Why the hydrate of cyclopropanone is stable is to be explained. Concept introduction: Ketones and aldehydes exhibit very similar chemical behavior because both contain a carbonyl group with alkyl groups or hydrogen atoms attached to the carbonyl carbon. However, the nucleophilic addition reactions they undergo differ noticeably both thermodynamically and kinetically. The rate of hydration and the extent of hydration at equilibrium are greater for the aldehydes than for the ketone. In a ketone, the steric repulsion from the two alkyl groups on the carbonyl carbon makes it more difficult for the nucleophile to attack. Furthermore, the bulky alkyl groups in the hydrate product overlap with the bulky OH groups, generating steric strain and decreasing stability. An aldehyde, on the other hand, has at the most one alkyl group bonded to the carbonyl carbon, so both these steric effects are diminished. However, this is not the case in cyclopropanone.

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Deducing the Peactants Can the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants, in one step, by moderately heating the reactants? ? Δ If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in any arrangement you like. If your answer is no, check the box under the drawing area instead. Explanation Check Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center X

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Question

Chapter 17, Problem 17.35P

Interpretation Introduction

Interpretation:

Why the hydrate of cyclopropanone is stable is to be explained.

Concept introduction:

Ketones and aldehydes exhibit very similar chemical behavior because both contain a carbonyl group with alkyl groups or hydrogen atoms attached to the carbonyl carbon. However, the nucleophilic addition reactions they undergo differ noticeably both thermodynamically and kinetically. The rate of hydration and the extent of hydration at equilibrium are greater for the aldehydes than for the ketone. In a ketone, the steric repulsion from the two alkyl groups on the carbonyl carbon makes it more difficult for the nucleophile to attack. Furthermore, the bulky alkyl groups in the hydrate product overlap with the bulky OH groups, generating steric strain and decreasing stability. An aldehyde, on the other hand, has at the most one alkyl group bonded to the carbonyl carbon, so both these steric effects are diminished. However, this is not the case in cyclopropanone.

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Deducing the Peactants Can the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants, in one step, by moderately heating the reactants? ? Δ If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in any arrangement you like. If your answer is no, check the box under the drawing area instead. Explanation Check Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center X

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