Fundamentals of Organic ChemistryChemistryAldehydes and Ketones
Consider the following reaction sequence: The number of possible stereoisomers in the final product mixture is:
Options
- A4
- B1
- C3
- D2
Correct answer
C. 3
Step-by-step solution
The first step is the Benzoin condensation. Benzaldehyde reacts with alcoholic KCN to form benzoin (A). 2C₆H₅CHO Alc. KCN C₆H₅-CH(OH)-CO-C₆H₅ Benzoin has one chiral center and is formed as a racemic mixture. In the second step, benzoin is reduced by LiAlH₄ , which converts the ketone group into an alcohol group, forming hydrobenzoin. C₆H₅-CH(OH)-CO-C₆H₅ (i) LiAlH₄ (ii) H₂O C₆H₅-CH(OH)-CH(OH)-C₆H₅ The product, 1,2-diphenyl-1,2-ethanediol (hydrobenzoin), has two identical chiral centers ( n=2 ). The number of possibl