Solved: Phosgene is the acid chloride of carbonic acid. Although phosgene was used as a

Chapter 0, Problem 21-51

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Phosgene is the acid chloride of carbonic acid. Although phosgene was used as a war gas in World War I, it is now used as a reagent for the synthesis of many useful products. Phosgene reacts like other acid chlorides, but it can react twice. (a) Predict the products formed when phosgene reacts with excess propan-2-ol. (b) Predict the products formed when phosgene reacts with 1 equivalent of methanol, followed by 1 equivalent of aniline. (c) tert-Butyloxycarbonyl chloride is an important reagent for the synthesis of peptides and proteins (Chapter 24). Show how you would use phosgene to synthesize tert-butyloxycarbonyl chloride.

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