12. Alcohols, Ethers, Epoxides and Thiols

Write balanced equations for the three preceding reactions.

Two products are observed in the following reaction.

a. Suggest a mechanism to explain how these two products are formed.

b. Your mechanism for part (a) should be different from the usual mechanism of the reaction of SOCl₂ with alcohols. Explain why the reaction follows a different mechanism in this case.

Provide the alcohol that would be used to make the bromoalkanes shown using PBr₃.

(a)

Provide the alcohol that would be used to make the bromoalkanes shown using PBr₃.

(b)

Provide the alcohol that would be used to make the bromoalkanes shown using PBr₃.

(c)

Besides PBr₃. and SOCl₂ , there are other ways of synthesizing haloalkanes. One such way is shown. Provide an arrow-pushing mechanism that rationalizes formation of the chloroalkane. [Hint: Dimethyl sulfide is a good nucleophile and Cl₂ is an electrophile. Start by reacting those two together.]

Identify the reagent that should be used to obtain each stereochemical outcome shown.

(a)

Identify the reagent that should be used to obtain each stereochemical outcome shown.

(b)

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (i) SOCl₂ ; (ii) PBr₃. If no reaction occurs, write 'no reaction.'  

(a)

Suggest the appropriate reagents to carry out the following transformations.

(g)

Draw structures for compounds A–F.

What is the product of each of the following reactions?

g.

Suggest the appropriate reagents to carry out the following transformations.

(b)

Suggest the appropriate reagents to carry out the following transformations.

(c)