12. Alcohols, Ethers, Epoxides and Thiols

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)

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

Draw the products of the following intramolecular reactions:

e.

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

Predict the product of the following reaction.

Draw the products of the following intramolecular reactions:

c.

d.

Show how you would accomplish the following synthetic conversions.

(a)

(b)

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.

Predict the product of the following reaction.

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