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I'm currently reading the Examkrackers 2015 Chemistry book(page. 100) and the mechanism for imine/enamine formation begins with the amine attacking the carbonyl carbon of the aldehyde/ketone as the first step. When i've looked up the mechanism on other sites, the first step of imine/enamine formation is protonation of the carbonyl oxygen THEN the amine attacking.
I'm not sure which mechanism is correct because the MCAT THINK question right below the mechanism states: What would happen if an acid catalyst were added at the beginning of the reaction instead of after the first reaction(amine attacking the carbonyl oxygen) had occurred? The explanation they provided was that the amine would be protonated and will no longer act as a nucleophile.
I'm not sure which mechanism is correct because the MCAT THINK question right below the mechanism states: What would happen if an acid catalyst were added at the beginning of the reaction instead of after the first reaction(amine attacking the carbonyl oxygen) had occurred? The explanation they provided was that the amine would be protonated and will no longer act as a nucleophile.