Nitriles & Hydroxynitriles (Cambridge (CIE) A Level Chemistry): Exam Questions

Exam code: 9701

26 mins17 questions
1a
2 marks

When 1-chloropropane is heated under reflux with ethanolic potassium cyanide, KCN, the following reaction occurs.

CH3CH2CH2Cl + KCN → CH3CH2CH2CN + KCl

i) Draw the displayed formula of the organic product formed in this reaction.

[1]

ii) State the systematic name of this organic product.

[1]

1b
1 mark

Suggest why this reaction is useful to chemists during the synthesis of other organic compounds.

1c
2 marks

The CH3CH2CH2CN can undergo hydrolysis.

i) Construct an equation for the acid hydrolysis of CH3CH2CH2CN.

[1]

ii) Draw the displayed formula of the intermediate formed when CH3CH2CH2CN is hydrolysed by sodium hydroxide.

[1]

2a
1 mark

This question is about hydroxynitriles.

The hydroxynitrile shown in Fig. 2.1 can be prepared from the reaction between propanal and hydrogen cyanide.

Structural formula of 2-hydroxybutanenitrile

Fig. 2.1

Give the systematic name of this hydroxynitrile.

2b
4 marks

Using 'curly arrows', complete the reaction mechanism shown in Fig. 2.2 for the reaction between propanal and the cyanide ion, CN.

Include any lone pairs of electrons and partial or whole charges.

Partially completed reaction mechanism for nucleophilic addition of CN⁻ to propanal

Fig. 2.2

2c
1 mark

Name the type of reaction mechanism shown in Fig. 2.2.