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Ch. 19 - Amines
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728당신이 사용하는 게 아니라요?교과서 변경
모든 교과서Wade 9th EditionCh. 19 - Amines문제 33d
19장, 문제 33d

Rank the amines in each set in order of increasing basicity.
(d)

검증된 단계별 안내
1
Step 1: Analyze the chemical structures provided. The three amines are aniline derivatives, each with a substituent on the benzene ring: (a) aniline (NH₂ group attached to benzene), (b) methyl-substituted aniline (CH₃ group attached to benzene), and (c) nitro-substituted aniline (NO₂ group attached to benzene).
Step 2: Understand the effect of substituents on the basicity of the amine group. Substituents can either donate or withdraw electron density from the benzene ring, which affects the availability of the lone pair on the nitrogen atom for protonation.
Step 3: Evaluate the electron-donating or electron-withdrawing nature of each substituent. The methyl group (CH₃) is an electron-donating group via hyperconjugation and inductive effects, increasing the electron density on the nitrogen atom and enhancing basicity. The nitro group (NO₂) is a strong electron-withdrawing group due to resonance and inductive effects, decreasing the electron density on the nitrogen atom and reducing basicity.
Step 4: Rank the amines based on their substituents' effects. The unsubstituted aniline (NH₂ group only) has intermediate basicity. The methyl-substituted aniline is more basic due to the electron-donating effect of the CH₃ group. The nitro-substituted aniline is the least basic due to the electron-withdrawing effect of the NO₂ group.
Step 5: Final ranking in order of increasing basicity: Nitro-substituted aniline < Unsubstituted aniline < Methyl-substituted aniline.

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주요 개념

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Basicity of Amines

Basicity in amines refers to their ability to accept protons (H+) in a chemical reaction. This property is influenced by the availability of the lone pair of electrons on the nitrogen atom, which can bond with protons. Factors such as steric hindrance and the presence of electron-donating or withdrawing groups can significantly affect the basicity of different amines.
추천 영상:
07:12
Reductive Amination

Inductive Effect

The inductive effect describes how the presence of electronegative atoms or groups near the amine can influence its basicity. Electron-withdrawing groups decrease basicity by stabilizing the lone pair on nitrogen, making it less available for protonation. Conversely, electron-donating groups enhance basicity by increasing electron density on nitrogen, facilitating proton acceptance.
추천 영상:
01:47
Understanding the Inductive Effect.

Steric Hindrance

Steric hindrance refers to the repulsion between atoms due to their physical size, which can impede the approach of protons to the nitrogen atom in amines. In bulky amines, steric hindrance can reduce basicity as the nitrogen's lone pair becomes less accessible for bonding with protons. Understanding steric effects is crucial for ranking amines based on their basicity.
추천 영상:
02:53
Understanding steric effects.
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Within each structure, rank the indicated nitrogens by increasing basicity.

(a)

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