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Topic 6: Organic Chemistry I Assessed homework 6

Reactions of halogenoalkanes

Name: ……………………………………………………… Date due: ......................................

Part 1: MCQs [10 marks]

1. Which of the following most readily undergoes a substitution reaction with sodium
cyanide (NaCN)? [1 mark]
A CH3CH2F
B CH3CH2Cl
C CH3CH2Br
D CH3CH2I

2. What is the product of the following reaction? [1 mark]

BrCH2CH2CH2CH2CH2OH + PCl5 →
A ClCH2CH2CH2CH2CH2OH
B ClCH2CH2CH2CH2CH2Cl
C BrCH2CH2CH2CH2CH2Cl
D ClCH2CH2CH2CH2CH2OCl

3. Which of the following equations does not involve a nucleophilic substitution. [1 mark]
A C3H7Br + KOH → C3H6 + KBr + H2O
B C3H7Br + KCN → C3H7CN + KBr
C C2H5Cl + C2H5ONa → C2H5OC2H5 + NaCl
D C2H5Br + NaOH → C2H5OH + NaBr

4. Which of the following reacts fastest by the SN1 mechanism? [1 mark]

A CH3CH2CH2CH2CH2Br
B CH3CH2CHBrCH2CH3
C (CH3)2CBrCH2CH3
D (CH3)3CCH2Br

5. Which of the following does not correctly describe SN2 reactions? [1 mark]
A Tertiary halogenoalkanes react faster than secondary halides.
B Rate of reaction depends on the halogenoalkane and nucleophile concentration.
C The halogenoalkane undergoes inversion of configuration.
D The transition state species can be described as a pentavalent carbon.
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6. Which of the following does not correctly describe SN1 reactions? [1 mark]
A Reaction rates increase as solvent polarity increases.
B Primary halogenoalkanes react faster than secondary halides.
C The reaction proceeds via a carbocation intermediate.
D Bromo halogenoalkanes react faster than chloro halogenoalkanes.

7. Which line in the table correctly describes the types of reaction in the following
sequence? [1 mark]
C3H8 Reaction 1 C3H7Br Reaction 2 C3H7OH Reaction 3 C3H 6

Reaction 1 Reaction 2 Reaction 3

A addition substitution elimination

B addition addition condensation

C substitution substitution elimination

D substitution addition condensation

8. Halogenoalkanes can undergo hydrolysis with AgNO3 / ethanol. Each C—X bond is
hydrolysed at a different rate. Which is the correct order of this rate and explanation?
[1 mark]
Rate of hydrolysis Explanation
A fastest C—F ............. C—I slowest fluorine is the most reactive halogen
B fastest C—F ............. C—I slowest fluorine is the most electronegative
C fastest C—I ............. C—F slowest iodine has a larger atomic radius
D fastest C—I ............. C—F slowest C—I has the lowest bond enthalpy

9. Which synthetic route will transform propan–1–ol into 2–bromopropane? [1 mark]

A NaBr / H2SO4
B Br2 / UV light
C H2SO4 / heat followed by HBr
D H2SO4 / heat followed by Br2 / UV light

10. Which of the following molecules is likely to produce the most stable carbocation
intermediate in a substitution reaction? [1 mark]
A CH3CH2I
B (CH3)CCl
C CH3CH2Cl
D CH3CHICH2CH3
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Part 2 [20 marks]
1. (a) The rates of hydrolysis of chloroethane, bromoethane and iodoethane are different.
• Describe how you would monitor the reaction rates.
• Explain why chloroethane, bromoethane and iodoethane react at different rates.
Use suitable equations in your answer. [6 marks]
(b) The equation for the reaction with 1-iodopropane is shown below.
CH3CH2CH2I + OH– → CH3CH2CH2OH + I–
(i) Outline the mechanism for this hydrolysis of 1–iodopropane.
Show curly arrows and relevant dipoles. [3 marks]
(ii) State the name of this type of mechanism. [1 mark]