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Question 1
Amines can be prepared by the reaction of haloalkanes with ammonia. |
a) | Write an equation for the formation of butylamine, CH3CH2CH2CH2NH2, from ammonia and 1-bromobutane.
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b) | Name the mechanism for the reaction in part a).
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c) | Explain why butylamine is a stronger base than ammonia.
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d) | Draw the skeletal formula of a tertiary amine which is an isomer of butylamine.
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Question 2
This question is about propylamine. |
a) | Draw the structure of a nitrile compound which can be reduced to form propylamine.
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b) | Suggest a suitable reagent for the reduction of a nitrile compound to form an amine.
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c) | Isomers of propylamine include a primary, a secondary, and a tertiary amine. Draw the structures of each of these three isomers.
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d) | Propylamine reacts with ethanoyl chloride to form an amide. Outline a mechanism for this reaction.
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e) | Name the amide formed in the reaction in part d).
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Question 3
a) | Name the compound with the structural formula (CH3)2NH.
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b) | (CH3)2NH can be formed by reacting CH3Br with an excess of CH3NH2. Outline a mechanism for this reaction.
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c) | Draw the structure of the product formed if a large excess of CH3Br is reacted with CH3NH2.
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d) | Name the type of compound formed in the reaction in part c).
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Question 4
Phenylamine can be prepared by the reduction of nitrobenzene. |
a) | Write an equation for the reduction of nitrobenzene to form phenylamine. Use [H] to represent the reducing agent.
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b) | Give a suitable reducing agent for the reduction of nitrobenzene.
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c) | The diagram below shows the structures of phenylamine and phenylethylamine. State and explain which of the two amines will be the stronger base.
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Question 5
a) | Draw the structure of the product formed in the reaction below.
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b) | State the reagent(s) needed for the reaction shown below.
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c) | The compound shown in the diagram below contains an amide group. Model answer Draw the structures of the two organic products formed when this compound is heated with HCl.
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Question 6
Amines can be prepared from halogenoalkanes. |
a) | Outline a mechanism for the reaction of NH3 with 1-bromohexane to form an amine.
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b) | Name the mechanism for the reaction in part a).
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c) | Draw the structures of a secondary amine and a tertiary amine that could form in the reaction in part a) if 1-bromohexane is in excess.
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d) | Primary amines can also be formed from the reduction of nitriles. Use your answer to part c) to suggest why reduction might be the preferred method for the formation of primary amines.
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Question 7
This question is about amines and amides. |
a) | Explain why ethylamine is basic.
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b) | Explain why phenylamine is less basic than ethylamine.
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c) | Ethylamine can react with CH3CH2COCl to form an amide. Write an equation for the reaction.
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d) | Name the amide formed in part d).
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