Consider all possible isomeric ketones, including stereoisomers, of MW = 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 Advanced 2014 Chemistry question

Consider all possible isomeric ketones, including stereoisomers, of MW = 100. All these isomers are independently reacted with (NOTE: stereoisomers are also reacted separately). The total number of ketones that give a racemic product(s) is/are

Answer: 5

Solution

MW 100 for a saturated acyclic ketone means . The isomers are: hexan-2-one, hexan-3-one, 4-methylpentan-2-one, 2-methylpentan-3-one, 3,3-dimethylbutan-2-one, and 3-methylpentan-2-one (chiral, existing as R and S). reduction creates a new stereocentre at the carbonyl carbon,

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Question ID VK-026274