n cu to: phn bit nhau v CTHH

I- ng ph
ph

NG
H A I C
C
NG
n 2 HA H
U C

Ph
Ph
H
C
Ni dung: Gm 7 chng
Chng I- i cng v Ha hu c
Chng II- Hidrocarbon
t hidroxi ca hidrocarbon
Chng III- Dn xu
xu
t carbonyl
Chng IV- Hp ch
ch
t
Chng V- Axit carboxylic v dn xu
xu
t ch
a nit

Chng VI- Hp ch
ch
ch
nit
Chng VII- Gluxit

ng phn cu to
ng phn
mch carbon

CH3

NG V
H
A H
U C

I C
C
NG
V
H
H
C

CH3 CH2 CH

ng phn lp th (khng gian) : cng cng thc

cu to nhng khc nhau v cch thc sp xp cc
nguyn t trong khng gian (khc nhau v cu hnh)

CH3

CH3

CH2 OH

CH3

CH3

CH2 CH2OH

CH3

CH3

Phn bit gia h bin v ng phn

Trong mt s trng hp, cht hu c c th tn ti di 2 dng

cu to khc nhau. Gia 2 dng ny tn ti mt cn bng lin tc
chuyn ha ln nhau khin cho chng ch x s nh mt cht duy
nht. Hin tng ny c gi l s h bin.
R

CH 2

OH

CH 3

O
Xeton

Enol

n lo
i : Ty thuc vo vic cc cht ng phn phn
Ph
Ph
lo
bit nhau v cu to hay phn bit nhau v cu hnh m
c 2 lai ng phn
ng phn cu to (phng) : cng cng thc phn
t nhng khc cng thc cu to.

CH

ng phn mch carbon, ng phn v tr : tnh cht vt

l khc nhau (khng nhiu), tnh cht ha hc tng
ng.
ng phn nhm chc : tnh cht vt l ha hc hon
ton khc nhau.

nh ngh
ngha : l hin tng cng mt cng thc c nhiu cht khc
nhau

CH3

CH3

N
NG PH
PH

CH2 CH2 CH2 CH3

ng phn
nhm chc

OH

NG I
CH
CH
NG

ng phn
v tr

'

OH

R'

Amid

Imid

Hai dng h bin khng th tch ring c do chng chuyn

ha (bin i) lin tc qua li nh vy h bin khng phi hin
tng ng phn.
C2H4O

:
V D
D

CH3 CH

CH2

CH

OH

n hnh hc ca ni i
ng ph
ph

n lp th
:
II- ng ph
ph
th
Cc ng phn lp th phn bit nhau v cu hnh
ngha l phn bit nhau v s phn b ca cc nhm
th trong khng gian

ng ph
phn lp th
th

ng phn
hnh hc

Hin tng ng phn c c l do c cu cng nhc

ca ni i khc vi ni n khng th xoay c (nu
khng s mt i s xen ph bn ca 2 vn o ).
Nh vy nu trn 2 carbon ni i c 2 nhm th khc
nhau th ta s c 2 c ch s p x p c c nh m th trong
khng gian (i vi mt phng - mt phng cha ni
v ) 2 ng phn hnh hc.

ng phn
quang hc

HOOC

COOH

Axit cis-2-butenoic
Axit maleic

nh ngh
ngh a : l nhng hp ch t c c ng CTPT, cng
cng thc khai trin phng ( cng CTCT ) nhng cch
sp xp ca nhng nguyn t hay nhm nguyn t khc
nhau i vi mt mt phng quy chiu.
Ty vo mt phng qui chiu l m t phng (mt
phng cha ni v ) hay mt phng vng carbon m
ta ng phn hnh hc tng ng.
ng ph
phn hnh hc
ng phn
ca ni i

HOOC

COOH

Axit trans-2-butenoic
Axit fumaric

n hnh hc hp ch
t vng no
ng ph
ph
ch
n xiclan )
( ng ph
ph

n hnh hc:
1- ng ph
ph

Cc hp cht vng no c th c 3, 4, 5, 6, 7, 8, carbon

Nhng vng 3,4 rt km bn (qu cng), trn thc t cc cht vng
ch yu l vng 5,6 (bn nht). Vng 7 tr ln rt t gp.

Mo hnh pha n t

Cau trang u a i
thc te

Da ng n gia n

ng phn
xiclan

Cong thc
khai trien phang

Ty vo s phn b ca cc nhm th so vi mt phng vng

carbon m ta c ng phn cis- hay trans-

:
V D
D

CH3

H 3C

H3 C

H
H

H
H

CH3

V d:

CH3 CHOHCOOH

CH3 CHBrCHOHCH3

Cis- v trans-1,2-dimetilxiclopropan

n quang hc:
2- ng ph
ph
2.1- Thuy
t carbon t di
n v qui c bi
u di
n c cu
Thuy
di
bi
di
n t trong kh
ng gian
ph
ph
kh
gian::
a- Thuyt carbon t din ( Lebel & VanHoff, 1874 ):
4 nguyn t, nhm nguy n t ni vi carbon c
phn b trong khng gian ti 4 nh ca t din u c
tm l nguyn t carbon :

3-brombutan-2-ol

Axit lactic

b- Qui c bi
u di
n c cu ph
n t trong kh
ng gian
bi
di
ph
kh
gian::
c ph
i cnh
th
ph
nh::
Cng th
Cc lin kt nm trong mt phng c biu din bng
nt lin mnh.
Lin kt hng ra pha trc mt phng c biu din
bng nt m.
Lin kt hng ra pha sau mt phng c biu din
bng nt t.

o
C 109 28'

H
H

Nu 4 nguyn t hoc nhm nguyn t lin kt vi

nguyn t carbon hon ton khc nhau th nguyn t
carbon trung tm c gi l carbon phi i xng hay
carbon bt i xng v c k hiu l C*.

H
H

Cng thc phi cnh cho hp cht c nhiu carbon:

Ni sang phi hng ra bn ngoi mt phng
Ni sang tri hng ra pha sau mt phng

n:
M hnh t di
di

b
d

c
=

c chi
u Fischer : t t din hoc cng
Cng th
th
chi
thc phi cnh sao cho 1 cnh nm ngang hng v
pha ngi quan st ri chiu xung mt phng giy.
Trc thng ng l mch carbon ng thi biu din
cc lin kt hng ra pha sau mt phng. Trc nm
ngang biu din cc lin kt hng ra pha trc mt
phng.

CT phi cnh dng i

CT phi cnh dng che khut

V d:
Cng thc phi cnh dng i v cng thc phi cnh
dng che khut ca axit 2-brom-3-clobutanoic
CH3-CHCl-CHBr-COOH

COOH

OH

CH3

CH 3
OH

COOH

COOH

COOH
H

CH 3

CH3

OH

COOH

COOH

COOH

Cl

Br

CH3

Br

CH3

Br

Cl

COOH
H

COOH

CH 3

OH

Br

Br

Cl

Cl

Cl
CH 3

Hoc
H

Cl

Br

Br

Cl

H
COOH

Br

COOH

CH 3

COOH

COOH
Br

CH 3

CH 3

Cl
CH 3

Cl
CH 3

Nh vy cng thc chiu Fischer ch biu din phn t

di dng che khut, v vy nu phn t dng i th
phi xoay v cu dng che khut ri mi chiu.
COOH

Br

Cl

Br

CH3

Nhn phn t dc theo lin kt gia hai nguyn t

cacbon trung tm thng gc vi mt phng giy v
chiu xung:

CH3

COOH

c chi
u Newman
Cng th
th
chi

CH3

CH3

Cl

H
H

H3C CH3
H

COOH
Br

CH3

Cl

H
H

CH3

900 trong

d
a

mp

c
180 0 trong
mp

CH3

H
CH3

Lin kt c c l do s xen ph gia hai orbital dc

theo trc ni ht nhn 2 nguyn t.
Nh vy lin kt c tnh i xng trc ngh a l khi
xoay 2 orbital xen ph , xen ph hay bn (n ng
lng) lin kt khng i. Do , 2 nguyn t ca lin
kt c th xoay quanh trc lin kt.

b
a

b
c

CH3

Thuyt quay gii hn ca lin kt n

C OOH
OH

C H3
C OOH

H
H

c Newman dng i
Cng th
th

C H3

HO

Cl
CH3

Qui c v s dng cng thc chiu:

Ton b cng thc chiu c th quay 180 o trn mt phng
nhng khng c php quay 90 o trn mt phng hoc
180o ngoi mt phng.
180o trong mf

c Newman dng che khu

t
Cng th
th
khu

COOH
H

Br

1800

ngoai

mp

sp3

sp 3
s

sp3

Do s quay t do ny m phn t hu c c th tn ti
di nhiu cu dng khc nhau, trong 2 cu dng u
t:
tin l cu dng i v cu dng che khu
khu

V d: cc CT phi cnh, Newman v Fischer ca n-butan

Cau dan g oi

ca u dan g che khuat

CH3 H H

CH3

CT phoi ca nh
H

H CH3

H
H

H
CH3

CH3
CH3

CH3

CT Newman

CH3
H

H
H

H
H
CH3

CT Fischer

khong co

H
H

H
H
CH3

n cc
2.2- nh s ng ph
ph
v hi n t ng quang
t:
ho
ho

nh sng phn cc: nh sng

c vect i n ch dao ng
theo 1 hng trong khng gian.
M t ph ng hp b i ph ng
truyn v phng vect in =
mf dao ng ca as phn cc.
Hin tng quang hot: hin
tng lm lch mt phng dao
ng ca nh sng phn cc
i 1 gc no y.
Ch t g y n n hi n t ng
quang hot c gi l cht
quang hot
( hay cht trin quang ).
c gi l gc quay cc

Nu mt phng dao ng lch v pha phi so

vi ngi quan st, cht quang hot c gi
t quay ph
i hay ch
t hu tri
n v c
l ch
ch
ph
ch
tri
tr
tr s dng
ng..
Nu mt phng dao ng lch v pha tri so
vi ngi quan st, cht quang hot c gi
t quay tr
i hay ch
t t tri
n v c tr
l ch
ch
tr
ch
tri
tr
s m.
V d: (+)-Glucoz ; (-)-Fructoz

o gc quay cc ngi ta s dng mt phn cc k

hay trin quang k ( Polarimeter )

ng kh
ng ch
ng kh
S ch
ch
kht & kh
kh
ch
kht vt - nh

iu kin cn v 1 cht c tnh quang hot l

phn t phi bt i xng hay phn t phi khng chng
kht ln c nh ca n trong gng ging nh bn
tay phi v bn tay tri: i xng qua 1 gng phng
nhng khng chng kht ln nhau v ngi ta gi l
s khng chng kht vt - nh gng

Khi c s khng trng vt-nh th s xut hin hai ng

phn i xng nhau qua mt phng gng, song khng
chng kht ln nhau c.

n quang hc do ph
n t c m t carbon
2.3- ng ph
ph
ph
phi i xng
ng::
Ngi ta nhn thy trong a s cc hp cht hu c c
t nh quang ho t, ph n t c a ch ng u c ch a
carbon phi i xng.
V d : Xt phn t axit lactic CH 3-CHOH-COOH. Ngi
ta thy c 2 loi axit lactic khc nhau:

M hnh t din v cng thc Fischer ca 2 loi axit lactic:

COOH

COOH

n quang h c do ph
n t c n C * kh
ng
2.4- ng ph
ph
ph
kh
ng
tng

ng::
Khi phn t c 2 C* khng tng ng:
Xt phn t 3-brom butan-2-ol: CH 3-CHBr-CHOH-CH3
Ngi ta thy c 4 ng phn quang hc c biu din
bng cng thc phi cnh nh sau:

CH3

CH3
H

Phn t ca 2 loi axit lactic ny c cu hnh i xng

nhau, c tnh cht vt l v ha hc ging nhau, ch khc
nhau tc dng vi nh sng phn cc, mt cht quay
phi cn cht kia quay tri. Hai axit ny c gi l 2
ng phn quang hc.
Vy: ng phn quang hc l nhng cht ng phn
c cu to ging nhau nn c tnh cht ha hc ging
nhau, nhng s phn b cc nhm th trong khng gian
khc nhau ( cu hnh khc nhau ) do vy tc dng vi
nh sng phn cc khc nhau.
Hai ng phn ca axit lactic ni trn c cu hnh i
xng nhau, tr s gc quay cc bng nhau nhng ngc
du. Chng c gi l 2 cht i hnh hay 2 cht i
quang.

OH

OH

Axit (-)-lactic

CH3
OH

OH

Br

Br

COOH

CH3

OH

CH 3
Axit (-)-lactic

Br

CH3
OH

OH

CH3
H

Axit (+)-lactic

COOH
H

CH3
H

OH

Cong thc chieu Fisher

CH3
Axit (+)-lactic

CH3

eritro () -3-brom butan-2-ol

H
CH3

Br

CH3

treo () -3-brom butan-2-ol

Dng eritro : 2 nhm ging nhau nm cng bn mch

carbon
CH3

CH 3
H

OH

Mc d c 2 C * nhng ch c 3 ng phn: 2 ng phn

treo- c tnh quang hot, 1 ng phn eritro- khng quang
hot v c i xng trong phn t v c th chng kht ln
nh ca n trong gng. ng phn ny c gi l
ng phn meso

Br

HO

Br

Dng
(1) treo : 2 nhm ging nhau nm hai bn mch(2)
carbon

H
Br

OH

HO

Br

OH

OH

OH

OH

COOH
COOH
Axit meso tartric

CH 3

CH3

COOH

COOH

CH3

CH 3

Nh vy quy tc Van Hoff c pht biu li l: Nu mt

cht c nC
nC** th s ng phn quang hc N 2n

CH 3

CH3

(3)

(4)

Tng qu
t : Khi phn t c nC
qu
nC** khng tng ng, theo qui tc
VanHoff ta s c 2 n ng phn quang hc.

2.6- K hi
u cu hnh
hi
nh::

n quang h c do ph
n t c carbon phi i x ng t ng
2.5- ng ph
ph
ph
ng: lc ny qui tc VanHoff khng p dng c, s ng phn quang

hc < 2n.
V d : axit tartric HOOC-CHOH-CHOH-COOH

HO

COOH

COOH

COOH
H

OH

HO

OH

HO

OH

COOH
H

OH
COOH

COOH

COOH

COOH

HO

k hiu cu hnh ca cc ng phn quang hc ngi ta

ly Glycerandehit CH2OH-CHOH-CHO lm chun v qui
c

Axit treo-()-tartric
COOH

COOH
H

OH

OH

OH

OH

COOH

COOH

L
mt

COOH

Dng eritro

HO

HO

COOH

HO

HO

COOH

H
COOH

Vi cc phn t kiu R-CHX-R( X= d t = O, N, S,

halogen, ), nhm b oxi ha su hn pha trn ca
cng thc chiu theo th t:
RH < RCH 2OH < RCHO < RCOOH

Nu s phn b ca X ging vi D- Glycerandehit th hp

cht c coi l c cu hnh D. Cn ngc li th c cu
hnh L. Tr s ca gc quay cc c xc inh nh phn
cc k.

Vi cc cht c nhiu C* chng hn cc cht Gluxit, cu

hnh phn t l cu hnh ca C* c ch s cao nht:

V d:
1 CHO

H
HO
H
H

2
3

4
5

OH
H
OH
OH

6 CH2OH

D-(+)-Glucoz