Nucleophilic Addition to the Carbonyl Group Aldehydes and Ketones Nucleophilic Addition to the Carbonyl Group
A. Aldehyde 1. Oxidation of primary alcohols PDC: Pyridinium Chlorochromate C5H5NHCrO3Cl
2. Reduction of acid chloride 3. Oxidation of methylaromatics Aromatic aldehydes only!
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
B. Ketone 1. Oxidation of secondary alcohols 2. Friedel-Crafts acylation Aromatic ketones (phenones) only
3. Coupling of RCOCl and R2CuLi
2o alcohol K2Cr2O7, etc. ketone acid chloride + ArH AlCl3 acid chloride + R2CuLi