Acid chlorides ketones

Hydride reagents Aldehyde Ketone Acid chloride Ester Carboxyhc acid Carboxyhc salt Amide... 

Acids and esters (see Esters, organic) are less easily brominated than aldehydes or ketones. Acid chlorides and anhydrides are more easily brominated (23). 

However, the most important methods for preparing alcohols are catalytic hydrogenation (H2/Pd-C) or metal hydride (NaBH4 or LiAlH4) reduction of aldehydes, ketones, carboxylic acids, acid chlorides and esters (see Sections 5.7.15 and 5.7.16), and nucleophilic addition of organometalhc reagents (RLi and RMgX) to aldehydes, ketones, acid chlorides and esters (see Sections 5.3.2 and 5.5.5). 

R = -Bu, s-Bu, f-Bu E-X = aldehydes, ketones, acid chlorides, TosCN, PhMe2SiCl... 

Oxidative metabolism of alkyl chlorides, bromides and iodides is initiated primarily by insertion of an oxygen atom into an a-C—H bond. The geminal halohydrin product rapidly loses hydrogen halide to form a carbonyl compound (an aldehyde, ketone, acid chloride or carbonyl chloride, depending on substrate structure). 

LiInH4 is increased by the introduction of phenyl group(s) LiPhInH3 and LiPh2InH2 readily reduce aldehydes, ketones, acid chlorides, and even esters to the corresponding alcohols. Hydroxy ketones and diketones are reduced with lithium indium hydride to give meso-diols selectively. a-Hydroxy ketones and a-diketones are reduced to meso-1,2-diols with high diastereoselectivities, whereas the selectivities of /3-hydroxyketones and /3-diketones are less satisfactory.365... 

Alane (AIH3) and its derivatives have also been utilized in the reduction of carboxylic acids to primary alcohols. It rapidly reduces aldehydes, ketones, acid chlorides, lactones, esters, carboxylic acids and salts, tertiary amides, nitriles and epoxides. In contrast, nitro compounds and alkenes are slow to react. AIH3 is particularly useful for the chemoselective reduction of carboxylic acids containing halogen or nitro substituents, to produce the corresponding primary alcohols. DIBAL-H reduces aliphatic or aromatic carboxylic acids to produce either aldehydes (-75 °C) or primary alcohols (25 C) Aminoalu-minum hydrides are less reactive reagents and are superior for aldehyde synthesis. ... 

A particularly useful and high-yielding reaction is that between indoles and oxalyl chloride, which gives ketone-acid-chlorides convertible into a range of compounds, for example tryptamines a synthesis of serotonin utilised this reaction." " ... 

Microcrystalline white powder when pure gray when aluminum impurity present. Monoclinic crystals, d 0.92. Stable in dry air at room temperature, decomp above 125, slowly loses hydrogen at 120. decomp in moist air. may ignite on grinding in air. Solv (parts/100 parts solvent) 30 (ether) 13 (tetrahydrofuran) 10 (dimethylcellosolve) 2 (dibutyl ether) 0.1 (dioxane). Reacts rapidly with water and alcohols reduces aldehydes, ketones, acid chlorides and esters to alcohols nitriles to amines aromatic nitro compounds to azo compounds. Does noi at lack olefinic double bonds unless they are conjugated with a phenyl group and a carbonyl or nitrile group. 

Electrophilic substitution of the carbonyl compounds occurs the more easily the less the carbonyl group is stabilized by mesomerism. It is increasingly difficult in the series ketone — acid chloride — acid anhydride — ester, carboxylic acid — carboxyamide.546 This gradation can be illustrated by, for instance, the bromination of levulic acid (4-oxovaleric acid) with 2 moles... 

Reductions. Aldehydes, ketones, acid chlorides, carboxylic acids, and N-Boc amino acids are reduced to the corresponding alcohols, generally in excellent yields. The reduction of a,P-epoxy ketones gives alcohols without affecting the heterocycle. ... 

Uses Reducing agent for aldehydes, ketones, acid chlorides, lactones, epoxides, and esters source of hydrogen and borohydrides Manuf./Distrib. Alfa Aesar http //www.alfa.com, Chemetall Chem. Prods. http //www. chemetall. com Lithium bromide... 

The ease of the electrophilic a-bromination of carbonyl groups decreases with increasing mesomeric stabilization of the carbonyl ketone>acid chloride>acid anhydride>acid, ester>amide. However, -bromination of esters can be... 

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