1. Acid Halides from Carboxylic Acids

2. Synthesis of Acid Halides
SOCl2 = thionyl chloride
PCl5 can also be used

3. Problems Give the major product for the following reaction:
Draw the products you would get from reacting the following molecule with PCl5. What product would you obtain from reacting it with PBr3?

4. Anhydrides from Carboxylic acids
Anhydride = “without water”
20.9 Conversion of Carboxylic Acids into Acid Chlorides and Anhydrides

6. Problem
The second reaction on the previous page happens through a nucleophilic acyl substitution reaction. Draw the mechanism.
What product might you get upon heating of succinic acid?

7. Reduction of Carboxylic Acids
The powerful reducing agent LiAlH4 is required
NaBH4 does not reduce carboxylic acids
The overall sequence for reduction is summarized as:
20.10 Reduction of Carboxylic Acids to Primary Alcohols

8. Problems
Draw the reactant that forms the following product upon reduction with lithium aluminum hydride:
How might you prepare 2-phenylehtanol from benzyl bromide? More than one step is necessary.

9. Decarboxylation of Carboxylic Acids
Decarboxylation: The loss of CO2 from RCO2H
Most ordinary carboxylic acids do not participate, but the following types do:
1. b-keto acids
2. Malonic acid derivatives (diacids)
3. Carbonic acid derivatives
20.11 Decarboxylation of Carboxylic Acids

10. Decarboxylation from b-keto acids
20.11 Decarboxylation of Carboxylic Acids

11. Decarboxylation from Malonic Acid Derivatives
This reaction also does not occur in base

12. Decarboxylation of Carboxylic Acids
Decarboxylation from carbonic acid derivatives

13. Problems
Give the products for the following reactions:

14. Draw the mechanism for the decarboxylation reaction below: