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Chapter 19: Q51E (page 648)

Primary amines react with esters to yield amides: RCO2R' + R"NH2 →RCONHR" + R'OH . Propose a mechanism for the following reaction of an a b-unsaturated ester.

Short Answer

Expert verified

When ester reacts with primary amine or ammonia in an acidic medium then they give amide as a product.

In this reaction, the first step includes a nucleophilic attack of nitrogen on the carbonyl center followed by proton transfer and the alcohol portion of ester is lost.

Step by step solution

01

Reaction of primary amine and ester to give amide

When ester reacts with primary amine or ammonia in an acidic medium then they give amide as a product.

In this reaction, the first step includes a nucleophilic attack of nitrogen on the carbonyl center followed by proton transfer and the alcohol portion of ester is lost.

02

Mechanism of the given reaction

In the given reaction first, the lone pair of nitrogen attack the double-bonded carbon and further rearrangements take place as shown below;

In the next step, intramolecular rearrangements take place. Lone pair of nitrogen attacks the carbonyl carbon and we get the desired product.

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Most popular questions from this chapter

Carvone is the major constituent of spearmint oil. What products would you expect from reaction of carvone with the following reagents?

  1. (CH3)2Cu-Li+, then H3O+
  2. LiAlH4, thenH3O+
  3. CH3NH2
  4. C6H5MgBr, thenH3O+
  5. H2/Pd
  6. CrO3, H3O+
  7. (C6H5)3P+CHCH3-
  8. HOCH2CH2OH, HCl

Imine formation is reversible. Show all the steps involved in the acid-catalyzed reaction of an imine with water (hydrolysis) to yield an aldehyde or ketone plus primary amine.

Each of the following reaction schemes contains one or more flaws.

What is wrong in each case? How would you correct each scheme?

(a)

(b)

(c)

Cyclohexanone forms a cyanohydrin in good yield but 2,2,6-trimethylcyclohexanonedoes not. Explain.

How might you use mass spectrometry to distinguish between the following pairs of isomers?

(a) 3-Methyl-2-hexanone and 4-methyl-2-hexanone

(b) 3-Heptanone and 4-heptanone

(c) 2-Methylpentanal and 3-methylpentanal
See all solutions

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