May/June 2026 Paper 11

2026 · 40 questions · 40 parts · 40 marks

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27Optical IsomerismHard1 mark
The structure of an ether X is shown. The C-O-C group is the functional group in the homologous series of ethers.
Structure of ether X, drawn in full displayed form: a propyl group (H3C-CH2-CH2-) joined through an oxygen atom to an ethyl group (-CH2-CH3), i.e. H-C-C-C-O-C-C-H with every C-H bond shown.
Y is a functional group isomer of X. Y exists as a pair of optical isomers. Which structure represents Y?
Structure A: a straight five-carbon chain with a hydroxy group on the terminal carbon, drawn in full displayed form as H3C-CH2-CH2-CH2-CH2-OH (pentan-1-ol), with no branching.
Structure B: a five-carbon chain with a hydroxy group on the fourth carbon, drawn in full displayed form as H3C-CH2-CH2-CH(OH)-CH3 (pentan-2-ol).
Structure C: a five-carbon chain with a hydroxy group on the middle (third) carbon, drawn in full displayed form as H3C-CH2-CH(OH)-CH2-CH3 (pentan-3-ol), symmetric about the carbinol carbon.
Structure D: an ethyl group (H3C-CH2-) joined to a carbon that carries a methyl branch, which is joined through an oxygen to a terminal methyl group, drawn in full displayed form as H3C-CH2-CH(CH3)-O-CH3 with the methyl branch shown below the carbon next to the oxygen, retaining a C-O-C ether linkage and no hydroxy group.