| Chapter 7 Alkenes and alkynes I: Properties and synthesis. Elimination reactions of alkyl halides | ||||
| 12th edition Solomons, Fryhle and Snyder Organic Chemistry | 11th edition Solomons, Fryhle and Snyde Organic Chemistry | |||
| Problems | Subject | Section | Subject | Problems |
| 7.1 | Introduction | |||
| Solved problem 7.1 Practice problem 7.1 | 7.2 | The E-Z system for designating alkene diastereomers | Solved problem 7.1 Practice problem 7.1 | |
| Solved problem 7.2 Practice problem 7.4, 7.5 | 7.3 | Relative stabilities of alkenes | Solved problem 7.2 Practice problem 7.4, 7.5 | |
| Required reading | 7.4 | Cycloalkenes | Required reading | |
| Synthesis of alkenes: Elimination reactions | 7.5 | Synthesis of alkenes via elimination reactions | ||
| Dehydrohalogenation Mechanism: See your class notes | 7.6 | Dehydrohalogenation of alkyl halides Mechanism: See your class notes | Solved problem 7.3 Practice problem 7.7, 7.8 | |
| Solved problem 7.3 Practice problem 7.7 | The E2 reaction Mechanism: See your class notes | 7.7 (omit 7.7C) | Acid-catalyzed dehydration of alcohols Mechanism: Acid-catalyzed dehydration of 2o and 3o alcohols: An E1 reaction Mechanism: Acid-catalyzed dehydration of a 1o alcohol: An E2 reaction | |
| The E1 reaction Mechanism: See your class notes | 7.8 | Carbocation stability and the occurence of molecular rearrangements Mechanism: See your class notes | Solved problem 7.6 | |
| Elimination and subsititution reactions compete with each other | 7.9 | The acidity of terminal alkynes | Solved problem 7.7 Practice problem 7.17 | |
| Elimination of alcohols: Acid-catalyzed dehydration Mechanism: Acid-catalyzed dehydration of 2o and 3o alcohols: An E1 reaction Mechanism: Acid-catalyzed dehydration of a 1o alcohol: An E2 reaction | 7.10 | Synthesis of alkynes by elimination reactions | Practice problem 7.18, 7.19 | |
| Solved problem 7.7 | Carbocation stability and the occurence of molecular rearrangements Mechanism: See your class notes | 7.11 | Terminal alkynes can be converted to nucleophiles for C-C bond formation | Solved problem 7.8 |
| Solved problem 7.8 Practice problem 7.19 | The acidity of terminal alkynes | 7.12 | Hydrogenation of alkenes | |
| Practice problem 7.21 omit A | Synthesis of alkynes by elimination reactions | 7.13 | Hydrogenation: The function of the catalyst | |
| Solved problem 7.9 | Terminal alkynes can be converted to nucleophiles for C-C bond formation | 7.14 | Hydrogenation of alkynes | Practice problem 7.22 |
| Hydrogenation of alkenes | 7.15 | An introduction to organic synthesis | Practice problem 7.23 | |
| Hydrogenation: The function of the catalyst | 7.16 | |||
| Practice problem 7.24 | Hydrogenation of alkynes | 7.17 | ||
| Practice problem 7.25 | An introduction to organic synthesis | 7.18 | ||
| End of chapter problems | End of chapter problems | |||
| 7.27 7.28 7.29 7.30 7.32 | 7.25 7.26, 7.27 7.28 | |||
| 7.34 omit F. Give E products only. Answer D - 1-methylcyclohexene is the only product. The double bond will not form outside of the cyclic structure. | ||||
| 7.35 Give E products only. Answer E - 1-methylcyclohexene is the only product. The double bond will not form outside of the cyclic structure. | 7.30 C. The reactant is concentrated H2SO4 / 180ºC given that it is a primary alcohol. 7.30 D. The reactant is 85% H3PO4 / 165-170ºC given that it is a secondary alcohol. | |||
| 7.37 Use the SN/E summary table we produced in class to predict the products. 7.38 | 7.31 7.32, 7.34 7.35 | |||
| 7.44 omit D Answers B - 2-methyl-2-butene (major) + 3-methyl-1-butene (minor) C - 3-methyl-2-pentene (major) + 2-ethyl-1-butene (minor) E - 1,4-dimethylcyclohexene is the only product. The double bond will not form outside | 7.37 omit F. Answer D - 1-methylcyclohexene is the only product. The double bond will not form outside of the cyclic structure. | |||
| 7.45 Answers C. The reactant is concentrated H2SO4 / 180ºC since it is a primary alcohol. D. The reactant is 85% H3PO4 / 165-170ºC since it is a secondary alcohol. | 7.38 B and D: E2 major and SN2 minor. E : 1-methylcyclohexene is the only product. The double bond will not form outside of the cyclic structure. | |||
| 7.46 7.47 Answer E 1-methylcyclohexene is the only product. The double bond will not form outside of the cyclic structure. | 7.39 7.40 7.41 (omit D) Answers B - 2-methyl-2-butene (major) + 3-methyl-1-butene (minor) C - 3-methyl-2-pentene (major) + 2-ethyl-1-butene (minor) E - 1,4-dimethylcyclohexene is the only product. The double bond will not form outside | |||
| 7.48 omit F |
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