L13 - Carbonyl Group Chemistry And Biochemistry
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Why are carbonyls reactive?
They are susceptible to nucleophilic attacks due to the dif in electronegativity
What are the steps in nucleophilic attacks in carbonyls?
• Nu- attacks the C in C=O • pi bond breaks, e- to O • tetrahedral intermediate • e- moves to reform db, LG leaves • stays as a 4 species if X isnt a LG
What can bases do to carbonyls?
Bases can attack the acidic proton - e- move to form db - e- move to break pi bond, to the O = enolate
What is more reactive between acyl chloride vs acid anhydride?
Acyl chloride is more reactive as Cl- better LG
What is more reactive between an aldehyde vs ketone?
Aldehyde - inductive effect is greater - less e- pushing towards delta+ C
What is more reactive between esters and amides?
Esters (Not v reactive due to mesomeric effects)
What can lead to rotamers?
Due to mesomeric effects - get some db in C-N bond that lead to rotamers
What is the rank order of reactivity of carbonyls?
Acyl chloride > acid anhydride > aldehyde > ketone > ester > amide