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Chapter 15: Q33P (page 712)

Problem:What acyl chloride and amine are required to synthesize the following amides?

a. N-ethylbutanamide b. N,N-dimethylbenzamide

Short Answer

Expert verified

Answer

a.

b.

Step by step solution

01

Acid chloride to amide

Amide is synthesized from the acid derivate, and themost reactive acid derivate is acid chloride.

The acid chloride reaction with the neutral amine (with at least one N-H group) is nucleophilic,attacking the carbonyl carbon of acid chloride to form atetrahedral intermediate,leaving chlorineformation of the desired amide.

02

Formation of N-ethylbutanamide

(acid chloride) reacts with the two moles of (amine) reaction goes by a nucleophilic addition-elimination mechanism.The nucleophile amine will attack the carbonyl carbon, leaving group (chloride). Finally, deprotonation forms the desired product, N-ethylbutanamide.

The reaction between the and the is shown below



03

 Step 3: Formation of N,N-dimethylbenzamide

Acid chloride reacts with the two moles of (amine)reaction goes bya nucleophilic addition-elimination mechanism. The nucleophile amine will attack the carbonyl carbon, leaving group (chloride) leave, and finally, deprotonation forms the desired product, N,N-dimethylbenzamide.

The reaction between the and the is shown as follows.

Formation of N,N-dimethylbenzamide

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Most popular questions from this chapter

Question: Is the acid-catalyzed hydrolysis of acetamide a reversible or an irreversible reaction? Explain.

Write the mechanism for the acid-catalyzed reaction of an amide with an alcohol to form an ester.

Information about the mechanism of the reaction undergone by a series of substituted benzenes can be obtained by plotting logarithm of the observed rate constant determined at particular pH against the Hammett substituent constant蟽 for the particular substituent. The 蟽value for hydrogen is zero. Electron-donating substituents have negative蟽 values; the more strongly electron withdrawing the substituent, the more positiveits s value. The slope of a plot of the logarithm of the rate constant 蟽versusis called the蚁 (rho) value. The 蚁value for the hydroxide-ion-promoted hydrolysis of a series of meta- and para-substituted ethyl

benzoates is +2.46; the蚁 value for amide formation for the reaction of a series of meta- and para-substituted anilines with benzoyl chloride is -2.78.

  1. Why doesone set of experiments give a positive role="math" localid="1652525783964" 蚁value, whereas the other set of experiments gives a negative蚁 value?
  2. Why were ortho-substituted compounds not included in the experiment?
  3. What do you predict the sign of the蚁 value to be for the ionization of a series of meta- and para-substituted benzoic acids?

a. Propose a mechanism for the formation of succinic anhydride in the presence of acetic anhydride.

b. How does acetic anhydride make it easier to form the anhydride?

What is the product of an acyl substitution reaction鈥攁 new carboxylic acid derivative, a mixture of two carboxylic acid derivatives, or no reaction鈥攊f the new group in the tetrahedral intermediate is the following?

a. a stronger base than the substituent that is attached to the acyl group

b. a weaker base than the substituent that is attached to the acyl group

c. similar in basicity to the substituent that is attached to the acyl group
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