I put together this summary sheet for the reaction of nucleophiles with carbonyls (click for larger image, see link to downloadable PDF below). It summarizes the two key concepts that are important to understand for these reactions: the effect of electronic and steric factors on nucleophilic addition.





I enjoyed doing this and I’d like to put together more of these types of sheets in the future. If you have suggestions for future topics, leave a comment.
Summary Sheet: Addition to carbonyls (PDF)


 

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{ 7 comments… read them below or add one }

Heero Fong

For weakly deactivating it says:

Deactivating due to electronegativity but are pi-donors.

Maybe I am confused, but the halogens have high electronegativity which would withdraw electrons from the carbonyl making it more electropositive and actually activating it. So shouldn’t it say:

Activating due to electronegativity but are pi-donors?

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James

I see your point. The “deactivating due to electronegativity but are pi donors” statement refers to how halogen substituents affect electrophilic aromatic substitution, where halogens “deactivate” the ring. In the case of carbonyls, the electronegative substituents should activate the carbonyl toward nucleophilic attack, but pi donation in this case would be “deactivating”. Thanks for pointing this out.

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Heero Fong

Right. I got confused with the deactivating and activating because I thought this was in respect to the carbonyl group.

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Rongson Pongdee

Have you considered making a summary sheet for Substitution and Elimination Chemistry or Electrophilic Aromatic Substitution?

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Jillen

These sheet are amazing!! I have an exam on Wednesday and this will help me memorize the reactions! :D

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Logic

You’re disgusting…memorizing organic chemistry? Why do you even take it if you’re going to not understand the material and keep anything for yourself after the class is over?

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Damn...

how could you possibly be this rude about something that everyone must do in ochem. You think I fully understand what is being taught? No, of course not–I’m not the professor. Sometimes you need to memorize stuff to understand it asshat.

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