What is the order of reactivity of the follow | vedclass

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

Question

(C) Sodalime decarboxylation involves the formation of a carbanion intermediate. The rate of decarboxylation is directly proportional to the stability

Vedclass · Accepted Answer

$ii > i > iv > iii$

Vedclass · Answer

(C) Sodalime decarboxylation involves the formation of a carbanion intermediate. The rate of decarboxylation is directly proportional to the stability of the carbanion formed. Electron-withdrawing groups $(EWG)$ stabilize the carbanion,while electron-donating groups $(EDG)$ destabilize it. The stability order of the carbanion intermediate is determined by the inductive effect ($-I$ effect) of the substituents. $(i)$ $m$-nitro group exerts a strong $-I$ effect. (ii) $p$-nitro group exerts a strong $-I$ effect. Since the $p$-position is closer to the reaction center in terms of inductive influence compared to the $m$-position in this specific structure,or considering the overall electron-withdrawing strength,the order is $ii > i$. (iii) $-OMe$ is an electron-donating group ($+M$ effect,though $-I$ at distance),which destabilizes the carbanion. (iv) $-CH_3$ is an electron-donating group ($+I$ effect),which also destabilizes the carbanion,but less than $-OMe$. Thus,the reactivity order is $ii > i > iv > iii$.

What is the order of reactivity of the following compounds towards sodalime decarboxylation?
$(i)$ $m$-nitro-phenylacetic acid
(ii) $p$-nitro-phenylacetic acid
(iii) $p$-methoxy-phenylacetic acid
(iv) $p$-methyl-phenylacetic acid

Similar Questions

What are $X$ and $Y$ respectively in the following reaction sequence?
Styrene $\xrightarrow[(ii) H_3O^+]{(i) KMnO_4 / KOH} X$ $\xrightarrow{Br_2 / FeBr_3} Y$

Identify the correct decreasing order of acidic strength for the following compounds:
$I$: $p$-Nitrobenzoic acid
$II$: Benzoic acid
$III$: $p$-Methoxybenzoic acid

Which of the following acids will form an $(a)$ anhydride on heating and $(b)$ an acid imide on strong heating with ammonia?

$CH_3COOH \xrightarrow{\Delta, P_2O_5} X$. Identify $X$.

Identify $A$ and $B$ in the following reaction:
$CH_3-CH_3 \stackrel{B}{\longleftarrow} CH_3COOH \stackrel{A}{\longrightarrow} CH_3CH_2OH$
$A \quad B$

Vedclass Test Series

Exam Paper Generator

Online Exam Module

What is the order of reactivity of the following compounds towards sodalime decarboxylation? $(i)$ $m$-nitro-phenylacetic acid (ii) $p$-nitro-phenylacetic acid (iii) $p$-methoxy-phenylacetic acid (iv) $p$-methyl-phenylacetic acid