Question

An ester (A) with molecular formula $C_9{H}_{10}{O}_2$ was treated with excess of $C{H}_{3}MgBr$ and the compound so formed was treated with conc. $H_{2}S{O}_4$ to form olefin (B). Ozonolysis of (B) gave ketone with formula $C_8{H}_{8}O$ which shows positive iodoform test. The structure of (A) is?

• A. $C_6{H}_{5}COO{C}_2{H}_5$
• B. $C{H}_{3}OC{H}_{2}CO{C}_6{H}_5$
• C. $C{H}_{3}CO-C_6{H}_5-COC{H}_3$
• D. $C_6{H}_{5}COO{C}_6{H}_5$

Answer 1

Answer: (A)

$C_6{H}_{5}COO{C}_2{H}_5$

$OH$ $C{H}_3$ $O$

$\underset{\left(A\right)}{C_6{H}_{5}COO{C}_2{H}_5}\stackrel{C{H}_{3}MgBr}{\to }{C}_6{H}_5-\stackrel{|}{\underset{|}{C}}-C{H}_3\underset{\Delta }{\overset{H_{2}S{O}_4}{\to }}\underset{\left(B\right)}{C_6{H}_5-\stackrel{|}{C}=C{H}_2}\stackrel{O_3}{\to }HCHO+\underset{\downarrow NaOI}{C_6{H}_5}-\stackrel{||}{C}-C{H}_3$

$C{H}_3$ $CH{I}_3+C_6{H}_{5}COONa$