This is the worksheet I created for my study group in preparation for their second midterm (Summer 2016).

1. Shashank Patil
Chem 3B Study Group
OH: Mon/Wed 1-2PM
shashankpatil@berkeley.edu
June 27, 2016
Worksheet 14: MT2 Review
1. Show the mechanism for the two steps & name the three molecules:
2. Carbonyls as Electrophiles
A. Circle the site at which 1,2 nucleophiles will attack. Box the site at which 1,4
nucleophiles will attack. What is the generic name of this molecule?
B. Are 1,2 nucleophilic attacks or 1,4 nucleophilic attacks reversible? Why?
C. Show a logical arrow pushing mechanism for the following:
D. Which mechanism & final product is more likely? Why?

2. 3. Carbonyls  Enols/Enolates act as nucleophiles
A. Aldol Condensation: Show Mechanism (Know the reverse mechanism as well!)
B. Michael (Conjugate) Addition: Show Mechanism [Analogous to Aldol]
1,5 dicarbonyl product
C. Robinson Annulation: Show mechanism [Analagous to Aldol Condensation]
4. Show a logical arrow pushing mechanism.
A. Enamine Chemistry (Recall: Enamines made from Secondary Amines + Carbonyls!)
D

3. B. Hidden Carbonyls & Analogous Hemiacetal/Acetal Chemistry
5. Bonus Mechanism: (One of Pete’s problems from class)
Final Points
- Be comfortable with naming generic molecules:
o Imines, Enamine, Imminium ions, Acetal, Hemiacetal, Aldol (= Beta hydroxyl
Carbonyl), Alpha-beta unsaturated carbonyl, 1,5 dicarbonyls, hydrates
- Review Sugar Chemistry Nomenclature
o Recall Sugar Chemistry is Hemiacetal Chemistry
- Know the mechanism of all reversible reactions
o Protecting Groups (Acetal Chemistry), Hydration/Dehydration, Cyanohydrin
Formation/Removal, etc.
- Focus on understanding the concepts & using intuition/logic to get to the answer
o DO NOT just MEMORIZE reactions
- Relax & Get Enough Sleep: DON’T CRAM! (I’m talking to YOU)
o You’ll do great! ☺