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An ester 'A' (C(4)H(8)O(2)) on treatment...

An ester 'A' `(C_(4)H_(8)O_(2))` on treatment with excess methyl magnesium chloride followed on acidification gives an alcohol 'B' as the sole organic product. Alochol 'B' as the organic product. Alcohol 'B' on oxidation with NaOCl followed by acidification gives acetic acid. Deduce structure of A and B. Show the reactions involved.

Text Solution

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(i) Since alcohol (B) on oxidation with NaOCl haloform reaction ) followed by acidification gives acetic acid thus it can be either ethyl alcohol or 2-propanol.

(ii) Since alcohol (B) is obtained by addtion of excess of `CH_(3)MgCl`, on ester (A), therefore the alcohol both the methyl group because esters and two molecules of the Grignard reagent that is its (CH - OH) part has come form acid part of ester . Thus (A) must be fomic ester .
(iv) Since molecular formula of ester (A) is `C_(4)H_(4)O_(2)`, therefore alkyl group of ester must contain three carbon atoms either n - propyl group or isopropyl group.
(v) Further , since 2 - propanol (B) is the sole organic product obtained when two molecules of `(CH_(3))_(3)`MgCl are added to ester (A). Therefore , the alkyl group of ester (A) must be isopropyl group.
Thus , ester is isopropyl formate .
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