Compound A is an optically active alcohol. Treatment with
chromic acid converts A into a ketone, B. In a separate reaction,
A is treated with PBr3, converting A into compound C.
Compound C is purified, and then it is allowed to react with
magnesium in ether to give a Grignard reagent, D.
Compound B is added to the resulting solution of
the Grignard reagent. After hydrolysis of the initial product (E),
this solution is found to contain 3,4-dimethylhexan-3-ol.
Propose structures for compounds A, B, C, D, and E.
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