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HALOALKANE

Total questions: 11

Worksheet time: 6mins

Name
Class
Date
1.

Haloalkane is a polar molecule that undergoes nucleophilic substitution through SN1 and SN2. Arrange the following haloalkanes in order of increasing rate of unimolecular nucleophilic substitution reaction:

I. 2-chloro-2-methylpropane

II. 2-chlorobutane

III. 1-chlorobutane

a)

I< II < III

b)

I< III < II

c)

III< I < II

d)

III< II < I

2.

Compound C easily undergoes hydrolysis to form compound D, which forms 2-methylpropene when heated with concentrated sulphuric acid. Using the information above, proposed the structural formula for compound C

a)

CH3CH2CH(Br)CH3

b)

CH3CH2CH2CH(Br)CH3

c)

CH3CH2(CH3)CH2Br

d)

(CH3)2C(Br)CH3

3.

Which of the following compounds is the rate of alkaline hydrolysis that is independent of the concentration of the hydroxide ion?

a)

CH3CH2CH2CH2Cl

b)

CH3CH(Br)CH3

c)

C6H5CH2CH2I

d)

(CH3)3CBr

4.

Which of the following is a chiral molecule?

a)

CH2BrI

b)

CH3CBr2Cl

c)

(CH3)2CHCl

d)

CH3CHBrCH2CH3

5.

Alkenes react with hydrogen halides, HX to formed haloalkane. In the reaction;

I. the pi electrons are used to form a bond with the hydrogen atom from HX

II. the intermediate product is carbocation

III. the rate of reaction increases in the order: HF, HCl, HBr, HI

a)

I only

b)

I and II only

c)

II and III only

d)

I, II and III

6.

Which of the following species is/are nucleophile(s)?

I. OH

II. H2O

III. R3C

a)

I only

b)

I and II only

c)

II and III only

d)

I, II and III

7.

A is a secondary haloalkane with formula C5H11Br and optically active. Identify A.

a)

CH3CH2CH2CH2CH2Br

b)

CH3CH(Br)CH2CH2CH3

c)

(CH3)2C(Br)CH2CH3

d)

(CH3)2C(Br)C(CH3)2CH2CH3

8.

Name compound B below according to IUPAC nomenclature.

a)

4-chloro-5-bromo-6-phenylhexane

b)

2-bromo-3-chloro-1-phenylhexane

c)

3-bromo-1-phenyl-2-bromohexane

d)

5-bromo-4-chloro-6-phenylhexane

9.

Which is a primary alkyl halide?

a)

CH3CH(Br)CH3

b)

C6H5Cl

c)

CH3CH(CH2Br)CH3

d)

CH3CH2C(Cl)2CH3

10.

The number of isomers (including structural and stereoisomers) of C4H9Cl is

a)

2

b)

3

c)

4

d)

5

11.

Arrange compound below according to decreasing boiling point;

Pentane, 2-chloropropane, 1-butanol, 2-methylbutane

a)

2-chloropropane, 1-butanol, 2-methylbutane, Pentane

b)

1-butanol, 2-chloropropane, Pentane, 2-methylbutane

c)

2-chloropropane, 2-methylbutane, Pentane, 1-butanol

d)

2-methylbutane, Pentane, 2-chloropropane, 1-butanol