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Chapter 21: Q56 E (page 726)

Treatment of 5- aminopentanoic acid DCC(dicyclohexylcarbodiimide) yields a lactam. Show the structure of the product and the mechanism of the reaction.

Short Answer

Expert verified

The product lactam will get by several by-products from 5- aminopentanoic acid DCC

Step by step solution

01

Overall reaction to yield a lactam product

On reaction with 5- aminopentanoic acid DCC will get lactam product and Di phenyl dicarbametic as an addition product.

02

Yield a lactam product from Protonated DCC

From the DCC and get protonated from amino acids.

03

Yield a lactam product from lactam

By the process of nucleophilic attack by a nucleophile on the carbon and furthermore process the product lactam is produced.

04

Yield a lactam product from lactam

And the process continues,

05

Conclusion

Therefore, the product lactam will get from several by-products from 5- aminopentanoic acid DCC

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Most popular questions from this chapter

21-52 How might you prepare the following compounds from butanoic acid?

  1. 1-Butanol
  2. Butanal
  3. 1-Bromobutane
  4. Pentanenitrile
  5. 1-Butene
  6. 2-Hexanone

How might you prepare the following esters using a nucleophilic acyl substitution reaction of an acid chloride?

(a)CH3CH2CO2CH3

(b) CH3CO2CH2CH3

(c) Ethyl benzoate.

Why is the saponification of an ester irreversible? In other words, why doesn’t treatment of a carboxylic acid with an alkoxide ion yield an ester?

21-30 Electrostatic potential maps of a typical amide (acetamide) and an acyl azide (acetyl azide) are shown. Which of the two do you think is more reactive in nucleophilic acyl substitution reactions? Explain.

Draw the structure of the polymer you would expect to obtain from
reaction of dimethyl terephthalate with a triol such as glycerol. Whatstructural feature would this new polymer have that was not present inDacron (Table 21-2)? How do you think this new feature might affectthe properties of the polymer?
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