Q15 / 60 · JEE Advanced 2014 (Paper 1) · Chemistry

Consider all possible isomeric ketones, including stereoisomers of MW = 100. All these isomers are independently reacted with NaBH4 (NOTE: stereoisomers are also reacted separately). The total number of ketones that give a racemic product(s) is/are

Correct answer: 5

Solution

The general formula of isomeric ketone having molecular mass 100 is C6H12O [6x12 +12x1 +16].

1] Will not give a racemic mixture on reduction with NaBH4. 

this  ketone have chiral center will give diastereoisomer.
Figure
2] Will give a racemic mixture on reduction with NaBH4
Figure
3] Will give a racemic mixture on reduction with NaBH4
Figure
4] Will give a racemic mixture on reduction with NaBH4
Figure
5] Will give a racemic mixture on reduction with NaBH4
Figure
6] Will give a racemic mixture on reduction with NaBH4
Figure

Hence, the correct answer is 5.

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