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Imine vs Enamine - Part 1 of 6
21. Aldehydes and Ketones: Nucleophilic Addition / Imine vs Enamine / Problem 3

In the benzoin condensation, what is the role of the cyanide ion? Why does the reaction fail if the hydroxide ion is used instead?

a) The cyanide ion generates an electrophile, allowing the reaction to occur. If a hydroxide ion is used, the electrophile is not generated, and the reaction will not continue.

b) The cyanide ion deprotonates methanol, allowing the reaction to occur. If a hydroxide ion is used, the methanol is not deprotonated, and the reaction will not continue.

c) The cyanide ion creates an umpolung to the carbonyl carbon, allowing the reaction to occur. If a hydroxide ion is used, the polarity of the carbonyl carbon will not be inverted, and the reaction will not continue.

d) The cyanide ion removes an α-hydrogen, allowing the reaction to occur. If a hydroxide ion is used, the α-hydrogen is not removed, and the reaction will not continue.

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