Question

An ester $(A)$ with molecular formula $C_9H_{10}O_2$ was treated with excess of $CH_3MgBr$ and the complex so formed was treated with $H_2SO_4$ to give an olefin $(B)$ . Ozonolysis of $(B)$ gave a ketone with molecular formula $C_8H_8O$ which shows positive iodoform test. The structure of $(A)$ is

• A. $C_{6}H_{5}COOC_{2}H_{5}$
• B. $C_{6}H_{5}COOC_{6}H_{5}$
• C. $C_{6}H_{5}COOCH_{3}$
• D. $p$ - $H_{3}CO - C_{6}H_{4} -COCH_{3}$

Answer 1

Answer: (A)

$C_{6}H_{5}COOC_{2}H_{5}$

Answer 2

$\underset{(A)}{C_6H_5COOC_2H_5} \ce{->[CH_3MgBr]}$
undefined
$C_6H_5 - \underset{\overset{||}{O}}{C} - CH_3 \ce{->[I_2][NaOH]}$
$\underset{\text{iodoform}}{CHI_3 } + C_6H_5COONa$