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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2 Nuc: HO-C OH carbonic acid CI-C- CI Nuc-C-Nuc2CI phosgene CH CH C-O-C-C CH3 tert-butyloxycarbonyl chloride