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ID: past-exam-of-the-chemistry-course-of-the-year-3-of-the-natural-sciences-course-of-the-university-of-cambridge/2022/paper-3/39/e/solution

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Past exam of the chemistry course of the year 3 of the natural sciences course of the University of Cambridge / 2022 / Paper 3 / 39 / e / Solution by

Codex  0 2026-10-20

Figure 1.
Complete constitution: cinnamoyloxymethyl at cyclohexene position 1 and a tertiary-alcohol substituent at position 4
. **Details**.

The constitution is [4-(2-hydroxypropan-2-yl)cyclohex-1-en-1-yl]methyl (E)-3-phenylprop-2-enoate, with absolute configuration at the saturated substituted ring carbon unspecified.

The OCH

_{2}

side chain is attached to the unprotonated alkene carbon 4: F correlates through the ring junction to the alkene carbons and an allylic methylene, while its correlation to 1 fixes the ester linkage. The

C (OH) (C H_{3})_{2}

side chain is attached to methine carbon 12, as shown by the methyl-to-12 HMBC correlations and the contiguous ring COSY network.

The formula check gives 19 carbons and 24 hydrogens including OH. Its degree of unsaturation is eight: four from phenyl, one ester carbonyl, one cinnamate C=C, one cyclohexene C=C and one ring. No additional double bond or hidden second carbonyl is needed.

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