Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.

(a)N,N-dimethylacetamide

(b)acetanilide (PhNHCOCH3)

(c)cyclohexanecarboxamide

(d)

Short Answer

Expert verified

(a)

(b)

(c)

(d)

Step by step solution

01

About the acetamide

(a) The acetic acid group attached to amide is called acetamide. This compound bears nitrogen and carbonyl groups. These compounds have a musty odor.

02

About N,N-dimethylacetamide

The acetamide that has two methyl groups at the nitrogen atom is N,N-diethylacetamide. The structure of this compound is given below.

03

About the reaction

The acyl chloride used is acetyl chloride and the amide used is dimethylamine. The resulting product will be N,N-dimethylacetamide. The by-product formed in this reaction is hydrochloric acid. The reaction is given below.

04

About acetanilide

(b) The organic compound that bears the benzene ring and group attached by NH bond is acetanilid. The structure of this compound is given below.

05

About the reaction

The acyl chloride used is acetyl chloride and the amide used is dimethylamine. The resulting product will beaniline. The by-product formed in this reaction is hydrochloric acid. The reaction is given below.

06

About cyclohexanecarboxamide

(c) The organic compound that bears benzene ring and group attached to bond cyclohexane is cyclohexanecarboxamide. The structure of this compound is given below.

07

About the reaction

The acyl chloride used is cyclohexanecarbonyl chloride.Ammonia isalso used. The resulting product will be cyclohexanecarboxamide. The by-product formed in this reaction is hydrochloric acid. The reaction is given below.

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Most popular questions from this chapter

(a) How many asymmetric carbon atoms are there in an aldotetrose? Draw all the aldotetrose stereoisomers.

(b) How many asymmetric carbon atoms are there in a ketotetrose? Draw all the ketotetrose stereoisomers.

(c) How many asymmetric carbon atoms and stereoisomers are there for an aldohexose? For a ketohexose?

Phosgene is the acid chloride of carbonic acid. Although phosgene was used as a war gas in World War I, it is now used as a reagent for the synthesis of many useful products. Phosgene reacts like other acid chlorides, but it can react twice.

(a) Predict the products formed when phosgene reacts with excess propan-1-ol.

(b) Predict the products formed when phosgene reacts with 1 equivalent of ethanol, followed by 1 equivalent of aniline.

(c) Iso-butyloxycarbonyl chloride is an important reagent for the synthesis of peptides and proteins. Show how you would use phosgene to synthesize iso-butyloxycarbonyl chloride.

Isobutyloxycarbonyl chloride

In the presence of a trace of acid, δ-hydroxyvaleric acid forms a cyclic ester (lactone).

HO-CH2CH2CH2CH2-COOH

δ-hydroxyvaleric acid

(a)Give the structure of the lactone, called δ-valerolactone.

(b) Propose a mechanism for the formation of δ-valerolactone.

Question:An unknown compound gives a molecular ion of m/z 70 in the mass spectrum. It reacts with semicarbazide hydrochloride to give a crystalline derivative, but it gives a negative Tollens test. The NMR and IR spectra follow. Propose a structure for this compound, and give peak assignments to account for the absorptions in the spectra. Explain why the signal at 1790 cm-1 in the IR spectrum appears at an unusual frequency.

Show how you would convert glycine to following derivatives. Show the structure of the product in each case.

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