Question

Which set of reaction conditions represents the best way to carry out the following transformation? Briefly explain your choice using one sentence.

T I 1111 CH ... CH3 H OCOCH Br OCOCH a) CH3COOCH2CH3 in water b) CH3COONa in DMSO c) CH3COONa in water d) CH3COONa in acetone

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Answer #1

correct option is c)

The above reaction went through the SN1 mechanism (via formation of carbocation intermediate) as the attack of nucleophile CH3COO- has taken place from the side of above and below the plane, so polar protic solvent (H2O) required and also CH3COONa has a charged nucleophile so will be preferable over CH3COOCH2CH3.

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