Neutral Nucleophilic Addition
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13 Terms
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
Note 
Flashcards (35)