Chapter 10. Reactions of Alcohols, Amines, Ethers, and Epoxides
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1 Chapter 10. Reactions of Alcohols, Amines, Ethers, and Epoxides Learning objectives: 1. Provide both IUPAC and common (when applicable) names for alcohols and ethers. 2. Describe the physical properties of alcohols, amines and ethers. 3. Remember the approximate pka values for alcohols, water, and hydronium ion. 4. Write the reaction equations of alcohols reacting with active metals, such as Li, Na, and K. 5. Write the reaction and electron-pushing (arrow-pushing) mechanism for the conversion of alcohols to alkyl halides. 6. Write the reaction and electron-pushing (arrow-pushing) mechanism for the conversion of alcohols to alkenes, and explain the regioselectivity when applicable. 7. Write the oxidation from primary alcohol to aldehydes then to carboxylic acids, and recognize the difference in using chromic acid versus PCC. 8. Know the reactions of amines and properties of ammonium salts. 9. Write the ring-opening of epoxides in acidic and basic conditions, and explain the observed stereochemistry of the products. 10. Differentiate primary, secondary, and tertiary alkyl alcohols and amines. Sections to be covered: 10.1 The Nomenclature of Alcohols 10.2 Reactions of Alcohols 10.3 Reactions of Amines 10.4 Reactions of Ethers 10.1 The Nomenclature of Alcohols A. Structure and classification R Know how to classify primary (1 ), secondary (2 ) and tertiary (3 ) alcohols. 1
2 B. Nomenclature 2
3 HO HO C. Physical Properties 3
4 D. Acidity of Alcohols Know the estimated pka of water, hydronium (H3O + ), methanol and ethanol. E. Self-assessment Questions Can you provide IUPAC and common (when applicable) names for alcohols? Can you describe the physical properties of alcohols? Can you remember the approximate pka values for alcohols, water, and hydronium ion? Can you differentiate primary, secondary, and tertiary alkyl alcohols? 10.2 Reactions of Alcohols 4
5 A. Reaction with Active Metals (Preparation of Alkoxides) 2 CH3 + 2 Na 2 CH3O - + H2 B. Conversion to Haloalkanes R HX R X X = Cl, Br, I (i) Examples Cl + H Cl + H + H Br (ii) Mechanism (SN1 and SN2) 5
6 C. Acid-Catalyzed Dehydration to Alkenes ( -elimination) (i) General Mechanism (ii) Relative ease of dehydration (iii) Dehydration and Zaitsev s rule H 2 SO 4 heating % 23% 3% 6
7 (iv) Comparison with Hydration Reaction of Alkenes 7
8 D. Oxidation of alcohols (i) General Reactions C H C H [O] C C O H [O] C C O C H C R [O] C C O R (ii) Examples CrO 3 H 2 SO 4 Na 2 Cr 2 O 7 H 2 SO 4 H 2 CrO 4 8
9 O CrO 3 H 2 SO 4 O Na 2 Cr 2 O 7 H 2 SO 4 PCC E. Self-assessment Questions Can you write the reaction equations of alcohols reacting with active metals, such as Li, Na, and K? Can you write the reaction and electron-pushing (arrow-pushing) mechanism for the conversion of alcohols to alkyl halides? Can you write the reaction and electron-pushing (arrow-pushing) mechanism for the conversion of alcohols to alkenes, and explain the regioselectivity when applicable? Can you write the oxidation from primary alcohol to aldehydes then to carboxylic acids, and recognize the difference in using chromic acid versus PCC? 9
10 10.5 Reactions of Amines A. Nomenclatures and Classification of Amines 10
11 B. Structure of Amines C. Acidity of amines 11
12 D. Common Roles of Amines and Properties of Ammonium Salts 12
13 E. Heterocyclic Amines and Plant Alkaloids F. Self-assessment Questions Can you provide IUPAC and common (when applicable) names for amines? Can you describe the physical properties of amines? Can you remember the approximate pka values for amines and ammonium ion? Can you differentiate primary, secondary, and tertiary alkyl amines? Can you describe the common roles of amines and properties of ammonium salts? 10.4 Reactions of Ethers 13
14 A. Structure and Nomenclature of Ethers 14
15 15
16 B. Ring-Opening of Epoxides (i) Stereoselectivity O H + H 2 O + (ii) Regioselectivity Ring-opening in acidic condition 16
17 Ring-opening in basic condition C. Self-assessment Questions Can you provide IUPAC and common (when applicable) names for ethers? Can you describe the physical properties of ethers? Can you write the ring-opening of epoxides in acidic and basic conditions, and explain the observed stereochemistry of the products? 17
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