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MHT CET Chemistry question

ChemistryOrganic Oxidation & Reduction ReactionsMHT CET

2, 2, 4, 4-tetramethyl-3-chloropentane on hydrolysis by aq.KOH gave 'A'. The compound 'A' on oxidation gave 'B'. The compound 'B' is neither able to reduce Fehling's solution nor aldol. This, on Clemmensen's reduction gives which of the following :

Answer: (A)

Solution

Hydrolysis gives (A), oxidation gives the ketone (B, no alpha-hydrogen so no aldol), and Clemmensen reduction converts C=O to

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Question ID VK-080757