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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
CH3
CH3
CH2 OH
CH3
CH3
CH2 CH2OH
CH3
CH3
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
nh ngh
ngha : l hin tng cng mt cng thc c nhiu cht khc
nhau
CH3
CH3
N
NG PH
PH
ng phn
nhm chc
OH
NG I
CH
CH
NG
ng phn
v tr
'
OH
R'
Amid
Imid
:
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
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
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
:
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
H
H
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.
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
Br
Cl
Br
CH3
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
b
a
b
c
CH3
C OOH
OH
C H3
C OOH
H
H
c Newman dng i
Cng th
th
C H3
HO
Cl
CH3
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
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
ng kh
ng ch
ng kh
S ch
ch
kht & kh
kh
ch
kht vt - nh
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:
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
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
CH3
Axit (+)-lactic
CH3
H
CH3
Br
CH3
CH 3
H
OH
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
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
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
V d:
1 CHO
H
HO
H
H
2
3
4
5
OH
H
OH
OH
6 CH2OH
D-(+)-Glucoz