Carboxylic acid derivatives reactions with organometallic reagents

The reactions of several carboxylic acid derivatives with organomagnesium and organolithium compounds were described in Section 14-12. The key step in these reactions is addition of the organometallic compound, as R60MS , to the carbonyl group. For a Grignard reagent,... 

Predict the products and propose mechanisms for the reactions of carboxylic acid derivatives with reducing agents, alcohols, amines, and organometallic reagents. Q Propose multistep syntheses using acid derivatives as starting materials and intermediates. 

Reaction of organometallic reagents with carboxylic acid derivatives... 

Reaction of Organometallic Reagents with Carboxylic Acid Derivatives... 

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. 

A diazonium salt reacts with copper(I) cyanide to form a benzonitrile. Because a cyano group can be hydrolyzed to a carboxylic acid, reduced to an amine or aldehyde, or converted to a ketone with organometallic reagents, this reaction provides easy access to a wide variety of benzene derivatives using chemistry described in Section 22.18. 

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... 

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