Ketones organolithium reagent reacting with

Organolithium reagents react with aldehydes and ketones in a manner similar to that of Grignard reagents to form alcohols... 

Both Grignard and organolithium reagents react with nitriles to form ketones with a new carbon-carbon bond. 

Organolithium reagents react with carboxylic acids to give ketones. 

Grignard reagents and organolithium reagents react with nitriles to give imine anions, but aqueous acid hydrolysis usually converts the imine anion to a ketone as the final product. Peroxyacids react with ketones to give esters in the Baeyer-Villiger reaction. 

Finally, organolithium reagents react with nitriles to give the imine, just as all the other carbon nucleophiles discussed in this section. If butyllithium reacts with 141, the product is butyl cyclopropyl ketone after acid hydrolysis. 

Organolithium Reagent Reacting with a Ketone (Section 16.5B)... 

The main synthetic application of Grignard and organolithium reagents is their reaction with carbonyl-containing compounds to produce alcohols. Carbon-carbon bond formation is rapid and exothermic when Grignard and organolithium reagents react with an aldehyde or ketone. 

Organolithium reagents reacts just like Grignard reagents. For example, reaction with aldehydes and ketones proceeds by nucleophilic addition to yield secondary and tertiary alcohols respectively. 

The real value of this acid-base reaction is to transform a weak acid into an anion by using a powerful base the organolithium reagent. Such anions behave as nucleophiles in various reactions. In Chapter 11 (Section 11.3.6), alkyne anions underwent Sn2 reactions with alkyl halides. In Chapter 18 (Section 18.3.2), alkyne anions react with aldehydes and ketones. Both Grignard reagents and organolithium reagents react as nucleophiles with aldehydes and ketones (also described in Chapter 18, Section 18.4). Lithium amides such as 45 react as bases with aldehydes or ketones in Chapter 22 (Section 22.3). Many such examples are discussed in this book. 

Grignard reagents and organolithium reagents react as carban-ions with aldehydes and ketones to give alcohols in a two-step process (1) acyl addition and (2) hydrolysis. The organometallic reagent reacts as a nucleophile with epoxides at the less substituted carbon atom. 

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