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Optical isomerism (A-level only)

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Question 1

The aldehyde (CH3)2CHCH2CHO\text{(CH}_3)_2\text{CHCH}_2\text{CHO}(CH3​)2​CHCH2​CHO reacts with KCN\text{KCN}KCN followed by dilute acid to form a racemic mixture of the two stereoisomers of (CH3)2CHCH2CH(OH)CN\text{(CH}_3)_2\text{CHCH}_2\text{CH(OH)CN}(CH3​)2​CHCH2​CH(OH)CN.

1.

Give the IUPAC name of (CH3)2CHCH2CH(OH)CN\text{(CH}_3)_2\text{CHCH}_2\text{CH(OH)CN}(CH3​)2​CHCH2​CH(OH)CN.

[1]
2.

Describe how you would distinguish between separate samples of the two stereoisomers of (CH3)2CHCH2CH(OH)CN\text{(CH}_3)_2\text{CHCH}_2\text{CH(OH)CN}(CH3​)2​CHCH2​CH(OH)CN.

[2]
3.

Explain why the reaction produces a racemic mixture.

[3]
4.

An isomer of (CH3)2CHCH2CHO\text{(CH}_3)_2\text{CHCH}_2\text{CHO}(CH3​)2​CHCH2​CHO reacts with KCN\text{KCN}KCN followed by dilute acid to form a compound that does not show stereoisomerism. Draw the structural formula of the compound formed and justify why it does not show stereoisomerism.

[2]

Optical isomerism (A-level only) Questions

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  3. /Optical isomerism (A-level only)