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Chapter 20: Q30E (page 678)

In the Ritter reaction, an alkene reacts with a nitrile in the presence of strong aqueous sulfuric acid to yield an amide. Propose a mechanism.

Short Answer

Expert verified

A mechanism of Ritter reaction is shown below

Step by step solution

01

Definition of mechanism

The sequence of elementary steps by which a chemical reaction occurs is defined as mechanism

02

Explanation

Protonation of the double bond in alkene by sulfuric acid leads to the formation of a tertiary carbocation.

The electrophilic nitrogen of the acetonitrile attacks the carbocation .

The nucleophilic attack of water on the nitrile carbon and subsequent removal of a proton yields the imidol.

The imidol then tautomerizes to yield the amide required

A mechanism of Ritter reaction is shown below


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Most popular questions from this chapter

Rank the following compounds in order of increasing acidity. Don’t look at a table of pKa data to help with your answer.

(a) Benzoic acid, p-methylbenzoic acid, p-chlorobenzoic acid

(b) p-Nitrobenzoic acid, acetic acid, benzoic acid

The following pKavalues have been measured. Explain why a hydroxyl group in the para position decreases the acidity while a hydroxy group in the meta position increases the acidity.

Draw structures corresponding to the following IUPAC names:

  1. cis-1,2-Cyclohexanedicarboxylic acid

  2. Hepatanedioic acid

  3. 2-Hexen-4-ynoic acid

  4. 4-Ethyl-2-propyloctanoic acid

  5. 3-chlorophthalic acid

  6. Triphenylacetic acid


  7. 2-Cyclobutenecarbonitrile

  8. m-Benzoyl benzonitrile

How would you prepare the following carbonyl compounds from a nitrile?

(a)

(b)

Acid-catalyzed hydrolysis of a nitrile to give a carboxylic acid occursby initial protonation of the nitrogen atom, followed by nucleophilicaddition of water. Review the mechanism of base-catalyzed nitrilehydrolysis in Section 20-7 and then predict the products for each reaction below and write all of the steps involved in the acid-catalyzedreaction, using curved arrows to represent electron flow in each step.
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