challenge_solutions_problem_set_10

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Chem 359 Problem Set 10 Chapter 10: Organic Chemistry: A Biological Approach Key Ideas: 1. Alkyl Halides 2. Substitution Reactions 3. Elimination Reactions Suggested Problems : 10.1-10.24, 10.30, 10.31, 10.32, 10.37, 10.39, 10.41, 10.43, 10.44, 10.45, 10.48, 10.50, 10.51, 10.54, 10.55, 10.57, 10.58, 10.59, 10.62, 10.64, 10.65, 10.66, 10.67, 10.70, 10.71 Challenge Problems 1. Separation of structural isomers in real life is very difficult. Devise a method to make B from A without getting a mixture. (i.e. no A, C, or D) A B HO H 1. BH 3 2. H 2 O 2 TsO H TsCl, Pyridine H t BuOK Base 2. Which of the following alkyl halides reacts faster with CN - in the S N 2 reaction?
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Unformatted text preview: > > > > Fast SN1 O O Fast SN1 Fast SN1 3. Explain the following strange observation. OTs EtO I EtO Acetone 5 days NaI 75% 25% I EtO NaI SN2 SN2 Fast Slow H H EtO I I H EtO Less Stable More Stable 4. Explain why 1-chlorobicyclo [2.2.1] is completely unreactive to S N 1 reaction. Very unstable due to constraints of bicycle 5. Which one of the following react faster in an S N 1 reaction? Br Br H > weaker C-Br Bond 6. Give the reagents to carry out the following synthesis O Br Br Br MgBr O BrMgO Br Mg 7. Rank the following compounds in order of decreasing rate in an E2 reaction. Br O Br O H > > Br H H > Br Br Br >...
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