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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
The diagram below shows the amino acids leucine, proline and glutamic acid. |
a) | Give the IUPAC name of leucine.
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b) | Draw the zwitterion of proline.
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c) | Draw the structure of the product formed when glutamic acid is dissolved in an acidic solution.
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d) | Draw the structure of the tripeptide leucine-proline-leucine, formed from one molecule of proline and two molecules of leucine.
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Question 4
The diagram below shows the structure of the amino acid aspartic acid. |
a) | Draw the structure of the product formed when aspartic acid is reacted with HCl.
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b) | Draw the structure of the product formed when aspartic acid is reacted with excess CH3OH and H2SO4.
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c) | Aspartic acid has an isoelectric point of 2.77. What is meant by the term isoelectric point?
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d) | Draw the structure of aspartic acid when it is dissolved in a solution with a pH greater than its isoelectric point.
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e) | Draw the structure of aspartic acid when it is dissolved in a solution with a high pH.
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Question 5
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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d) | Phenylamine reacts with nitrous acid (HNO2) to form a diazonium salt. Draw the displayed formula of the salt.
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e) | What type of compound would be formed if the diazonium salt in part d) was reacted with phenol?
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Question 6
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 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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e) | The diagram below shows a series of reactions to form the dye X. Name the reagents for steps 1 and 2.
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Question 8
The diagram below shows the structure of the amino acid alanine. |
a) | Outline the mechanism for the formation of alanine from CH3CHClCOOH and ammonia.
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b) | Draw the structure of the zwitterion formed by alanine.
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c) | Draw the structure of the product formed when alanine reacts with CH3OH in the presence of concentrated H2SO4.
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