Which is most reactive towards soda-lime deca | vedclass

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

Question

(B) The decarboxylation of carboxylic acids with soda-lime $(NaOH + CaO)$ proceeds through the formation of a carbanion intermediate. The rate of deca

Vedclass · Accepted Answer

$p-O_2N-C_6H_4-CH_2-COOH$

Vedclass · Answer

(B) The decarboxylation of carboxylic acids with soda-lime $(NaOH + CaO)$ proceeds through the formation of a carbanion intermediate. The rate of decarboxylation is directly proportional to the stability of the carbanion formed after the loss of $CO_2$. Electron-withdrawing groups (EWGs) stabilize the carbanion,thereby increasing the rate of decarboxylation,while electron-donating groups (EDGs) destabilize it. Comparing the substituents: $1$. $-NO_2$ is a strong electron-withdrawing group $(EWG)$ due to both $-I$ and $-M$ effects. $2$. $-OCH_3$ is an electron-donating group $(EDG)$ due to its $+M$ effect. Between the nitro-substituted compounds,the $-NO_2$ group at the ortho or para position exerts a stronger electron-withdrawing effect via resonance ($-M$ effect) compared to the meta position. However,in the case of $p-O_2N-C_6H_4-CH_2-COOH$,the $-NO_2$ group is at the para position relative to the $-CH_2COOH$ group. The electron-withdrawing effect of the $-NO_2$ group stabilizes the negative charge on the benzylic carbon formed during the transition state. Thus,$p-O_2N-C_6H_4-CH_2-COOH$ is the most reactive.

Which is most reactive towards soda-lime decarboxylation?

Similar Questions

Dimerization in carboxylic acids is due to which of the following?

When an acyl chloride is heated with $Na$ salt of a carboxylic acid,the product is

Order of acidity of benzoic acid $(I)$,$4-$methoxybenzoic acid $(II)$,acetic acid $(III)$ and $4-$nitrobenzoic acid $(IV)$ is

$CH_3CH_2COOH$ $\xrightarrow{Br_2/P} X$ $\xrightarrow{NH_3} Y$. What is $Y$ in the above reaction?

Treatment of benzoic acid with $Cl_2/FeCl_3$ will give

Vedclass Test Series

Exam Paper Generator

Online Exam Module