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Question
Consider all possible isomeric ketones, including stereoisomers of MW=100. All these isomers are independently reacted with NaBH4 (NOTE: stereoisomers are also reacted separately). What is the total number of ketones that give a racemic product(s)?
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Solution
The general formula of isomeric ketone having molecular mass 100 is C6H12O [6×12+12×1+16].The possible structure will be :a) CH3−CH2−CH2−O||C−CH3
b) CH3CH2CH2−O||C−CH2CH3
c)CH3−C|HCH3−CH2−O||C−CH3
d) CH3−CH2−CH3|CH−O||C−CH3
e) CH3−CH3|CH−O||C−CH2−CH3
f) CH3−CH3|C|CH3−O||C−CH3The number of ketones that gives racemic mixture with NaBH4 is 5 as the ketone with chiral center will give diastereoisomer with NaBH4
The possible structure will be :
a) CH3−CH2−CH2−O||C−CH3
b) CH3CH2CH2−O||C−CH2CH3
c)CH3−C|HCH3−CH2−O||C−CH3
d) CH3−CH2−CH3|CH−O||C−CH3
e) CH3−CH3|CH−O||C−CH2−CH3
f) CH3−CH3|C|CH3−O||C−CH3
The number of ketones that gives racemic mixture with NaBH4 is 5 as the ketone with chiral center will give diastereoisomer with NaBH4
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