Question

A $\left[ C _{6} H _{10} O _{3}\right.$ (keto ester) $] \ce{->[{ NaOH + I _{2}}][{\Delta}]}\,\,$ yellow $p p t + B \ce{->[{ H ^{+}}]} C \ce{->[{- C O _{2}}][{\Delta}]} C H _{3} C O O H$. Hence, $A$ is

• A. $CH _{3} \overset{\underset{||}{O}}{C}CH _{2} \overset{\underset{||}{O}}{C}OC _{2} H _{5}$
• B. $CH _{3}CH_2 \overset{\underset{||}{O}}{C}CH _{2} \overset{\underset{||}{O}}{C}OCH _{3}$
• C. Both are correct
• D. None is correct

Answer 1

Answer: (A)

' $A$ ' gives iodoform test thus $A$ has $- \overset{\underset{||}{O}}{C} CH _{3}$ group. ' $C$ ' eliminates $CO _{2}$ on heating hence, $C$ has two $- COOH$ groups at same (gem) position.
Since, only (a) has $- \overset{\underset{||}{O}}{C}CH _{3}$ group, therefore,
compound ' $A$ ' is $CH _{3} \overset{\underset{||}{O}}{C}CH _{2} COC _{2} H _{5}$.