Question: Draw the products formed when ethylene oxide is treated with each reagent.

$$\begin{gathered} \mathbf{a}\mathbf{.}\mathbf{}\mathbf{HBr} \\ \mathbf{b}\mathbf{.}\mathbf{}{\mathbf{H}}_{\mathbf{2}}\mathbf{O}\mathbf{}\left(H_2{\mathrm{SO}}_4\right) \\ \mathbf{c}\mathbf{.}\mathbf{}\left[1\right]\mathbf{}{\mathbf{CH}}_{\mathbf{3}}{\mathbf{CH}}_{\mathbf{2}}\mathbf{O}\mathbf{}\mathbf{;}\mathbf{}\left[2\right]{\mathbf{H}}_{\mathbf{2}}\mathbf{O} \\ \mathbf{d}\mathbf{.}\mathbf{}\left[1\right]\mathbf{}{\mathbf{CH}}_{\mathbf{3}}\mathbf{C}\mathbf{\equiv }\mathbf{N}\mathbf{}\mathbf{;}\mathbf{}\left[2\right]{\mathbf{H}}_{\mathbf{2}}\mathbf{O} \\ \mathbf{e}\mathbf{.}\mathbf{}\left[1\right]\mathbf{}\stackrel{\mathbf{-}}{\mathbf{O}}\mathbf{H}\mathbf{;}\mathbf{}\left[2\right]{\mathbf{H}}_{\mathbf{2}}\mathbf{O} \\ \mathbf{f}\mathbf{.}\mathbf{}\left[1\right]\mathbf{}{\mathbf{CH}}_{\mathbf{3}}\mathbf{S}\mathbf{;}\mathbf{}\left[2\right]{\mathbf{H}}_{\mathbf{2}}\mathbf{O} \end{gathered}$$

The compound ethylene oxide is highly reactive. Neutral nucleophiles will attack it at the most substituted carbon of the epoxide. Negatively charged nucleophiles would attack the epoxide ring at less substituted carbon.

Ethylene oxide can react with strong acids as well as nucleophiles and form the respective addition products containing $-\mathrm{OH}\mathrm{group}$.

The products of the given reaction are as shown below:

a.

Reactions of ethylene oxide with reagent a

b.

Reactions of ethylene oxide with reagent b

c.

Reactions of ethylene oxide with reagent c

d.

Reactions of ethylene oxide with reagent d

e.

Reactions of ethylene oxide with reagent e

f.

Reactions of ethylene oxide with reagent f