For each of the following pairs, predict which substance is more soluble in water. (a) CH3CH2NH2 or NH3 (b) (CH3)3COH or CH3(CH2)5OH (c) CH3CH2CH2OH or CH3CH2CH2CH3 (d) CH3CH2CN or CH3CH2OCH3 (e) CH3CH2OH or CH3CH2CH2OH (f) CH3CH2OCH3 or CH3CH2CO2H

For each of the following pairs, predict which substance is more soluble in water. (a) CH3CH2NH2 or NH3 (b) (CH3)3COH or CH3(CH2)5OH (c) CH3CH2CH2OH or CH3CH2CH2CH3 (d) CH3CH2CN or CH3CH2OCH3 (e) CH3CH2OH or CH3CH2CH2OH (f) CH3CH2OCH3 or CH3CH2CO2H

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter5: Alkenes: Bonding, Nomenclature, And Properties

Section: Chapter Questions

Problem 5.16P

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Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

For each of the following pairs, predict which substance is more soluble in water.

(a)

CH₃CH₂NH₂ or NH₃

(b)

(CH₃)₃COH or CH₃(CH₂)₅OH

(c)

CH₃CH₂CH₂OH or CH₃CH₂CH₂CH₃

(d)

CH₃CH₂CN or CH₃CH₂OCH₃

(e)

CH₃CH₂OH or CH₃CH₂CH₂OH

(f)

CH₃CH₂OCH₃ or CH₃CH₂CO₂H

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