12. Alcohols, Ethers, Epoxides and Thiols

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

g.

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

b.

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

a. 1-bromopropane

b. propan-1-amine, CH₃CH₂CH₂NH₂

Predict the product for each of the following reactions.

(a)

Predict the product for each of the following reactions.

(b)

Predict the product of the following sulfonylation reactions.

(a)

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

Predict the product for each of the following reactions.

(d)

A trifluoromethanesulfonate (triflate) can be used in a manner similar to tosylates. Which would you expect to be a better leaving group? Why?

Predict the product of the following sulfonylation reactions.

(b)

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

(a)

(a) Show how you would affect the following transformation using a tosylate.

(b) Why might this not be the most sustainable method?

(c) What reagent might you use instead?

What is the product of each of the following reactions?

c.

d.