In the alkylation of cyclohexanone, better yields are obtained by first reacting

Question

In the alkylation of cyclohexanone, better yields are obtained by first reacting cyclohexanone with an equivalent of lithium diisopropylamide in THF and then adding the alkyl halide, rather than mixing cyclohexanone, alkyl halide, and a catalytic amount of sodium ethoxide in ethanol. Explain this observation by pointing out what the problems with the second reaction conditions might be and how the first set of reaction conditions help alleviate the problems. When cyclohexane is placed in a solution of sodium ethoxide in ethanol, the enolate generated in small amounts in the presence of large amounts of conditions that are good for Ketotes for aldol self-condensation. After the aldol enolate, and produce mixtures result.

Explanation / Answer

In Second set of conditions it is more favourable for self aldolcondensation.

But in order to obtain better yields of alkylation of cyclohexanone, better to add LDA first whic is good reagent to abstract alpha hydrogen, and then add RX to produce corresponding alkylated cyclohexanone.

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