Question

Oxidation of compound A with ozone with a zinc/acid workup yielded compound B as the sole organic product, which upon reaction with one mole equivalent of ethylene glycol under acidic conditions gave compound C. Reduction of C with lithium aluminium hydride produced compound D. Compound D has a molecular formula of C9H18O3. Acid hydrolysis of compound D yields compound E. Compound E has a molecular formula of C7H14O2. Compound A decolourises a solution of Br2 in CCl4 while B, C and E produced a yellow precipitate with 3,5-dinitrophenylhydrazine. Compounds D and E produced a cloudy precipitate within 3 minutes when subjected to a Lucas test.

What is compound A?

Answer 1

The first step is ozonolysis process, this provides that the starting molecule A is an alkene. Again, since it exclusively gives only one product, so other may be a cyclic alkene. In another side, since the molecule absorbed 1mol of ethylene glycol, that means the starting must contain a methyl substitution that is methyl alkene. By this way you can reach to the origin. Hence compound A is 1-methyl cyclohexene.

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