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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

Olestra庐is a fat-based fat substitute that became available in snack foods such as potato chips in 1998. Previous fat substitutes were carbohydrate-based or protein-based mixtures that did not give as good a sensation in the mouth and are not suitable for frying. With Olestra庐, the glycerol molecule of a fat is replaced by sucrose (p. 1237). In Olestra庐, the sucrose molecule has six, seven, or (most commonly) eight fatty acids esterified to its hydroxy groups. The fatty acids come from hydrolysis of vegetable oils such as soybean, corn, palm, coconut, and cottonseed oils. This unnaturally bulky, fat-like molecule does not pass through the intestinal walls, and digestive enzymes cannot get close to the sucrose center to bind it to their active sites. Olestra庐 passes through the digestive system unchanged, and it provides zero calories.Draw a typical Olestra庐 molecule, using any fatty acids that are commonly found in vegetable oils.

Bisphenol A is made on a large scale by a condensation of phenol with acetone. Suggest an appropriate catalyst, and propose a mechanism for this reaction. (Hint: This is a condensation because three molecules are joined with loss of water. The mechanism belongs to another class of reactions though.)

Polychloroprene, commonly known as neoprene, is widely used in wetsuits and in rubber parts that must withstand exposure to gasoline or other solvents.

(a) Is neoprene an addition polymer or a condensation polymer?

(b) What monomer is used to make this synthetic rubber?

Give the structure of the polyurethane formed by the reaction of toluene diisocyanate

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