CHNG I

NG PHN HA HC

GV: PHAN TH HONG ANH

NG PHN

Cng cng thc phn t

Isomers

ng phn
lp th

ng phn
cu trc
Constitutional isomers
Khc trt t sp xp nguyn t
trong phn t

ng phn
cu dng
Conformational isomers

ng phn
hnh hc
Geometric isomers

ng phn quang
hc i quang
Enantiomers

Cng trt t sp xp nguyn t

trong phn t, khc nhau trt t
sp xp trong khng gian

Stereoisomers

ng phn
cu hnh
Configurational isomers

ng phn
quang hc
Optical isomers

ng phn quang hc
khng i quang
Diastereomers

A. NG PHN CU TRC
I. NG PHN MCH C

II. NG PHN V TR NHM CHC, LIN KT

BI

III. NG PHN LOI NHM CHC

B. NG PHN LP TH (Stereoisomers)

Cng trt t sp xp nguyn t trong phn t, khc nhau trt

t sp xp trong khng gian
ng phn lp th
ng phn
cu dng

ng phn
cu hnh
ng phn
hnh hc

ng phn
quang hc

II. NG PHN CU DNG

(Conformational isomers)
Hnh thnh do s quay cc nhm th xung
quanh lk n C-C

Cc cu dng c th chuyn ha ln nhau (khng phi l

nhng cht khc nhau)
Khng th tch nhng ng phn cu dng ring l
Cht tn ti ch yu nhng cu dng bn

NG PHN CU DNG
1. CCH BIU DIN
1. NT M, NT RI

2. CT PHI CNH

3. CT CHIU NEWMAN

2. CU DNG CA ETHANE C2H6:

CHE KHUT

XEN K

3. CU DNG CA n-BUTHANE C4H10:

XEN K K

XEN K I

3. CU DNG CA CYCLOHEXANE:

Cu dng gh

Cu dng thuyn (km bn)

Ring flipping (ring inversion)

Khi chuyn t cu dng gh 1 sang cu dng gh 2, cc nhm

th v tr trc s chuyn thnh v tr xch o v ngc li

DN XUT TH CA CYCLOHEXANE

NG PHN HNH HC
(Geometric isomers)
Phn t c h thng cng nhc (lin kt pi hoc
mp vng 3,4,5 cnh)

DANH PHP NG PHN HNH HC

1. CIS TRANS : H abC=Cac
2. E Z: H abC=Ccd

DANH PHP E-Z

H abC=Ccd: sp xp a>b, c>d
a,c cng pha Z,
a,c khc pha E

(E is for entgegen, German for opposite).

(Z is for zusammen, German for together)

Quy tc Cahn-Ingold-Prelog

Quy tc 1:
Nguyn t c s th t ln hn th hn cp

Quy tc Cahn-Ingold-Prelog

Quy tc 2:
So snh t trong ra ngoi

2
Sp xp tnh hn cp cc nhm th sau:
a) C(CH3)3 , CH(CH3)2 v CH2CH3
b) CH2CH2OH v CH(CH3)2
c) CH2OH v C(CH3)3

Quy tc Cahn-Ingold-Prelog

Quy tc 3:
Lk i = 2 lk n, lk ba = 3 lk n

NG PHN QUANG HC
(Optical isomers)
1. NH SNG PHN CC

2. CHT HOT NG QUANG HC

Lm quay mt phng nh sng phn cc sang

phi hoc sang tri mt gc :

Gc quay cc ring:

3. IU KIN C P QUANG HC

Cha yu t khng trng vt -nh (chirality)

Cc phn t c tnh cht khng trng vt-nh s

c tnh quang hot (chiral molecule)

 C bt i xng: lin kt vi 4 nhm th khc nhau

 Phn t cha 1 C bt i xng s c tnh chiral -->

c th tn ti 1 trong 2 dng ng phn quang hc
i quang gi l enantiomer.

ENANTIOMERS (ng phn quang hc i quang)

Enantiomers have identical physical properties except for the rotation of planepolarized light and how they react with other chiral molecules

4. BIU DIN P QUANG HC

NT M, NT RI

CHIU FISCHER

5. CU HNH TNG I

Cc cht dng: RC*HXR

Cht chun: Glyceraldehyde

D-(+)-Glyceraldehyde

L-(-)- Glyceraldehyde

p dng cho cc cht ng , lipid, aminoacid

S dng cng thc chiu Fischer (C nm trn cng c s oxy ha ln nht)

ng: nguyn t C bx cha nhm OH c s th t ln nht

Amino acid: nguyn t C bx cha nhm NH2 c s th t nh nht

6. CU HNH TUYT I (R,S)

R: clockwise
S: anti-clockwise

Nhm th nh nht (4) phi t hng ra xa ngi quan st

QUY C

Quay CT Fischer 90o hoc 270o cu hnh o

Xoay CT Fischer 180o cu hnh khng i

HN HP RACEMIC
50% (R-) + 50% (S-) khng hot ng quang hc

 TINH KHIT QUANG HC CA HN HP 2

ENANTIOMER
tinh khit quang hc (%ee) = % enantiomer d trong hn hp

If the mixture has a 40% S enantiomeric excess (or

optilcal purity = 0.4), 40% of the mixture is excess S
enantiomer and 60% is a racemic mixture.
(40 + 60/2) = 70% of the mixture is the S
enantiomer and 70-40 =30% is the R enantiomer.

7. HP CHT C 2 TRUNG TM BT I
Cng thc chiu Fischer

(2R,3R)-dihydroxybutanoic acid.

DANH PHP THREO - ERYTHRO

Cabx Caby hoc Cabx Cacy

DANH PHP R-S

 Mt hp cht c n C bt i xng c th c ti a 2n
ng phn quang hc.

3-bromo-2-butanol c 4 ng phn quang hc l 2

cp i quang

ng phn quang hc khng i quang

(DIASTEREOMERS)
enantiomers

diastereomers

8. NG PHN MESO

Cha nhiu hn 1 trung tm bt i, v c mp

i xng trong phn t.
Khng hot ng quang hc

Hp cht c tnh i xng dng Cabx-Cabx 3

ng phn lp th : 1 meso + 1 cp i quang

Nu mp i xng i qua C gi bt i 2 meso + 1 cp i quang