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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!. K 2 Cr 2 O 7 , special cond.
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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
2o alcohol K2Cr2O7, etc. ketone acid chloride + ArH AlCl3 acid chloride + R2CuLi