Sign In

Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.

Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering this, specific reaction conditions, such as excess ammonia, must be used to exclusively make primary amines.

Since tertiary halides are more hindered, they are not the substrates of choice for alkylation reactions. Although secondary alkyl halides are far less hindered and can be alkylated, they are also not preferred as substrates due to their tendency to undergo elimination reactions.

Since ammonia is cheaply available, alkylations using ammonia as the substrate are the most common.

Tags
Amine PreparationAlkylationAmmonia AlkylationAmine AlkylationSN2 ReactionQuaternary Ammonium SaltExhaustive AlkylationNucleophilicityPrimary AmineTertiary HalideSecondary Alkyl HalideElimination ReactionAmmonia Substrate

From Chapter 19:

article

Now Playing

19.12 : Preparation of Amines: Alkylation of Ammonia and Amines

Amines

3.1K Views

article

19.1 : الأمينات: مقدمة

Amines

4.0K Views

article

19.2 : تسمية الأمينات الأولية

Amines

3.2K Views

article

19.3 : تسمية الأمينات الثانوية والثالثية

Amines

3.5K Views

article

19.4 : تسمية الأمينات الحلقية غير المتجانسة

Amines

2.2K Views

article

19.5 : هيكل الأمينات

Amines

2.3K Views

article

19.6 : الخصائص الفيزيائية للأمينات

Amines

2.8K Views

article

19.7 : أساسيات الأمينات الأليفاتية

Amines

5.5K Views

article

19.8 : أساسيات الأمينات العطرية

Amines

6.9K Views

article

19.9 : أساسيات الأمينات العطرية غير المتجانسة

Amines

5.3K Views

article

19.10 : التحليل الطيفي بالرنين المغناطيسي النووي للأمينات

Amines

8.1K Views

article

19.11 : قياس الطيف الكتلي للأمينات

Amines

4.0K Views

article

19.13 : تحضير 1 ° الأمينات: تخليق الأزيد

Amines

3.7K Views

article

19.14 : تحضير 1 ° أمين: Gabriel Synthesis

Amines

3.4K Views

article

19.15 : تحضير الأمينات: تقليل الأوكسيم ومركبات النيترو

Amines

3.2K Views

See More

JoVE Logo

Privacy

Terms of Use

Policies

Research

Education

ABOUT JoVE

Copyright © 2025 MyJoVE Corporation. All rights reserved