CHM207 (ORGANIC CHEMISTRY)

TUTORIAL 5
CHAPTER 5: ALKYL HALIDES
1.

2.

Give the structures of the following compounds:

a)

trans-1,2-dichlorocyclopentene

b)

3-chloro-4-phenylheptane

c)

1,2-dibromo-3-methylpentane

d)

1-Bromo-2,2-dimethylpropane

e)

trans-1,4-diiodocyclohexane

f)

1-bromo-3-methylhexane

g)

3-bromo-2,4-dimethylpentane

Give systematic (IUPAC) names for the following compounds.

a)

Br

b)

Cl
CH3

c)

Cl

CH3

d) (CH3)2CHCH2Br

e)

Br
Cl

f)

Cl

Cl
1

CHM207 (ORGANIC CHEMISTRY)

3.

Write the IUPAC names of the following alkyl halides, and classify them as
primary, secondary or tertiary alkyl halides.

a) CH3CH2CHFCH(CH3)2
b) (CH3)2CHCH2Cl
c) CH3CH2CHBrCH3
d) CH3CH2Cl
e) (CH3)3CBr

4.

Give the reagents for the reactions below:

a)

CH3CH=CHCH3

CH3CH=CHCH2Cl

b)

CH3CH=CHCH3

CH3CHCHCH3
Br Br

c)

CH3C=CH2

Cl

Cl

CH3CCH3
Cl

d)
Br

5.

Give the product(s) for the following reactions:

a)

b)

2CH3CH2CH2 Cl

2Na

(CH3)3CI + NaOH (aq)

c) (CH3)2CHI + KCN

d) (CH3)2CHCH2CH2Cl +

CH3OH
NaH

CHM207 (ORGANIC CHEMISTRY)

6.

Predict the products of E1 elimination of the following compounds. Label

the major products.
a) (CH ) C
3 3

CH

d)

CH3

Cl
CH3

Br

b)

e)

CH3

CH3

Cl CH3

H3C CH CH2 C

Br

CH CH3

CH3

c)

CH3 CH3
CH3CHCBr
CH2CH3

7)

Predict the compound in each pair that will undergo the S N2 reaction
faster:
a)

Cl

or
Cl

b)

Cl

or

c)

Cl

d)

or

CH2Cl

or

Br

Br

e) CH3CH2CH2CH2Cl

or

CH3CH2CHCH3
Cl

CHM207 (ORGANIC CHEMISTRY)

8)

Draw the structure of the major product when the following compound
reacts with sodium hydroxide solution, NaOH, under reflux.
i)

CH3
H3C

CHCH2Br

ii)

CH3CH2CH2CH2Cl

iii)

CH3
H3C

Cl

CH3