1. Tardigrade
  2. Question
  3. Chemistry
  4. An ester (A) with molecular formula C9H10O2 was treated with excess of CH3MgBr and the complex so formed was treated with H2SO4 to give an olefin (B) . Ozonolysis of (B) gave a ketone with molecular formula C8H8O which shows positive iodoform test. The structure of (A) is

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Q. 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

MHT CETMHT CET 2008Aldehydes Ketones and Carboxylic Acids

Solution:

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