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C–C Bond Cleavage: Retro-Aldol Reaction

C–C Bond Cleavage: Retro-Aldol Reaction

The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.

Crossed Aldol Reaction Using Weak Bases

Crossed Aldol Reaction Using Weak Bases

This lesson deals with the crossed aldol reaction using weak bases. The self-condensation of an aldehyde having α hydrogen is prevented by adding it slowly to a mixture of formaldehyde and weak bases like hydroxide and alkoxide. Upon slow addition of the aldehyde, the base deprotonates the α carbon of the aldehyde to form the corresponding enolate. The enolate subsequently attacks the formaldehyde to form a single crossed product. Figure 1 depicts the aforementioned reaction.

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.

Radical Substitution: Allylic Bromination

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is activated by...

Crossed Aldol Reactions: Overview

Crossed Aldol Reactions: Overview

Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.

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Updated: Jun 1, 2026

Environmental Modulations of the Number of Midbrain Dopamine Neurons in Adult Mice

Environmental Modulations of the Number of Midbrain Dopamine Neurons in Adult Mice

Published on: January 20, 2015

β-d-Altrose.

Yuji Watanabe, Hiromi Yoshida, Kosei Takeda

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

This study details the crystal structure of a glucose molecule, revealing its chair conformation and extensive hydrogen bonding network. The molecule forms helical chains through intermolecular interactions, contributing to its solid-state arrangement.

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A Strategy for Sensitive, Large Scale Quantitative Metabolomics

A Strategy for Sensitive, Large Scale Quantitative Metabolomics

Published on: May 27, 2014

Area of Science:

Carbohydrate Chemistry
Crystallography
Supramolecular Chemistry

Background:

Understanding the solid-state structure of simple carbohydrates like glucose is fundamental in chemistry and biology.
The hydrogen bonding patterns in carbohydrates dictate their physical properties and biological functions.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(6)H(12)O(6) ((2R,3S,4R,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol).
To analyze the hydrogen bonding interactions and supramolecular assembly in the crystalline state.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of intermolecular O-H⋯O interactions was performed to characterize the hydrogen bonding network.

Main Results:

The glucose molecule adopts a (4)C(1) chair conformation with the anomeric hydroxyl group in an equatorial position.
Ten intermolecular O-H⋯O hydrogen bonds were identified, involving all hydroxyl groups.
Two independent helical chains along the z-axis were formed through these hydrogen bonding interactions.

Conclusions:

The study provides detailed insights into the hydrogen bonding and packing of glucose in the solid state.
The observed helical structures highlight the self-assembly capabilities of monosaccharides through directional intermolecular forces.