When the three benzaldehydes shown below were exposed to HCN under identical conditions it was found that the equilibrium constants, K, for the three cyanohydrin formation reactions were different. Based on principles that govern equilibrium processes for reversible carbonyl addition reactions, place the K values for the three reactions in ascending order (smallest to largest). Briefly justify your answer. (Hint: Recall that electron deficient carbonyls tend to react faster with nucleophiles and have larger equilibrium constants for the addition reaction.) H X + HCN pH ~9-10 X = H, NO2, OCH 3 OH H HCN X
When the three benzaldehydes shown below were exposed to HCN under identical conditions it was found that the equilibrium constants, K, for the three cyanohydrin formation reactions were different. Based on principles that govern equilibrium processes for reversible carbonyl addition reactions, place the K values for the three reactions in ascending order (smallest to largest). Briefly justify your answer. (Hint: Recall that electron deficient carbonyls tend to react faster with nucleophiles and have larger equilibrium constants for the addition reaction.) H X + HCN pH ~9-10 X = H, NO2, OCH 3 OH H HCN X
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
Section19.SE: Something Extra
Problem 28VC
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Question
![When the three benzaldehydes shown below were exposed to HCN under identical
conditions it was found that the equilibrium constants, K, for the three cyanohydrin formation
reactions were different. Based on principles that govern equilibrium processes for reversible
carbonyl addition reactions, place the K values for the three reactions in ascending order
(smallest to largest). Briefly justify your answer. (Hint: Recall that electron deficient carbonyls tend
to react faster with nucleophiles and have larger equilibrium constants for the addition reaction.)
H
X
O
+ HCN
pH ~ 9-10
X = H, NO₂, OCH 3
OH
H+CN
X](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F277d8e9e-796c-4923-a9a2-4c05d5ad95df%2F776f0d46-8aff-4543-bb16-45b0cd84d67e%2F3td42sf.jpeg&w=3840&q=75)
Transcribed Image Text:When the three benzaldehydes shown below were exposed to HCN under identical
conditions it was found that the equilibrium constants, K, for the three cyanohydrin formation
reactions were different. Based on principles that govern equilibrium processes for reversible
carbonyl addition reactions, place the K values for the three reactions in ascending order
(smallest to largest). Briefly justify your answer. (Hint: Recall that electron deficient carbonyls tend
to react faster with nucleophiles and have larger equilibrium constants for the addition reaction.)
H
X
O
+ HCN
pH ~ 9-10
X = H, NO₂, OCH 3
OH
H+CN
X
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