Nucleophilic Addition to the Carbonyl Group

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Presentation transcript:

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