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Question

A 3o optically active alcohol C9H18O (A) on dehydration with conc.H2SO4 produces C9H16 (B) which exists in two stereoisomeric forms. Reductive ozonolysis of B produces acetaldehyde and C7H12O (C).
C on treatment with LiAlH4 produces D (C7H14O)
D on dehydration produced following product 
Identify the correct answers.
  1. D is 
  2. A is 
  3. A is 
  4. B is 


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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