Consider the following compounds: (1) C6 H5-NH2 (2) C6 H5-NH-C6 H5 (3) (C6 H5)3 N (4) CH3-CH2-N

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Consider the following compounds: (1) C6 H5-NH2 (2) C6...

Consider the following compounds: (1) $\mathrm{C}_6 \mathrm{H}_5-\mathrm{NH}_2$ (2) $\mathrm{C}_6 \mathrm{H}_5-\mathrm{NH}-\mathrm{C}_6 \mathrm{H}_5$ (3) $\left(\mathrm{C}_6 \mathrm{H}_5\right)_3 \mathrm{~N}$ (4) $\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{NH}_2$ Arrange these compounds in decreasing order of their basicity. (a) $1>2>3>4$ (b) $2>3>1>4$ (c) $3>2>1>4$ (d) $4>1>2>3$

Consider the following compounds:
(1) $\mathrm{C}_6 \mathrm{H}_5-\mathrm{NH}_2$
(2) $\mathrm{C}_6 \mathrm{H}_5-\mathrm{NH}-\mathrm{C}_6 \mathrm{H}_5$
(3) $\left(\mathrm{C}_6 \mathrm{H}_5\right)_3 \mathrm{~N}$
(4) $\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{NH}_2$

Arrange these compounds in decreasing order of their basicity.
(a) $1>2>3>4$
(b) $2>3>1>4$
(c) $3>2>1>4$
(d) $4>1>2>3$

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Key Concepts

Resonance Effects on Basicity

Resonance effects involve the delocalization of the nitrogen lone pair into adjacent ? systems, such as aromatic rings. This delocalization reduces the electron density available on the nitrogen for protonation, thereby decreasing the basicity of the amine.

Inductive Effects

Inductive effects arise from the transmission of electron density through sigma bonds due to the presence of electron-donating or electron-withdrawing groups attached to the amine. Electron-donating groups increase the electron density at the nitrogen, enhancing basicity, while electron-withdrawing groups have the opposite effect.

Basicity of Amines

Basicity in amines refers to the ability of the nitrogen atom to donate its lone pair of electrons to bond with a proton. The extent of this donation is influenced by various structural and electronic factors, which are key to understanding how different amines behave when subjected to protonation.

Steric Hindrance

Steric hindrance refers to the impact of bulky groups around the nitrogen atom, which can physically obstruct the approach of protons or other electrophiles. This spatial congestion can adversely affect the ability of the amine to react, thus reducing its effective basicity.

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