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Chapter 25: PROBLEM 25.19 (page 1017)

Question: Which compound in each pair is more basic:

a. CH32NHandNH3

b. CH3CH2NH2andClCH2CH2NH2 ?

Short Answer

Expert verified

Answer

a.CH32NH

b.CH3CH2NH2

Step by step solution

01

Basicity of amines

Primary 1°,2°and3°alkylamines are more basic than NH3 because of the electron-donating inductive effect of the R groups. The alkyl groups increase the electron density at the nitrogen.Therefore, the electrons at the nitrogen become freer to donate.

02

Explanation

a.CH32NHis a more basic compound because it has two methyl groups bonded to the nitrogen atom.

NH3is not bonded with an alkyl group.

b. CH3CH2NH2is a more basic compound because it has an ethyl group bonded to the nitrogen atom.

ClCH2CH2NH2is bonded with the Cl group, which is an electronegative atom. Therefore, theClCH2CH2NH2compound is less basic.

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