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Q. Consider all possible isomeric ketones, including stereoisomers of $M W=100$. All these isomers are independently reacted with $NaBH _{4}$ (NOTE: stereoisomers are also reacted separately). The total number of ketones that give a racemic product(s) is/are

JEE AdvancedJEE Advanced 2014Aldehydes Ketones and Carboxylic Acids

Solution:

1 image Will not give a racemic mixture on reduction with $NaBH _{4}$
2 image Will give a racemic mixture on reduction with $NaBH _{4}$
3 image Will give a racemic mixture on reduction with $NaBH _{4}$
4 image Will give a racemic mixture on reduction with $NaBH _{4}$
(5) image Will give a racemic mixture on reduction with $NaBH _{4}$
(6) image Will give a racemic mixture on reduction with $NaBH _{4}$