CHAPTER 14

HALOALKANES
2
 14.1 Learning outcomes

a) Give the general formula of haloalkane.

b) Draw the structures, classify and name 1, 2 and
3 haloalkanes according to the IUPAC
nomenclature.
c) Describe haloalkanes: contain polar bond,
carbon bearing the halogen is susceptible to
nucleophilic attack.

3
 Introduction
Haloalkanes or alkyl halides
- compounds that contains halogen atom as functional
group.
- In alkyl halides, halogen atoms are bonded to sp3
hybridized carbon atom.
General formula : R-X
or CnH2n+1X (acyclic)
or CnH2n-1X (cyclic)
where X : halogen atom (F, Cl, Br or I)

4
 Classification of Haloalkanes
Haloalkanes are classified based on the carbon
atom to which the halogen is directly attached.
General Formula Classification

methyl halide
CH 3 X
- halogen is bonded to methyl group

R CH 2 X Primary (10) halide

- halogen is bonded to 10 carbon atom

R Secondary (20) halide

R CH X - halogen is bonded to 20 carbon atom

5
General Formula Classification

R Tertiary (30) halide

R C X - halogen is bonded to 30
R carbon atom

X Aryl halide
- halogen is bonded to
aromatic ring

CH 2 X ** Not a aryl halide

- This is primary (10)
halide
6
7
 Example :
Classify the following haloalkanes :

No. Haloalkanes Classification

i. CH 3 CH 2 Br 1o

CH 3 CH(Cl)CH 3
ii. 2o

iii. (CH 3 ) 3 C(Br) 3o

H3C Cl
iv. 3o

8
Common names
Named alkyl group first before its halide

CH3CH2Cl - ethyl chloride

F
CH3CHCH3 - isopropyl fluoride
I CH3CHCH2CH3
Br
Cyclohexyl iodide sec-butyl bromide
 IUPAC Nomenclature

Haloalkanes are named as alkanes with halogen as

substituents.
Locate and number the parent chain from the
direction that gives the substituent encountered
first the lower number.
Show halogen substituents by the prefixes flouro-,
chloro-, bromo- and iodo-, and list them in
alphabetical order along with other substituents.

10
 Example :

i. CH 3 CHCH 2 CH 3
Br
2-bromobutane

Cl

ii. BrCH 2 CH 2 CHCHCH 2 CH 3

CH 3
1-bromo-3-chloro-4-methylhexane
11
 1
CH3 CH3

CH3CH2-C-CH2CHCH3
4 3
6 5 F 2

4-fluoro-2,4-dimethylhexane

chlorocyclohexane
(2) Cl
 Example :

iii. CH 2 CH 2 F
CH 3 CH 2 CH 2 CHCH 2 CH 2 CH 3

4-(2-flouroethyl)heptane

H3C CH 3
iv. Cl

2-chloro-1,1-dimethylcyclopentane
13
 Example :

v. vi. CH 2 Cl
Br

4-bromocyclohexene (chloromethyl)benzene

CH 3
vii. Cl

2-chlorotoluene Video 2
14 (name & class)
 POLYHALOALKANES NAMES
COMPOUNDS IUPAC NAMES COMMON NAMES

CH2Cl2 Dichloromethane Methyl dichloride

CHCl3 Trichloromethane Chloroform

CCl4 Tetrachloromethane Carbon tetrachloride

 EXERCISE
Give these haloalkanes IUPAC name & classified them :
1. CH3-CH(CH3)-CH2-CH(CH3)-CH(Br)-CH2-CH3
2. Br-CH2-CH2-CH(Cl)-CH(CH3)-CH3
3. CH3-CH(CH3)-CH2-CH2-CH(Br)-CH2-CH3
4. CH3
F 6. CH3-C-Cl
5. CH3
I
 ANSWERS.
1. 5-bromo-2,4-dimethylheptane (2)

2. 1-bromo-3-chloro-4-methylpentane (1)

3. 5-bromo-2-methylheptane (2)

4. 1-fluoro-3-methylbutane (1)

5. Iodocyclohexane (2)

6. 2-chloro-2-methylpropane (3)
Physical properties
Boiling point :
Higher than alkane with the same number
of carbon atom electronegativity of halogen
CH3CH3 CH3CH2Cl

Mr = 30 Mr = 64.5
-smaller size -bigger size, polar
-non-polar -Greater no. of e-

For isomerism, 3 < 2 < 1 ( surface area )

Physical Properties of Haloalkanes
Boiling point.

Formula Substituent X and boiling point, oc

X=F X = Cl X = Br X=I
CH3X -78 -24 3 42
CH3CH2 X -32 12 38 72
CH3CH2CH2X -3 47 71 103
 Have a low solubility in water
fluoro- and chloro- less dense than water
bromo- and iodo denser than water
 14.2 Learning outcomes

(a) Explain nucleophilic substitution reaction of

haloalkanes
(b) Explain SN1 and SN2 mechanisms.

(c) Compare the relative reactivities of 1, 2 and 3

haloalkanes toward hydrolysis. .

21
 Chemical Properties of Haloalkanes
Nucleophilic Substitution Reaction
Haloalkanes undergo nucleophilic substitution reactions in
which the halogen atom is replaced by a nucleophile.
Example of nucleophiles: H2O/NaOH, KCN, NH3
In this reaction, the nucleophile attacks the partially positive
charge (+) carbon atom bonded to the halogen (-).
General reaction:

_ _
R_ X + Nu: R _ Nu + X:
22 Substituting group X V1 Intro
 Structure of Haloalkane
Alkyl halides are polarized at the carbon-halide bond,
making the carbon electrophilic

+ - electrophilic
C X
site

The polar C X bond causes the carbon bearing the halogen

is susceptible to nucleophilic attack.
electronegative
-
Nu: - attack + halogen polarizes C-X
at positive C X bond
center Video 3
23 (Physical Properties)
 Substitution Reactions

+ - -
C C + Nu: C C + X:
H X - H Nu

As a result from Nu:- attack at electrophilic C+, the C-

X bond breaks heterolytically and X- leaves.
The group replacing X- is a nucleophile.

Haloalkanes are reactive and undergo nucleophilic

substitution.
24
 Nucleophilic Substitution Reaction

Heterolytic
cleavage

Leaving group

25
 Nucleophilic Substitution Reaction

(a) Hydrolysis of Haloalkane with Aqueous Solution

of NaOH (H2O/NaOH)
Alkaline hydrolysis is carried out by boiling R-X with
NaOH (aq) to form alcohol.
H2O
R _ X + NaOH R_ OH + NaX

Example :
CH 3 CH 3
H2O
CH 3 _ C _Br + NaOH CH 3 _ C _OH + NaBr
26
CH 3 CH 3
 (b) Reaction of Haloalkane with
Potassium Cyanide (KCN)

When R-X is refluxed with KCN in alcohol, the halogen atom

is substituted by the CN- to produce a nitrile compound.

_ _
R_ X + CN alcohol R_ CN + X
reflux
Example :

CH 3 CH 2 Br + KCN alcohol CH 3 CH 2 CN + KBr

reflux
27
 (c) Reaction of Haloalkane with
Ammonia (NH3)

When R-X is heated with excess concentrated NH3, the

halogen atom is replaced by the amino group, NH2-.

NH 3 _ NH 3 _
R _X RN H 3 + X _ +
R N H2 + N H 4 X
Example :
(amine)

Alcohol _
CH3CH2Cl + excess NH3 +
CH3CH2NH2 + NH4 Cl

28
 (d) Reaction of Haloalkane with
Sodium Ethoxide (NaOCH2CH3)
When R-X is heated with excess concentrated NH3, the
halogen atom is replaced by the amino group, NH2-.

R X + NaOR' ROR' + NaX

Example : (ether)

CH3CH2Cl + NaOCH3 CH3CH2OCH3 + NaX

30
 Nucleophilic Substitution Reaction
General reaction :
NaOH (aq)
R OH + NaX

NH3
R NH2 + NH4X
CH3CH2OH,
R-X
KCN
R CN + KX
CH3CH2OH,

CH3CH2ONa
R OCH2CH3 + NaX

30
 Mechanisms of Nucleophilic Substitution
Reaction

They are 2 important mechanisms for the

substitution reaction:

1. Unimolecular Nucleophilic Substitution

Reaction (SN1)

2. Bimolecular Nucleophilic Substitution

Reaction (SN2)

31
 Mechanisms of Nucleophilic Substitution
Reaction

- The SN1 and SN2 Reactions

Follow first or second order reaction kinetics

Ingold nomenclature to describe characteristic step:

S=substitution

N (subscript) = nucleophilic

1 =rate determining step involves only one reactant

(unimolecular)
2 =rate determining step involves two reactants (bimolecular)

32
 Unimolecular Nucleophilic Substitution
Reaction (SN1)

The term unimolecular means there is only one

molecule involved in the rate determining step.
SN1 reaction is a two steps reaction :

1. Formation of carbocation as an intermediate (slow)

2. Nucleophilic attack

33
 The mechanism of SN1 reaction involves 2 steps.

Step 1 : Formation of a carbocation

(rate determining step)

R R
slow _
R_ C _ X R_ C + + X
R R

3o alkyl halide carbocation halide ion

34
 Step 2 : Nucleophilic attack on the carbocation

R R
_ _ fast
R C + + Nu: R_ C _ Nu
R R

35
 Unimolecular Nucleophilic
Substitution Reaction (SN1)

The slow step of reaction is the reaction that will determine

the rate of overall reaction.
rate = k [R3C-X]

The rate of SN1 reaction does not depend on the concentration

of nucleophile.
The rate depends only on the concentration of the alkyl
halide.
* SN1 is a first order reaction

36
 Example 1 : Hydrolysis of haloalkane
Reaction of 2-bromo-2-methylpropane with H2O.

CH 3 CH 3
CH 3 _ C _Br + H 2 O CH 3 _ C _ OH + HBr
CH 3 CH 3

SN1 mechanism :
Step 1 : Formation of a carbocation

CH 3 CH 3
slow _
CH 3 _ C _Br CH 3 _ C + + Br
CH 3 CH 3

37
 Step 2 : Nucleophilic attack on the carbocation

CH 3 CH 3
H
CH 3 _ C + + H 2 O fast _ _
CH 3 C O
+ H
CH 3 CH 3
Loss of proton, H+ to solvent

CH 3 CH 3
H
_ _
CH 3 C O + H2O CH 3 _ C _ OH + H 3 O +
+ H
CH 3 CH 3

38
 Relative Reactivities of Unimolecular
Nucleophilic Substitution Reaction (SN1)
SN1 reactions are governed mainly by the relative stabilities of
carbocations.
Tertiary alkyl halides react rapidly by a mechanism that
involves departure of the leaving group prior to addition of the
nucleophile
Relative reactivities of haloalkanes in an SN1 reaction :

CH3X <<< R-CH2-X < R2-CH-X < R3-C-X

1o 2o 3o
increasing reactivity

39
 Relative Reactivities of Unimolecular
Nucleophilic Substitution Reaction (SN1)

More stable ion requires less energy to form

H CH3 CH3 CH3

Br C Br C Br C Br C
H H H CH3
H H CH3 CH3

less reactive more reactive

Reactivity in SN1 reaction

Therefore 3o haloalkanes is more reactive towards SN1

hydrolysis compare to 2o, 1o & methyl halide
40
 Relative Rates Alkyl Bromides SN1 Reaction

Ralph H. Petrucci Prentice Hall V4 haloalkanes V5 haloalkanes

class hydrolysis (diff. X) hydrolysis
 SN1 mechanism involving rearrangement of
carbocation :
Carbocations can rearrange to form a more stable carbocation.

Rearrangement occurs in two ways:

i. Hydride shift(1,2-H-): H- on adjacent(1,2) carbon bonds with C+.
ii. Methyl shift(1,2--CH3): CH3- moves from adjacent(1,2) carbon if no
Hs are available.

Rearrangement is a serious side reaction when there is

carbocation formation involved in the reactions!

42
 Rearrangement - Methyl shift(1,2--CH3):

Example 1: Write the mechanism for the following reaction.

CH 3 CH 3
CH 3 _ C _CH 2 Br + NaOH(aq) CH 3 _ C _CH 2 CH 3 + NaBr
CH 3 OH
Step 1 : Formation of carbocation :

CH 3 CH 3
_
CH 3 _ C _CH 2 _Br slow _ _
CH 3 C CH 2 + Br
+
43
CH 3 CH 3
 Rearrangement - Methyl shift(1,2--CH3):

the migration of a methyl group together with its pair of

electrons - more stable tertiary carbocation is formed.

CH 3 CH 3
1,2-methyl shift
CH 3 _ C _ CH 2 CH 3 _ C _ CH 2
+ +
CH 3 CH 3
Step 2 : Nucleophilic attack on the carbocation

CH 3 CH 3
_
CH 3 _ C _ CH2 + OH fast CH 3 _ C _ CH 2 CH 3
+
44
CH 3 OH
 Rearrangement - Hydride Shift (1,2-H-)

Step 1 : Formation of carbocation

H H
1,2-H- shift
CH3 C C CH3 CH3 C C CH3
H CH3 H CH3

the hydride shift converts the initially formed

secondary carbocation to a more stable tertiary
45
carbocation.
Rearrangement - Hydride Shift (1,2-H-)

1,2-H- shift
CH3 C C CH3 CH3 C C CH3
H CH3 H CH3

46
Exercise 2 : (Mac 2002)

The structure of compound A is as follows:

CH3
CH3 C Br
i. Give IUPAC name for A CH3
ii. Compound A react with OH- forming an alcohol. Write the
mechanism for the formation of this alcohol and name the
reaction.

47
 Bimolecular Nucleophilic Substitution
Reaction (SN2)

The term bimolecular means that the transition state of the

rate limiting step involves the collision of two molecules.
Example of SN2 reaction:

60oC
HO- + CH3 Br CH3 OH + Br-
H2O / NaOH

to make it happen: CH3Br & OH-must collide, a bimolecular

reaction An SN2 reaction : substitution, nucleophilic,
bimolecular
48
 Bimolecular Nucleophilic Substitution
Reaction (SN2)
General Mechanism :

R R R
slow - + -
fast Nu C
C X Nu C X + X-
Nu:- H H
H H H H
transition state

Single step with no intermediate

Concerted reaction: new bond forming and old
bond breaking at same time.
The mechanism of SN2 occurs in a single step. 49
 Bimolecular Nucleophilic Substitution
Reaction (SN2)
General Mechanism :
R R R
slow - + -
C X Nu C X fast Nu C + X-
Nu:- H H
H H H H
transition state
The rate of reaction involves two reactants.
The rate of reaction depends on the concentration of
the haloalkane and the concentration of nucleophile.
rate = k [R-X] [Nu:-]
* SN2 is a second order reaction. 50
 SN2 = Bimolecular Nucleophilic Substitution

SN2 reactions always lead to inversion of configuration

H
H H
- + - + Br
-

C Br HO C Br HO C
HO: H H

H H
H H
t r a n s i t io n s t a t e

In SN2 reaction, the nucleophile attacks from the back

side of the electrophilic carbon, that is, from the side
directly opposite bonded to the halogen.

51
 SN2 = Bimolecular Nucleophilic Substitution

Back-side attack causes the product formed has inverse

configuration from the original configuration.
H
H H
- + - + Br
-

C Br HO C Br HO C
HO: H H
H H
H H
t r a n s i t i o n s t at e

*turns the tetrahedron of the carbon atom inside out, like

umbrella caught by the wind.

52
 SN2 = Bimolecular Nucleophilic Substitution

Nu: C X

Nu: + C X Nu C + X
53
 SN2 = Bimolecular Nucleophilic Substitution

Nu: C X

A Transition State

Nu: + C X Nu C + X
54
 SN2 = Bimolecular Nucleophilic Substitution

backside attack

Nu C X
Inversion occurs at
carbon

Nu: + C X Nu C + X
55
 SN2 = Bimolecular Nucleophilic Substitution

Nu C X

A Transition State

The transition state involves partial bonding between the

attacking nucleophile and the haloalkane.

Nu: + C X Nu C + X
56
 Another example :

Reaction of ethyl bromide with aqueous sodium

hydroxide.

CH 3 CH 2 Br + NaOH (aq) CH 3 CH 2 OH + NaBr

SN2 Mechanism :

CH3 CH3 CH3

:OH- fast
slow - + -
C Br OH C Br OH C + Br-
H H
H H H H

transition state 57
 Relative Reactivities of Unimolecular Nucleophilic
Substitution Reaction (SN2)

The reactivity on SN2 reaction depends on the size of the

groups attached to the C - X atom that being attacked.

Relative reactivities of haloalkanes in an SN2

reaction (opposite to SN1):
R3-C-X<<< R2-C-X < R-C-X < CH3-X
3o 2o 1o
increasing reactivity
58
 Relative Reactivities of Unimolecular
Nucleophilic Substitution Reaction (SN2)

The reaction will be fast when the groups are small,

and will slow considerably when larger groups are
attached. The presence of bulky alkyl groups will
prevent the nucleophilic attack.

SN2: Reactivity of Substrate on hydrolysis reaction.

H H CH3 CH3
H C Br CH3 C Br CH3 C Br CH3 C Br
H H H CH3
59
 H H CH3 CH3
H C Br CH3 C Br CH3 C Br CH3 C Br
H H H CH3
SN2: Reactivity of Substrate on hydrolysis reaction.
 Relative Reactivities of Unimolecular
Nucleophilic Substitution Reaction (SN2)

SN2 reactions are governed mainly by steric factors (steric effect).

The more alkyl groups connected to the reacting carbon, the

slower the reaction.

61
 Relative Reactivities of Unimolecular Nucleophilic
Substitution Reaction (SN2)

Steric hindrance

- the spatial arrangement of the groups near the

reacting site hinders(retards) a reaction
-Large groups can often hinder the formation
Steric effect

- is an effect on relative rates caused by the space-

filling properties of those parts of a molecule
attached at or near to the reacting site.
62
 Relative Reactivities of Unimolecular
Nucleophilic Substitution Reaction (SN2)

Carbon must not be sterically hindered.

Tertiary halides do not react via the SN2 mechanism,
due to steric hindrance.

63
 Relative Reactivities of Unimolecular Nucleophilic
Substitution Reaction (SN2)

NOTE: 1o haloalkanes with large alkyl groups (e.g

(CH3)3CCH2Br) will not undergo SN2 reaction due to
steric hidrance.

64
 CH3 CH3

CH3 C CH2Br + Nu- CH3 C CH2CH3

CH3 Nu

1 haloalkane SN2

SN1 ??
65
 CH3 H CH3 H

CH3 C C Br CH3 C C H
+
CH3 H CH3
1 carbocation

CH3 H CH3 H
Nu- + CH3 C C H CH3 C C H
+
CH3 Nu CH3

66
3 carbocation
 Exercise 1 : (Feb 2003)

Write a reasonable structures of products formed when 1-

iodobutane reacts with
i. KCN
ii. NaOH/H2O
iii. excess NH3
Write the mechanism for the reaction in (ii).

67
 Comparison of SN1 and SN2 Reactions

SN1 SN2

A two-step mechanism A one-step mechanism

A unimolecular rate- A bimolecular rate-

determining step determining step
First order : Second order :
rate = k [RX] rate = k [RX] [Nu]
No carbocation
Carbocation rearrangement
rearrangement
Reactivity order : Reactivity order :
3o > 2o > 1o methyl > 1o > 2o
 Learning outcomes
d) Explain elimination reaction of haloalkanes.
e) Explain the use of haloalkanes in the synthesis of
Grignard reagent, RMgX.
f) Describe the preparation of alkanes and alcohols (1,
2and 3) from Grignard reagents.

70
 d). Elimination Reaction
(dehydrohalogenation of haloalkanes)

A review from alkenes synthesis:

Halogen can be removed from one carbon of a haloalkane

and hydrogen from an adjacent carbon to form a carbon-
carbon double bond in the presence of a strong base.
General reaction :

H
_ C _ C _ + :B _ _
C C + X
_

71 haloalkane base alkene

 Example :

Br
i. CH 3 CHCHCH 3
CH 3CH 2ONa
CH 3 C CHCH 3
CH 3CH 2OH
CH 3 CH 3
major

CH 3 CHC CH 2
CH 3 minor

ii. Br CH 3CH 2ONa CH 3 CH2

CH3 CH 3CH 2OH +
72
major minor
Nucleophiles that are strong Brnsted bases
can produce elimination
Nucleophiles that are strong Brnsted bases
can produce elimination

In aqueous

In alcohol
 e). Use of haloalkanes in the synthesis of
Grignard reagent, RMgX

Grignard reagents are examples of organometallic

compounds because they contain a carbon-metal bond.
Grignard reagents are called organomagnesium halides, of
empirical formula R-Mg-X.
Grignard reagents results from the reaction of haloalkanes
with magnesium metal. This reaction is always carried out in
an ether solvent.

75
 The French chemist
(Francois Auguste) Victor Grignard :
1871-1935
Grignard found that, in the presence
of ether, magnesium reacts with alkyl
and aryl halides at room temperature
to form organomagnesium
compounds.
These solutions, called "Grignard
reagents" react with most functional
groups in a synthetically useful way.

76
 The French chemist

For this discovery, tremendously

useful in laboratory and industrial
synthesis, he was awarded the 1912
Nobel Prize in Chemistry (shared
with Paul Sabatier, discoverer of
catalytic hydrogenation).

77
 Synthesis of Organomagnesium
Compound ( Grignard Reagent )

R-X + Mg ether R-MgX

Grignard Reagent
(alkylmagnesium halide)
Example :
i. CH 3 CH 2 CH 2 Br + Mg ether CH 3 CH 2 CH 2 MgBr

ii.
ether
Cl + Mg MgCl

78
 f)Synthesis of Alkanes, Alcohols and Carboxylic
Acids from Grignard Reagents.

The Grignard reagents undergo many reactions that make

them useful as a starting materials in the synthesis of other
organic compounds.

(i) Synthesis of alkane

The Grignard reagent is hydrolyzed to an alkane when
warmed with H2O.

H+
RMgX + H2O R-H + Mg(OH)X
79
 Example :

H +
i. CH3CH2MgBr + H2O CH3CH3 + Mg(OH)Br

ii. CH3CH-MgBr + H2O H+ CH3CH2CH3 + Mg(OH)Br

CH 3

H 2O/H +
iii. CH 2 MgCl CH3
+ Mg(OH)Cl

80
 (ii) Synthesis of 1o alcohol

Methanal reacts with the Grignard reagent, followed by the

hydrolysis produces primary alcohol.
O H
R-MgX + H-C-H R-C-OMgX
H

H 2 O,H +

H
R-C-OH + Mg(OH)X
81
H
 Example :

i.
O H
H 3 O+
CH 3 MgBr + H - C - H C H 3 - C - O H + Mg( O H ) B r
H

ii.
Mg B r O CH 2 O H
H 3 O+
+ H - C- H + Mg ( O H ) B r

82
 iii) Synthesis of 2o alcohol

Grignard reagent reacts with aldehydes to produce

secondary alcohol.
O R'
R-MgX + H-C-R' R-C-OMgX
H

H 2 O,H +

R'
R-C-OH + Mg(OH)X
83
H
 Example :

O
i. CH 3 CH 2 MgBr + CH 3 CH 2 -C-H

H 2 O/H +
H
CH 3 CH 2 -C-CH 2 CH 3 + Mg(OH)Br
OH

ii. CH 3
O
MgCl H 2 O/H + C-OH
+ CH 3- C-H + Mg(OH)Cl
84 H
 (iv) Synthesis of 3o alcohol

Grignard reagent reacts with ketones to produce the

tertiary alcohol.
O R'
R-MgX + R'-C-R" R-C-OMgX
R"

H 2 O,H +

R'
R-C-OH + Mg(OH)X
85
R"
 Example :

O
i.
CH 3 CH 2 MgBr + CH 3 -C-CH 3

H 2 O/H +
CH 3
CH 3 CH 2 -C-CH 3 + Mg(OH)Br

ii. OH

CH 3
O
MgCl
H3O+ C-OH
+ CH 3- C-CH 3 + Mg(OH)Cl
86 CH 3
 Conclusion: The carbon-magnesium bond is
polarized, making the carbon atom
nucleophilic and basic

RMgX + H3O+ yields R-H

+
Mg-X Nucleophile attack on electrophilic
site
-C

Reagents Electrophile Product

H-OH / H+ H+ C-H
(alkanes)

87
 Reagents & Electrophile Product
Metanal / O OH
H+ H C H H C H 1o alcohol
C
Reagents & Electrophile Product
Aldehyde O OH
/ H+ R C H R C H 2o alcohol
C
Reagents & Electrophile Product
Ketone / O OH
H+ R C R R C R 3o alcohol
C
88
 (v) Synthesis of carboxylic acid

Grignard reagent reacts with carbon dioxide(CO2)

followed by hydrolysis to form carboxylic
acid.
O
RMgX + O C O R-C-O-MgX

O O
H+
R-C-O-MgX + H 2 O R-C-OH + Mg(OH)X

89
 Example :

O
CH 3 CH 2MgI + CO 2 CH 3 CH 2- C-O-MgI

O O
H+
C H 3 CH 2 - C - O - MgI + H 2 O CH 3 CH 2 COH + Mg( OH ) I

Reagents & Electrophile Product

i. Carbon
dioxide O C OH Carboxylic
O C O
ii. H2O / H+ acid
C

90
 END OF
SLIDE SHOW