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In the alkylation of cyclopentanone, better yields are obtained by first reacting cyclopentanone with an equivalent of lithium diisopropylamide in THF and then adding the alkyl halide rather than mixing cyclopentanone, 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.

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