Question

Please write neatly.

3. Show the products formed in the tollowing reactions draw two enols 1) Mg. Et O 2) CO2 3) H:O NHz Jo .OTo. 쁘. pyridne CI NH Ci CI 0 SOCl OH heat NH 1) CH3MgBr excess CH, CH, -OCH,C 2) H2O COOMe LIAIH OH Ci 0

Answer 1

There are two types of alpha hydrogens, therefore, two enols are formed as shown in reation scheme он H3C The alkyl bromide forms grignard reagent with Mg. This Grignard reagent reacts with CO2 to form carboxylic group as shown below H2C 1) Mg. Et,o Hsc MgBr 2)CO2 CH 3) H3O CH C The amide group is dehydrated with diphosphorous pentaoxide ad forms nitrile as shown below CN iv) Acyl chloride reacts with alcohol to from ester as shown below Pyridine v) Acyl chloride reacts with ammonia to from amide as shown below CI + NH CI CI vi) Carboxylic acid is converted into acyl chloride with thonyl chloride as shown below Нас H3C vii) Ester reacts with excess Grignard reagent to form the tertiary alcohol as given below он CH3MgBr (excess) CH H3C CH3