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Chapter 26: Q18P (page 1337)

Propose a mechanism for the reaction of phenyl isocyanate with methanol.

Short Answer

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Complete mechanism for the reaction

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01

Urethanes (or carbamate ester)

They are commonly made by treating an isocyanate with an alcohol or a phenol. The reaction is highly exothermic and it gives a quantitative yield of carbamate ester.

02

Mechanism for the reaction of phenyl isocyanate with methanol

In this reaction, nucleophilic addition of methanol takes place in a concerted way across the nitrogen double bond carbon (N=C) of the phenyl isocyanate. Another methanol molecule adds to the reaction as a result of which a protonated methyl alcohol is formed. The double bond around N=C gets rearranged to give the final product as methyl-N-phenylcarbanate .

Complete mechanism for the reaction

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Most popular questions from this chapter

Show the intermediate that would result if the growing chain added to the other end of the styrene double bond. Explain why the final polymer has phenyl groups substituted on alternate carbon atoms rather than randomly distributed.

The polyester named LactomerRis an alternating copolymer of lactic acid and glycolic acid. Lactomer is used for absorbable suture material because stitches of Lactomer hydrolyze slowly over a two-week period and do not have to be removed. The hydrolysis products, lactic acid and glycolic acid, are normal metabolites and do not provoke an inflammatory response. Draw the structure of the Lactomer polymer.

(a) Isobutylene and isoprene coplymerize to give 鈥渂utyl rubber鈥�. Draw the structure of the repeating unit in butyl rubber, assuming that the two monomers alternate.

(b) Styrene and butadiene copolymerize to form styrene-butadiene rubber (SBR) for automobile tires. Draw the structure of the repeating unit in SBR, assuming that the two monomers alternate.

Draw the structure of isotactic poly(acrylonitrile) and syndiotactic polystyrene.

The mechanism given for cationic polymerization of isobutylene (Mechanism 26-2) shows that all the monomer molecules add with the same orientation, giving a polymer with methyl groups on alternate carbon atoms of the chain. Explain why no isobutylene molecules add with the opposite orientation.
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