PIE A SK BEI SR A A EEG LP 4.11 (2) HEIN AS TA), BRK SY F BA HB FF BL TDS « 2 WN HAG a 5 WORRY HH DR HE AB62 Rig w JE 6 SN Dk PAE AF» Ba HB SE BB TAR HD RBS HE RAE LP 4. 11, 4.2 Ff & & FS BENE 1B) PR IG KE) See 35 WR AL 2 (aromatic compound) (ty BEA, IF FE HEAL ty HE HE LAE BARRE IEG Ue AE SE A 7 EHH) — AT FO AY A PD EAA eS A HH HEPES FG PEPE AC ED 5 DERE AR BLAIS — 1G BE A A 2B A SL AS a A AL D1 A TERE —— 5B AE (aromaticity), AIL FPL CY SR EE FE A AUER E LY. ERR URL EE APA RE RAI BD. REA HAS ES ORE K. 4.2.1 FRBOD AMS Le HEREIN FEB HB (Corene) HUE JE BF A KH OT 4} Hy FE AY FF FAB (benzenoid hydrocarbon) AlaE WF #12 (nonbenzenoid hydrocarbon) MV CL) ERLE PERS ARIE FH hE AR BO BCD AE He Do KAO I] BY 5} MR RS MEK HK. D RAGA. PEAR HIE ABE ARIES. GO O4 oO ve * LIE © BREE. DEP RAAT RPL ER I ES. ARE RI AY EE I RAR AL aT AUF IL: ae SARTRE « WG ESD BS BBS AS ke RE FE A AP EAR ARE. ~—CHI) OPO gqaamg ei NZ Seite POR (be REA BIR Be RE ey SB AS A ET A FPA WIE SE od OD YG BRE FF PP RA Se FB PA RF BF BS II,128 BB 63 = cm oc Y =) J oe CO OC ony-% : DERDKER BEPRERK AAG EE FRAY. AER. EMIS Hi SR a Hy A A TA LA GE. v-V O- © Se OF FRR AO HAF 2, RIFE BYR] SF HD AEF OY ADF Be BE BAR TE RIE TS TAN AY AT EO OEY TA. AOE Ct PAN BE) 3 PAR 3 LE FL He PA TEP SE, ER a BE TERRA CAINE « DIRE AE A RY BE 7 A BH a, CH,CH, CH,CH,CH, cCHCH)s cH, cH, CO a (al on ~ S cH, ze iE He HOP soo 3. PIRI KE A thr % AE BSA AE O01) RE Ot JE AA SSE IC RO A 0 RA AR A OMY RD ON AR ZTE FEY — We MEIC 3 ASE RIYA. tit Oy T Ae a AE OY AR TE TE DB Tal XP 42a o— Cortho) .m— (meta), p- (para) ik Ag AR BUH 1,2-51,3-,1,4-2eR. BO, (7 y-cH } OU one wot cence = once 0m (p~dimethyl benzene) FANS Be AEA LAL 3 UT TPT OES Le RE) Wf. lan:64 Bik RB cH, cH, A ‘pe CL Hew cH, cH Lads 1357 RE a= IED 1,2,3-trimethyl benzene? (1,2.4=trimethyl benzene) (1,3,5 trimethyl benzene) RR ei $B AS Be REE eR Oe ei” 4 A A Jt AS DAH TY AS ON 180 HE A A ly RE A oH da cH. (7 CHCCH, I HyCCCH.), 7S 1-5 TE 2— I (5~butyl~2—isopropyl—1—methyl benzene) REA bit AT BL FRE IG aR AB A AIS «LT AR UE BE ETT A CH,CHCH, CH.CH, CH=CH, e oH (CH, —CH—CH=CH, a 2 O O eats eo Ro SEMA T (2—phenylpentane) (Pheaylethene) —_Cphenylethyne) (3—phenylbut=1 ened SF PEKE SDF pS Ba — PE JF 09 GA OY AB Caryl) SAD" Aj #%B(— C,H, .phenyl) , A A] Ph— eA. MEARS Eh Ay EE IM — BY AKI C,H CH: — #5 aR HE, PRE AB benzyl). (OME 4.5 GREASE A RI EE Z ROM HI 4.2.2 Re 1. R69 Kekule st HE CH SP i BAAS St FH A «GET ORAS FE Cy eB (benzene) 4} F Hf sie RF 5 RF 4 BC We LS Zea D1 a EA AS AVES LA RO HE D8 RATA 6 A « TRA RAS ee Fw 5 AS a A 3 A Salt, ABR SOY 1 BLA — AAS EE EH ATL BA BR ALT Me Be TB EL AT AN HR 9 2 A EB — BR FESR EAT BRIE IAS P SURF 08 10 EEA I]. 1865 AF PE LEK Kekule $e th TMH AR EB HED I AR OPI SAP — A ANT BRA BB Se Zi] BS Ra AL FD RO RP RF LAE —T ARF AREA Kekule xt.128 & @ 65 H u Hu a x OTE aes O) Crk Y AEHY Kekcule 20301 TRS} F (9 24 A 2H Be RF 1 8 BC ALS RRR Se RA) BRAM AT 3 4 CC RUBE EL AB ORF AS BH RI 5 EB I AT I A RS HO ETE. J Kekule Re ROO RS Be FR Se tk PNA 3X 120 kJemol”' = 360 kJ+mol”! RE HY SUE HAH 120 kJ emol”") . SBR IW AE FE AY ALE, RAL 208 kJ emol” | He ALTE HIER CE LH OC IEE 152 J+ mol! BEB ER = MSE 2B BES AEH Kekule AS R656 2 TE Wi Sb 1 WR HE AY AS a Hy 2. REF BAH BY AC RE RE HX SRA EH SD TEE RSE 6 PRUE A 6 4 URE AB AE De] FM 6 ALISA ASO TE» Ta RE FF: 120° 5 Be — RR BE AC) 7 139 pm. HNL 4. 12Ca) Co) HEAR. PUM Ae He RIED ESD FA 6 SRIF BE sp* Ae Ae ERIE UL sp? A HE LE A BIEMC—C o HE MIE ARIE PRE HT sp CPL SUT AY 1s PU IE 6 CHA o Bit AG SRF AUF ABE — POP RF ASSAY p PELE OF FF TT EAP A» UT ART RAL AY oe ae SERA RH 2 OA OA HL FEF BSR FA] 23 PA HA RAY AD 4. 12 BR. RR AA PE HAIER FR TE I Ag OS ARE” OR A s eo oo nde " ow C= . : CO) RAF ae () p NIE RI HA ot (BECK F412 ea eee KF RBS HK PROVE AA Kekule 29h , 8 RAW TE A a JEP ots — 7 Be a EO oO Pas HD AL 2 EDF A ES Fe Se HRA I= 1 i66 Rik RB SSE BES AT Al, Kekule | 0 CAE A SR ARE. AE LRA RAR HE FT SCAN IT SC 96 FT Be Aa 9 TT HE I SS AY. TE FT AA MT HE eS WAY» HE He 9 A EF HE A «TB SP” EH MBAR HS. 4.2.3 FRC MEER A BST 0 — RR» SLAG EK « Sb RE » ARE AE RRA EAT OIE GE EY AT 5 ALP SR A A 7 A HBA PRE OY eB a SH RE AS Be A ARIE AD HE aa HBB TA BLT) HR A 5 I HSH FE 4 Rid RAAM RO we ee HEC © HK /Cgrem * 80.1 0.8765 110.6 0. 8669 Mad 0. 8802 139.1 0. 8642 138. 0.8610 176. 0. 8942 168. 0. 8758 164 0, 865 1 138, 0. 8667 0. 8620 0.8617 A) kL HAL Sp a HG «EHF HL 4S CHL HB FPG 20~30 °C, PAA BR DR BE AA EB ADEA A FEU PR OE EB FET en 9 IE EAE ERE RIE ICT RAB A Pk ELE BA LILA fH) BRE PEER. 4.2.4 SOC SER Le A A) HH A LS AIRE — PH SABE OAR « AS BEAL ARS AR» HA se A HAR PR HE EO HIF BY LL BR HL ik Hl —X, NO, , -SO,H, —R AFR RAE PBR CL) TCR IM LIE Be FETA] Hy OY AR BR WL HB HR A BU AR (electrophilic substitution) BRIM, MEDC IAI JERR MBH Celectrophili reagent), KLIMA HEIGL wo FEE TR FAL EIU UHL BILE eee f +E 4-E Me Or 2G *425 #8 B 67 a wf at 4 Che: i = 6x] omae J {CM Qe (a th E Ee oe BOLE te eee EY ES AAR SB PEAY oe HL PE 13 HB Cr complex) « MHRA E ATE OY HY. PRI x BEE ES BNA ARE LE SAY — A BDA E28 AF TE SUB TE PF Th] Hs ——- BB Hy Co — complex) » IK) 4 AH SE ME HE FRAG BB SY WEG RMA A co BL 2 a APH , BK RH FA HY TEBE RAR, CE BRM Nu READ EBT, BOR BLA RR o ROAD AY ARN 5 TE ET ME — TAA I AE BNL BR OARS (2) BARR D MRR Chalogenation) . 4 2 EK MR ALF AG Cle aR Bre FE FH. He OAL A RR, KH HCI Be HBr; Cte Be CP Hx cecum Xe TEP ACR BY EF Be A i SF RE TE OK) XE AB TE, X,+FeX, —= Xt +(FeX.J FR 4. 6 RB SA yc AA ACL YO A @ MU RM nitration), #-FWRM CK HNO, Al H,SO, (i OD) HAA IEE, NO: ay 1:80, ] +HoNo, +H: we 3560 wae SR — Ab 7 He MS ESPRE TES NOS fe — aR AY 6 EE OR AE wo AM ARR RE » EGBR Js — RF 2H,S0, + HO—NO, == 2HS0; +NO! +H,0* QD MURA (sulfonation) , H 7H MLA — AL HN AR RS BEANE AR HH EB OS 48(—SO, BUR REAR. TO +001 ABBR SD EET AK SM De WIS BA 0 hc MR «LF | k $0; H +H.068 wie RB TYE. BE ZLB: 2H,S0, —= H,0° +HS0; +80, or Oe OD SO; re i ey +Hs0, $0; SO, H Ch ino —C} +n0 0 } +H.so, ae He AR BRIA SO, . SO, Se — 7 Hs FBR EB EE SD FB SE Ha: fe i eH i FA De SHE BCA RT MR ICA OD» FE Bs — PH a 7. A I SIL IN, 5 FR BPR 5G OR — A I A, «TBR A I I «BE RE A OR A SHAR FAL BO EG A FE EWR» SL GARTER SO. fA cH, cH om oH, Q a ore Ww oapa Y Y @ Friedel-Crafts #2 RM (F-C alkylation), 7EI6 7 = CAB AEE Fo ES aR RE HE JAD RAGE MEE ALN AR BT R—CI+ AICI, Rt + AlCl, : Cl ™ ae “CO encem TEER CNY BY ARE PEMA ZS BR. HF AICI, BY PEE RP A eG 2 BT RS 6 2 BT PAS AS a «I HE A 2 8 TE AT MRE LAO HBR. PUN:69 cnr: zama, | od (CH, CH,CH,Cl RBHECT0%) (OCH. CH.CH, EAPRC0%) © Friedel-Crafts RBH RB CF—C acylation). AE = AC $8 REA F 5 AR 5 AR PE A A HERO AD. C,H. + RCOC] —» C,H.COR + HCI eR MER ss PR A AR Bz ONL 5 A A Bk AL MEAG A A EA TE BS FCRCO* ) .RCO* PEED A HG He TR AB AC BI “RH EB A—NO2+ Friedel~C SO, H,—COR Ct AE ) 3 8 FE IBY rey 3k A HBA BB ts FE FAL MCAS BY IIE PE BEAIK , Friedel — Crafts 456 3 46 APM A 652 IMLS AS AEE AT (AME 4.7 Gel; Friedel-Crafts MMR MLOLA, 2. Hi RR He Be HN) HR) «AR By BEF BIE» TEL RBA PE SR at EH CL) HMPA A IRL FE AEF J FE BE HIE A EE 3 TI EH Chem MBE O) C2) SR FERRITE AES Cle PEF AE AN RUE AR (Co He Cle) a aoe acre oO t3Ch oe" at a a DACA AG KB RASA AN” 5 — PR AS A AL nn Sve Fe BLE Be ke AE 3. FR UE HY BZ ONE CL) A AEHRAR SEINE ERE PG aE ORE ARTS Foe RE A A ~ B AL FUR LIES BEE ARR AEE A RL. AS cH, cH.CL CHCl, 6206 2020 Ae eee RSM RR70 Bie R C2) AGRI AER SEDAN E78 BD PAE FESR AA. ELAR SRE AT oH KE EAE TB i A AL TAAL HE KEE ay oH RR TRF RE FAR AR, GH AOR — AR ER A cH, cooH KivnouHe 804, >) 5 O29 PEREIRA FG AE CH RE IC A) AR AA TR Ae AR TAS oe? V205 HC—CO J +o, ae 1 Yo+co, Ae ER LR va AR BI aE AY BA CL) RERUN ARR LBA ACE EET HR RB IRA CARA Se ME Si PIE BT BAR ARREARS OS CO) t0vo, neo ol NO, CH; CH, CH, CH CF ry 28 Om ©) os ‘Ol J No. (novo, one & OC NO; TE BREA ON BE « FR 8S A A A Re A BA A A A BOA HP RG A A, «WA 5 Se BE Le BA WE LAH TT SR,» PRES SGC A BD Ay Ss BA A AT SC SBRCAEUE A ARR AUB SR BICAT AY EAC BE Rp OY FE AHL BE (orienting group). (09K AYIK APE FHB6 A He AM EAL Corienting effect) . ALI ME {i257 978 IA HF SE LAL 5) BK425 B® a RET AE AUB AHEM, ERTS] A AURA SE BEUE AB RTL FORK F 60% sR DRT RET — ABBE ART AK, « By BR As A I HS EA 0 PAE OAT ERE A & BE BRM HF lk Fk se (10M B47; NR, » -NHR, ~NH OH, —OR,—NHCOR, COR, Ry Ar X(Ch Br. SEE BU TE.E TS| AB AR E EE A T A ARC 40% 5 HEE SRE (RL ORE BE Bt A A I SL A a 6 HO ALS A LAE a ER A A TE a ApJ GK SB id BE 19 47: — NR NO, » —CN, ~ SO, HH CHO,—COR, COOH, A SS a 4 A ET AR ALD SAI BO A aE 2H TE AH TH ELS EC BY A A RTA AN AT KZ AE HE EH Fe EB AA AK + AG A a Fs SE A I A AY BTC AC EA FE AA AT US DB AE AE A 9 Pe AD AC A a D BARA A He A FLA I HE + D BABAR —BARMEA 1,3 BACAR AY 2 fe. ‘TL FRD aE (SE EY 2 ak PR A BR A BI BR 7 (2) ERNE AO MERE ERIE — TAISEN AR BR oe EZ PIS), RR AS TBAR ARIE IARI (ARI bY LF SSP A HE CE PE SPE CE 2 AAU] i BAS ta ze EF SILLA FEA yf BF] — 2S 17 4 AB BEE eps BO ht OR AY SPF TR Dt FG 9 C—H o SUNS ER AWK we ETE HE ox RG SE AG CON «A PR A DT] — BC BE CH BBR BY HHL 25 1) ARR SH A HY AUS Ai HLF Ze EE AT RS 3H 1 HEF AEE PE SSR AE TOPE hh hat RO A EAB A. FOR LC AR BSD Be APLAR RL ARE EEA EA SB. 0- 0 Ae — 0.017 FRA RAE aE (80 RIN, « WA a ROM ak PH a TE OO Co A A EH RE, FO a He ewe CM Ae A ET SH CE* 9g ADDa @ @ ‘FE TBE RS Fa) GA C1) C3) ELA bs FPR A Ag SR AB STE A OE RFID «RTE 8 45793 38) BFA AB TE SF Ae TT CS a, SE MESH RICE SE PE AB BAT 5 HELIER BIA EAS a 7 SLA AE yf DBP) AS ie A EA SS A a FA ELAR a ~ T INY E PLA —C Re E E ROAST) — BB ERE 2 SE AA 8 0 ZS Be Td 2 RFE ATX AEG 2 DL i REE A AS PAL «SC Be A Te By, RE HEE EE ARB BAS HE PTB A BE ALE aS Oo NO, Nok . O + 0.058 a (So. 001 ey ¥o.082 ws AEA HE Be A CA eH EE RCE 3 = Eo TA w o @ SSA RTE STL AA, CA) 16) of HAE A AE BS} TE of OAc AE BES FE FL TE A RE ED | RE Fad C5 RE A AF AB SP TE LT BY RE BAR ALE TE LMA BK (4) (6) 9 TES FS) REE He) AAA. Be FRA BR IN BY 0D VAT iy 3 PUA. BLA He es Med LI RE Ny FE ZEA 4.2.5 BREE 1. CD 2% (naphthalene) i) 44 #4) ALT AE) BY tt FRADE AO Cio Hy» RAE A BY —12% 8B 2B AMS} HLT US 5.6 ZEA. RANA RIL ANDRO FP RIF Bo SO AAs ap ol Se FEW Cy Cy Cy AC, LEIA BEART PRD a — BRI 6 Ce Cy Ce ALC, BE BRE PEG — TOA LB SR ATA SP SAD TRE A ~ 42 — BR a 5B PULA DH s PRB Be TH Ae A EF BP A a A cH, as = i JU K = 80 RD 2-H AD (1~methylnaphthlene) (2 methylnaphthalne) sO, H aya 6 —2— Rae 5~diniteonaphthalene) (-amino~2-naphthalene sulfonie acid PERETTI FE AAT SRL EAN. ER IR A AS SE AR TIS 5 SE TRAGER AE ADF A Ep OLE A BE AB JE I GO PEAR APF 9 {AML 10 LATE AY p MLL RT AMR Oh SPS 1.8 BAS IRE AY p OLR AH oO FEAR RHIAN. (BLEEP C—C RRA EC Ey UE 4. 13: Dita. 142 pm_136 pm Clee} ae oe Kw HRA TE A Co eC CHE PE 4.13 RAP Sit Ade AI SABRI ARE AS TG HY « BR PF A BRE A Fy AE AB AS EE CAL AW 80. 5 C Ub 218 CITE REF OK HEME FS ‘SLAR. (aM 4.9 — mange An ARR aLm4 Bie Re (2) REMC EL APRRSD EY Hs Fe Sh ARH) ERR A TL BE LAG AB ABZ INCRE «AR AH BAR So a Ae. D FAC, FRACTAL ME Ae Ae ea ARR A LN BAR LAL LEAN Friedel —Crafts RMS. WERT o HERE pL. HEMET — A At, EBA a HBR mo. Os CC A SO, oa BRA «BR A A «LEAST TA AST) AP. PA SR BE SPCR. AG HT BUA — eR. SR A SZ SO,H rene se 1) 2 EBLE TS) +H,s0, 6 CO ft See 5 SOK aay In ABR. FR CAE ASD HEAT AR OM PNG BR Pe A AB A A PEE Ey. CO ader OO we 1234 USCA bate GD WALI. BERLE BRIE AME, V2.0, Oy REAL TAL 6 HEL 35 SRT HE A ea EO, TS S838 FFARR COR : ¥00~500% ‘° 2. BONAR WE Canthracene) #1 #E (phenanthrene) % 46 F ME TH HP, WOON JE AR Ah HELO 216 °C PS 240 Ca AAT IT BY FE OA ABE WY 101°C ELOY 340°C. OMAR AY SR FOB Coc Ho » BUA EL FAS EIS CES ABT TAT EB SE UR I FE A SP Aa AAS S105» AH Be FB BL J ML 48 AR LCP 9A AL 10 RAE ISR. Es ATTY 2 Bk A HK144,558 (0 AAI] PRY o 12 5253,6,7 (ie BEAD), PRY 2 1h 9 A 10 fe ANIA EW 7 10 IR BL Be SE FAS A AR os J UD eA A CANE AB FL Aa — AR A 5 PR A HB» EE AF A ‘BER HG A 9 Ae PE Fa RH SB HE RS AE Ch RE FEL ASS RR ASS SHE SH FB SI AE AE A EE AR 3. BONIS FERS 1955 B (carcinogenic aromatic hydrocarbon) ER RAASARRKMED. BMY FBG ALLE EP BR GE Le Ae FFE IE BR AT BB HE 4 ORR 5 PORE OY BH IH HEB CANT A BB ST A a RE «6 AS OY 5 HEB SP EB. BF RR D5 HNTB AA BME HEF TT SE 9 NH AE BL bE OY RE a. ANY poe COC MOTE EBS SA SDP BS — 4 RAG Ho — > Ph RM tI TET FESS IH BY De F 9 S S T O — E S E E E E E asbye SRA, HMM, 2 EE ORS BAS I SEL 2 BB eA ES TS oS AT PR AAA 1.2 2.3 BUAF EE a boc FHA » PRB IO EM WAI (2,3-0)E. WIE EOF Bh He 180° HA,L238) ASP Lb JE ey SB BB Ra «FRIES BEB AR} AS WE A ea 32a MH BA OD EP CO HRS A a nO PSE ke RIEL CE AY BEA 250 CARAT AH 4.2.6 HRDS BE AS LAT RR EG PY APL LAY 28 DOE IF A HEB REE LD a a HS, 1. Hickel BLS 1930 46 WPA LF Hisckel FH fii 4609 SbF BLA CHMOD tk Ht PYF SLR HS A eT AE, Me ABE EN TEU DOE 5 PH A) LA « TER HB A Son RO SE BL IRE ABE sp* He Ne HE LA A RR IE oe EF dn +202 = 041,230 EA a FAT HE HELIN Fk 7 Hiickel $2 (Huckel rule), RH 4n+2 MIM. RAL —A MTSE AG 6 Sw LF, HAL Anh 2 SRS C= 1), PA LAG SF AE. TL A Hck LY, AB te. 2. RBH TE CHF AEF BE 28 BN PAE BI BSF RE TE FA AS AS TE. DOO oO oO FRA SBS FLA BE MST RS BA TB PD Ao SA RS Po FL OE Ant 20n= 1) BUI ALA HG PEER 6x TR REVERE Ant 2 SLI BEATE RHE. AR HE ME aR — OP Fe HE 10, FERS Amt 2 2. SALI HE AS a WT TE GI eR I FORA IF iE Aa HE. Eh BT MS RE BF ALE MG A AE AS Hacked ALI ABER 3. Bi(azulene) BUDE Th FER A TIA BHF i Hy EO SE PAE DSA tt FEO 10, REE An 2 2) SOLID IE BA LAT TG RE I 2.1L, C2 ES BOK IIR REY 99°C HEE GE HAL AI Friedel —Crafts J ie » EAR AE TH AY SP LATHE DA As EAD. 4. 448 Cannulene) SEMI ATES ARR ER OAT EL CBR A a. CLOSE EBON 10, AF & Hiickel SUI) ELPA ERAS ly 5 LER AB DF SL eR of Pe A AR A FR DT AE Eb BRU A AE CE FA) TA. AEE RA REA RG EEC18 DE AAC VS 5 ALU A OS SR HD RU DB] — Te EAA Hckel LW FLA Oe ARE. cieeee BEAL AD EE A EB OTE A Hike! SLM. AD Be A a & % i Pullerenc, @ 4. 142445 4%. IRA CRRAS % MR (Buckyball) ,¥ M&M) BELLE RARARHBAM BSA HR, 1985 +, 2H 40$ @ H.W. Kroto H+ 4 & WF K RE, Smalley FAR PARE RA DS SEM P HK HG 60 PRAT BRE RABDF Co. Bie, Kroto HERA 1996 + RSM AK HF R, Kroto st AF K R.B. Fuller i #4 OF HMMA FRAG OL TRA He RIOD AAA Coo TRE RA ISR AR HY 88 HB) tt 4 % A “Buckminster Fullerene” (i 4H HM), HH te L-ANRRARMRT RMD, CMR WEF HH RAR, ATR AE HRA AE AY KE cs A SA AGH SE ES LP Bel eens BEB Coo tC, TAP, Coo PF PEA 32 hh oh IRB, R60 PMR A 20D RAR fo 12S BSR Aha MY BAT 30 AN a RR a RIK ES DF HM AEH 710 pm, UL SM La HRM. Coo BEAL, RD RIF A sp’ Ae Ae Hill fe AN ES RR HOE ALAR pM Ae Coo BF Sb fe RE CPE RAF AE TRE A Be Es Coo AIM ML Co AB BB AEM Co PFA AE AAPA HEBER) AEG 9 AR ARB RD IE a a AES Cus FE th —— EAA BADR AAR HE RA HER A RATHER RA A 2 DMR RU AE ERLE SGA SERA ER ORE RUE ARAM, TAR RAAT TRAE A TIM SH MEA A Rb MR IEA AE RD io BIH EET EO RA. Bey8 wig wR OB Coo R KATE th RBA EAR IMR He AEE ME OO AR oe, oth. 4 a + HERESY FAR Cy Ha LR 1 ORF SA OTB ESA IE 2. ARF SH A at BH 2 Ha A a 0 ©O CoH cl oy a co) H A i ocr oO (9) 14-2. ape RE (10) 1 — FRR CD) =H#(2. 2. 1]-2,5- Be (12) 1~MoHK[S. 2. 1 BE (13) M-1,3-= PARR He Newman #8 x0) OD R-14- SERA RHR (5) 2,6~ =i aE (16) fa) aR 3. SER IA BRS ww DX] tram, oD or CH—CHCHS 4 ip, Hel eo) He CH, CH. et w OY" wise3 8 79 Fes os) J let : Co a 4. EEF SAG Oo Oy A A OE oO oO 0B SO,H oO) 0 Ole An ory oO NO; a Lo ~ ONS 5. FACED te a IF HA os C) PIR SIM (2) DIRE SIRE 3) RHE @D R5RE (3) RAE 1-1 B.A a BOR 2 NF SE 2 9 SEE FL CD RA AR (2) VASE HF wR (3) NERA A A) (RAE AR 7. HEI Hlockel S250 4 WEF 94 29 JB 2 SA I APH oF oO oO »pP “QH 9D #D 8. ELF 3 Ae A (2) PhCH; — PhCH(CH,), — PRC(CH,), PAH PhCH © goer Oeoonen — C)-ogen. ° oO80 Bie RB 9. HERE A BEES Cio He + A MEARE ZK AE 5 AL RAR HE HE HE FAB A CB Sb FE Cy Hes AOR AR HERA HC I SPER C,H.O, CHEE A.B. HE. 10, AeA A OSD FW Ca His BHF BEAR, ELAR AEE KM nO, PREHEAT HBr BRITA HG BCC. Hi BO A S46 2,3-— A T Ea A,B HMR ER Be LL, MS AMEEM ALB. FIN CHa. MA KMnO, (SRR EERE RAUGIS «ATE — JERR Bey TFERMR.C MEH = TEMA, ELEM HINO, AI HeSO, AG A AB 455 A — EA A TE CAE 1 MEE DO ALB AC AHR, 12, AGA ACC Hig) 5 A HE OTT ECC ho HsBOD, AB KM nO, AR PERE HERG A BRR A BM Co HO, HE HE LAE A — A RTCA 9 (CyHOWNO,), BEA A MVHS, CRE te RDRSH ath HH FiBL Ps IBLE Be A EA, SEU EB A a FE HE A B® Cisome- ris) «fil PS. 5F PY BER. (A Sb 9 Sb 3 489 3B SAY (constitutional isomerism) Ml XZ Hk S44 (stereo isomerism) YAK. PUA FR HD ALTE SbF SAB IA] . SbF DF Be MG AD AD HE A BY eS A AD TOD AE A SPA RR 5 SARA St 9 A a ALU» AR oD FR A AE Ud HE SK AB 51 a) SA) «EH oka FH 9 AST > 2D A 9} FY BY HD SS HCP 5.1), EA LSE A BRT BIT Sh A SRS 8 AT A — BR TE ay SPH TERRA 9 ARTE BE HST HE RT RE AM UR RY RSE HS A FAY RT RB I HE PAAR IC Sh READE HK RI EEN. pra pas EE FEY |e te Se ar ai DD aah se — WE L. wane SL TO SEH se P51 Sree ap 5.1 st ek A ALR HAF OE RRA SES ATR FOR. BERRA MAA OLE BAR LR, ARSE A SLR STE TE RS F A Ag LAL 0 2B SS HE A A ET SAA SE SERA 18 19 ALIA EEA OL ES 5.1.1 SRR RHR RAO EE ARF CAF BRS th AMHR. EMMA CMM SRRMKAR. AH CUA REE SRR ASHS AER MA MEF AAP ENR AES CRA AARNE HAM 5.2), KHAFAHFRWAEWSRRKAR HAMEL HA 4E RSs FH (chirality). BRE LLSb BA EEA ABE A HE 982 BSR NRF AF FO @) EKFEHED SARE aF : ) AREA ES 5.2 FERRE AMET F HEED S URN KA RBM 5 B.3), WH 5.3 Brae) Thea 2-H TRE F BMD Te StF BFE He 5 BARK HE TE HAST 2— ROT eo BO RAQMIA EEE HA. LN 2 molecule). f£ iB H. RVG FAA EE. AA ELE DF FED F (chiral 5 BAB TG 7 ME EE 2S Ha 9 yt ft BR A Cena tiomer) . 7 4 RY BRE HS FR 8 3 AAO SRY SAR SF AY DM Cenantiomerism) , Xf we HAH 5} Teh AY TRF i BAN OPS ee Do AB AT) «A AL AV HB 9) AS) Ee HH. ‘oni H,CH,C T (butane) ‘ei HCH,C | xf Sa 2TH (2-chlorobutane) om ‘iti & xX E53 WAL FS SR PLR St F (CH, CHOHCOOH) fs — 4 Ft SbF 5 AF WR ADF ES AT Se AT I5.1 RRO 83 ADAH Gy IR AD we SE SED TH a POMEL 5. 4 Phas. ' ASUS FAT ELE HH IE Ce 5 NAT ' SRF RAR BLAME. GREAT DUAR LF wk aE ' FAB Bk FA HERR F chiral carbon oH} RECEP (chiral center) JH"C’ "fea. CH HT ! 2— TNR 2-9-3 — EEN SE Hh RAAT COOH HRT. BIS.4 RRR MOLAR Br CH,CH, CH,CH, HR I. WAN & Aa ch,\P# cHy’ Xq 27m 23 (2-butanod> (3~bromo~2-chloropentane) FED IRF BE T-tEDF bY — A te bE a AE EAT tA WR FARES. FIG ANA PHRMA 7 PATI «alt co I NE 1. CH,CH,CHCH.CH,CL 2. CH,CHCHC—H 3. cree | a on FI cH, CH,COOH, CH H 1 4. chon « ¢ ‘ CHC 7 CH, ch cH.cooH 5 on 1 5.1.2 SFM FAT RE FEE OR HE RE. — YE ES HR AF Bt EAR BAT AG Ae A AT FE SL I DF He EP EE STALE BPR AA 1. RAST Fa TT BLA Fe 9 — AF HE LL a eA 9 BS BD Fi BBP AS BEAR» NF PR SPF 9 HAR TH (symmetrical plane), #€ 1,1-—&-1-2a hE WF A Br HELP RE OF SF CL—C—Cl AF oi CPR 5. 5 Ca) ) BEF ti DH BEF By wR 6 A ABTA] 9D ABD KP TB BBR Oh PAP LE A 9 DRE RE LAG ILE HE MD AF HS AA ME eS © ALAR FES F (achiral molecule) , Ask BEA A BLE84 BSR NRE (11-1 aR 0b) E)=1,2- (.-bromo~1+1 =dichloromethane) (E)=1,2-dichloroethene 5.5 Rit GBF 1 DAT AF ABE FE BA CE) — 1,2 ZBL 5. 5b) ) GRE TE aE By Fy RY AT» DN ths 2. MRR JL SP 8 — ELAR SS 5 EL ae A) HE a — WE Ha RA TA LE SL 49 AEN) 4 UR FAD «ABCA SR 9 TP FB AR EBLLs (symmetrical center), MIP 5. 65 (5.7 BEAR. amb 5.6 Zhe FO5.7 0 1,3-=M-24- RT SAY RL AE BE BY BAG HE LA Ete EL ZEA 3-H - 2.4 - RY See FEAF AT ROR IH. RRS TL Te PL aS At PAL BR Et DA SLADE AS FAG Xt BST RNY PL, BR ABE BN EE DE RR BS AE PRIS BY AE Fe} FI Ae RE HH 5.2 BRIE Aa KS HR EE Sa HP ET i HG 9 a A ES HH 4 — OT PE Fs — PARA HE Te ME» FE DL AD 3p Dy ME JE SA BR IEE S44 optical isomerism) . 5.2.1 FM RIE We Fa — A REE» SLA BE AA «BF He LS He AL. A IE CBE K 400 ~ 800 rarm P 3 AE ABY G ) HB J F 66, CB — AI) » PE BE AB Te SE ee5.2 Rik AeA tk Me HE tt 85 LR. Wn SEAS BA EAE —HR Nicol BE (obi Dy BHT ih RD Bw A Cada BZ BO AD HAF Nicol 8 6 2468 aR He Ft VF 55 0 AB Bh AEE 47 9 BB IE CAA) a, Paik a BE 9 PATH HbR. RAR ET ii LR oH BOG OK Oh HF TB A HE (plane polarized light) fi) PRR AEIE (polarized Light +P 5.8). MDE HE Ma AY Ay (61 Ao HE AL AS He BA TL TH A OF it Bs 9 He oh Td mee tt UIT cr td Nicol #8 Fm MRR PAS. 8 AR AOE uote 5.2.2 METER MEE Ami A Ne SO SL DL 5 AG AE BC ZPD SD AS A HO a 5 A Re COL PS Sk A A) eH He — FO BE Ca) AL 5. 9 HFS BK A AR APA He 9 FT Be CS 9 BME HEHE (optical activity) , Lm HABE. , , B { D > ze D | B’ FRAO , . B. Dp >| ’ AR See iz D B wetom Fi FO 5.9 nie EH FLAT ME HEHE 1 Oy By EEE EE TK te. PLR HH TB Re HEH VE OD TT AK ZR PS Ee HH BE Te LEA HG 9B As DAS AS A LA +B dB 8 A Hf a TT] Ze CONS SI A AS A Ze HE LAS SB BRR A RE Ht i TH HE BY Be Te 4 OY FE gy Me IE BE (rotation) 5H “a” RA.86 Be RE 5.2.3 REEL AN EL MEE BE Se Be FALE HE OR BE FE A EE. EEA AN SE BEB ALF BB Nicol BE BE CR Be BEATER AR BED — PRE A — 4 HE A, SLA RN MNP 5. 10 AECL RA 5 . 10, PAS. 10 eA a USE ANY Ay i he A eb AL FB EEO HE ER TB HA AH A eA Be OY WI RE AY A i i A 5 A A BA «AER Th PE AR ME OF OO» ABA He 2 Sa HF» FAH yD «SPB Ai HE AN 9 A 1B He A A «i Zs TH eB AL EE, A EER Se. HEUTE A 2 SE kL 0 A HR AR IE BE BRA — Me sy II» SB A BE HEH ASU SE «hy IE 5 I SE ARCA KBE A AE BH AC A HET ee BE SIE HE BS ASE 1 mL 1g fH 0 FE EH» EL dm A 4 0 Ey BBE IE EC specific ro- tation) FN “La li” 28 7. ¢ Hy WM sat mt OY AML IE sa EIN 8 IR, — ORG Ce 589. 3 nm, JAS D #7). PARIS PB I A) PL AY He ie He BE 9 [a]? = 4-3. 8°, TR AEH WLS FLARE 20 “CHR FH ANE ESE RINE SE He We HG IE ON AT HE 3. 8°, SBA ENS A ARR AA BEARS 1 dm PE HE Age LS eB RLF A HEHE]: (al SOP co OT TE IE BE (—— RARE (dm) 5 oF HB FB PRE (ge mL!)5.3 RR AOR MARIE ey t WE ECC: DFE RUE AC EN IE D AE. HEC 589.3 nm, BRAS AB DA FHLB ae ae YS I MN «BA A WHE IE IME Ay + 66° « FAV hrm 4 fy RE BRR EE AE A MY EE BE y+ 10. 75” 5 Be AY HEE -[ehxd 081 4(g+mL "> A J BE J eH I) — A AE «AA st EA I 2 IE elit. FH BRAD AAS LIE — AP ZI A — AS A A ATT 8 Ws A LB IEA TA HANK 5.3 spe FF A RAY ARID 5.3.1 RRR RK CF) L205 SARE A as aR AN Td AL ACA fi fe a Hy AY. PLR RY BE SF HY TAT HN Sh BERD CL PRL 9. 4) BET HK aR EB SN AR A FE HOLD 5.110. coon { coon coon i i i I c. ; c. c. HO athe Ht ae Hi aiee OH = Hie \E On) cH i cH, CH, EK eee awk PHS.11 FUNRS FBI RSL SSL Re A Ty Ws AR BE EL WL AES 5 SBR PR AT «A A SB Le 9 FRE RST A Fy MMT HA. HW Fischer MW AAA. Fischer BX HH = MEM ASA HH A eB BETA BN SAH. BRE 9 5 BOR FOF Ha ER i $B yd FB ta] COKE Ae OL) OS RO) A TO 9 SF a 9 CRE FLD Wah) 381 AE TT «HG RS A — A RE EB Ei DR eH PLE BOR SP FY OF BRAG BI Fischer BRIN SLAM 5.12). PUR EL RL TEBE EHUB Fisher 9520 BAR 19 JE FA] — 9 2B AB PB SEF 9 (1) Hf Fischer 41% 2050 Tie 180° HR SEA I, HU 7S ES Cy DF RL) 5 FHS AT Ee 90" HR HE AG A AB UH ms WR HB A