12. Alcohols, Ethers, Epoxides and Thiols

Show how 1-propanol can be converted into the following compounds by means of a sulfonate ester:

a. CH₃CH₂CH₂SCH₂CH₃

Show how you would convert propan-1-ol to the following compounds using tosylate intermediates. You may use whatever additional reagents are needed.

c. CH₃CH₂CH₂OCH₂CH₃, ethyl proyl ether

d. CH₃CH₂CH₂CN, butyronitrile

Predict the major products of the following reactions, including stereochemistry where appropriate.

(a) (R)-butan-2-ol + TsCl in pyridine

(b) (S)-2-butyl tosylate + NaBr

What is the product of each of the following reactions?

a.

Complete the following multistep syntheses using tosylate formation as one of the steps. The optimum number of steps for each synthesis is shown.

(b)

Predict the products of the following reactions.

(a) cyclohexylmethanol + TsCl/pyridine

(b) product of (a) + LiAlH4

Using an appropriate tosylate intermediate, synthesize the following molecules starting from the appropriate alcohol.

(a)

Predict the major product(s) of each of the following reactions.

Complete the following multistep syntheses using tosylate formation as one of the steps. The optimum number of steps for each synthesis is shown.

(a)

Using an appropriate tosylate intermediate, synthesize the following molecules starting from the appropriate alcohol.

(b)

Predict the product of the following sulfonylation reactions.

(d)

Predict the product of the following sulfonylation reactions.

(c)

Complete the following multistep syntheses using tosylate formation as one of the steps. The optimum number of steps for each synthesis is shown.

(c)

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iii) SOCl₂ , NEt₃, and (iv) 1. TsCl, Et₃N 2. NaCN. If no reaction occurs, write 'no reaction.'

(k)

Write the appropriate reagent over each arrow.