Chapter 11

Supplemental Problems

1)  How would you prepare the following ethers using a Williamson ether synthesis?(18.3)

  1. Methyl propyl ether
  2. Anisole (methyl phenyl ether)
  3. Benzyl isopropyl ether
  4. Ethyl 2,2-dimethylpropyl ether

2)  Rank the following halides in order of their reactivity in the Williamson ether synthesis(18.4):

  1. Bromoethane, 2-bromopropane, bromobenzene
  2. Chloroethane, bromoethane, 1-iodopropene

3)  How would you prepare the following disulfide? What would you call it?

4)  How would you prepare diethyl ether using a single alcohol?

5)  How would you prepare diethyl ether from an alkene and excess alcohol?

6)  Write the mechanism for the alkoxymercuration of 1-methylcyclopentene with ethanol. (18.5)

7)  How would you prepare the following ethers?

  1. Butyl cyclohexyl ether
  2. Benzyl ethyl ether
  3. Sec-butyl tert-butyl ether
  4. Tetrahydrofuran (18.6)

8)  Predict the products of each of the following reactions (18.7)

9)  Write the mechanism for the acid-catalyzed cleavage of t-butyl cyclohexyl ether to yield cyclohexanol and 2-methylpropene (18.8)

10) Why are HI and HBr more effective than HCl at cleaving ethers? (18.9)

11) What product would you expect from the reaction of cis-2-butene with mCPBA? Draw all steps and stereochemistry. (18.11)

12) The reaction of trans-2-butene with mCPBA yields a different epoxide than obtained with the cis isomer. Explain. (18.12)

13) Draw the mechanism for the epoxidation of trans-2-butene via a halohydrin mechanism instead of mCPBA