12. Alcohols, Ethers, Epoxides and Thiols

On the reaction coordinate diagram for the disfavored nucleophilic displacement of hydroxide, predict the curve that would demonstrate how using a tosylate makes the substitution favorable.

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

(a)

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

(a)

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 for each of the following reactions.

(a)

Predict the products of the following reactions.

(a) cyclohexylmethanol + TsCl/pyridine

(b) product of (a) + LiAlH4

Predict the product of the following sulfonylation reactions.

(d)

Predict the product of the following sulfonylation reactions.

(c)

What is the major product(s) of each of the following reactions?

g.

Predict the product for each of the following reactions.

(d)

Predict the product for each of the following reactions.

(b)

What is the product of each of the following reactions?

a.

Write the appropriate reagent over each arrow.

The sulfur atom in toluene sulfonyl chloride (TsCl) is strongly electrophilic. Why?

Predict the product of the following sulfonylation reactions.

(a)