Nucleophilic Addition and Reduction Reactions of Aldehydes and Ketones, Exams of Organic Chemistry

Download Nucleophilic Addition and Reduction Reactions of Aldehydes and Ketones and more Exams Organic Chemistry in PDF only on Docsity! Chapter 9 Rxn Summary (Aldehydes and Ketones) 1. Nucleophilic Addition a. Formation of Acetals CH3-C-CH3 O CH3OH H+ CH3-C-CH3 OH OCH3 (excess) CH3-C-CH3 OCH3 OCH3 hemiacetal acetal and Hemiacetals CH3CH2-C-H O CH2CH2 O H+ HOCH2CH2OH CH3CH2-C-H O b. Reaction with Glycols (Hydrolysis of acetal and hemiacetal back to the carbonyl CH3CH2-C-H OCH3 OCH3 H2O H+ CH3CH2-C-H O ) Formaldehyde (methanal) gives 1o alcohols; other aldehydes give 2o alcohols. Ketones give 3oalcohols. CH3CH2-C-H OH CH3 2. H2O, H + 1. CH3MgBr CH3CH2-C-H O c. Reaction with Grignard Reagents (to form alcohols) d. Reaction with Amines to form imines CH3CH2-C-H O NH3 CH3CH2-C-H NH 2. Reduction of Carbonyl a. H2/Pt reduces aldehydes and ketones and adds across C=C double bonds. b. NaBH4 and LiAlH4 reduce aldehydes and ketones, but do not add across C=C. c. LiAlH4 also reduces carboxylic acids (see Chapter 10). CH3-CH=CH-C-H O H2, Pt 1. NaBH4 2. H2O CH3-CH2-CH2-CH2-OH CH3-CH=CH-CH2-OH (or LiAlH4)