Ha Hc Hu C

TS Phan Thanh Sn Nam

B mn K Thut Hu C
Khoa K Thut Ha Hc
Trng i Hc Bch Khoa TP. HCM
in thoi: 8647256 ext. 5681
Email: ptsnam@hcmut.edu.vn
http://hhud.tvu.edu.vn

Ti liu tham kho

[1] Paula Y. Bruice, Organic chemistry, fifth edition, Pearson
Prentice Hall, 2007
[2] Graham T.W. Solomons, Craig B. Fryhle, Organic chemistry,
eighth edition, John Wiley & Sons, 2004
[3] Francis A. Carey, Organic chemistry, fifth edition, McGrawHill, 2003
[4] Robert T. Morrison, Robert N. Boyd, Oragnic chemistry, sixth
edition, Prentice Hall, 1992
[5] Trn Th Vit Hoa, Phan Thanh Sn Nam, Ha hu c, NXB
i Hc Quc Gia HCM, 2007
[6] Trn Th Vit Hoa, Trn Vn Thnh, Bi tp ho hu c, NXB
i Hc Quc Gia HCM, 2004
[8] Thi Don Tnh, C s l thuyt ho hu c, NXB Khoa Hc
K Thut, 2000
[9] Trn Quc Sn, C s l thuyt ha hu c, NXB Gio Dc,
1979
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NI DUNG CHNH
ng phn ca hp cht hu c
Hiu ng trong hp cht hu c
C ch cc phn ng ca hp cht hu c
Alkane
Alkene
Alkyne
Alkadiene
Hp cht hydrocarbon thm
Dn xut halogen
Alcohol Phenol
Aldehyde Ketone
Carboxylic acid
Amine Hp cht diazonium http://hhud.tvu.edu.vn

Chng 1:

NG PHN

ng phn: nhng hp cht hu c c

cng thc phn t ging nhau, cng thc
cu to khc nhau tnh cht ha hc, vt
l, sinh hc khc nhau
Phn loi:
+ ng phn cu to (phng)
+ ng phn lp th: ng phn hnh hc
(cis, trans), ng phn quay (cu dng),
ng phn quang hc
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I. ng phn cu to
Do c s sp xp khc nhau ca cc nguyn t
trong mch C
I.1. ng phn mch C
n-butane
iso-butane

C6H12

methyl cyclopentane

cyclohexane
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I.2. ng phn do v tr cc lin kt bi, nhm chc

butene-1

C4H8

OH

butene-2

OH

OH

OH
OH
1,2-

1,3-

OH
1,4-

dihydroxy benzene

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I.3. ng phn c nhm nh chc khc nhau

dimethyl ketone
C3H6O

propan-2-one
O

acetone

CHO

propionaldehyde
propanal
propionic aldehyde

C3H6O2

COOH

Propionic acid

O
O

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methyl acetate
7

I.4. ng phn c nhm th khc nhau lin kt vi

nhm nh chc

C4H10O

diethyl ether

methyl propyl ether

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II. ng phn lp th
II.1. ng phn hnh hc
II.1.1. iu kin xut hin ng phn hnh hc
Xut hin khi phn t c 1 b phn cng nhc
cn tr s quay t do ca cc nguyn t

2 nguyn t lin kt vi cng 1 nguyn t ca

b phn cng nhc phi khc nhau
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 Thng xut hin cc hp cht c cha:

C=C, C=N, N=N, h lin hp, vng phng 3
hay 4 cnh
abC=Ccd: a b, c d

Cl
H

Cl
H

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II.1.2. Danh php ca ng phn hnh hc

a. H cis-trans: abC=Cab
Nhm th tng ng nm cng pha
mt phng lin kt cis
Khc pha trans

H3C
H

CH3

H3C

cis-butene-2

H
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H
CH3

trans-butene-2

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b. H Z-E: abC=Ccd

a>b c>d

Quy tc Kahn-Ingold-Prelog: da theo th

t u tin trong bng HTTH ca nhm th
a, c cng pha so vi mt phng ni i: Z
(zusammen)
a, c khc pha so vi mt phng ni i: E
(entgegen)
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35
Br

17
Cl

(E)-1-Bromo-2-chloro-2-fluoro-1-iodoethene

F
9

53
Br

Cl

(Z)-1-Bromo-2-chloro-2-fluoro-1-iodoethene

Lu : Khi dng Z-E, ch Z, E khng

phi lun trng vi cis, trans
Cl

Cl

Cl

Cl

Z-, cis-

Br

E-, cishttp://hhud.tvu.edu.vn

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II.1.3. ng phn hnh hc ca abC=Nd v

aN=Nb
a. abC=Nd
Trc y, dng h syn-, anti-, nhng
khng chnh xc nn hin nay dng h Z-E
a>b: a, d khc pha so vi mt phng ni
i E, cng pha Z
i vi aldoxime
H3C
OH
C N
H
anti-acetaldoxime
(Z)-acetaldoxime

H3C
C N
OH
H
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syn-acetaldoxime
(E)-acetaldoxime

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 i vi ketoxime: Cng 1 cht, c th gi l

syn- hay anti- !!!
H3C

H3C
OH
C N

C N

anti-phenyl-p-tolylketoxime
syn-p-tolyl-phenylketoxime

OH

syn-phenyl-p-tolylketoxime
anti-p-tolyl-phenylketoxime

h syn-anti khng chnh xc

chuyn sang h Z-E
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b. aN=Nb

C6H5
N N

N N

C6H5

C6H5

C6H5

syn-azobenzene

anti-azobenzene

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II.1.4. ng phn hnh hc ca hp cht cha C=C

lin hp
a(HC=CH)nb
CH
H
6 5

H
H

C6H5

C6H5
H

H
C6H5
H

C6H5

trans,trans-1,4-diphenyl-1,3-butadiene

cis,cis-1,4-diphenyl-1,3-butadiene

C6H5
H

cis,trans-1,4-diphenyl-1,3-butadiene

* S p hnh hc ca h lin hp C=C

N = 2n-1 + 2p-1
n: s ni i lin hp
p = n/2
nu n chn
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p = (n + 1)/2 nu n l

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II.1.5. ng phn hnh hc ca vng no 3, 4

cnh
c b tr trn 1 mt phng cc nhm th
khng th quay t do xut hin ng phn
hnh hc
* Cc nhm th tng ng cng pha mt phng
cis, khc pha trans
HOOC
H

COOH

HOOC

cis-cyclopropane-1,2-dicarboxylic acid

H
COOH

trans-cyclopropane-1,2-dicarboxylic acid

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II.1.6. Cch xc nh v so snh cc ng phn

hnh hc
a. xc nh khong cch gia cc nhm th
Khong cch gia 2 nhm th tng ng
trong ng phn cis < trans
H
Cl

H
Cl

H
Cl

Cl
H
4.7

3.7

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b. Moment lng cc
2 nhm th ging nhau aHC=CHa
H
Cl

Cl

Cl

Cl
H

cis (1.89D) > trans (0D)

2 nhm th khc nhau aHC=CHb (a b)
2 nhm th cng ht hay cng y in t:
cis > trans
2 nhm th c tnh cht in t ngc nhau:
cis < trans
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