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Preparation of Benzene and Homologues

A 3∘ opticall...

Question

A $3^{o}$ optically active alcohol $C_{9} H_{18} O$ $(A)$ on dehydration with $c o n c . H_{2} S O_{4}$ produces $C_{9} H_{16}$ $(B)$ which exists in two stereoisomeric forms. Reductive ozonolysis of $B$ produces acetaldehyde and $C_{7} H_{12} O$ $(C)$ .
$C$ on treatment with $L i A l H_{4}$ produces $D (C_{7} H_{14} O)$ .
$D$ on dehydration produced following product
Identify the correct answers.

A

D is

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B

A is

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C

A is

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D

B is

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Solution

The correct options are
C A is
D B is
Back tracing the reaction, we can assume that D may either be (i) or (ii).

Since D is a reduced carbonyl, which is possible for (ii) only.
Hence (C) will be
Now, constucting the reaction sequences:

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