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7 Cards in this Set

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  • Back
Aldehydes and unhindered ketones react with HCN to yield ?
cyanohydrins, RCH(OH)C=-N
cyanohydrin formation is ?
reversible and base-catalyzed.
Addition of HCN rxns occur _______ when pure HCN is used but ______ when a small amount of a base is added to generate the nucleophilic cyanide ion, CN-.
- slowly

- rapidly
a small amount of ____ can be added to HCN to catalyze the rxn
KCN
Addition of CN- to an aldehyde or ketone occurs by _____________________________ , yielding a _______ _______ that is protonated by HCN to give
- a typical nucleophilic addition pathway

- tetrahedral intermediate

- cyanohydrin product plus regenerated CN-
Cyanohydrin formation is unusual because ?
it is one of the few examples of the addition of a proticacid (H-Y) to a carbonyl group
Reagents such as H2O, HBr, HCL. and H2SO4 don't normally yield carbonyladditionproducts because their equilibrium constants for rxn are unfavorable. With HCN, the equilibrium favors
the cyanohydrin adduct