Which beta-keto acid shown will not undergo d | vedclass

Name: Exam Paper Generator | JEE NEET Paper Generator | Vedclass
Brand: Vedclass
Rating: 5 (35 reviews)

Question

(B) Decarboxylation of $\beta$-keto acids typically proceeds through a cyclic six-membered transition state to form an enol intermediate,which then ta

Vedclass · Accepted Answer

Vedclass · Answer

(B) Decarboxylation of $\beta$-keto acids typically proceeds through a cyclic six-membered transition state to form an enol intermediate,which then tautomerizes to a ketone.Option $B$ represents a bicyclic $\beta$-keto acid where the carboxyl group is at the bridgehead position.Decarboxylation would require the formation of a double bond at the bridgehead position in the resulting enol intermediate.According to Bredt's rule,the formation of a double bond at the bridgehead of a small bicyclic system is highly unstable and prohibited.Therefore,the compound in option $B$ will not undergo decarboxylation.

Column-$I$ (formula)	Column-$II$ (name)
$A$. $RCH=NH$	$i$. Diisobutyl aluminium hydride
$B$. $AlH(i-Bu)_2$	$ii$. Benzalchloride
$C$. $C_6H_5-CH(OCOCH_3)_2$	$iii$. Imine
$D$. $C_6H_5CHCl_2$	$iv$. Benzylidene diacetate

Which $\beta$-keto acid shown will not undergo decarboxylation?

Similar Questions

Identify $Z$ in the following reaction sequence:
$CH_3COONH_4$ $\xrightarrow{\Delta} X$ $\xrightarrow{P_2O_5} Y$ $\xrightarrow{H_2O/H^+} Z$

What are $X$ and $Y$ respectively in the following reactions?

Hydrolysis of an ester gives acid $A$ and alcohol $B$. $A$ reduces Fehling solution and oxidation of $B$ gives $A$. The ester is

Match the formulas in Column-$I$ with their names in Column-$II$.

Column-$I$ (formula) Column-$II$ (name)

$A$. $RCH=NH$ $i$. Diisobutyl aluminium hydride

$B$. $AlH(i-Bu)_2$ $ii$. Benzalchloride

$C$. $C_6H_5-CH(OCOCH_3)_2$ $iii$. Imine

$D$. $C_6H_5CHCl_2$ $iv$. Benzylidene diacetate

The total number of carboxylic acid groups in the product $P$ is

Vedclass Test Series

Exam Paper Generator

Online Exam Module