What is the best way to prepare the following ethers using an alkyl halide and an alkoxide ion?
c.
d.

Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.

(a)

Provide the reagents necessary to carry out the following synthesis. What is the purpose of steps (a) and (e)?

How could you synthesize isopropyl propyl ether, using isopropyl alcohol as the only carbon-containing reagent?

Draw the product of each of the following reactions:

2.

A chemist wanted to synthesize the anesthetic 2-ethoxy-2-methylpropane. He used ethoxide ion and 2-chloro-2-methylpropane for his synthesis and ended up with no ether. What was the product of his synthesis? What reagents should he have used?

Design a synthesis for each of the following, using an intramolecular reaction:

e.

The compound shown below has three different types of OH groups, all with different acidities. Show the structure produced after this compound is treated with different amounts of NaH followed by a methylating reagent. Add a brief explanation.

(a) 1 equivalent of NaH, followed by 1 equivalent of CH₃I and heat

(b) 2 equivalents of NaH, followed by 2 equivalents of CH₃I and heat

(c) 3 equivalents of NaH, followed by 3 equivalents of CH₃I and heat

Show how you would use the Williamson ether synthesis to prepare the following ethers. You may use any alcohols or phenols as your organic starting materials.

(d) ethyl n-propyl ether (two ways)

(e) benzyl tert-butyl ether (benzyl = Ph–CH₂–)