Download Carbonyl Compounds II: Nomenclature, Reactivity, and Reactions of Aldehydes and Ketones and more Assignments Chemistry in PDF only on Docsity! 1 Chapter 17: Carbonyl Compounds II Learning Objectives: 1. Recognize and assign names to aldehydes and ketones. 2. Write the mechanism for nucleophilic addition and nucleophilic addition-elimination reactions of aldehydes and ketones, and be able to predict the products of such reactions. 3. Be able to explain the relative reactivity of carbonyl compounds toward nucleophilic addition. 4. Be able to describe the concept of employing protecting groups. 5. Predict the products of the reactions of carbonyl compounds with Grignard reagents, hydride ion donors, sulfur nucleophiles, and with phosphonium ylides (the Wittig reaction). 6. Be able to recognize Re and Si faces of carbonyl compounds, and the stereochemistry outcomes from a nucleophilic addition. 7. Predict the products of addition reactions to α,β-unsaturated carbonyl compounds. Sections: 17.1 Nomenclature of Aldehydes and Ketones 17.2 Relative Reactivities of Carbonyl Compounds* 17.3 How Aldehydes and Ketones React* 17.4 Reaction of Carbonyl Compounds with Grignard Reagents* 17.5 Reaction of Carbonyl Compounds with Acetylide Inos 17.6 Reaction of Carbonyl Compounds with Hydride Ion* 17.7 Reaction of Aldehydes and Ketones with Hydrogen Cyanide 17.8 Reaction of Aldehydes and Ketones with Amines and Derivatives of Amines* 17.9 Reaction of Aldehydes and Ketones with Water 17.10 Reaction of Aldehydes and Ketones with Alcohol* 17.11 Protecting Groups* 17.12 Addition of Sulfur Nucleophiles 17.13 The Wittig Reaction Forms an Alkene* 17.14 Stereochemistry of Nucleophilic Addition Reactions: Re and Si Faces # 17.15 Designing a Synthesis VI: Disconnections, Synthones, and Synthetic Equivalents 17.16 Nucleophilic Addition to α,β-Unsaturated Aldehydes and Ketones* 17.17 Nucleophilic Addition to α,β-Unsaturated Carboxylic Acid Derivatives 17.18 Enzyme-catalyzed Additions to α,β-Unsaturated Carbonyl Compounds # * Sections that will be focused # Sections that will be skipped Recommended additional problems 17.45 – 17.65, 17.67 – 17.70, 17.73 – 17.77, 17.79 – 17.82, 17.84 2 Class Note 17.1 Nomenclature of Aldehydes and Ketones O H O H O H O H H H O O O H O H HO H OCH2CH3 O O OCH2CH3 CHO O Cl 5 B. In acidic condition H B B + H R H (R) O R H(R) O BH R H (R) O H 6 17.4 Reaction of Carbonyl Compounds with Grignard Reagents* A. Carbon nucleophile (basic or acidic?) B. Reaction of aldehydes and ketones with Grignard reagent 7 C. Reactions of ester and carboxylic acid with Grignard reagent 10 17.6 Reaction of Carbonyl Compounds with Hydride Ion* A. Source of hydride B. Reduction of aldehydes and ketones 11 C. Reduction of esters 12 D. Reduction of carboxylic acids 15 C. Addition of secondary amines D. Addition of hydrazine, hydroxyamine 16 E. Mechanism of Wolff-Kishner reduction 17 17.9 Reaction of Aldehydes and Ketones with Water A. Addition of water (formation of hydrate, gem-diol, geminal diol) R H (R) O R H(R) HO OH H2O (i) Consideration of pKa (ii) Stability consideration 20 17.11 Protecting Groups* A. Stability of acetals and ketals B. Example O HOCH2CH2OH+ OO + H2O (i) O OCH3 O ? O OH 21 C. More examples (i) NH2 ? NH2 NO2 (ii) NH2 ? NH2 CO2H 22 17.12 Addition of Sulfur Nucleophiles 17.13 The Wittig Reaction Forms an Alkene* A. Wittig reagents (C6H5)3P CH2 phosphonium ylide (C6H5)3P CH2 B. Formation of Wittig reagents 25 (ii) Arbuzov (Perkow) reaction 26 17.15 Designing a Synthesis VI: Disconnections, Synthones, and Synthetic Equivalents A. Retrosynthetic analysis Example OH OH synthesis of from 27 17.16 Nucleophilic Addition to α,β-Unsaturated Aldehydes and Ketones* A. Analysis of α,β-unsaturated aldehydes and ketones R O α β B. Direct addition (1,2-addition) and conjugate addition (1,4-addition)
