1. Nucleophilic Addition to the Carbonyl Group
Aldehydes and Ketones
Nucleophilic Addition to
the Carbonyl Group

4. A. Aldehyde
1. Oxidation of primary alcohols
PDC: Pyridinium Chlorochromate C5H5NHCrO3Cl

5. 2. Reduction of acid chloride
3. Oxidation of methylaromatics
Aromatic aldehydes only!

6. K2Cr2O7, special cond.
or C5H5NHCrO3Cl
1o alcohol
Ar-CH3
Aromatic only
1. CrO3 /(AcO)2O
2. H2O/H+
aldehyde
acid chloride
LiAlH(O-t-Bu)3

7. B. Ketone
1. Oxidation of secondary alcohols
2. Friedel-Crafts acylation
Aromatic ketones (phenones) only

8. 3. Coupling of RCOCl and R2CuLi

9. 2o alcohol
K2Cr2O7, etc.
ketone
acid chloride + ArH
AlCl3
acid chloride + R2CuLi