Q51P Phosgene is the acid chloride of... [FREE SOLUTION]

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Chapter 20: Q51P (page 1038)

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-1-ol.
(b) Predict the products formed when phosgene reacts with 1 equivalent of ethanol, followed by 1 equivalent of aniline.
(c) Iso-butyloxycarbonyl chloride is an important reagent for the synthesis of peptides and proteins. Show how you would use phosgene to synthesize iso-butyloxycarbonyl chloride.
Isobutyloxycarbonyl chloride

Short Answer

Expert verified

(a)

Phosgene propan-1-ol propyl carbonochloridate

Formation of propyl carbonochloridate

(b)

Phosgene Ethanol Ethyl carbonochloridate

Formation of ethyl carbonochloridate

Ethyl carbonochloridate Aniline

Formation of the desired product

(c)

Formation of isobutyloxycarbonyl chloride

Step by step solution

Phosgene

Phosgene is an organic compound with chemical formula COLCl2and is used in industrial work for the production of polycarbonate plastics.

The reaction of phosgene with propan-1-ol

(a) Treatment of phosgene with the excess of propan -1-ol gives propyl carbonochloridate. This reaction proceeds through the nucleophilic acyl substitution. The reaction is represented as:

Phosgene propan-1-ol propyl carbonochloridate

Formation of propyl carbonochloridate

The reaction of phosgene with ethanol and aniline

When phosgene is reacted with ethanol, then it gives ethyl carbonochloridate. Here, the ethyl carbonochloridate reacts with aniline and gives the desired product.