Decide on the mechanism for each substitution, and then pick the solvent that affords the faster reaction. a.(CH3CH2)2CClCH3 + CH3OH in CH3OH or DMSO b.CH3CH2CH2Br + −OH in H2O or c. DMF (CH3CH2)2CHCl + CH3O− in CH3OH or HMPA

Q: NH, 1) CI 2) Br, (might also require catalytic FeBr3) 3) H300 NH2 [H°] + NABH3CN

A:

Q: 1. Br2./ NAOH i) CH3-CH2-C-NH2 2. H20 NO 2 CN HN CH3 CN fH3 CHNH2 OH k.

A:

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Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.