Organometallic Reagents for Alcohol Synthesis

We have already encountered one type of organometallic compound with a negative charge on carbon sodium acetylides, covered in Section 9-7. Terminal alkynes are weakly acidic, and they are converted to sodium acetylides by treatment with an unusually strong base, sodium amide. These sodium acetylides are useful nucleophiles, reacting with alkyl halides and carbonyl compounds to form new carbon-carbon bonds. 

Grignard reagents may be made from primary, secondary, and tertiary alkyl halides, as well as from vinyl and aryl halides. Alkyl iodides are the most reactive halides, followed by bromides and chlorides. Alkyl fluorides generally do not react 

Like magnesium, lithium reacts with alkyl halides, vinyl halides, and aryl halides to form organometallic compounds. Ether is not necessary for this reaction. Organolithium regents are made and used in a wide variety of solvents, including alkanes. 

The electrostatic potential map (EPM) of methyllithium is shown at left. The blue (electron-poor) color of the metal results from its partial positive charge, and the red (electron-rich) color of the methyl group shows its partial negative charge. 

Which of the following compounds are suitable solvents for Grignard reactions  

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Structure and Classification of Alcohols 425 10-3 Nomenclature of Alcohols and Phenols 427 10-4 Physical Properties of Alcohols 430 10-5 Commercially Important Alcohols 433 10-6 Acidity of Alcohols and Phenols 435 10-7 Synthesis of Alcohols Introduction and Review 438 Summary Previous Alcohol Syntheses 438 10-8 Organometallic Reagents for Alcohol Synthesis 440 10-9 Addition of Organometallic Reagents to Carbonyl Compounds 443... 

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