Question

Identify the final product $B$ of the reaction
$C_6H_5COOH + NaH\overset{*}{C}O_3 $ gas $(A)$
$\ce{ ->[{(i) CH_3MgBr}][{(ii) H_2O^+}] }(B)$
Here $\overset{*}{C}= C^{14}$

• A. $\overset{*}{C}H_3COOH$
• B. $C_6H_5\overset{*}{C}OOH$
• C. $CH_3\overset{*}{C}OOH$
• D. $H\overset{*}{C}OOCH_3$

Answer 1

Answer: (C)

$C _{6} H _{5} COOH + NaH\overset{*}{C}O _{3} \rightarrow C _{6} H _{5} COONa+ H _{2} O +\overset{*}{C}O_{2}$

$\overset{*}{C}O_2 \ce{ ->[1. CH_3MgBr] }CH_3 \overset{*}{C}OOMgBr \ce{ ->[H_3O^+] }CH_3\overset{*}{C}OOH$

Please not that when carboxylic acids are treated with $NaHCO _{3}$ solution, $CO _{2}$ liberated comes from $NaHCO _{3}$.