Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl - Lecture Outline - Prof. Sil, Study notes of Organic Chemistry

Download Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl - Lecture Outline - Prof. Sil and more Study notes Organic Chemistry in PDF only on Docsity! SCB CH232 summer 2007 Chapter 19 Lecture Outline "Aldehydes and Ketones. Nucleophilic Addition to the Carbonyl" (problems: 25-27, 28, 30-31, 32-33, 34, 36, 38, 39-40, 41-42, 44-45, 49, 51, 52, 57-59, 61-62, 63, 67) I. General Properties & Nomenclature II. Preparation of Aldehydes A. Oxidation of 1°Alcohols by PCC in CH2Cl2 B. Ozonolysis of Alkenes C. Controlled Reduction (by DIBAL-H) of Esters III. Preparation of Ketones A. Oxidation of 2° Alcohols by Cr(VI) Reagents B. Ozonolysis of Alkenes C. Friedel-Crafts Acylation of Arenes D. Hydration of Alkynes E. Cuprates reaction with Acid Chlorides IV. Reactions of Aldehydes and Ketones A. Oxidation of Aldehydes to Carboxylic Acids (via Aldehyde Hydrate) B. Nucleophilic Addition Reactions - Some General Comments C. Nucleophilic Addition Reactions 1. Hydration (addition of H2O) a. acid catalysis b. base catalysis 2. Cynaohydrin Formation (addition of HCN) 3. Alcohol Formation (addition of hydride or Grignard reagents) 4. Imine Formation (addition of R-NH2) a. Oxime Formation b. Semicarbazone Formation c. 2,4-Dinitrophenylhydrazone Formation 5. Wolff-Kishner Reduction (addition of H2NNH2 under basic conditions) 6. Clemmensen Reduction (reduction under acidic conditions) 7. Enamine Formation (addition of R2NH) 8. Acetal Formation (addition of ROH) 9. Wittig Reaction (addition of phosphonium ylides) V. Nucleophilic Addition to α,β-Unsaturated Aldehydes and Ketones A. Conjugate addition of 1° and 2° amines B. Conjugate addition of "R-" as organocuprates (R2CuLi) VI. Spectroscopy of Aldehydes and Ketones A. IR B. NMR (1H and 13C) C. MS 1. McLafferty Rearrangement of aldehyde and ketone radical cations 2. α-cleavage of aldehyde and ketone radical cations