Question

NaBr OH Br CH3 CH20 Na CH3CH2OH Explain what problems are associated with the following reaction in each case.
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Answer #1

The deisred product can not be formed in both cases .

reaction 1.

Bromide is a weaker nucleophile and base than hydroxide ion. Thus nucelophilic substitution cannot takeplace.

Secondly , -OH being a strong base, is a poor leaving group , making the substrate also less reactive. Thus NO Reaction takes place.

Reaction2.

Though using a strong base like ethoxide io , we expect elimination to take place, a different reactionoccurs here.

In the substrate along with Br(a primary alkyl halide) we have a keto group also, which is more electrophilic than the carbon attached to the bromide.

Thus the nucelophile/base ethoxide ion attacks preferably the carbonyl carbon rather than the carbo n with halogen. Thus acyl nucleophhilic attack is done rather than elimination.

Secondly a primary halide is less reactive towards elimination.

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