Q1.

This question is about the primary amine CH3CH2CH2NH2

(a) The amine CH3CH2CH2NH2 reacts with CH3COCl

Name and outline a mechanism for this reaction.

Give the IUPAC name of the organic product.

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(6)

(b) Isomers of CH3CH2CH2NH2 include another primary amine, a secondary amine and a
tertiary amine.

(i) Draw the structures of these three isomers.

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(ii) Use Table 1 on the Data Sheet to explain how you could use infrared spectra
in the range outside the fingerprint region to distinguish between the
secondary amine and the tertiary amine.

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(2)

(c) The amine CH3CH2CH2NH2 can be prepared by two different routes.

Route A is a two-stage process and starts from CH3CH2Br.

Route B is a one-stage process and starts from CH3CH2CH2Br.

(i) Identify the intermediate compound in Route A.

Give the reagents and conditions for both stages in Route A and the single
stage in Route B.

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(7)

(ii) Give one disadvantage of Route A and one disadvantage of Route B.

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(2)
(Total 20 marks)

Q2.Each of the following conversions involves reduction of the starting material.

(a) Consider the following conversion.

Identify a reducing agent for this conversion.

Write a balanced equation for the reaction using molecular formulae for the
nitrogen-containing compounds and [H] for the reducing agent.

Draw the repeating unit of the polymer formed by the product of this reaction with
benzene-1,4-dicarboxylic acid.

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(5)

(b) Consider the following conversion.

Identify a reducing agent for this conversion.

State the empirical formula of the product.

State the bond angle between the carbon atoms in the starting material and the
bond angle between the carbon atoms in the product.

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(4)

(c) The reducing agent in the following conversion is NaBH4

(i) Name and outline a mechanism for the reaction.

Name of mechanism ............................................................................

Mechanism

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(ii) By considering the mechanism of this reaction, explain why the product formed
is optically inactive.

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(3)
(Total 17 marks)

Q3. The amide or peptide link is found in synthetic polyamides and also in naturally
occurring proteins.

(a) (i) Draw the repeating unit of the polyamide formed by the reaction of
propanedioic acid with hexane-1,6-diamine.

(2)

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 (ii) In terms of the intermolecular forces between the polymer chains, explain why
polyamides can be made into fibres suitable for use in sewing and weaving,
whereas polyalkenes usually produce fibres that are too weak for this purpose.

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(3)

(b) (i) Name and outline a mechanism for the reaction of CH3CH2COCl with CH3NH2

Name of mechanism............................................................................

Mechanism

(5)

(ii) Give the name of the product containing an amide linkage that is formed in the
reaction in part (b) (i).

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(1)

(c) The dipeptide shown below is formed from two different amino acids.

Draw the structure of the alternative dipeptide that could be formed by these two
amino acids.

(1)

(d) The amino acids serine and aspartic acid are shown below.

(i) Give the IUPAC name of serine.

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(1)

(ii) Draw the structure of the species formed when aspartic acid reacts with
aqueous sodium hydroxide.

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(iii) Draw the structure of the species formed when serine reacts with dilute
hydrochloric acid.

(1)

(iv) Draw the structure of the species formed when serine reacts with an excess of
bromomethane.

(1)
(Total 16 marks)

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