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  4. Which of the following on reaction with excess of NaHSO3 in aqueous solution will give mixture of salts which can be separated into two fractions by fractional crystallization?

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Q. Which of the following on reaction with excess of $NaHSO_3$ in aqueous solution will give mixture of salts which can be separated into two fractions by fractional crystallization?

Aldehydes Ketones and Carboxylic Acids

Solution:

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In the above reaction, four stereoisomers, two pairs of enantiomers are formed. Each member of a pair of enantiomer is diastereomer of each member of other pair of enantiomer. Hence, fractional crystallisation would give two fractions, each containing racemic mixture.