Organometallic reagents reactions with carboxylic acid

Organometallic reagents react with carboxylic acid derivatives (RCOZ) to form two different products, depending on the identity of both the leaving group Z and the reagent R-M. The most useful reactions are carried out with esters and acid chlorides, forming either ketones or 3° alcohols. 

Q Predict the products and propose mechanisms for the reactions of carboxylic acids with reducing agents, alcohols, amines, and organometallic reagents. 

Reaction of organometallic reagents with carboxylic acid derivatives... 

Reaction of Organometallic Reagents with Carboxylic Acid Derivatives... 

This chapter will discuss methods for the preparation of esters, acid chlorides, anhydrides, and amides from carboxylic acids, based on acyl substitution reactions. Acyl substitution reactions of carboxylic acid derivatives will include hydrolysis, interconversion of one acid derivative into another, and reactions with strong nucleophiles such as organometallic reagents. In addition, the chemistry of dicarboxylic acid derivatives will be discussed, as well as cyclic esters, amides, and anhydrides. Sulfonic acid derivatives will be introduced as well as sulfate esters and phosphate esters. Finally, nitriles will be shown to be acid derivatives by virtue of their reactivity. 

Aldehydes and ketones have a central role in organic synthesis, and efficient procedures for their preparation are of great importance. Such compounds are synthesized in a number of ways, including hydration or hydroboration-oxidation of alkynes (Eqs. 16.10 and 16.11, respectively, and Chap. 11) and reaction of carboxylic acids or their derivatives with organometallic reagents or reducing agents... 

Nitriles are similar in some respects to carboxylic acids and are prepared either by SN2 reaction of an alkyl halide with cyanide ion or by dehydration of an amide. Nitriles undergo nucleophilic addition to the polar C=N bond in the same way that carbonyl compounds do. The most important reactions of nitriles are their hydrolysis to carboxylic acids, reduction to primary amines, and reaction with organometallic reagents to yield ketones. 

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