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Chapter 24: Q24P. (page 1287)

Question. Propose a mechanism for the coupling of acetic acid and aniline using DCC as a coupling agent.

Short Answer

Expert verified

Representation of DCC as c-Hx

Mechanism for the coupling of acetic acid aniline

Step by step solution

01

Step1: Introduction to DCC

DCC or N,N鈥�-Dicyclohexylcarbodiimide is used in the coupling reactions of amino acids during peptide synthesis. It has a low melting point and can be handled easily. Often, in reactions, we use the abbreviation 鈥榗-Hx鈥� to stand for cyclohexyl in DCC.

Representation of DCC as c-Hx

02

Mechanism for the reaction

The nitrogen of aniline firstly abstracts hydrogen from acetic acid-forming acetate ion and anilinium ion. Then, the oxygen of the acetate ion acts as a nucleophile and attacks thecarbon center of DCC, which is an electrophile. DCC thereby activatesthe carboxyl group,converting it into an excellent leaving group. Further, a reaction with another molecule of aniline occurs inthis activated carboxyl group, and lastly, the leaving group leaves, which is resonance-stabilized, and the final product is formed.

Mechanism for the coupling of acetic acid aniline

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Most popular questions from this chapter

Aspartame(Nutrasweet庐) is a remarkably sweet-tasting dipeptide ester. Complete hydrolysis of aspartame gives phenylalanine, aspartic acid, and methanol. Mild incubation with carboxypeptidase has no effect on aspartame. Treatment of aspartame with phenyl isothiocyanate, followed by mild hydrolysis, gives the phenylthiohydantoin of aspartic acid. Propose a structure for aspartame.

Write the complete structures for the following peptides. Tell whether each peptide is acidic, basic, or neutral.

  1. Methionylthreonine
  2. Threonylmethionine
  3. Arginylaspartyllysine
  4. Glu-Cys-Gln

Draw the complete structure of the following peptide Met-Ser-Gln-NH2

Draw the structure of the phenylthiohydantoin derivatives of

(a) Alanine (b) Tryptophan (c) Lysine (d) proline

After treatment with peroxyformic acid, the peptide hormone vasopressin is partially hydrolyzed. The following fragments are recovered. Propose a structure for vasopressin.

Phe-Gln-Asn Pro-Arg-Gly.NH2 Cys-Tyr-Phe

Asn-Cys-Pro-Arg Tyr-Phe-Gln-Asn

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