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Chapter 12
Aldehydes and Ketones

Structures of Aldehydes and Ketones
Vanillin—a flavoring agent in vanilla, cinnamaldehyde—a molecule responsible for the distinct smell of cinnamon, and acetone—a…
IUPAC Nomenclature of Aldehydes
Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the…
IUPAC Nomenclature of Ketones
Like aldehydes, ketones are named using IUPAC rules; in this case, by replacing “e” in the name of the longest hydrocarbon chain with…
Common Names of Aldehydes and Ketones
Some common aldehydes and ketones are popularly known by their common names used historically and predate the IUPAC…
IR and UV–Vis Spectroscopy of Aldehydes and Ketones
Infrared spectroscopy, also known as vibrational spectroscopy, is mainly used to determine the types of bonds and functional groups in molecules. In…
NMR Spectroscopy and Mass Spectrometry of Aldehydes and Ketones
In aldehydes, the hydrogen atom connected to the carbonyl carbon helps distinguish aldehydes from other carbonyl compounds using ¹H NMR…
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes
Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used…
Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids
Although it is possible to reduce a carboxylic acid to an aldehyde, strong reducing agents, like lithium aluminum hydride (LAH), prohibit a…
Preparation of Aldehydes and Ketones from Carboxylic Acid Derivatives
Aldehydes are more reactive than carboxylic acids and hence, can get over-reduced to alcohol in the presence of strong reducing agents. Therefore,…
Nucleophilic Addition to the Carbonyl Group: General Mechanism
The carbonyl carbon in an aldehyde or ketone is the site of a nucleophilic attack due to its electron-deficient nature. Depending on the strength of…
Aldehydes and Ketones with Water: Hydrate Formation
An oxygen-based nucleophile, like water, can undergo addition reactions with aldehydes and ketones. The reaction leads to the formation of hydrates,…
Aldehydes and Ketones with Alcohols: Hemiacetal Formation
Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl…
Protecting Groups for Aldehydes and Ketones: Introduction
Protecting groups are compounds that can bind to a specific functional group in the presence of other functional groups to protect them from…
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases,…
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the…
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism
Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes…
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview
The Wittig reaction is the conversion of carbonyl compounds—aldehydes and ketones—to alkenes using phosphorus ylides, or the Wittig…
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic…
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named…
Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of…
Aldehydes and Ketones with Amines: Enamine Formation Mechanism
Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the…
Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction
Wolff–Kishner reduction involves converting aldehydes and ketones to alkanes using hydrazine and a base. The reaction converts a carbonyl group…
Oxidations of Aldehydes and Ketones to Carboxylic Acids
Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily…
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…
Keto–Enol Tautomerism: Mechanism
The keto and enol forms are known as tautomers and they constantly interconvert (or tautomerize) between the two forms under acid or base catalyzed…
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
α-Functionalization of ketones via umpolung of enolates by hypervalent iodine reagents is an important concept in synthetic organic chemistry.…
Determination of Carbonyl Functional Groups in Bio-oils by Potentiometric Titration: The Faix Method
Carbonyl compounds present in bio-oils are known to be responsible for bio-oil property changes upon storage and during upgrading. Specifically,…
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Heteroarylation introduces heteroaryl fragments to organic molecules. Despite the numerous available reactions reported for arylation via transition…

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