Mechanism

2
A I+X
B + I Y

LOGO

I
(intermediate)

Thitiphan Chimsook
Department of Chemistry, Faculty of
Science, Maejo University

1. Carbocation 6 electron
3
+

3. Free radical
1

2. Carbanion 3

C

4. Carbene 2
2
..

C
3
4

1. (Substitution)

2. (Addition) 2
1
3. (Elimination)
2

4. (Rearrangement)


5.

2
- (nucleoplilic)

1.
2. 3. C=C

(nucleophile) (electron-donors)
7

- (electrophilic)

1.
2. +

(electrophiles) (electronacceptors)
8

 (cabocation)

(Addition reaction)

1. primary carbocation, 1 RC+H2
2. secondary carbocation, 2 R2C+H
3. tertiary carbocation, 3 R3C+

1.
- Hydrogenation
Ni
CH3CH=CH2 + H2

CH3CH2CH3

10

(Addition reaction)

(Addition reaction)
Hydrogenation
+ 2H2

Hydrohalogenation
Ni

CH2=CH2

+ HCl

CH3CH2Cl

Halogenation
Br

+ Br2

Br

CCl4

CH3CH=CH2 + HBr

CH3CH - CH3

+ CH3CH2CH2Br

Br

CH3CH2CH=CH2 + Br2

CCl4

Br

Br

CH3CH2CH - CH2
11

12

 (Addition reaction)

(Addition reaction)

CH2=CH2 +

H2SO4

H2O

H2SO4

CH3CH=CH2 + H2O

2.
HC

CH3CH2OH
OH

CH3CH - CH3 + CH3CH2CH2OH

CH

H2, Ni

CH2=CH2

H2, Ni

CH3CH3

3.
C=O
C O

14

13

(Addition reaction)

(Addition reaction)

-
O

H - C - H + H2O

OH

H-C-H

RCH

CH3OH, H+

RCH

CH3CCH3 +

OH

H2O

hemiacetal

OCH3

OH
O

OH

CH3 - C - CH3
OH

15

RCR

CH3OH, H+

OH

RCR

hemiketal

OCH3
16

 (Addition reaction)

(Addition reaction)

2
1.

2.

C

CH2=CH2 + HCl

CH3CH2Cl

CH2=CH2 + HCl
+
CH3 - CH2

+
CH3 - CH2

Cl-

OH

OH

H - C - H + H2 O

H-C-H

H-C-H

OH

+ Cl-

OH

CH3CH2Cl
17

18

(Substitution reaction)


1. Halogenation
light
CH3CH3 +

Cl2

CH3CH2Cl

Br

Br2

light

20

 (Substitution reaction)

(Substitution reaction)

2.

3.

CH3CH2 - Br

NaOH

H2O

CH3CH2 - OH

NaBr

CH3CH2 - OH + HCl
(CH3)2CH - OH + HBr

CH3CH2 - I + CH3ONa

alcohol

CH3CH2 - OCH3 + NaI

(CH3)3C - OH + HI

light
light
light

CH3CH2 - Cl +
(CH3)2CH - Br +

22

(Substitution reaction)

(Substitution reaction)

4.
Cl

Cl2

Fe
or FeCl3

+ HCl

5.

CH3

+ Br2

Fe
+ CH3Cl

H 2O

(CH3)3 - I + H2O

21

H 2O

hv or heat

Br

+ HBr

+ HCl

or FeCl3
23

24

 (Substitution reaction)

(Substitution reaction)

6.

7.

CH3CCl + 2NH3

+ CH3CNH2 + NH4Cl

C17H35 - C - OCH2CH3 + CH3OH

C17H35 - C - OCH3 + CH3CH2OH

ethyl octadecanoate
O

hydrolysis
COH + CH3OH

COCH3 + H2O

methyl octadecanoate

H+

CH2 = CH - C - OCH3 + CH3CH2OH

methyl propenoate

esterification

H+ or OH

CH2 = CH - C - OCH2CH3 + CH3OH

ethyl propenoate

25

26

SN1

1.
2.
2
SN1 2


SN2

1 leaving group Cl-

27

CH3

CH3
H3C

slow
Cl

CH3

H3C

C
CH3

+ Cl-

 SN1

SN1

(S)-3-bromo-3methylhexane (R) (S)-3-methyl-3hexanol

2
CH3

CH3
H3C

fast
H3C

H2O

CH3

fast

CH3

CH3 H

CH3

H3C

+ H2O

H3C

OH

+ H3O

CH3

CH3 H

SN1

SN2

CH3

H3CH2CH2C

Br

H3CH2C

OH(S)-3-bromo-3-methylhexane

CH3

CH3

H
C

Cl

H2CH3C

(S)-2-chlorobutane
H3C
HO

CH2CH2CH3
CH2

CH3

H3CH2CH2C

H2O

-H

(R)-3-methyl-3-hexanol

-H

CH2CH3

H2O

CH2CH3

carbocation

H3CH2CH2C

CH3
C

OH

H3CH2C

(S)-3-methyl-3-hexanol

HO

CH3
C

Cl

CH2CH3

transition state

H
HO

+ Cl-

CH2CH3

(R)-2-butanol

 (Elimination reaction)

(Elimination reaction)

1. Dehydration

2. Dehydrohalogenation
H

Br

conc. H2SO4
CH3CH2OH
CH3

CH3CHOH

180 C

CH2=CH2 + H2O

CH3

CH3CH=CH2 + H2O

CH3CH=CH2 + H2O + BrCH3

CH3 - C - CH3 + OH-

conc. H2SO4
100

CH3CHCH3 + OH-

CH3C=CH2 + H2O + Cl-

Cl

33

34

1. E1


2. E2


35

1.
2.

36

KMnO4
CH3 - CH2 - CH2 - OH

CH3 - CH = CH2

CH3 - CH2 - C - H
KMnO4

Pt
CH3 - CH = CH2 + H2
CH3 - COOH

CH3 - CH - CH2
OH

CH3 - CH2 - CH3

LiAlH4
H+

OH

37

38

H+
CH2 = CH - CH2 - CH3
CH3

CH3 - CH - CH2 - OH

CH3 - CH2 - OH

CH3 - CH = CH - CH3
H+
CH3 - CH = CH - CH3 + H2O
39

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