Answer to Question #104706 in Organic Chemistry for Chem

Question

). Draw a full arrow pushing mechanism for the hydration of acetaldehyde, illustrating carefully the reversibility or irreversibility of each reaction step.
(ii). Account for the relative K values for acetone, acetaldehyde and chloral (it is important to consider the factors that can favour each side of the equilibrium). Which carbonyl compound is the least hydrated at equilibrium?
(iii). Predict if the equilibrium constant K for the hydration of benzaldehyde (PhCHO) would be larger or smaller than that for acetaldehyde, giving reasons for your answer.

Answer 1

1. On the attached picture

2. Acetone

3. It is less because of the M- effect of the phenyl ring comparing to the M+ effect of methyl group in acetaldehyde