12. Alcohols, Ethers, Epoxides and Thiols

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

(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?

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)

Starting with (R)-1-deuterio-1-propanol, how could you prepare

a. (S)-1-deuterio-1-propanol? 

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(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)

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

a. CH₃CH₂CH₂SCH₂CH₃

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

(b)

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

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

(b)

What is the product of each of the following reactions?

c.

d.

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

b.

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