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Question

Complete the following reactions with appropriate structures of products/reagents:

From the options, choose one that can replace the question marks in the above scheme.
Only major products can be considered.


A

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B

Benzaldehyde made to react with cyclohexanone in the presents of a strong base

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C

A is the final product; B gives the reagent/conditions/solvent for the first part.

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D

Neither A nor B can sufficiently explain the reaction scheme

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Solution

The correct option is C

A is the final product; B gives the reagent/conditions/solvent for the first part.


In the first step - observe how the cyclohexanone structure has been “retained”. Further - there is αβ unsaturation on a carbonyl. This should remind you of aldol condensation elimination. Since the blueprint of the cyclohexanone is undisturbed, it is the enol/enolate provider!
Clearly, that leaves us with the unenolizable benzaldehyde.


In the above reaction, we get cyclohexanone to react with benzaldehyde in the presence of a strong base like NaOEt in EtOH.

As shown in this reaction, the LiAlH4 reduces only the carbonyl, which becomes an alcohol on reduction plus workup.



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