Neutral Nucleophilic Addition

Steps of Nucleophilic Addition with Nitrogen

1. Protonate carbonyl

2. Nucleophilic addition

3. Proton Transfer

4. Proton Transfer

5. Pi donation

6. Deprotonation

draw the mechanism for imine formation

Usually protonation is first step

draw the mechanism for enamine formation

Usually protonation is first step

Steps of Nucleophilic Addition with Oxygen or Sulfur

1. Protonate carbonyl

2. Nucleophilic addition

3. Proton Transfer

4. Proton Transfer

5. Pi donation

6. Nucleophilic addition

7. Deprotonation

draw the mechanism for acetal formation

reaction of acetone with HSCH2CH2SH, H+

thioacetal

how to remove an acetal protecting group

H+, H2O

how to remove a thioacetal protecting group

Hg+2, H2O

How do you drive the reversible acetal formation to product?

Le Chatelier:

Remove product (water)

Product of a Grignard (CH3CH2MgBr) with nitrile (CH3CN)?

Product of ketone with methylamine, H+, NaCNBH3

Hydrolysis of an imine

Stork Enamine Reaction