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Fischer's Esterification Process

An organic ac...

Question

An organic acid $A (C_{5} H_{10} O_{2})$ reacts with $B r_{2}$ in presence of phosphorus to produce a resolvable compound B. B on dehydrobromination yields C. C does not show geometrical isomerism and on decarboxylation gives an alkene D. D on ozonolysis gives E and F. Compound E gives positive Schiff's test but F does not. Give structures of A to F.

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Solution

Bromination will occur next to the $C O O H$ group as the $C O O H$ group make stable the carbocation
$C$ does not show geometrical as the both groups on left side are same of double bond
Ozonolysis will break the bond and form secondary carbon to ketone and primary carbon to aldehyde
$F$ ( formaldehyde) does not give the Schiff base test.

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