Concept explainers
Interpretation:
It is to be determined which of the two given molecules D and E would be expected to undergo hydration to a greater extent.
Concept introduction:
The carbon atom in the carbonyl group is relatively electron-poor, and a nucleophile such as water can attack this carbon. This bond formation and subsequent solvent-mediated proton transfer result in the formation of a geminal
In
The presence of bulky groups on the carbonyl carbon makes it more difficult for the nucleophile to attack, reducing the extent of hydration. The steric crowding in the hydrate with two bulky alkyl groups also makes it less stable.
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Organic Chemistry: Principles and Mechanisms (Second Edition)
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