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
CH3-CH2-CH2-CH2 CH2CH3

10
9
8
1CH -CH CH
3

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

CH2-CH3

6-Butyl-3-etyl-4-metyl-5-propyl ecan
CH2-CH2-CH2-CH2CH3
1

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
|

CHO
|

(CHOH)n

(CHOH)n

|
|
*
H - C - OH
HO- C*- H
|
|
Dy D
Dy L
CH
OH
CH
OH
2. Danh php
R/S
2
2
* 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

H2N

NH2

H
CH3

CH3

(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
OH
HO

CH3S)-2,3,4-trihiroxi
OH
OH
(2S, CH
3R)-2,3,4-trihiroxi
butanal
(2R,
butanal
2
2
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
OH

HO

OH

HO
HO

H
H

OH

CH2OH
OH
CH2OH
i i quangCH
threo
i
i
quang
erythro
2
CH2OH
Trong trng hp R = R; X = Y, ta ch c 1 dng erythro gi l ng phn
meso, cng i i quang threo

HO
H
OH

CHO

CHO

CHO

H
OH

H
OH
HO

CHO
i
i quang threo CHO

HO
HO

H
OH

CHO
H
H

CHO
Hai ng phn ny l 1 gi
CHO
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