The two most generally used compounds of this type are alkyl lithium reagents and Grignard reagents. They are ready from alkyl and aryl halides, as discussed previous. These reagents are powerful nucleophiles and extremely strong bases (pKa's of saturated hydrocarbons range from 42 to 50), therefore they bond readily to carbonyl carbon atoms, giving alkoxide salts of the lithium or magnesium. Due to their ring strain, epoxides go through many carbonyl-like reactions, as noticed previously. Reactions of such type are among the most significant synthetic techniques available to chemists, because they allow simple starting compounds to be joined to form more complex structures. Instances are displayed in the diagram below.
A common example, displayed in the shaded box at the top is observed in all these reactions. Organometallic reagent is a source of a nucleophilic aryl or alkyl group (colored blue in the diagram), that bonds to the electrophilic carbon of the carbonyl group (colored magenta in the diagram). The result of this addition is a metal alkoxide salt and the alcohol result is produced from the weak acid hydrolysis of the salt. The first two illustrations display that water soluble magnesium or lithium salts are also produced in the hydrolysis but these are rarely listed among the products, like in the last four reactions. Ketones act with organometallic reagents to give 3º-alcohols; mainly aldehydes react to produce 2º-alcohols and formaldehyde and ethylene oxide react to form 1º-alcohols (instances no.5 & 6). When a chiral center is created from achiral reactants (instances no.1, 3 & 4) the product is all the time a racemic mixture of enantiomers.
Two additional instances of the addition of organometallic reagents to carbonyl compounds are informative. The first illustrates that active metal derivatives of terminal alkynes function in similar way like an alkyl lithium and Grignard reagents. The second instance again demonstrates the use of acetal protective groups in reactions with powerful nucleophiles. The Following acid-catalyzed hydrolysis of the acetal, the resulting 4-hydroxyaldehyde is in equilibrium with its cyclic hemiacetal.
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