Primary alcohols organometallic reagent

Grignard reagents react with ethylene oxide to yield primary alcohols containing two more carbon atoms than the alkyl halide from which the organometallic compound was prepared... 

Primary and tertiary alcohols are obtained conveniently from esters by the reduction of LiAlH4 and two molar equivalents of organometallic reagents (R MgX or R Li), respectively (see Sections 5.7.22 and 5.5.5). A less powerful reducing agent, diisobutylaluminium hydride (DIBAH), reduce an ester to an aldehyde (see Section 5.7.22). 

Addition of organometallic reagent to formaldehyde preparation of primary alcohols... 

The reaction of an organometallic reagent with formaldehyde produces a primary alcohol ... 

Perhaps the greatest use of organometallic compounds is in the transfer of alkyl groups to carbon atoms that are bound in organic molecules. For example, the reaction of a Grignard reagent with a primary alcohol can be shown as... 

The dialkylzinc additions catalyzed by N,N-di-n-alkylnorephedrines (most typically DBNE) are not limited to primary organometallic reagents. Diisopropylzinc (with a secondary alkyl substituent) adds to benzaldehyde in the presence of a catalytic amount of DBNE to afford the corresponding alcohol with high ee (entry 4). The reaction of diisopropylzinc in the presence of other types of catalysts may result in the reduction of aldehydes. 

The irreversible addition of organometallic reagents and metal hydrides provides a simple synthesis of primary, secondary, and tertiary alcohols. But you have to be careful to choose your reagents properly, so that the desired substitution pattern is achieved. 

How many different poly(organophosphazenes) are accessible by this synthesis route Taking into account the available alcohols, phenols, primary and secondary amines, and organometallic reagents, it seems clear that the phosphazene homopolymers accessible by known synthesis routes rival in numbers all the known organic polymers. 

The synthetic method (b) combines the formation of a primary or secondary alkynol [from formaldehyde or an aldehyde respectively and an organometallic acetylenic reagent (Section 5.4.2, p. 532)] with the semihydrogenation of the triple bond to a double bond. As noted in Section 5.2.2, p. 493, appropriate selection of catalyst is necessary in the hydrogenation step to ensure the formation of either the ( )- or the (Z)-isomer. The specific formation of the allylic alcohol, CH2=CH-CH(OH),R, is from a vinylmagnesium halide (Expt 6.41) and an aldehyde. 

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