1. Hydrolysis of Acid Derivatives
Acid chlorides and anhydrides
Y = Cl or OCOR - room temperature
USUALLY UNWANTED SIDE REACTIONS

2. Hydrolysis of Esters and Amides
Require acid or base catalyst and heat
ESTERS - REVIEW SAPONIFICATION
AMIDES - 6M HCl or 40% NaOH and prolonged heating
DEPROTECTION OF ACETANILDES

3. Cyclic compounds
RNH2 +
Phthalic acid

4. Reactions of Cyclic Anhydrides with ROH
Half Acid

5. Lactones with ROH & Amines
HO-(CH2)4COOR
HO-(CH2)4CONHR

6. Reduction Reactions RCO2R RCH2OH LAH
Recall Reduction of amides to give amines
Acid chlorides to aldehydes

7. Look over carefully: Summary of the Chemistry of Acid Chlorides
1) Synthesis - acid + SOCl2
2) Reactions
a. Conversion to all other acid derivatives: NO catalyst
b. Rx with organmetallics (p. 977)
RMgX or RLi ----> alcohols
LAH ---> primary alcohols
R2CuLi >
ketones
Li(t-BuO)3H >
aldehyde
Friedel-Acylation (AlCl3)

8. Acid Anhydrides
1. Preparation - from acid chlorides and carboxylic acids
2. Reactions
1. Conversion to less reactive acid derivatives No Catalyst
2. Friedel-Craft Acylations - catalyst required +
NOTE above: One part of anhydride adds to ring: the other is
sacrificed

9. Mechanism of FC THINK OF THE MECHANISM AS A TYPICAL ACID
CATALYZED ADDITION-ELIMINATION MECHANISM
OF NUCLEOPHILIC ACYL SUBSTITUTION Y Y Y
ELIMINATION
ADDITION
Think of AlCl3 as big proton!!!!! IT IS E+
WHAT IS Y?
WHERE DOES E+ (AlCl3) ADD?
The C=O oxygen
WHICH IS NUKE?
ELECTRON PAIR ON AROMATIC RING

10. ACTUAL MECHANISM
AlCl3 - -

11. Please don’t do problem 31a, but please do problem 32c

12. Chapter 22 Alpha Substitutions and Condensations of Enols and Enolate Ions
Actually this the chemistry of a-hydrogen atoms
enolate ion
Aldehydes, ketones and esters
IMPORTANT: enolate is a nuke; attacks via of its alpha carbon

13. Reactions of Enolates with Electrophiles

14. ALDOL REACTION - Borodin

15. C

16. EXAMPLES Dangle the group attached to alpha carbon nuke portion
electrophilic portion

17. MECHANISM OF ALDOL REACTION+ H