Question

Maximum decarboxylation occurs in:
A. \[C{{H}_{2}}COOH\]
B. \[{{C}_{6}}{{H}_{5}}COOH\]
C. \[{{C}_{6}}{{H}_{5}}C{{H}_{2}}COOH\]
D. \[C{{H}_{3}}COC{{H}_{2}}COOH\]

Answer 1

Hint: Decarboxylation is the way toward eliminating a carboxyl gathering (a carbon atom twofold attached to an oxygen atom) from a molecule. In the cannabis world, this cycle happens when a carbon atom is taken out from a carboxylic acid.

Complete step by step answer:
Oxidative decarboxylation reactions are oxidation reactions in which a carboxylate group is removed, forming carbon dioxide. They often occur in biological systems: there are many examples in the citric acid cycle. This type of reaction probably started early at the origin of life.
Option 4 is most reactive towards decarboxylation. The structure is of a\[\beta \] keto acid, which forms amuch stable carbanion than any other carboxylate ion.
\[C{{H}_{3}}COC{{H}_{2}}COOH\]is a \[\beta \] −keto acid.
Thus decarboxylation is maximum in a carboxylic acid containing an electron withdrawing group such as >CO or \[-COOH\]at the \[\beta \] −carbon atom with respect to the \[-COOH\] group.

Hence, The correct option here is D. \[C{{H}_{3}}COC{{H}_{2}}COOH\]

Additional Information:
The identified structural changes prevent decarboxylation
(i) by strengthening the bond of glutaconyl-coenzyme A,
(ii) by reducing the leaving group potential of, \[C{{O}_{2}}\] and
(iii) by increasing the distance between the atom (negatively charged in the enolate transition state) and the adjacent glutamic acid.

Note:
\[\beta \]Keto acids are truly precarious and promptly go through the disposal of carbon dioxide or essentially decarboxylation under mellow conditions. Ketones are acquired in these responses. Decarboxylation happens promptly at whatever point a carboxyl gathering is clung to the α carbon of another carbonyl gathering for two reasons.