Acetal formation [ROH/H+]
Aldehydes and ketones can be converted into acetals and ketals when treated with alcohols and acids.
Aldehydes & Ketones
26 reactions in this topic, each with the reagents, the mechanism and the structure of the product.
Acetal hydrolysis [H3O+]
Addition of aqueous acid to acetals will transform them back into aldehydes or ketones. This is often referred to as “deprotection
Aldol addition reaction
The Aldol Addition Reaction is an addition of an enolate ion on an aldehyde or ketone to produce aldol.
Aldol Condensation
When heated in acidic or basic conditions, the product of an will undergo elimination to produce aldol addition reactionunsaturati
Alkylation of enolates
Enolates of carbonyl compounds will react with alkyl halides in SN2 reactions to give alkylation products.
Baeyer-Villiger Reaction
When treated with a peroxyacid (RCO3H), ketones can be converted into esters via the insertion of an oxygen atom. This transformat
Cannizzaro Reaction
When two moles of aldehyde is treated with sodium hydroxide, a reaction occurs in which one mole of aldehyde is oxidized (giving c
Clemmensen reduction to alkanes
Addition of zinc amalgam, Zn(Hg) and acid to a ketone results in an alkane. This is called the Clemmensen reduction.
Conversion to ketones [Gilman reagents]
Addition of organocuprates (Gilman reagents) to acid chlorides results in ketones.
Cyanohydrin formation [CN(–)]
When treated with hydrogen cyanide (HCN), aldehydes and ketones are converted into cyanohydrins which are characterized by the pre
Enamine formation [R2NH]
When ketones are treated with secondary amines and heated with an acid catalyst, a condensation reaction occurs, resulting in the
Enamine Hydrolysis
Treatment of enamines with water and aqueous acid leads to the formation of aldehydes or ketones and secondary amines.
Enolate formation
When treated with a strong base, the α position of a ketone or aldehyde is deprotonated to give a resonance-stabilized intermediat
Halogenation [Cl2, Br2, I2]
In the same way as alkenes, alkynes are also observed to undergo halogenation. The one major difference is that alkynes have two π
Hydrate formation [H2O]
Treatment of a carbonyl compound with H2O in the presence of acid or base catalyst adds the elements of H and OH across the carbon
Imine formation [RNH2]
The reaction of a primary amine with an aldehyde or ketone results in an imine and one equivalent of water.
Keto-Enol tautomerism
Ketones and other carbonyl compounds containing a hydrogen adjacent to the carbonyl are in the equilibrium with a constitutional i
Oxidation to carboxylic acid [H2CrO4 or KMnO4]
Chromium trioxide and water will oxidize aldehydes to carboxylic acids.
Oxidation to carboxylic acids [Tollens]
When Ag2O is added to aldehydes, carboxylic acids are formed. The results in the formation of silver metal (“silver mirror”) a rea
Reduction of aldehydes [LiAlH4]
Addition of lithium aluminum hydride to aldehydes leads to the formation of primary alcohols (after addition of acid).
Reduction of aldehydes [NaBH4]
Addition of sodium borohydride, NaBH4 to aldehydes gives primary alcohols (after adding acid).
Reduction of ketones [LiAlH4]
Addition of lithium aluminum hydride to ketones leads to the formation of secondary alcohols (after addition of acid).
Reduction of ketones [NaBH4]
Addition of sodium borohydride (NaBH4) to ketones gives secondary alcohols (after addition of acid).
Thioacetal formation
In analogy for the formation of acetals from alcohols and acid, treatment of aldehydes or ketones with thiols in the presence of a
Wittig reaction: alkene formation
The Wittig reaction is a useful way of forming alkenes from phosphorus ylides (Wittig reagents) and aldehydes or ketones.
Wolff-Kishner: reduction to alkanes
The Wolff-Kishner reduction is a reaction for converting carbonyls (such as aldehydes or ketones) into alkanes.