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ِFormation of New C-C for Aldhydes and ketones

To understand this simple reaction try to convert Acetone into t-butyl alcohol.

Organometalic nucleophile usage

Examples of organometallic reagent: R-Li , Grignard reagent.

As you see you can add what ever group you need R to the carbonyl by adding it to lithium which make it suitable nucleophile (HOMO) to attack carbonyl group (LUMO).

Mechanism:

Li–C as we know metals are positive so Li+ – C here carbon referes to the group with lithium ex: Me , Ph , …

when carbon bound to electropositive metal the sigma bond is nucleophile (types of nucleophile) so it attacks the carbonyl group at C due to its partial positive chrage formed. After attack alkoxide is formed so we use water as solvent to protonate this oxygen as we did in cyanide (see.) to form an alcohol with the new added group.

Grignard reagent:

C–Mg–X

Mg in ether can eract with alkyl halide or halobenzne making what is know by grignard reagent:

CH3–Cl + Mg —–> CH3 – MgCl

Ph–Br + Mg —–> Ph – MgBr

These are called grignard reagents.

ph bound to electropositive element then the sigma bon is nucleophile that will attack carbonyl group leading to formation of alkoxide which then needs water to be protonated.

Note:

Water reacts with organometalic compounds making alkanes so we add water seperatelt in second step after grignard reagent reacts with carbonyl. Adding of water in seperate step secondly is refered by word workup.

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