When ethylene oxide is treated with a strong nucleophile, the epoxide ring is opened to form an alkoxide ion that can function as a nucleophile to attack another molecule of ethylene oxide. This process repeats itself, and a polymer is formed.

The resulting polymer is called poly(ethylene oxide) or poly(ethylene glycol). It is sold under the trade name Carbowax and is as an adhesive and a thickening agent.

(a) Draw a mechanism showing the formation of a segment of poly(ethylene oxide).

(b) Ethylene oxide can also be polymerized when treated with an acid. Draw the mechanism of formation of a segment of poly(ethylene oxide) under acidic conditions.

(c) Identify the monomer you would use to prepare the following polymer:

(d) Determine whether you would use basic conditions or acidic conditions to prepare the following polymer. Explain your choice.

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Nuc Nuc Ethylene oxide Poly(ethylene oxide)