QUI TC CHUNG CA VIC GI TN THEO DANH PHP TH IUPAC

I HIROCACBON C 3 bc chnh: 1. Xc nh hirua nn ( mch chnh, vng chnh) - Theo qui tc c th ty vo loi hirocacbon VD: + Vi hirocacbon no mch h th chn mch chnh l mch C di nht, c cha nhiu nhnh nht lm mch chnh + Vi hirocacbon khng no mch h, l mch vi s lng lin kt kp ti a v khi cn th u tin cho ni i hn l ni ba,... Cch gi tn cc loi hirua nn: a) Hirua nn n nhn: ch cha mt nguyn t ca nguyn t c kho st cn li l cc nguyn t hiro. Tn = tn ca nguyn t tng ng + hu t an VD: BH3: Boran; CH4 : metan, cacban; SiH4: Silan; PbH4: Plumban; OH2: Oxian; SH2: Sunfan; NH3: Azan; PH3: Phosphan (Phosphin)..... b) Hirua axiclic a nhn + Hiro cacbon no: ngoi tr 4 hirocacbon u dy ng ng, cc hirocacbon cn li u c tn c hnh thnh t tin t ch s lng nguyn t C v ui l -an S Tin t S Tin t S Tin t 1 Mono11 Uneca21 Henicosa2 i12 oeca30 Triaconta3 Tri13 Trieca40 Tetraconta4 Tetra14 Tetraeca60 Hexaconta5 Penta15 Pentaeca100 Hecta6 Hexa16 Hexaeca200 icta7 Hepta17 Heptaeca300 Tricta8 Octa18 Octaeca400 Tetracta9 Nona19 Nonaeca500 Pentacta10 eca20 Icosa1000 Kilia* Ch : bt u t oeca- hu ht cc tin t c hnh thnh bng cch t hp cc tin t hp phn theo trnh t ngc vi trong s Rp VD: 13: triecan; 22: ocosan; 31: Hentriaconta; 32: otriacontan; 33Tritriacontan; 132: otriacontahectan + Hirua khc hirocacbon Tn = Tin t c bn v bi + tn hirua n nhn VD: NH2-NH2: iazan (hay Hirazin) + Hirua d t: l nhng mch c cha C v d nguyn t v cng c th khng cha cc bon: CH3 O - CH2 CH2 O CH3 : 2,5-ioxahexan

c) Hirua n vng + Hirocacbon n vng: a s c tn t hirocacbon mch h tng ng c thm tin t xiclo Vi h vng n c ni i lun phin , s C > 6 c gi l cc annulen km theo ( pha trc) con s trong du mc vung ch s nguyn t C mt vng VD:

[10]Annulen 2. nh s th t cc nguyn t C trn mch chnh - Ty theo hirocacbon m c qui tc c th + Vi hirocacbon no: nh s th t t u no gn nhnh nht sao cho tng ch s ca C c mch nhnh l nh nht + Vi hirocacbon khng no cn nh s t u no gn lin kt kp hn ( ni ba u tin hn ni i =) nhng khi cn thit th u tin cho ni i C = C. 3. Gi tn y Ch s ca cc nhnh + Tn ca cc nhnh (theo trnh t ch ci khng tnh n tn ca bi) + Tn ca hirua nn + Ch s ca lin kt kp (nu c) + Hu t ca lin kt kp (theo trnh t en trc in) VD:
CH2-CH3
10 9 8 1CH -CH CH
3 2

CH3-CH2-CH2-CH2 CH2CH3
7 6 5

2-CH2-CH-CH-CH-CH-CH2-CH3

CH2-CH3

6-Butyl-3-etyl-4-metyl-5-propyl ecan CH2-CH2-CH2-CH2CH3

1 2 3 4 5

CH2 = C-CH2-C C - CH-CH3 CH3 2- Pentyl-6-metyl hept-1-en-4-in II- DN XUT CA HIROCACBON 1. Xc nh cc nhm c trng thuc v loi A hay loi B; nu c nhiu nhm loi B cn xc nh nhm chnh a) Phn loi nhm c trng - Cc nhm c trng ch c tn dng tin t (nhm loi A) Nhm c -Br -Cl -F -I -IO2 -NO -NO2 - OR - SR trng -Brom -Clo -Flo -Iot (R)-Ioyl -Nitroso -Nitro -(R)-OxiTn -Bromo - Cloro -Fluoro -Ioo sunfanyl - Cc nhm c trng c th c tn dng tin t hoc hu t (nhm loi B) 2

-SeR (R)selanyl

Loi hp cht Axit cacboxylic Este Axyl halogenua Amit Nitrin Anehit Xeton Ancol, phenol Thiol Amin

Nhm -(C)OOH -COOH -(C)OOR -COOR -(C)OHal -COHal -(C)ONH2 -CONH2 -(C) N -C N -(C)H=O -CH=O -(C)=O | -OH -SH NH2

Tin t Cacboxi (R)oxicacbonyl HalogencacbonylAminocacbonylXiano- (Xian-) OxoFomylOxo Hiroxi Sunfanyl(Mecapto-) Amino-

Hu t Axit ....-oic Axit ....-cacboxylic R....-oat R ....-cacboxylat ...-oyl halogenua ....cacbonyl halogenua ....amit ....-cacboxamit ... nitrin ...- cacbonitrin ...-al ...-cacbanehit ...-on ...-ol ...-thiol ...-amin

Cc ch (C) ch ra rng nguyn t C ny c tnh trong tn ca hirua nn b) u tin ca cc nhm c trng Khi trong phn t c mt 2 hoc hn nhm loi B cn xc nh nhm chun gi tn di dng hu t, cn cc nhm khc c gi tn di dng tin t Nhm chnh c u tin cao hn trong dy sau: Axit cacboxylic > Anhirit axit > Este > Halogenua axit > Amit > Anehit > Xeton > Ancol v phenol > Amin > Ete 2. Xc nh hirua nn L mch cha nhm chc chnh vi s lng ti a, sau n cc nhm chc v nhm th khc vi s lng cng nhiu cng tt 3. nh s mch chnh t u no gn nhm chc chnh nht. Cc hu t ch cha bo ha (-en, -in) c t ngay trc tn ca nhm chnh 4. i vi cc hp cht n chc v a chc ng nht cha nhm c trng loi B th nhm c trng c th hin dng hu t cng vi ch s (t ngay trc hu t) 5. i vi cc hp cht n chc v a chc ng nht ch cha nhm chc loi A th gi tn cc nhm c trng dng tin t cng vi ch s (t trc tin t) ri n tn ca hirua nn 6. i vi hp cht tp chc cha nhiu nhm chc c trng khc nhau, trong s c nhm chc loi B, th gi tn tt c cc nhm khng phi l chnh dng tin t cng vi ch s (t ngay trc mi tin t) ri n tn hirua nn (mch chnh) cng vi cha bo ha (nu c) v sau cng l tn nhm chnh dng hu t vi ch s (t ngay trc hu t) Tm tt trnh t gi tn dn xut ca hirocacbon : 3

Ch s + Nhm th v nhm chc khng chnh ( dng tin t, trnh t ch ci)+ Mch chnh + ch s + cha bo ha (dng hu t en, -in,..)+ ch s + Nhm chc chnh (dng hu t) VD: 1) CH3-CH2-OH v HO-CH2-CH2-OH Nhm chc chnh: -OH (loi B) c hu t ol Hirua nn: CH3-CH3 c tn etan Tn hp cht : Etan-1,2-iol 2) CH2- CH CH = C - C CH3 | | | || OH CH3 Cl O Nhm chnh: C=O hu t on Hirua nn: CH3CH2CH2CH2CH2CH3 hexan Cc tin t: -Cl, -OH, -CH3 : cloro-; hiroxi-; metylTn hp cht: 3-Cloro-6-hiroxi-5-metyl hex-3-en-2-on

DANH PHP NG PHN CU HNH

I- NG PHN HNH HC - Cc trng hp xut hin ng phn hnh hc iu kin cn v : - Phn t phi c lin kt i ( mt hoc nhiu lin kt i) hoc c vng no - mi nguyn t C ca lin kt i v t nht 2 nguyn t C ca vng no phi c 2 nguyn t hoc nhm nguyn t khc nhau abC=Ccd (a b, c d) 1. Trng hp c 1 lin kt i a) H abC=Ccd s c hai ng phn hnh hc nu a b, c d b) H abC = Nc cng c 2 ng phn hnh hc nu a b ( c ng phn hnh hc v nguyn t N cn 1 i e cha lin kt c th coi l mt nhm th) c) H aN = Nb d a ging b hay khc b u c 2 ng phn hnh hc 2. Trng hp c nhiu lin kt i a) H c mt s l lin kt C=C lin nhau: abC=(C=)n=Ccd (n l), nu a b, c d s c 2 ng phn hnh hc b) H c nhiu lin kt C=C lin hp - H abC = CH - (-CH=CH-)n-2 -CH = C cd, s ng phn l 2n nu Cab Ccd. Th d: - H abC = CH - (-CH=CH-)n-2 -CH = Cab, s ng phn t hn 2n c) H c n ni i bit lp: xt tng ni i , s ng phn hnh hc l 2n 3. Trng hp cc hp cht vng no Cch gi tn cc dng ng phn hnh hc 1. H danh php cis-trans - Hai nhm th ln cng phn b v 1 pha ca lin kt i C= C th gi l cis, nu phn b v 2 pha ca lin kt i C = C gi l ng phn trans - H danh php ny gp kh khn trong trng hp c nhiu nhm th phc tp 4

VD: ClBr C= CHBr 2. H danh php syn-anti - p dng vi cc hp cht khng no ca N nhng khng p dng c vi anken - syn : cng; anti: khc Ring vi loi R-CH = N-OH ly H lm chun 3. H danh php Z-E - Khc phc c nhc im ca 2 h danh php trn abC=Ccd; abC = Nc Cch xc nh: + So snh a vi b, c vi d v hn cp. C s xc nh hn cp l s th t Z ca nguyn t nh trc tip gn vo ni i. Z cng ln th hn cp cng cao + Nu cc nguyn t trc tip gn vo ni i l ng nht th cn xt cc nguyn t trc tip lin kt vi nguyn t C ; phi nhn i hoc nhn ba i vi nguyn t c ni i hoc ni ba + Sau khi xc nh hn cp thy a>b; c>d; xt v tr khng gian ca a v c; nu chng cng mt pha gi l dng Z; khc pha gi l dng E a c a d a c a C = C C=C C=N C=N b d b c b b c Z E Z E VD: II- NG PHN QUANG HC iu kin xut hin ng phn quang hc - C yu t khng trng vt nh ngha l phn t 2 ng phn khng th lng kht ln nhau ging nh nh v ngi trong gng. Yu t khng trng vt nh ph bin nht l C bt i (C*): C*abcd (a b c d)

Br | I - C - Cl | H

Br | Cl - C - I | H

K c nhng nguyn t l ng v ca nhau cng c coi l cc nguyn t hoc nhm nguyn t khc nhau vn c ng phn hnh hc Br Br | D - C*- Cl | H | Cl- C*- D | H

1.Danh php D/L Xut pht t Glixeranehit: (+)-Glixeranehit c kh nng lm quay mt phng nh sng phn cc sang bn phi nn gi l D- Glixeranehit (-)-Glixeranehit c kh nng lm quay mt phng nh sng phn cc sang bn tri nn gi l L- Glixeranehit CHO CHO | H - C*- OH | | HO- C*- H |

CH2OH CH2OH D- Glixeranehit L- Glixeranehit Tt c nhng cht c cu hnh tng t D- Glixeranehit v L- Glixeranehit u c k hiu bng ch D- v L- bt k du ca [ ] VD: COOH COOH | H - C*- OH | CH3 D- Lactic COOH | H - C*NH2 | CH3 | HO- C*- H | CH3 L- Lactic COOH | H2N- C*- H | CH3

D- Alanin L- Alanin * Qui tc: Khi biu din cc ng phn quang hc ta mch C theo chiu thng ng, nhm chc c cha nguyn t C c s oxi ha cao nht quay ln pha trn. Khi nhm OH, -NH2 ca nguyn t C bt i, vi s th t cao nht v pha bn phi gi l ng phn D- , pha bn tri gi l ng phn LH danh php D/L ch ni ln cu hnh tng i, ch c ngha so snh v ch tin li i vi cc hp cht kiu RC*HYR vi Y l d t. Vi cc hp cht nhiu C* th vic p dng danh php ny gp rt nhiu kh khn i vi dy monosaccarit ngi ta cn c vo v tr khng gian trn cng thc Fis ca nhm OH C* c nh s ln nht xp vo dy D hay dy L

VD:

CHO | (CHOH)n

CHO | (CHOH)n

| | * H - C - OH HO- C*- H | | Dy D Dy L CH2OH CH2OH 2. Danh php R/S * Theo cng thc phi cnh - Bn nguyn t hoc nhm nguyn t C* c sp xp theo s gim dn hn cp a > b > c > d. Khi nhn phn t theo hng C *-d, nu thy th t a > b > c i theo chiu kim ng h th phn t c cu hnh R ( rectus phi), tri li nu th t ngc vi chiu kim ng h th phn t c cu hnh S (sinister tri) VD: CH2OH C*HOH CHO Xt hn cp: - OH > - CHO > - CH2OH > H * Theo cng thc Fis: Nu nhn vo cng thc m d cnh ngang th ng phn R trnh t a > b > c li ngc chiu kim ng h, cn ng phn S th theo chiu ngc li COOH COOH VD: H NH2 CH3 H2N CH3 H

(R)-Alanin (S)-Alanin H thng R/S c th p dng cho nhng hp cht c nhiu C*, khi y ngi CHO CHO ta ghi thm ch s cho R, S. VD: HO H OH H H OH HO H

CH2OH (2S, CH2OH 3R)-2,3,4-trihiroxi butanal (2R, 3S)-2,3,4-trihiroxi butanal 3. Danh php erythro/threo i vi cc hp cht cha 2 nguyn t C* m ni trc tip vi nhau ngi ta chn cc ng phn lp th ca 2,3,4- trihiroxibutanal lm c s 7

i vi phn t R-CHX-CHY-R, i i quang no m cc nguyn t C* c th a v v tr che khut hon ton theo tng cp R-R, X-Y, H-H th c gi l i quang erythro, i i quang cn li l threo CHO CHO CHO CHO VD: HO H OH H H OH HO H H OH H OH HO HO H H

CH2OH CH2OH CH2OH i quang threo i i i quang erythro CH2OH Trong trng hp R = R; X = Y, ta ch c 1 dng erythro gi l ng phn meso, cng i i quang threo CHO HO H OH H H OH HO H CHO H OH H OH CHO CHO HO HO H H

CHO i i quang threo CHO

CHO Hai CHOng phn ny l 1 gi l ng phn meso

DANH PHP HIROCACBON

I- HIROCACBON NO MCH H A. Hirocacbon no mch h khng nhnh: Tr 4 cht u dy ng ng cn li tn ca tt c cc ng ng cao hn u c hnh thnh bng cch t hp tin t c bn v bi vi hu t an B. Hirocacbon no mch nhnh 1. Xc nh hirua nn: Chn mch C di nht, c cha nhiu nhnh nht lm mch chnh 2. nh s cc nguyn t C trn mch chnh xut pht t u no gn nhnh nht cho tng ch s ca cc nhnh l nh nht 3. Xc nh tn ca cc nhnh: sp xp theo trnh t ch ci v chn tin t v bi thch hp nu c 2 nhnh ging nhau Cc nhnh n gin c xp theo trnh t ch ci u ca tn nhnh, khong dng ch ci u ca tin t v bi VD: Butyl Etyl imetyl Propyl 8

Cc nhnh phc tp (c nhm th trong nhnh) cng c sp xp theo trnh t ch ci u, nhng l tn hon chnh cho d l ch ci u ca nhm th tong nhnh hay tn ca tin t c bn v bi VD: (1,2-imetylpentyl) Etyl Metyl (1-Metylbutyl) (2-Metylbutyl) Khi c mt 2 nhnh phc tp ging nhau cn dng cc tin t nh bis-, tris, tetrakis-,.... VD: bis(1-metyletyl) hoc iisopropyl bis(2,2-imetylpropyl) hoc ineopentyl 4. Thit lp tn y : Ch s ca nhnh + Tin t bi + Tn ca nhnh+ Tn hirua nn VD: II- NHM (GC) HIROCACBON NO 1. Gc hirocacbon no ha tr I C 2 cch gi tn: a) i ui an -yl: Trong nhm c mch chnh th chn mch di nht k t nguyn t C mang ha tr t do (c nh s 1) lm mch chnh ri gi tn nhm theo danh php th b) Thm ui yl vo tn ca ankan km theo ch s cho ha tr t do, nh s mch C sao cho ch s c gi tr nh nht VD: CH3CH2CH2CH2CH3 pentan CH3CH2CH2CH2CH2a) Pentyl b) Pentan-1-yl CH3CH2CH2CH CH3 a) 1-Metylbutyl b) Pentan-2-yl | Kiu gi tn th 2 thng dng cho cc nhm m cu to phc tp (cha nhiu lin kt kp, nhiu vng,..) v cc nhm a ha tr Mt s tn gc na h thng c s dng (CH3)2CH-: Isopropyl (CH3)2CHCH2CH2- : Isopentyl (CH3)2CHCH2-: Isobutyl CH3CH2-C(CH3)2-: tert-Pentyl CH3CH2CH(CH3)-: sec-Butyl (CH3)3C-CH2-: Neopentyl (CH3)3C-: tert-Butyl 2. Gc hirocacbon no ha tr 2 - Nu hai ha tr t do c dng to lin kt i th: -an -ylien hoc thm ylien vo tn ankan - Nu 2 ha tr t do c dng to 2 lin kt n th thm -iyl vo tn ca hirua nn - i vi cc gc ha tr 2 c cng thc chung [CH2]n- c th gi: thm tin t ca bi vo metylen tr trng hp n = 1, 2 -CH2- -CH2-CH2- -CH2-CH2-CH2metylen etylen trimetylen 3. Gc ha tr 3 v cao hn - Ba ha tr t do: triyl - Ha tr t do to lin kt 3: -yliin - 3 ha tr t do dng to 1 lin kt i, 1 lin kt n: -yl-ylien 9

Tng t vi cc gc ha tr cao hn ta cng kt hp cc ui yl, ylien, yliin km theo ch s ch v tr, tin t v bi III- HIROCACBON KHNG NO MCH H - Chn mch C di nht c cha nhiu lin kt bi lm mch chnh (u tin mch c s ni i nhiu hn) - nh s th t sao cho tng ch s ca lin kt bi l nh nht k c khi ch s ni 3 nh hn - Gi tn: ch s nhnh+tn nhnh + tn hirua nn + ch s lin kt i+ ( bi)en + ch s lin kt ba+ ( bi)in IV- GC HIROCACBON KHNG NO 1. Gc ha tr 1 - Thm hu t yl km theo ch s cho v tr ha tr t do vo tn ca hirocacbon tng ng - Chn mch chnh cho gc khng no theo s gim dn u tin: + S lin kt kp l ti a + S nguyn t C l nhiu nht + S ni i l nhiu nht 2. Gc ha tr cao hn Tng t vi hirocacbon no V- HIROCACBON MCH VNG NO V KHNG NO 1- Hirocacbon n vng no + Khng nhnh: xiclo + tn ankan tng ng + C nhnh: nh s th t nhnh sao cho tng ch s nhnh l nh nht Gc hirocacbon n vng no: gi tng t gc hirocacbon no 2- Hirocacbon n vng khng no: tng t hirocacbon khng no mch h thm tin t xiclo3- Hirocacbon hai vng c chung 1 nguyn t mt vng: Spiro + [cc ch s nguyn t C ring] + tn hirocacbon mch h tng ng (ghi t s nh n s ln) Mch C c nh s ht vng nh n vng ln, bt u t 1 nguyn t k nguyn t chung

10