1. Chemistry
2. Organic Chemistry
3. Organic Reactions
4. Organic Reaction Intermediates and Mechanisms
5. 33889

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Three compounds A, B and C all have the formula C5H10. A and B rapidly decolourise bromine dissolved in CH2CL2 but compound C is unreactive.

Compound A reacts rapidly with acidified water and a tertiary alcohol D is formed; however compound B yields a secondary alcohol.

(a) Draw a possible structure for each of A, B and C.

(b) Are other structures possible for A,B and C?

(c) Formulate the reaction A --> to D and give mechanism of reaction.