12. Alcohols, Ethers, Epoxides and Thiols

Predict the product of the following reaction.

Predict the product of the following reaction.

Show how you would accomplish the following synthetic conversions.

(a)

(b)

Draw the products of the following intramolecular reactions:

e.

Draw the products of the following intramolecular reactions:

c.

d.

The following pseudo-syntheses (guaranteed not to work) exemplify a common conceptual error.

(a) What is the conceptual error implicit in these syntheses?

(b) Propose syntheses that are more likely to succeed.

Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.

(e) 1-ethoxy-1-methylcyclohexane from 2-methylcyclohexanol

Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.

(f) trans-2,3-epoxyoctane from octan-2-ol

Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.

(d) 1-methoxydecane from a decene

Show how you would synthesize each compound, starting with alkenes or cycloalkenes that contain no more than six carbon atoms. You may use any additional reagents you need.

(b)