Sng kin kinh nghim

Ho Hu c

PHN I
Thut ng ho hu c theo ngha rng bao gm tn gi hp cht hu c ( danh php ho hc hu c) v cc cm t biu t khi nim chung v ho hu c- l mt b phn ca thut ng khoa hc ni chung hay ni rng hn l ca thut ng ting Vit. Danh php ho hc hu c l mt b phn ln nht bi s lng cc hp cht hu c bit c hin nay ln ti khong trn mi triu hp cht , mi hp cht t nht phi c mt tn ho hc, mi tn ho hc li ch dng cho mt cht. Th nhng vn tn gi hin nay ca cc hp cht hu c vn cha thng nht trn c nc. nc ta u nht tr dng danh php IUPAC(International Union of Pure and Applied Chemistry) l chnh, song cn cha thng nht hon ton v i khi cn c iu cha chnh xc trong vic p dng quy tc, danh php lp th li khng c cp nhiu trong chong trnh ph thng v i hc. Vn v tr ca ch s ch v tr ca cc nhm th, nhm chc, ni i, ni ba vn cha thng nht. Ngoi v tr ca cc ch s ch v tr , vn vai tr v v tr ca cc du phy, du mt chm, du hai chm, gch ni , ngoc n, ngoc vung, cng nh trng hp khong trng, ch in nghing, vit thu gn cng cha c qun trit mt cch cht ch. Mc khc theo chng trnh bi dng thng xuyn ca B Gio dc i vi gio vin trung hc ph thng v vn danh php ho hu c y l mt ni dung cp bch, b ch v quan trng i vi gio vin trng trung hc ph thng. V th, cp nht nhng thng tin mi nht, ng thi tm hiu vn nu trn, ti chn ti: Mt s quy nh ca IUPAC khi c tn hp cht hu c v bi tp

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I.

Ho Hu c

A.

LC S TI NGHIN CU Nm 1892 hi ngh quc t cc nh ho hc Ginev qui nh mt h thng danh php cc cht hu c. l danh php quc t Ginev, c s dng rng ri trong thi gian di. Nm 1954 xut hin danh php quc t mi, gi l danh php IUPAC (International Union Pure and Applied Chemistry). V thc cht danh php IUPAC khng phi hon ton mi m n sa cha b sung v hon thin thm nhng quy tc ca danh php Ginev cho ph hp vi tnh hnh pht trin ca ho hc hu c hin i. Danh php IUPAC ngy cng c s dng rng ri hn danh php Ginev. Nm 1979 danh php ho hc hu c do Rigaudy (Php) v Klesney (M) bin son c coi l y nht. Nm 1993 ra i thm ti liu ch dn v danh php IUPAC. T nm 1998 n nay c s b sung thm v cc nguyn tc trong danh php ho c bit hai ti liu quan trng l Principle of nomenclature-1998 v IUPAC Provisional Recommendations-2004. trong nc: Nm 1942 gio s Hong Xun Hn bin son cun sch danh t ho hc. Nm 1973 min Nam c ti liu danh php ho hc hu c ca L Vn Thi. Nm 1998 Trn Quc Sn b sung thm v nguyn tc, quy tc ca danh php ho hc hu c. Ngoi ra cng c cc tc gi khc nh: Nguyn Minh Chu, Trn Vn Thnh, L Huy Bc, cng cp n danh php ca hp cht hu c. II. GII HN TI NGHIN CU Phm vi ca danh php ha hc hu c th rt a dng v phong ph . Tuy nhin do iu kin thi gian c hn nn ti ny ch gii hn nghin cu mt s qui nh ca IUPAC v danh php ca cc hp cht hu c v cch c tn cc hidrocacbon. PHNG PHP NGHIN CU Tng hp kin thc c hc, cc ti liu v danh php cc hp cht hu c tm hiu cc qui nh chung ca IUPAC trong cch c tn ca cc hp cht hu c. T thng k cc tn gi c s dng i vi tng hp cht hu c. i vi mi hp cht ring, tm v tng hp thnh cc dng bi tp khc nhau v danh php cc hp cht hu c. III. NI DUNG NGHIN CU L THUYT. Phn loi danh php hu c Mt s quy nh chung ca IUPAC khi c tn hp cht hu c. Danh php ca mt s hp cht hidrocacbon thng dng Danh php cu hnh B. Bi tp : Cc dng bi tp gi tn ca mt cht cho trc Cc dng bi tp vit cng thc ca cht t tn gi

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Ho Hu c

PHN II
A-L THUYT
I. PHN LOI CHUNG. I.1. Danh php thng. Danh php thng l loi danh php c tn gi c hnh thnh theo ngun gc tm ra hay theo tnh cht l hc (mu sc, mi v, ...), v khng c tnh h thng. V d: Ure c ngun gc t urine( ting Php c ngha l nc tiu) v ure ln u tin c tch t nc tiu. I.2. Danh php h thng. Danh php h thng l loi danh php c cu to t nhng t, nhng vn, nhng ch ci v nhng ch s cn thit, c tnh h thng. V d: C5H11OH: pentanol = penta + an + ol ( ancol)

( ting HiLp ch s 5) ( hp cht no) I.3. Danh php na h thng hay na thng thng. L loi danh php trong ch c mt vi yu t h thng.

V d: Stiren, glixerol c tn cng l en v ol l hu t ca anken v ancol. II. PHN LOI DANH PHP IUPAC. II.1. Tn thay th. Tn thay th l tn c to ra trn c s thay th mt hay nhiu nguyn t hidro trong phn nn ca hp cht hu c bng mt hay nhiu nhm nguyn t khc. Phn thay th c th gi tn theo tin t hoc hu t ty theo tng cht. V d:

CH3 CH CH3
Phn nn 2-metylpentan

CH2

CH2 CH3

Nhm th

( nhm CH3 c gi di dng tin t)

HO

CH2 CH2

CH2 CH2

OH

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Nhm th phn nn Butan-1,4-diol ( hai nhm OH c gi tn di dng hu t) Mt tn thay th y bao gm:

Ho Hu c Nhm th

TIN T

PHN NN

KT THC

HU T

Tin t tch ra c

Tin t hidro/ dehidro Tin t khng TN PHN tch ra c NN

Kt thc an/en/in

Hu t nhm chc

II.2 Tn gc chc: ( Tn loi chc) Tn gc chc l tn c to thnh t tn nhm chc v tn gc trong phn t. II.2.1 Tn gc chc s dng tn nhm chc: tn gi c hnh thnh bng cch ghp tn ca nhm chc ca hp cht v phn cn li ca phn t. Tn ca phn cn li c t trc tn ca nhm chc. V d: CH3-OH metyl ancol CH3CH2COOCH3 metyl propanoat C6H5COCN benzoyl xianua CH3COCl axetyl clorua Khi tn gc chc c lin quan n nhm chc c hai ha tr t do th ta c tn ca hai nhm th ni vi n, c ring tng nhm v sp xp theo a,b,c, V d: CH3CH2COCH3 etyl metyl xeton CH3CH2OCH2CH3 dietyl ete II.2.2 Tn gc chc s dng thay i nhm chc: nhiu dn xut ca mt s nhm c trng c th c tn bng cch thay i tn ca nhm c trng hoc cng thm vo tn dn xut. Phn thay i hoc phn cng thm c t sau tn ca phn nn. V d: CH3COOCOCH3 anhidrit axetic ( axit c thay bng anhirit) CH3-CH2-CH=N-OH propanal oxim ( oxim c thm vo tn ca hp cht cacbonyl) CH3CH2CH(OCH3)2 propanal dimetyl axetal ( dimetyl axetat c thm vo hp cht cacbonyl) II.3. Tn trao i: Tn trao i l tn c to ra khi c s trao i mt nhm nguyn t hay mt nguyn t khc hidro cho nguyn t hay nhm nguyn t khc. C hai cch trao i: GV:Nguyn Xun Phong Trang 4

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Ho Hu c II.3.1. Tn trao i b khung: thng gp l s trao i xy ra b khung cacbon, khi c ta thm tin t i din cho phn t c trao i. Cc phn t quan trng thng dng trong danh php hu c thay th cho nguyn t cacbon nh: O, S, Se, Te, N, P, As, Sb, Bi, Si, Ge, Sn, Pb, B, Al, Ga, In, hoc Tl. Cu trc mi hnh thnh c thm tin t a nh: oxa, sila, aza, thia V d:

Xiclotetradecan Silaxiclotetradecan CH3-S-SiH2-CH2-CH2-SiH2-O-CH3 2-oxa-7-thia-3,6-disilaoctan II.3.2. Trao i nhm chc: s trao i nguyn t oxi hoc nhm nguyn t cha oxi bi cc nguyn t khc. Tn mi c th c thm tin t hoc trung t. Cc ph ng thio, seleno, teluro bo s thay th mt nguyn t O bi S, Se, Te. V d: C6H5-COOH C6H5-C{O,Se}H Axit benzoic Axit Selenobenzoic (Se c th thay th cho =O hoc O) CH3 [CH2]4 COOH CH3 [CH2]4 C(S)SH Axit hexanoic Axit hexandithioic
4

OHC

COOH

SeHC

COOH

Axit 4- focmylbenzoic

Axit 4-metanselenoylbenzoic Hoc axit 4-(selenofocmyl)benzoic

II.4. Tn kt hp. i vi cc hp cht hu c cha ng thi mt b phn mch h c nhm chc chnh v mt b phn mch vng, ngi ta c th dng thao tc kt hp tn ca b phn mch h v tn ca h vng, mc d to nn hp cht cn gi tn ta phi bt i mt s nguyn t H ch ni. V d: CH2OH + CH3OH Xiclohexan
+

Metanol
CH3COOH

Xiclohexanmetanol

CH2COOH

Benzen Axit axetic Axit benzenaxetic II.5. Tn cng: Tn cng c hnh thnh bng cch cng cc hp phn c trong cu trc m khng lm mt i thnh phn hay nhm chc no. C th biu th vi cch nh sau. II.5.1.Cng tin t. V d: GV:Nguyn Xun Phong Trang 5

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1 2 3 4

Ho Hu c

Naphtalen II.5.2. Cng hu t. V d:

1,2,3,4 - tetrahidronaphtalen
+

N
+

NH H
+

Piridin Piridinium + (hu t ium xc nh cng mt H ) _ _ + BH3 H BH4 Boran Boranua (hu t ua xc nh cng mt H ) II.5.3. Cng thm mt t ring bit. - Cng theo tn ca mt cu trc ring r. V d:

CH3C N
-

CH3C NO
Axetonitrin oxit

Axetonitrin Cng theo 2 cu trc tr ln. V d: CH3Metyl + -OH Ancol

+

CH3OH Metyl ancol

O

Xiclohexyl Xiclohexyl Xeton dixiclohexyl xeton C6H5-CH2+ -CN C6H5-CH2-CN Benzyl Xianua Benzyl xianua II.6. Tn tr. Tn tr c hnh thnh t tn ca mt cht tng t quen bit bng cch dng mt tin t hoc mt hu t ni ln s loi bt mt s nguyn t hay mt nhm nguyn t. C hai cch sau: II.6.1. Tn tr c hnh thnh bng cch dng hu t tr. V d:
CH4 Metan _ H Ion monohidro + _ H

CH3

Metyl

CH3 CH3
Etan

Ion hidro

CH3 CH2 Etanua

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CH3CH2CH2CH3
Butan

Ho Hu c

C6H5 SO2 OH
Axit benzensunfonic

Ion hidrua + _ H Ion hidro

CH3CH2CH CH3 But-2-ylium _ C6H5 SO2 O Axit benzensunfonat

2 1

CH3CH2CH3

CH3CH CH2 Propan hidro propen II.6.2. Tn tr c hnh thnh bng cch dng tin t tr cho cc hp cht n
V d:

H2

gin.

Oxepan 2,3-didehidrooxepan II.6.3. Tn tr c hnh thnh bng cch dng tin t tr s dng trong danh php cho cc hp cht t nhin. Trong danh php cc hp cht thin nhin, vi tin t c s dng ch s mt i mt nhm, chng hn s trao i mt nhm cho hidro. S dng tin t de hoc des. Tin t de thm trc tn mt nhm hay nguyn t khc hidro, biu thi s loi b mt nhm hay nguyn t (khc hidro) v s thm vo nhng nguyn t hidro cn thit.
CHO OH OH OH CH 2OH CHO H OH OH CH2 OH

D-Ribozo D-2-deoxiribozo Tin t des biu th s loi b mt phn cn li hp cht hu c c trong protein ca mt polypeptit vi s ni li ca dy chuyn hay s loi b mt thit b u hoc cui ca mt cu trc nn. V d:
18
CH3

18 17
CH 3

1 A 4

19
CH3

C
H H

14 8
H

19
CH 3

C
H H

17 14 8
H

10 5
H

10 5

5--androstan des-A-androstan - S dng tin t anhidro: c s dng khi c s loi b phn t H2O t hai nhm OH trong phn t monosacarit hay dn xut ca monosacarit. Tin t anhidro c t trong tn theo vn ca ch ci. V d:

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Ho Hu c

2,4,5-tri-O-metyl-D-mannitol 3,6-anhidro-2,4,5-tri-O-metyl-D-mannitol - S dng tin t nor: ( thng c s dng trong tn cc hp cht t nhin) dng ch ra s thay th tt c cc nhm CH3 cu trc vng bng cc nguyn t H.

V d:

Norcaran Norpinan Norbornan II.7. Tn nhn: Tn nhn dng t tn cho nhng cu trc nn tng t nhau, ni vi nhau bng mt nhm a ha tr i xng. Trnh t ca cc b phn ca tn nhn nh sau: Tn nhm i xng + tin t ch bi ( di, tri, tetra) + tn ca cu trc nn. V d:

benzonitrin

metylen

benzonitrin

2,2-metylendibenzonitrin

Xiclohexan II.8. Tn dung hp.

oxi

Xiclohexan

1,1-oxidixiclohexan

Trong h thng a vng ngng t, c mt b phn c coi l chnh v mt b phn c coi b phn ghp. Vic la chn b phn chnh da vo u tin ca cc b phn . Tn thnh phn gn lin bng vic thay th ch cui e bng ch o trong tn hp thnh, v d nh indeno t indene. Hoc bi vic thm o khi tn thnh phn gn lin khng c ch e, v d nh: pirano t piran hoc cho bi mt tn khc. Cc ch s ch v tr dng m t cu trc hp thnh, nh v tr ca nguyn t khc loi c gi vi tn v c bao bn trong nhng mc ngoc vung. V d: cc ch s 1, 2, 3, ch v tr nguyn t, cc ch ci a, b, c, ch v tr cc cnh trong h thng vng. GV:Nguyn Xun Phong Trang 8

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Quy c:

Ho Hu c

i vi vng chnh: cc ch s ch v tr s dng l cc ch ci in thng, a cho v tr 1,2, b cho v tr 2,3, i vi vng ghp: cc ch s ch v tr s dng l cc ch s 1, 2, 3, i vi nhng cu trc khng phc tp, vic thay th c th b qua cc ch s v tr. V d:

Azulen ( phn chnh)

naphtalen ( phn ghp)

naphto[2,1-a]azulen

II.9. Tn d vng theo Hantzsch v Widman. i vi cc d vng n vng c mt hay nhiu d t vi s cnh t 3 n 10, IUPAC p dng h thng tn theo xut ca Hantzsch v Widman. Theo cch gi tn ny, tn ca mt d vng c cu thnh t hai thnh phn chnh : - Tin t a dng ch ra d nguyn t trong vng. Th d: oxa-, thia-, aza-, - Phn c s t hp vi hu t dng ni ln kch thc ca d vng, cha bo ha, d vng c cha nit hay khng Th d: -iriin, -iran, -ole. s cnh Vng cha bo Vng cha bo ca ha ha cha nit vng 3 -iren -irin 4 -ete -ete 5 -ole -ole 6 -in -in 7 -epin -epin 8 -ocin -ocin 9 -onin -onin 10 -ecin -ecin Bng 1: Phn c s v hu t d vng. V d:
H N

Vng bo ha -iran -etan -olan -inan (-an) -epan -ocan -onan -ecan

Vng bo ha cha nit -iridin -etidin -olidin

NH

N O

Aziridin

1,2-oxazetidin

1,2,5-oxadiazol

1,3-oxathiolan Trang 9

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Ho Hu c Khng phi hp cht d vng no cng tun theo quy tc Hantzsch v Widman trn. Nhng tn thng thng thng cho thy du vt ca danh php h thng, nhng khng hon ton tun theo lut l. V d:
N

c tn l thiazol thay v tn h thng l 1,3-thiazol.

S

c tn l thiophen thay v tn h thng l thiol. II.10. Tn thng v tn na h thng c IUPAC lu dng trong h thng tn ca IPUAC l tn ca 1 s hidrocacbon mch h, mch vng, nhm ( hay gc hidrocacbon, dn xut hidroxi,) Cc tn loi ny chia lm 3 nhm a. Nhm 1 gm cc tn c dng khi khng c nhm th v khi c nhm th bt k v tr no VD: axetilen, etan, benzen, phenol b. Nhm 2 gm cc tn c dng khi khng c nhm th v khi c nhm th 1 s v tr nht nh (thng l mch vng) VD: toluen c. Nhm 3 gm cc tn ch c ng khi khng c nhm th VD: isopentan, neopentan, isopren III. MT S QUI NH V CCH CHN NHM CHC CHNH, MCH CHNH, CCH NH S, CCH C TN THEO TRNH T CH CI TRONG DANH PHP TH IUPAC. III.1. Cch chn nhm chc chnh. Cc nhm chc c chia lm hai nhm: III.1.1. Cc nhm ch c gi di dng tin t: gm Br Cl F I -NO -NO2 - OR -SR Tn gi : brom clo flo iot nitrozo nitro R-oxi R-sunfanyl Khi trong phn t ch c nhng nhm th loi ny th tn gi c t trc tn ca mch chnh v xp theo trnh t ch ci. V d:
Cl NO2

3-Clo-4-nitroxiclohex-1-en III.1.2. Cc nhm c th gi dng tin t hoc hu t: gm axit, este, axyl halogenua, amit, nitrin, andehit, xeton, ancol, phenol, thiol, amin, ete... Theo danh php IUPAC, trong hp cht tp chc cha nhiu nhm chc trong phn t th phi chn nhm chnh gi tn di dng hu t v nhm khng

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Ho Hu c phi nhm chnh gi tn di dng tin t. u tin ca cc nhm c trng c sp xp nh sau: a. Gc t do b. Anion c. Cation
d. Axit ( RCOOH > RSO3H > SO2H )

e. Anhidrit axit f. Este g. Halogenua axit h. Amit i. Hidrazit j. Nitrin k. Anderhit l. Xeton m. Ancol v phenol n. Hidroxi peoxit o. Amin p. Imin q. Ete i vi chc cha O, S, Se nu cng cu trc nh nhau th trnh t s gim dn -OH > -SH > -SeH; -COOH > CSSH > CSeSeH. V d: OH : Axit 5-hidroxihexanoic COOH - Cc tin t cng nh cc hu t c s dng cho mt s nhm chc quan trng c th hin trong bng sau theo th t u tin gim dn: Hu t khi Hu t khi cacbon ca cacbon ca Tn ca nhm nhm chc nhm chc Nhm chc Tin t chc c tnh khng c trong mch tnh trong mch chnh chnh Axit Axit -COOH Axit -oic Cacboxicacboxylic -cacboxylic

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Anhidrit axit este Halogen axit Amit Nitrin -COOR -COX -CONH2 -CN Anhidrit -oic Ankyl-oat -Oyl halogen -amit -nitrin Anhidrit -cacboxylic Ankylcacboxylat -cacbonyl halogenua -cacboxamit -cacbonitrin -

Ho Hu c

Alkoxicacbon ylHalocacbonyl-

CacbamoylXianoOxoAndehit -CHO -al -cacbandehit ( Focmyl-) Xeton -CO-on OxoAncol -OH -ol HidroxiThiol -SH -thiol MecaptoAmin -NH2 -amin AminoImin =NH -imin IminoAnken C=C -en Ankin C C -in Bng 3: Cc tin t v hu t c s dng cho mt s nhm chc quan trng. V d: CH3-CH2-CH2-CH2-COOH : Axit pentanoic
COOH

Axit xiclohexan cacboxilic

III.2. Cch chn mch chnh. III.2.1. Cch chn mch chnh i vi hp cht mch h. * Theo ti liu (4) : i vi hp cht mch h th vic chn mch chnh da theo cc tiu chun sau vi mc u tin gim dn: a. mch chnh l mch c cha nhiu nhm chc chnh nht b. mch chnh l mch cha tng s ni i v ni ba ln nht. c. mch chnh l mch di nht d. mch chnh l mch c cha nhiu ni i nht e. mch chnh l mch c ch s ch v tr thp nht cho nhm chc chnh. f. mch chnh l mch c ch s ch v tr thp nht cho cc lin kt kp. g. mch chnh l mch c ch s ch v tr nh nht cho cc lin kt i. h. mch chnh l mch c s ln nht cc nhm th dng tin t. i. mch chnh l mch c ch s ch v tr nh nht cho mi nhm th dng tin t. j. mch chnh l mch c nhm th c nu u tin theo trnh t ch ci. * Theo ti liu (5) : Trt t cho th t u tin c s thay i, mch di hn s u tin hn mch c cha lin kt kp, tc l mc u tin c c a ln trc b v c b sung thm cch chn mch chnh trong trng hp mch xut hin d t. C th nh sau: a. mch chnh l mch c cha nhiu d t nht. b. mch chnh l mch di nht. c. mch chnh l mch cha s lng cc d t l ln nht theo th t u tin sau: GV:Nguyn Xun Phong Trang 12

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Ho Hu c O > S > Se > Te > N > P > As > Sb > Bi > Si > Ge > Sn > Pb > B > Al > Ga > In > Tl. d. mch chnh l mch cha tng s ni i v ni ba ln nht. e. mch chnh l mch c cha nhiu ni i nht. f. mch chnh l mch c ch s v tr thp nht cho d t. g. mch chnh l mch c ch s v tr thp nht cho cc d t xut hin theo u tin sau: O > S > Se > Te > N > P > As > Sb > Bi > Si > Ge > Sn > Pb > B > Al > Ga > In > Tl. h. mch chnh l mch c ch s ch v tr thp nht cho nhm chc chnh. i. mch chnh l mch c ch s ch v tr thp nht cho cc lin kt kp. j. mch chnh l mch c ch s ch v tr nh nht cho cc lin kt i. k. mch chnh l mch c s ln nht cc nhm th dng tin t. l. mch chnh l mch c ch s ch v tr nh nht cho mi nhm th dng tin t. m. mch chnh l mch c nhm th c nu u tin theo trnh t ch ci. V d 1: theo qui nh a.

6-(pentyloxi)-2,5,8,11,14-pentaoxahexadecan V d 2: theo qui nh b

Theo IUPAC 2004 : Theo IUPAC 1998 : V d 3: theo qui nh c

3-metylidenoctan 2-etylhept-1-en

9-(propylsunfanyl)-2,5,8,11-tetraoxatridecan V d 4: theo qui nh d

3-etyl-4-metylpent-3-en-1-in V d 5 : theo qui nh e

HO-CH2-CH2-C C
9 8 7 6 5 4 3 2 1

HO-CH2-CH2-CH CH

CH-CH2CH CH-CH2-OH

5-(4-hidroxibut-1-inyl)nona-2,6-dien-1,9-diol V d 6: theo qui nh f GV:Nguyn Xun Phong Trang 13

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Ho Hu c

4-(etylsunfanyl)-2-oxa-6,9,12-trithiatetradecan V d 7: theo qui nh g

4-[(metylsunfanyl)metyl]-2-oxa-6,9,12-trithiatetradecan V d 8: theo qui nh h

8-clo-5-(3-hiroxi-1-metylpropyl)octan-1,7-diol V d 9: theo qui nh i

6-(pent-2-in-1-yl)undeca-2,4-dien-7-in V d 10: theo qui nh j

5-(but-2-en-1-yl)nona-1,6-dien V d 11: theo qui nh k

3-etyl-2-metylhexan ( khng c 3-isopropylhexan) V d 12: theo qui nh l

5-metyl-4-(2-metylprop-1-en-1-yl)hepta-1,5-dien

GV:Nguyn Xun Phong

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 Sng kin kinh nghim

Ho Hu c V d 13 :theo qui nh m, c 2 cch c tn cho cc nhm th trong v d sau, ta so snh 2 dy tn ca cc nhm th xp theo trnh t abc, mch chnh l mch m tn ca nhm th ti im khc nhau u tin c xp trc.

4-brom-2-(2-cloetyl)butan-1-ol khng c 2-(2-brometyl)-4-clobutan-1-ol Dy 1: brom, cloetyl Dy 2: brommetyl, clo Do brom c xp trc brometyl theo trnh t abc.

1,6-dibrom-1-clo-5-(clometyl)hexan khng c 1-brom-5-(brommetyl)-1,6diclohexan Do dy 1: brom, brom , clo, clometyl dy 2: brom, brommetyl, clo, clo brom phi xp trc brommetyl theo trnh t abc. III.2.2 Cch chn mch chnh i vi hp cht mch vng. 1. Khi hp cht c cha c mch vng v mch h th nhm chc chnh nm mch no ta chn mch lm mch chnh. V d:
CH2CH2CH2CH2CH2CH3 OH CH3 C CH = C CH2 COOH CH2OH Cl

Axit 3-clo-6-hidroxi-5-metyl-5-xiclohexylhex-3enoic 2. Khi nhm chc chnh c mt c mch h v mch vng th mch chnh l mch no c nhiu nhm chnh hn. Nu s nhm chc chnh nh nhau th mch vng c chn lm mch chnh.
HO CHCH2CH2CH2CH2OH OH CH3CH2 C CH2 O O

2-hexylxiclohexan-1-ol

1-(4-hiroxixiclohexyl)pentan-1,5-diol 4-(2-oxobutyl)xiclopentan-1,2-dion 3. Khi hp cht c hai hoc hn 2 mch cacbon b ngn cch bi 1 vng hoc 1 d nguyn t th mch mang s nhm chc chnh nhiu hn s c chn lm mch chnh. Nu s nhm chc nh nhau th th chn mch chnh theo nguyn tc chn mch chnh nu. V d :

1-4-[3-(hidroxipropyl)phenyl]etan-1,2-diol V d : S nhm chc chnh nh nhau ta chn mch di hn lm mch chnh. GV:Nguyn Xun Phong Trang 15

 Sng kin kinh nghim

Ho Hu c

3-4-[2-(hiroxietyl)phenyl]propan-1-ol 4. Nu s nhm chc chnh l nh nhau trong c hai phn ca hp cht th ta chn mch vng lm mch chnh.

3-(7-oxoheptyl)xiclohexan-1-cacbandehit 5. Khi hp cht c cha c mch vng v mch h v khng c cha nhm chc th ta da vo s nguyn t cacbon chn mch chnh. V d:
CH2CH2CH2CH2CH3 CH2CH2CH2CH2CH2CH3

pentylxiclopentan 1-xiclopentylhexan 6. Khi nhm chc chnh c mt 2 h vng trong phn t th ta chn h vng no c u tin cao hn lm mch chnh. u tin ca vng tun theo qui lut sau: a. S vng ngng t cng nhiu u tin cng cao V d:
HOOC
3 1 1 7 2

COOH

Axit 7-(3-cacboxiphenyl)naphtalen-2-cacboxilic b.Nu s vng ngng t nh nhau th ln vng cng cao u tin cng cao. V d:
<

c. Cc vng thm cacboxilic c u tin km d vng

V d:
< NH < N

d. Khi mc hidro ha ca vng cng ln th mc u tin cng cao. V d:

O

(xiclopentyloxi)benzen e. Vng c s lng lin kt bi nhiu hn s c u tin hn. V d:

benzen > xiclohexen f. Vng c s lng lin kt i nhiu hn. V d:

>

xiclohexan

GV:Nguyn Xun Phong

Trang 16

 Sng kin kinh nghim

Ho Hu c

1,4-dihidronaphtalen

>

1,2,3,4-tetrahidronaphtalen

g. Vng c ch s thp hn cho nguyn t hiro ch nh bn trong.

V d:

2H-piran >

4H-piran

h. Vng c ch s v tr thp hn cho cc nhm th nh vo.

V d:

Piridin-2-yl

>

Piridin-3-yl

i. Vng c ch s v tr thp hn cho mt nhm th c th hin di dng hu

t. V d:

2H-piran-2-on > 4H-piran-4-on j. Vng c ch s v tr thp hn cho nhng kt thc hay nhng tin t biu th s thay i mc hidro ha. V d:

1,2-dihidronaphtalen > 1,4-dihidronaphtalen k. C s lng t a nhm th c trch dn l tin t. V d:

1,2-dibromnaphtalen > 2-clonaphtalen l. C ch s v tr thp hn cho nhm th c biu din di dng tin t. GV:Nguyn Xun Phong Trang 17

 Sng kin kinh nghim

V d:

Ho Hu c

N-metylanilin > 3-metylanilin m. C ch s v tr thp hn cho nhm th c biu din di dng tin t v c trch dn u tin. V d:

1-etyl-2-propylnaphtalen > 2-etyl-1-propylnaphtalen III.3. Cch nh s trong mch khi gi tn hp cht hu c 1. Ta nh s trong mch chnh theo nhiu cch, xc nh nh s theo cch no ta phi so snh cc b ch s(trong mi b c ghi theo th t tng dn), b ch s nh nht l b ch s c im khc nhau u tin nh nht. Khi b ch s theo 2 hng nh l nh nhau th phi u tin s nh c nh vo nhm c xp u tin theo trnh t ch ci. V d 1:

2,2,6,6,7-pentametyloctan 2,3,3,7,7- pentametyloctan (ng) (khng ng) V khi so snh hai b ch s ta thy im khc nhau u tin l hng th hai: 2< 3 nn chn b ch s 2,2,6,6,7 V d 2 :
1 2 4 1 2 4

4-sec-butyl-1-etyl-2-metylxiclopentan 4-sec-butyl-2-etyl-1-metylxiclopentan (ng v 1 c nh vo etyl xp trc) (khng ng) V d 3 :

5 4

CH3
6 1 3 2

CH3 CH3
4 5 3 6 2 1

CH3

1,6-dimetylxiclohexen (ng) GV:Nguyn Xun Phong

2,3-dimetylxiclohexen(khng ng) Trang 18

 Sng kin kinh nghim

1 2 3

Ho Hu c V so snh 2 b ch s : 1,6 v 2,3 th im khc nhau u tin l hng th nht :1< 2 V d 4:

2 1 3 5 4

2-metyl-3-vinylxiclopentan (khng ng) V d 5:

1 3 4 6

1-metyl-5-vinylxiclopentan (ng)
6 5 3 1

3-etinylhexa-1,4,6-trien 5-etinylhexa-1,3,6-trien (khng ng) ( ng ) 2. Ch s ch v tr c du phy tng ng c t sau ch s ch v tr khng c du phy tng ng, ch s ch v tr bao gm s v ch c t sau ch s ch v tr bng s tng ng vi c hoc khng c du phy v tip theo l cc ch s ch v tr c s vit bn trn. V d : 2 nh hn 2 3 nh hn 3a 8a nh hn 8b 4 nh hn 4a 12 nh hn 2 Ch in nghing v ch ci a,b nh hn ch ci Hy Lp(, ..) v nh hn ch s. V d : N, ,1,2 nh hn 1,2,4,6 3. Khi c nguyn t ng v th nh s u tin ng v c ch s nh hn. Nu c nhiu nguyn t ng v khc nhau th nh s sao cho cc nguyn t ng v c b ch s l nh nht. Khi b ch s l nh nhau theo cc hng nh th ta u tin nh s nh vo ng v no c in tch ht nhn ln hn. Khi ng v ca cng mt nguyn t th ta u tin nh s nh hn vo ng v c in tch ln hn. CH3-14CH2-CH2-CH3 CH3-14CH2-C2H2-CH3 (2-14C)butan (3-14C,2,2-2H2)butan Khng c (3-14C)butan khng c (2-14C,3,3-2H2)butan 14 CH3- CH2-CH2H-CH3 (2-14C,3-2H1)butan khng c (3-14C,2-2H1)butan (R)-(1-2H1)propan-2-ol V 2H c u tin nh s nh hn

4. Khi c s la chn nh s trong cc cht c ng phn lp th, ch s ch v

tr thp hn c u tin nh vo Z hn E, R hn S.

GV:Nguyn Xun Phong

Trang 19

 Sng kin kinh nghim

Ho Hu c

Axit (2Z,5E)-hepta-2,5-diendioic

(2Z,4E,5Z)-4-etylidenhepta-2,5-dien

(2R,4S)-2,4-diflopentan 1-[(2R)-butan-2-yl]-3-[(2S)-butan-2-yl]benzen * C s thay i so vi quy nh ca danh php 1979: D t trong mch c xem nh l mt phn ca phn nn, nn chng c u tin hn hu t khi nh s.

Axit 3,6,9,12-tetraoxapentadecan-15-oic Khng c axit 4,7,10,13-tetraoxapentadecanoic. V hu t ch nhm chc axit nh hn nhng ch s ch d t s ln.
8 6 4 2 1

CH3 - SiH2 - CH2- SiH2- CH2- SiH2-CH2- SiH2-COOH axit 2,4,6,8-tetrasilanonanoic

khng c axit 2,4,6,8-tetrasilanonan-9-oic. V ch s ch d t theo 2 cch nh s l nh nhau nn u tin ch s ch nhm chc axit nh hn. III.4. Cch vit tn gi theo trnh t ch ci - Khi nhm th n gin th ta xp theo trnh t ch ci, khng tnh tin t ch bi(i, tri, tetra..). V d :

1-etyl-4-metylxiclohexan 2,5,8-triclo-1,4-dimetylnaphtalen - Khi nhm th phc tp(nhm th c thm nhm th na) th ta xp theo trnh t ch ci v tnh ngay t ch ci u tin. V d:
13 8 7 5 1

CH3[CH2]4CH2CHCH2CH[CH2]3CH3 CH3CH2 CH CH F F CH2CH3

GV:Nguyn Xun Phong

Trang 20

 Sng kin kinh nghim

Ho Hu c

7-(1,2-diflobutyl)-5-etyltridecan - Khi xp theo trnh t ch ci th ly ch ci u tin l i trong isobutyl, ch n trong neopentyl, nhng ch b trong sec-butyl hoc tert-butyl. V d:

4-tert-butyl-6-isopropylnonan - Khi ch ci La tinh khng quyt nh c th ch ci in nghing c xem xt. V d :

CH3 CH3CH2 CH
1 2 3

C(CH3)3

1-sec-butyl-3-tert-butylbenzen - Khi hai tin t bao gm cc ch ci ging nhau, ta xp nhm no c ch s ch v tr thp nht ti im khc nhau u tin. V d:
CH2CH3

Cl CH3 CH ClCH2CH2
6 5

4 1

CHCH2CH3

NH
2

CH3CH CH2CH2CH3

6-(1-cloetyl)-5-(2-cloetyl)indol 1-(pentan-2-yl)-4-(pentan-3-yl)benzen IV. DANH PHP IUPAC CHO TNG HP CHT C TH. IV.1. Hirocacbon no, mch h (Ankan). IV.1.1. i vi ankan khng phn nhnh. Bn nguyn t cacbon u tin trong dy ng ng c s dng tn na h thng. Chng c t hn mt trm nm trc, chnh thc c cng nhn bi hip nh Ginev nm 1892 v c s dng n by gi. V d: Metan CH4 Etan CH3CH3 Propan CH3CH2CH3 Butan CH3CH2CH2CH3 Tn gi metan xut pht t metyl trong tn gi ancol metylic, m ting Hi Lp metyl c ngha l cn, ru vang,v hyle l g ( ancol metylic sinh ra trong qu trnh chng khan g) Tn gi etan c lin quan n t HiLp aithein c ngha l chy bng, v etan l mt trong nhng cht d chy khi c ngn la. Ngun gc ca tn gi propan l t axit propionic axit u tin m n gin c tch ra t cht bo. ( proto ngha l u tin, pion l cht bo) Butan l tn gi bt ngun t axit butiric thnh phn gy mi trong b, m ting La Tinh butyrum c ngha l b. Tuy nhin i vi nhng ankan c 5C tr ln th c tn l s kt hp ca tin t ch bi ca 5, 6, 7, vi hu tan. V d: pent(a) +an = pentan CH3-[CH2]3-CH3 GV:Nguyn Xun Phong Trang 21

 Sng kin kinh nghim

n Ankan n Ankan n 1 Metan 11 Undecan 33 2 Etan 12 Dodecan 35 3 Propan 14 Tetradecan 40 4 Butan 16 Hexadecan 50 5 Pentan 18 Octadecan 60 6 Hexan 20 Icosan 100 7 Heptan 21 Henicosan 101 8 Octan 22 Docosan 102 9 Nonan 30 Triacontan 132 10 Decan 31 Hentriacontan 200 Bng 4: Tn h thng ca mt s ankan. IV.1.2. i vi ankan c nhnh: mt s s dng nh:

Ho Hu c Ankan Tritriacontan Pentatriacontan Tetracontan Pentacontan Hexacontan Hectan Henhectan Dohectan Dotriacontahectan Dictan tn na h thng, v d

(CH3)2CH-CH3

(CH3)2CH-CH2-CH3

(CH3)4C

isobutan isopentan neopentan Nhng a s chng c gi theo tn h thng theo IUPAC. Tn h thng y bao gm: Ch s v tr cho nhnh + tin t bi + tn nhnh + tn hirua nn Vic xy dng tn thay th ca ankan cng tun theo trnh t sau: La chn mch chnh, n s c dng lm hidrua nn. Xc nh v c tn nhnh. Xc nh v tr ca nhnh trn mch chnh v la chn ch s v tr theo cc nguyn tc khi chn ch s v tr thp nht. La chn cc tin t ch bi thch hp. Xy dng tn y . V d: CH3

CH3CH2CH2CH2CHCH2CH3
7 6 5 4 3 2 1

3-metylheptan IV.1.3. Tn gc hirocacbon no. 1. Gc hirocacbon no ha tr mt. Cc nhm ha tr mt c hnh thnh bng cch loi bt mt nguyn t H ra khi phn t ankan v c gi chung l ankyl. C hai cch gi tn: a. i hu t -an ca ankan thnh yl.

b. Thm hu t -yl vo tn ca ankan km theo ch s ch v tr cho

ha tr t do. V d: CH3-CH2-CH2-CH2-CH3 (pentan) CH3-CH2-CH2-CH2-CH2(a) pentyl hoc (b) pentan-1-yl.

GV:Nguyn Xun Phong

Trang 22

 Sng kin kinh nghim CH3 -CH2 -CH2 -CH-CH3

(a) 1-metylbutyl (b) Pentan-2-yl

Ho Hu c CH 3 -CH2 -CH-CH 2-CH 3 (a) 1-etylpropyl (b) pentan-3-yl

IUPAC lu dng tn na h thng cho cc nhm ha tr mt sau y. (CH3)2-CH(CH3)2-CH-CH2(CH3)2-CH-CH2-CH2isopropyl isobutyl isopentyl (CH3)3-C-CH2CH3-CH2-CH(CH3)CH3-CH2-C(CH3)2neopentyl sec-butyl tert-pentyl (CH3)3-Ctert-butyl 2. Gc hirocacbon no ha tr hai. Tn ca cc gc ha tr hai c hnh thnh v c bn theo hai cch tng t nh cc nhm ha tr mt nu trn. - Nu hai ha tr t do c dng to lin kt i th p dng phng php a tc i hu t -an ca hirua nn thnh ylien ( hay thm ien vo tn nhm ha tr mt tng ng) hoc phng php b l thm ylien vo tn hirua nn.

- Nu hai ha tr t do c dng to hai lin kt n th p dng

phng php b, tc thm hu t -iyl vo tn hiua nn ( km theo ch s ch v tr). V d: CH3-CH= a) etyliden b) etanyliden
CH3 -C-CH3

CH3 -C-CH3 a) 1-metyletyliden hoc isopropyliden b) propan-2-yliden

CH3-CH2-CH2-CH= a) butyliden b) butan-1-yliden

CH 3-CH-CH 2-CH 2-CH2-CH2-CH2-CH2b) Propan-2,2-iyl b) propan-1,3-iyl b) butan-1,3-iyl i vi cc gc ha tr hai c cng thc chung -[CH2]- tn cn c hnh thnh bng cch thm tin t ch bi vo metylen, tr trng hp n=1 v 2. V d: -CH2-CH2-CH2-[CH2]3-[CH2]4-[CH2]6Metylen Etylen Trimetylen Tetrametylen Hexametylen 3. Gc hidrocacbon ha tr ba v cao hn. Cc hu t ca gc ho tr ba c th l: -triyl ( ba ho tr t do ring r), -yliin ( ho tr t do dung to lin kt ba) v ylylien ( ba ho tr t do dng to mt lin kt n v mt lin kt i), V d:

CH3 CH2 C
Propan-1,1,1-triyl

CH2 CH

CH2

CH3 CH2 C
propylidin propanylidin

propan-1,2,3-triyl

GV:Nguyn Xun Phong

Trang 23

 Sng kin kinh nghim CH3 CH2 C

Ho Hu c

Propan-1-yl-1-yliden propan-2-yl-1-ylidenpropan-1-yl-3-yliden Cc hu t ca gc ho tr bn bao gm: -tetrayl ( bn ho tr t do ring r), -ylyliin ( bn ho tr t do dng to mt lin kt n v mt lin ba), -iylien ( to hai lin kt i) v iylylien ( to hai lin kt n v mt lin kt i). V d:

CH3 CH

CH

CH2 CH2 CH

CH2 C CH2
propan-1,3-diyl-2-yliden

HC CH2 CH2 CH
butan-1,4-diyliden

Cc gc ho tr t do cao hn cng c gi tn theo cch tng t. C CH2 CH2 CH V d: : butan-1-yliden-4-ylidin IV.2 Hirocacbon khng no mch h. IV.2.1.Hirocacbon cha mt hay nhiu lin kt i: Nguyn tc c tn ca anken v c bn l ging nh vi ankan. Tuy nhin khi chn mch chnh cn u tin mch di hn l chn mch cha lin kt i. V d:

3-metylidenoctan Hexa-1,4-dien (khng c: 2-etylhept-1-en) (Khng c 1,4-hexadien) - Trng hp hirocacbon cha ni i c yu t lp th th theo quy nh ca IUPAC trc v sau 1998 khng thay i. V d:

(2Z)-but-2-en ( Hoc cis-but-2-en) - Mt s tn c IUPAC lu dng tn theo tn na h thng sau y: CH2=C=CH2 Anlen ( khng hn ch nhm th) CH2=C(CH3)-CH=CH2 isopren ( ch dng khi khng c nhm th)

IV.2.2. Hirocacbon cha mt hoc nhiu lin kt ba. Tn ca hirocacbon cha mt hoc nhiu lin kt ba cng xut pht t tn ca hirocacbon no tng ng ch i hu t -an thnh in ( mt ni ba), aiin ( hai ni ba), -atriin ( ba ni ba), Cch chn mch chnh, cch nh s mch cacbon v cch gi tn ni chung cng tng t nh i vi hp cht cha ni i. GV:Nguyn Xun Phong Trang 24

 Sng kin kinh nghim

V d:
1 2 7 6 5 4 3

Ho Hu c

4-etyl-6-metylhept-1-in (Khng c 4-etyl-6-metylheptin-1)

1 2 3 4

4-etinylheptan (khng c 3-propyl-5-metylhex-1-in)

5 6

3-metylhexa-1,4-diin (Khng c 3-metylhexiin-1,4) IV.2.3.Hp cht hirocacbon cha ng thi lin kt i v lin kt ba. Tn ca cc hirocacbon thuc loi ny c hnh thnh bng cch i hu t -an ca ankan tng ng thnh enin ( mt ni i v mt ni ba), -aienin ( hai ni i v mt ni ba), -eninin ( mt ni i v hai ni ba), mch chnh c chn l mch di nht cha tng s lin kt bi l ln nht. Khi c la chn, cc lin kt i c u tin cao hn lin kt ba, do cacbon lin kt i s c s thp hn cacbon lin kt ba. 1

V d:

3 4 5 6 7

Hept-2-en-5-in Tuy nhin nu lin kt i v lin kt ba khng phi cc v tr tng ng nhau, s nh s s u tin s khc bit u tin hai pha cacbon u mch. 7 V d: 6 5
4 3 2 1

Hept-4-en-2-in IV.2.4. Gc hirocacbon khng no. 1. Gc hirocacbon khng no ho tr mt. Gc hidrocacbon khng no ho tr mt c hu t nh: -enyl, -inyl, -ienyl, km theo ch s ch v tr cho lin kt kp v cho v tr ca ho tr t do. V d:

CH C
GV:Nguyn Xun Phong

: Etinyl

Trang 25

 Sng kin kinh nghim

CH C CH2
: Prop-2-in-1-yl : Prop-1-en-1-yl

Ho Hu c

CH3

CH CH

CH2 CH CH CH

: Buta-1,3-dien-1-yl

CH2 CH

CH2

CH2

: But-3-en-1-yl : Pent-2-en-4-in-1-yl

CH C

CH CH

CH2

Khi cn la chn mch chnh cho gc khng no, ta vn dng cc tiu chun sau y theo th t gim dn u tin. a. S nguyn t cacbon l nhiu nht. b. S lin kt bi ( lin kt i + lin kt ba) ti a. c. S ni i l nhiu nht. Tn cc gc khng no c lu dng:
-

Khng hn ch nhm th:

CH2=CHVinyl

CH2=CH-CH2Anlyl

Khng nhm th:

-CH2=C(CH3)Isopropenyl

2. Gc hirocacbon a ho tr: Cch gi tn cc gc hirocacbon khng no a ho tr cng tng t nh cch gi tn cc gc no.

a. Dng cc hu t t hp nh: -enylen, -dienylen, -inylen,

V d:
CH2 CH CH
: Propenylen

b. Dng cc hu t t hp nh: -endinyl, -entrinyl, -indiyl, -enyliden,

V d:
C CH2 CH CH C CH CH2 CH CH

: Pent-2-endiylidin : Hepta-1,6-dien-3,5-diyl

CH2 CH

IV.3. Hirocacbon mch vng GV:Nguyn Xun Phong Trang 26

 Sng kin kinh nghim

IV.3.1 Hirocacbon n vng no.

Ho Hu c

1. Hidrocacbon n vng no khng nhnh: c tn c hnh thnh bng cch thm tin t xiclo- vo tn ca ankan khng nhnh tng ng. V d:

Xiclopropan

xiclohexan

xiclotetradecan

2. Hidrocacbon n vng no c nhnh: c gi theo tn thay th vi cch nh s sao cho tng ch s ch v tr l nh nht. V d:
CH3 CH3 CH3 CH2CH3 CH3

CH3

CH2CH3

1,4-dimetylxiclohexan 1-etyl-3-metylxiclohexan 2-etyl-1,3-dimetylxiclohexan 3. Nhm (gc) hidrocacbon no n vng. Cc nhm ho tr mt c tn c hnh thnh bng cch i hu t -an ca xicloankan thnh hu t -yl hoc thm hu t -yl vo tn ca xicloankan. V d:
CH3

CH3

Xiclopropyl Hoc xiclopropanyl

xiclohexyl hoc xiclohexanyl

2,4-dimetylxiclohexyl hoc 2,4-imetylxiclohexan-1-yl

Cc nhm ho tr hai m hai ho tr t do tp trung cng mt nguyn t cacbon to ni i vi nguyn t khc c tn mang hu t -yliden. Trong trng hp hai ho tr c mt hai nguyn t khc nhau th tn ca nhm c tn cng bng ylen hoc diyl ( cng vi ch s ch v tr). V d:

GV:Nguyn Xun Phong

Trang 27

 Sng kin kinh nghim

Ho Hu c

Xiclopentyliden

xiclopent-1,3-ylen Hoc xiclopentan-1,3-diyl

xiclohex-1,2-ylen hoc xiclohexan-1,2-diyl

IV.3.2. Hidrocacbon n vng khng no. Hidrocacbon n vng khng no c gi tn tng t nh hidrocacbon khng no mch h: ngoi tin t xiclo-, cn dng cc hu t -en, -atrien, -in, -adiin, thay cho an.

CH3

Xiclohexen

3-metylxiclohex-1-en

xiclohexa-1,3-dien

Xiclooctin

xicloocta-1,3,5trien

Tn ca cc nhm (gc) hidrocacbon n vng khng no cng c hnh thnh theo cch tng t nh cc nhm khng no mch h, tc l cng c cc hu t nh: -enyl, -enylen, -yliden,

Xiclopent-2-en-1-yl xiclohex-3-en-1,2-diyl xiclohexa-2,4-dien-1-yliden IV.4. Hirocacbon thm . IV.4.1. Hirocacbon thm n vng v a vng. Tn chung ca hirocacbon n vng v a vng c cha nhn benzen l aren.
a. Tn thng ca nhiu aren c IUPAC hay dng.

+ Cc tn c dng khi khi khng c nhm th hoc c bt k v tr no. GV:Nguyn Xun Phong Trang 28

 Sng kin kinh nghim

8 7 6 5 4 1 2 3 7 6 5 10 4 8 9 1 2 3 7 6 8

Ho Hu c
9 10 1 2 5 4 1 3

Benzen

Naphtalen

Antraxen

Phenantren

+ Cc tn c dng khi khng c nhm th v ch khi c nhm th dng tin t trong vng. C6H5-CH3 Toluen C6H5-CH=CH2 Styren C6H5-CH=CH-C6H5 Stinben

+ Cc tn ch c dng khi c nhm th.

C6H4(CH3)2 Xilen ( 3 ng phn o-, m-, p-)

C6H5-CH-(CH3)2 Cumen

CH3

CH3-C6H4-CH(CH3)2

CH3

CH3

Ximen ( 3 ng phn o-, m-, p-)

b. Tn ca aren c nhm th.

Mesitylen

Tn ca aren c nhm th c hnh thnh theo tn thay th IUPAC . i vi khung benzen, vic nh s sao cho tng ch s v tr cc nhm th l nh nht. i vi cc khung a vng ngng t, vic nh s cc nhm th phi tun theo cch nh s v tr ca cc nguyn t cacbon b khung. V d:
8 7 6 5 4 1 2

C(CH3)3

CH3

8 7 6 5

CH3

1 2 3

10

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 Sng kin kinh nghim

Tert-butylbenzen 2-metylnaphtalen

Ho Hu c 9-metylantraxen

CH=CH2 CH3

CH3 CH3

CH2CH2CH2CH3 CH2CH2CH3 CH2CH3

CH=CH2

1,4-divinylbenzen 1,2,3-trimetylbenzen 1-butyl-3-etyl-2-propylbenzen i vi cc dn xut hai ln th ca benzen c th dng cc k hiu o(ortho), -m (meta), -p (para) ln lc cho cc v tr 1,2-, 1,3-, 1,4- (t c s dng hn). V d:
CH2CH3 CH=CH2 CH2CH3

CH3 CH3
CH2CH2CH3 CH2CH3 CH2CH3

o-imetylbenzen hoc o-metyltoluen

p-etylpropylbenzen

m-ietylbenzen

p-etylstiren

IV.4.2. Nhm hay gc hirocacbon thm. a. Nhm ( gc) c tn thng hay tn na h thng hay dng. + Cc tn dng khi khng c hoc c nhm th.

C6H5Phenyl
8 7 6 5 4 1 2 3 7 6 5 8

-C6H4Phenylen (o-, m-, p-)

9 1 2 3 10 4 7 6 5 4 3 9 8 10 1 2

2-naphtyl vng. C6H5-CH2GV:Nguyn Xun Phong

2-antryl

2-phenantryl

+ Cc tn c dng khi khng c nhm th hoc ch khi c nhm th C6H5-CH= C6H5-CH2-CH2Trang 30

 Sng kin kinh nghim

Benzyl benzyliden

Ho Hu c phenetyl

C6H5-CH=CH- C6H5-CH=CH-CH2Stiryl xinamyl

(C6H5)2-CHbenzhidryl

(C6H5)3Ctrityl

+ Cc tn ch c dng khi khng c nhm th. CH3-C6H4Tolyl (o-, m- v p-) b. Cc nhm ( gc) thm khc. - Dn xut ca cc nhm c tn thng hoc tn h thng c lm nn trong tn thay th. V d:
8 7 6 5 4 1 8 1 2 3 5 4 1 6 5 3 6 2 3 4

2,4,6-(CH3)3C6H12mesityl

CH2CH2CH3

CH2CH2CH3

7-(2-naphtyl)-2-naphtyl

2,4-dipropylphenyl

- Tn ca cc gc c ho tr hai hoc hn hai cng c hnh thnh nh tn ca cc gc hidrocacbon mch h. V d:

8 7 6 5 4 1 2

C6H5

C6H5CH=CH-CH= Xinamyliden

CH3

Benzylidin

6-metylnaphtalen-2,3-diyl

V.DANH PHP CU HNH V.1. Danh php ng phn hnh hc VII.1.1. H danh php cis- trans Theo h danh php ny, nhng dng c hai nhm th c phn b cng mt pha i vi mt phng ca ni i hay vng no th c gi l cis, tri li nu khc pha th c gi l trans. i vi anken phc tp ta chn mch di nht c cha lin kt i lm mch chnh:

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 Sng kin kinh nghim

CH3CH2 CH2CH2CH3 CH3 trans-4- etyl-3-metylhept-3-en C=C CH2CH3

Ho Hu c

Vic p dng h danh php ny gp kh khn trong cc trng hp nh cc th d sau: Cl Br C=C Br I 1,2- dibrom-1-clo-2- iotetylen CH3 CH2CH3 1-sec-Butylideninden V.1.2. H danh php syn- anti H danh php ny thng dng cho cc hp cht c lin kt N=N- v C= N-. ng ch l i vi oxim ca anehit RCH = NOH ngi ta cn c vo v tr trong khng gian ca H v OH gi cu hnh l syn ( tng t cis) hay anti ( tng t trans ). CH3 OH H OH C N C N H CH3 Anti-etanal oxim syn-etanal oxim Ngy nay ngi ta rt t dng h danh php ny. V.1.3. H danh php Z E H danh php Z-E bao trm c c hai h danh php trn v c th p dng c vo nhng trng hp m hai h trn gp kh khn. Mun gi tn cu hnh ca hp cht c ni i cn thc hin hai bc sau y: a. Bc 1:So snh hn cp ca cc nguyn t hoc nhm nguyn t ni i. abC = Ccd abC = Nc - C s xc nh hn cp l s th t Z ca nguyn t trc tip gn vo ni i. Z cng nh hn cp cng thp. V d: -Br > - Cl > - F > -OH > - NH2 > - CH3 > - H Z: 35 17 9 8 7 6 1 - Nu hai nguyn t trc tip gn vo ni i l ng nht, v d cng l cacbon, th cn xt n nguyn t tip theo. V d:-CH2 Cl > - CH2 OH > - CH2 CH3 > - CH2 H Do C(Cl, H, H) > C(O, H, H) > C(C, H, H) > C(H, H, H) Hoc -CH2 CH2 Cl > -CH2 CH2- OH > - CH2 CH2 CH3 - Nhng nguyn t ( nhm th ) mang ni i hoc ni ba c coi nh tng ng hai hoc ba ni n vi cc nguyn t gi nh v c ghi trong du ngoc:
V du: COOH , CH2OH , CHO , CH3 C(O,O,O) > C(O,O,H) > C(O,H,H) > C(H,H,H) theo thu tu Z giam dn

b. Bc 2: Xc nh tn cu hnh Z E Gi s sau khi xc nh hn cp tng i thy a > b v c > d, ta xt v tr khng gian ca a v c, nu chng cng pha ta c dng Z ( t ting c Zusammen c GV:Nguyn Xun Phong Trang 32

 Sng kin kinh nghim

a c C=C Z d

Ho Hu c ngha l cng), tri li nu chng khc pha ta c dng E ( ch ci u ca Entgegen c ngha l i ) :

a b b C=C E H Cl Br CH3 d c

V d:
CH3 CH3 H (E)- but-2-en C=C

I Br (Z)- 1,2-dibrom-1-clo-2-iotetilen
Cl CH3

C=C

C=N OH H (E)-axetandoxim

V d:

Cl H C C

CH2OH CH(CH3)OH

C=N

CH(CH3)(CH2Cl) CH(CH2OH)(CHOHCH3)

Cl>H C(O,C,H)>C(O,H,H) Suy ra cu hnh E

v bn phi c cng C(C,C,H) nn phi xt tip C(Cl,H,H)>C(H,H,H)>H nhm trn C(O,C,H)>C(O,H,H)>H nhm di So snh ta thy C(Cl,H,H)>C(O,C,H) nn nhm trn ln hn nhm di v ta c cu hnh Z.

B-CC DNG BI TP
I.HYDROCACBON NO Bi 1: Hy gi tn ca cc hp cht sau theo danh php thay th ca IUPAC

GV:Nguyn Xun Phong

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 Sng kin kinh nghim

Ho Hu c

13)

14

CH4

14)

CH32H 16)

15)

17)

18)

19)

20)

21)

22)

23)

GV:Nguyn Xun Phong

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 Sng kin kinh nghim 24) 25)

Ho Hu c

26)

27)

p n:
1) 3-etyl-7-metyl-5-propylnonan 2) 2,3,5-trimetyl-4-propylheptan 3) 2,5-dimetyl-4-(2-metylpropyl)heptan hoc 4-isobutyl-2,5-dimetylheptan 4) 2,7,8-trimetyldecan 5) 3-etyl-2,2-dimetylhexan 6) 6-(1,2-dimetylbutyl)-5-etylundecan 7) 3-etyl-4-metylhexan 8) 7-(1-metylbutyl)-9-(2-metylbutyl)pentadecan 9) 5,5-bis(1,2-dimetylpropyl)nonan 10) 5-tert-butyl-6-isobutyldecan 11) 5-tert-butyl-6-sec-butyldecan 12) 4,6-diisopropylnonan hoc 4,6-di(propan-2-yl)nonan 13) (14C)metan 14) (2H1)metan 15) 4-Etyl-3,3-dimetylheptan 16) 7-(1,2-dimetylpentyl)-5-etyltridecan 17) 6-(1-metylbutyl)-8-(2-metylbutyl)tridecan 18) 7,7-bis(2,4-dimetylhexyl)-3-etyl-5,9,11-trimetyltridecan 19) 2,2,6,6,7-pentametyloctan GV:Nguyn Xun Phong Trang 35

 Sng kin kinh nghim

20) 5,5-Bis(1,1-dimetylpropyl)-2-metyldecan 21) 2,3,4,5-tetrametylhexan 22) 4-sec-butyl-1-etyl-2-metylxiclopentan hoc 1-etyl-2-metyl-4-(1-metylpropyl)xiclopentan 23) 3-(1-metylxiclobutyl)pentan 24) 3,6,7-trietyl-2,3,4,8-tetrametylnonan 25) 2-tert-butyl-5-isopropyl-1-metyl-4-xiclopentylxicloheptan 26) 4-etyl-5-isopropyl-3,6-dimetyloctan 27) 3-(2-sec-butylxiclopropyl)-4-etyl-2,5-dimetylhexan

Ho Hu c

Bi 2: Hy chn trong s cc cng thc t A-L cho trc, cng thc no ng cho nhng tn gi theo IUPAC c cho bn di:
A B C D

1) 4-metylheptan 2) 2,2-dimetylhexan 3) 2,4-dimetylhexan 4) 2-etyl-1,1,3,3-tetrametylxiclopentan 5) 2,3-dimetypentan 6) 3-etyl-2-metylpentan p n: 1-H; 2-F; 3-B; 4-K; 5-E; 6-D. Bi 3: Chn tn IUPAC cho CH3CH2C(CH3)2CH2CH(CH3)2?
A) 3,3,5-trimetylhexan B) 2,2,5-trimetylhexan C) 2,4,4-trimetylhexan D) 1,1,3,3-tetrametylpentan

p n: C Bi 4: Hy vit cng thc cho cc tn gi sau:

a. b. c. d. e. 6-isopropyl-2,3-dimetylnonan 4-tert-butyl-3-metylheptan 4-isobutyl-1,1-dimetylxiclohexan Sec-butylxicloheptan cis-1,2-dimetylxiclohexan Trang 36

GV:Nguyn Xun Phong

 Sng kin kinh nghim

f. g. h. i.
j. k.

Ho Hu c

trans-1,2-dimetylxiclohexan trideca-1,2,11-trien-5,7,9-triin 4-isobutyl-3,6-dimetylhept-3-en But-2-enylxiclohexan (2S,4R)-(4-H1 ,2-H1 )pentan (R)-(1-H1 )propan-2-ol

p n: a.

hoc

b.

hoc

c.

hoc

d.

hoc

e.

f.

g.

CH2 CH CH CH C C

C C

C C

CH CHCH3

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 Sng kin kinh nghim

h. CH3 CH3

Ho Hu c
i.

CH3CHCH2CCH2CHCH3 CH3 CH2CH3

j.

k.

Bi 5: c tn theo danh php h thng ca bixiclo v spiro c cng thc sau: 1) 2) 3) 4)

5)

6)

7)

8)

. 9) 10) 11) 12)

13)

14)

15)

16)

CH2

17)

CH2

p n:
1) 2) 3) 4)

bixiclo[4.1.0]heptan 1-metyl-8-propylbixiclo[4.3.0]nonan 7,7-dimetylbixiclo[2.2.1]heptan 4-etyl-2-isopropylbixiclo[4.1.0]heptan Trang 38

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 Sng kin kinh nghim

5)

Ho Hu c

1,9-dimetylbixiclo[4.2.1]nonan 6) 2,6,6-trimetylbixiclo[3.1.1]heptan
7) 2-metylbixiclo[2.1.0]pentan 8) 2-etyl-3-metylbixiclo[2.2.2]octan 9) 1,4-dimetylbixiclo[2.2.0]hexan 10) 1,4-diisopropylbixiclo[2.2.2]octan 11) 2,6-dimetylspiro[4.5]decan 12) 2,6-dimetylspiro[3.3]heptan 13) 1,2,4,8-tetrametylspiro[2.5]octan 14) 2,7-dietylspiro[5.6]dodecan 15) 8-isopropylspiro[4.5]decan 16) 1-isopropyl-2,4-dimetylidenbixiclo[3.1.0]hexan 17) 5-isopropylbixiclo[3.1.0]hex-2-en

II. HYDROCACBON KHNG NO Bi 1: Hy gi tn ca cc hp cht sau theo danh php h thng ca IUPAC 1) 2) 3) 4)

5)

6)

7)

8)

9)

10)

11)

12)

13)

14)

GV:Nguyn Xun Phong

Trang 39

 Sng kin kinh nghim

Ho Hu c

15)

16)

17)

C
18)
HC

CH3 CCCH CH2 CH3

19)
CH3 CH3

CH2 CHC CHCH2CH CCH3

20)

21)

22)

23)

24)

25)

p n:
1) 2-etyl-4-metylpenta-1,4-dien 2) 2-etyl-3,4-dimetylpenta-1,4-dien 3) 1-xiclobutyl-3-metylbut-1-in 4) 4-vinylhept-1-en-5-in 5) 2,5-dimetyl-3-propylhex-2-en

GV:Nguyn Xun Phong

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 Sng kin kinh nghim

6) 1-etyl-4,4-dimetylxiclohepten 7) 2,3-dietyl-4-metylpenta-1,3-dien 8) 6,6-dimetylhept-2-in 9) 5-xiclohexylpent-1-en-3-in 10) 6-alylxicloocta-1,4-dien 11) 2-metylpent-1-en 12) (3Z)-4-butyl-3-clo-6-isopropyl-5,7,9,9-tetrametyldec-3-en
13) (3E)-7-metyloct-3-en

Ho Hu c

14) (2E,4E)-3-metylhexa-2,4-dien 15) 4-Etenylidenheptan hoc vinylidenheptan

16) (E)-(1-2H1)propen

17) (3E)-3,4-dietylhexa-1,3,5-trien 18) 3,3-dimetylpent-1-en-4-in 19) 3,7-dimetylocta-1,3,6-trien 20) cis-trans-cis-octa-2,4,6-trien 21) cis-cis-octa-3,5-dien 22) 5-etylhept-3-in 23) (E)-7-isopropylnon-2-en-5-in 24) (3Z)-3,4-dietylhexa-1,3-dien-5-in 25) 3-metyliden-5-(prop-1-in-1-yl)decan

Bi 2: 1.Tn IUPAC cho (CH3)2CHCH(CH3)CH2CH=CH2 l g?

A) 4,5-dimetylhex-1-en B) 4,5,5-trimetylpent-1-en C) 2,3-dimetylhex-5-en D) 4-metyl-4-isopropylbut-1-en

p n: A 2. Mt tecpen c tn IUPAC l (3E)-3,7-dimetylocta-1,3,6-trien, u l cng thc ng

GV:Nguyn Xun Phong

Trang 41

 Sng kin kinh nghim

Ho Hu c

p n: D Bi 3: Gi tn cc cht sau theo danh php h thng ca IUPAC, c km theo cu hnh: 1) 2) 3)

4)

5)

6)

7)

8)

9)

10)

p n:
1)
2)

(E)-3-etyl-2,4-dimetylhex-3-en cis-1-isopropyl-4-vinylxiclohexan (Z,Z,Z)-1-metylxicloocta-1,3,6-trien (Z)-3-metylnon-2-en-7-in (R)-3-etyl-3,5-dimetylhexen (R)-3-metyl-3-vinylxiclohexen (2S,3R)-1,1,3-trimetyl-2-vinylxiclohexan trans-1-isopropyl-4-vinylxiclohexan (4S)-4-metylnon-2-in (E)-2,4-dietylidenxiclobutan

3) 4) 5) 6) 7) 8) 9) 10)

Bi 4: Tm li sai trong tn ca cc cng thc sau vit li tn ng ca cng thc theo tn thay th IUPAC.

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 Sng kin kinh nghim

1-propylbut-1-en

Ho Hu c

Tn IUPAC ng : .
2-metylxiclopropen

Tn IUPAC ng :.
2-etyl-1,3-imetyl-1-xiclohexen

Tn IUPAC ng : .
cis-4,5-imetylhex-4-en

Tn IUPAC ng : .
e. 3-propylpent-1-en CH2CH2CH3 Tn IUPAC ng: . f.
CH3 C C H H C C H CH2CH2CH3 H

CH3CH2CHCH CH2

trans-cis-oct-2,4-ien

Tn IUPAC ng: .
g. CH2CH2CH2CH3 CH3CCH2C CH CH CHCH3

4-butyl-4-metylpent-5-en-1-in

Tn IUPAC ng:.
p n: a. b. c. d. e. 3-metylhex-1-en Metylxiclopropen 2-etyl-1,3-imetylxiclohex-1-en 2,3-imetylhex-2-en 3-vinylhexan hay 3-etenylhexan Trang 43

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 Sng kin kinh nghim

f. g. Trans-trans-octa-2,4-ien hoc (2E,4E)-octa-2,4-dien 4-(prop-2-in-1-yl)-4-metyloct-2-en

Ho Hu c

III. HYDROCACBON THM c tn theo danh php h thng IUPAC 1) 2) 3)

4)

5)

6)

7)

8)

9)

p n:
1) 2) 3)
4)

5) 6) 7) 8) 9)

p-clometylbenzen (clometyl)benzen 1-alyl-2-etylbenzen naphtalen o-xilen stiren mesitilen 9,10-dihidro-9,10-but[2]enoantraxen perhidro-1,4-etano-5,8-metanoantraxen

PHN III
Qua qu trnh nghin cu ti: Mt s quy nh ca IUPAC khi c tn hp cht hu c v bi tp c th rt ra mt s kt lun sau: 1.Nhn r danh php IUPAC khng phi l mt danh php thun khit m l t hp ca nhiu dng danh php khc nhau, trong quan trng v ph bin nht l danh php thay th, sau n danh php gc chc v cc danh php khc. C rt nhiu tn thng thng vn c IUPAC lu dng. 2. Danh php trc v sau nm 1998 c nhng im khc nhau c bn sau: V v tr ch s ch v tr ca nhm chc v cha bo ho. S i mi ny c p dng trong chng trnh i mi sch gio khoa cc trng ph thng . 3.Danh php IUPAC 2004 c mt s thay i nh cch chn mch chnh v cch nh s trn mch chnh khi xut hin d t. Tuy nhin s i mi ny vn cha c cp nht trong cc sch Ha hu c bc i hc cng nh bc ph thng do nhn chung hin nay gio vin v hc sinh u p dng theo qui nh ca IUPAC 1998 l GV:Nguyn Xun Phong Trang 44

 Sng kin kinh nghim

Ho Hu c mch cha lin kt bi c u tin hn mch di hn v nh s t pha nhm chc c u tin hn l t pha d t. 4. ti tng quan c cch chn mch chnh, cch nh s, cch vit tn theo trnh t ch ci mt cch tng qut nht, gip ch rt nhiu cho vic c tn mt hp cht hu c. 5. Bi tp di cc dng khc nhau gip cng c, nng cao k nng c tn, vit cng thc, xc nh cu hnh, ca mt cht hu c mt cch nhanh v chnh xc. y l mt ti hay, l hnh trang gip bn thn ti rt nhiu trong vic hc v ging dy. Nhng do hn ch v ch quan v khch quan nn ti cha trnh by y ht danh php cc hp cht hu c. V vy ti mong mun rng cc bn tip tc pht trin thm nhng mt thiu st ca ti ti hon chnh hn.

1. Danh php hp cht hu c-Trn Quc Sn(ch bin)- Trn Th Tu-Nh xut
bn Gio dc.

2. C s ha hc hu c- Thi Don Tnh- nh xut bn Khoa Hc v K Thut. 3. Gio trnh ha hu c- Nguyn Hu nh( ch bin)- nh Rng- nh xut
bn gio dc.

4. Theo Principle of nomenclature-1998 5. Theo IUPAC Provisional Recommendations-2004 6. Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H, Pergamon
Press, Oxford, 1979.

7. A Guide to IUPAC Nomenclature of Organic Compounds (Recommendations

1993)

8. Mc Graw-Hill-Deans handbook of organic chemistry.

9. Cc trang wed hu c: - http://chemistry.boisestate.edu/people/richardbanks/organic/nomenclature/ organicnomenclature1.htm. GV:Nguyn Xun Phong Trang 45

 Sng kin kinh nghim Ho Hu c http://www.chem.qmul.ac.uk/iupac/. - http://www.acdlabs.com/iupac/nomenclature/. - http://en.wikipedia.org/wiki/IUPAC_nomenclature_of_organic_chemistry. - http://www.chemguide.co.uk/basicorg/conventions/names.html. - http://old.iupac.org/publications/books/author/connelly.html. - http://www.chembio.uoguelph.ca/educmat/chm19104/nomenclature/quize
s.html. - http://www.mhhe.com/physsci/chemistry/carey5e/nomenclature/tutorialsnew.html. - http://www.scribd.com/doc/14024052/IUPAC-Nomenclature-Exercisesin-Organic-Chemistry. - Stereocenter Nomenclature Tutorial and Exercises

Trang Li cm n:.... 1 M u:........ 2 Tng quan: ... 3 IV. L C S TI NGHIN CU: . 3 V. GII HN TI NGHIN CU: 3 VI. PHNG PHP NGHIN CU:. . 3 VII. NI DUNG NGHIN CU: :. 4 Ni dung: A-L THUYT: I.PHN LOI CHUNG. .. 5 II. PHN LOI DANH PHP IUPAC. II.1. Tn thay th. . 5 II.2 Tn gc chc: 6 II.3. Tn trao i: . 6 II.4. Tn kt hp. .. 7 II.5. Tn cng: 7 II.6. Tn tr: ... 8 II.7. Tn nhn: 8 GV:Nguyn Xun Phong Trang 46

 Sng kin kinh nghim

Ho Hu c II.8. Tn dung hp. 9 II.9. Tn d vng theo Hantzsch v Widman. 11 II.10. Tn thng v tn na h thng c IUPAC lu dng trong h thng tn ca IPUAC.. 12 IV. MT S QUI NH V CCH CHN NHM CHC CHNH, MCH CHNH, CCH NH S, CCH C TN THEO TRNH T CH CI TRONG DANH PHP THAY TH IUPAC. IV.1. Cch chn nhm chc chnh. 20 IV.1.1.Cc nhm ch c gi di dng tin t : .21 IV.1.2. Cc nhm c th gi dng tin t hoc hu t : .21 IV.2.Cch chn mch chnh : . 22 IV.2.1.Cch chn mch chnh i vi hp cht mch h : . 22 IV.2.2 Cch chn mch chnh i vi hp cht mch vng: : 25 IV.3. Cch nh s trong mch khi gi tn hp cht hu c : 28 IV.4. Cch vit tn gi theo trnh t ch ci : 31 V. DANH PHP IUPAC CHO TNG HP CHT C TH. V.1.HIROCACBON NO, MCH H. V.1.1.i vi ankan khng phn nhnh: . 32 V.1.2.i vi ankan c nhnh: 33 V.1.3.Tn gc hirocacbon no: . 33 V.2.HIROCACBON KHNG NO MCH H. V.2.1.Hirocacbon cha mt hay nhiu lin kt i: ... 34 V.2.2. Hirocacbon cha mt hoc nhiu lin kt ba: 35 V.2.3.Hp cht hirocacbon cha ng thi lin kt i v lin kt ba: . 35 V.2.4. Gc hirocacbon khng no: . 36 V.3. HIROCACBON MCH VNG

V.3.1 Hirocacbon n vng no: . 37 V.3.2. Hidrocacbon n vng khng no: . 38 V.3.3. Hirocacbon kiu spiro: . 39 V.3.4. Hirocacbon kiu bixiclo: 39 V.4. HIROCACBON THM.

V.4.1. Hirocacbon thm n vng v a vng: . 39 V.4.2. Nhm hay gc hirocacbon thm: . .41 VI.DANH PHP CU HNH

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 Sng kin kinh nghim

Ho Hu c

VI.1. Danh php ng phn hnh hc VI.1.2. H danh php cis- trans : 69 VI.1.3. H danh php Z E : 69 VI.1.1. H danh php syn- anti: 69 B-CC DNG BI TP I. Hydrocacbon no: 77 II. Hydrocacbon khng no: 84 III. Hydrocacbon thm: 88 Phn 3: kt lun:..104 Ti liu tham kho: .105

GV:Nguyn Xun Phong

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