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Lecture 7 Problems

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Lecture 7 Problems

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Lesson 7 Problems

1. Suggest which alcohol and alkyl bromide you would use to synthesize the following ethers using a Williamson Ether Synthesis. If two possible reagent pairs may work, show both pairs. If no combination is expected to work, note that as well. a) b) c) d) e) Ethyl methyl ether Diethyl ether t-butyl propyl ether Di-t-butyl ether Isoprypyl methyl ether

2. Predict the major products of the following reactions a. b. c. d. Ethoxide with 1-bromopropane T-butoxide with 1-bormopropane Ethoxide with 3-ethyl-3-bromopentane T-butoxide with 3-ethyl-3-bromopentane

3. In some cases, halohydrins (see lesson 6) can react in the presence of a suitably strong base to form a cyclic ether known as an epoxide. Draw a mechanism for the reaction of 3-bromo,(2,3)dimethyl-2-butanol to form such a compound.

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