Organic compound A does not undergo decarboxy | vedclass

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(C) The compound $A$ is a bridged bicyclic carboxylic acid. Decarboxylation typically involves the formation of a carbanion or a carbocation intermedi

Vedclass · Accepted Answer

Intermediate does not follow Bredt's rule

Vedclass · Answer

(C) The compound $A$ is a bridged bicyclic carboxylic acid. Decarboxylation typically involves the formation of a carbanion or a carbocation intermediate. In this specific bridged system,the formation of a double bond at the bridgehead position (which would be required for the transition state or intermediate during decarboxylation) is forbidden by Bredt's rule. Bredt's rule states that a double bond cannot be placed at the bridgehead of a bridged ring system unless the rings are large enough to accommodate the strain.

Organic compound $A$ does not undergo decarboxylation reaction because?

Similar Questions

$CH_3COOH + C_2H_5^{18}OH \xrightarrow{Conc. H_2SO_4} (X)$
$CH_3COOH + (CH_3)_3C^{18}OH \xrightarrow{Conc. H_2SO_4} (Y)$
In the above reaction $(X)$ and $(Y)$ are respectively:

$R-CO-OR' + R''OH \xrightarrow{H^{\oplus}} R-CO-OR'' + R'OH$
The above reaction is an example of:

The correct order of acidic strength is

Which of the following rings is highly strained?

The decreasing order of acidic strength for the following acids is:
$(A)$ $CH_3COOH$
$(B)$ $CH_3CHClCH_2COOH$
$(C)$ $ClCH_2COOH$
$(D)$ $Cl_2CHCOOH$

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