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Question

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

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Solution

Molecular weight of the ketone is 100
So, molecular formula =C6H12O
Degree of unsaturation =(6+1)122=1
According to question, compound contains ketone group. Since, the compound which contain chiral centre lead to the formation of diastereomer while other produces enantiomers. Various isomers and their possible reduced product are as shown below.

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