question_answer

An ester with molecular formula \[{{C}_{9}}{{H}_{10}}{{O}_{2}}\] was treated with excess of \[C{{H}_{3}}MgBr\] and the complex so formed was treated with \[{{H}_{2}}S{{O}_{4}}\] to give an olefin . Ozonolysis of gave a ketone with molecular formula \[{{C}_{8}}{{H}_{8}}O\] which shows +ve iodoform test. The structure of is: [AIPMT 1998]

A) \[{{C}_{6}}{{H}_{5}}COO{{C}_{2}}{{H}_{5}}\]

B) \[{{C}_{6}}{{H}_{5}}COO{{C}_{6}}{{H}_{5}}\]

C) \[{{H}_{3}}COC{{H}_{2}}CO{{C}_{6}}{{H}_{5}}\]  

D) \[p-{{H}_{3}}CO-{{C}_{6}}{{H}_{4}}-COC{{H}_{3}}\]

Correct Answer: A

Solution :

[a]