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α-Alkylation of Ketones via Enolate Ions

α-Alkylation of Ketones via Enolate Ions

Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the strong interaction...

Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction

Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction

The reaction between two different carbonyl compounds comprising α hydrogen in the presence of a strong base like lithium diisopropylamide (LDA) to form a crossed aldol product is known as a directed aldol reaction. The directed aldol reaction is depicted in Figure 1.

Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

Acid Halides to Ketones: Gilman Reagent

Acid Halides to Ketones: Gilman Reagent

Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

Preparation of 1° Amines: Azide Synthesis

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...

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Related Experiment Video

Updated: Jul 16, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

Published on: November 12, 2016

Lithium diisopropylamide: solution kinetics and implications for organic synthesis.

David B Collum¹, Anne J McNeil, Antonio Ramirez

¹Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, NY 14853-1301, USA. dbc6@cornell.edu

Angewandte Chemie (International Ed. in English)

|March 28, 2007

Summary

Lithium diisopropylamide (LDA) is key in organic synthesis. This review details LDA reaction kinetics, solvation, aggregation, and mechanisms to optimize yields and selectivity in organolithium chemistry.

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Area of Science:

Organic Chemistry
Physical Chemistry
Chemical Kinetics

Background:

Lithium diisopropylamide (LDA) is a widely used reagent in organic synthesis.
Understanding the kinetics and mechanisms of LDA-mediated reactions is crucial for optimizing synthetic outcomes.

Purpose of the Study:

To review rate studies of LDA-mediated reactions within the broader context of organic synthesis.
To provide insights into solvation and aggregation effects on reaction kinetics.
To guide the optimization of yields, rates, and selectivities in organolithium reactions.

Main Methods:

Analysis of solution kinetics, focusing on solvation and aggregation effects.
Summarization of substrate- and solvent-dependent reaction mechanisms.
Integration of mechanistic understanding with empirical methods for optimization.

Main Results:

Detailed explanation of characteristic rate behavior in LDA reactions due to solvation and aggregation.
Elucidation of basic principles governing solvation and aggregation in these systems.
Demonstration of how mechanistic insights can improve organolithium reaction performance.

Conclusions:

A comprehensive understanding of LDA reaction kinetics and mechanisms is essential for effective organic synthesis.
Solvation and aggregation are dominant factors influencing LDA reaction rates.
Combining mechanistic knowledge with empirical methods offers a pathway to optimize LDA-mediated transformations.