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Chapter 20: Q18P b. (page 1065)

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.

(a)

(b)

(c)

Short Answer

Expert verified

(b)

Step by step solution

01

Synthesis of acetanilide

(b) When aniline is treated with acetic acid , an acetate ion is formed along with a phenyl ammonium ion. Further, on heating, acetanilide is formed.

02

Reaction of acetanilide

Synthesis of acetanilide

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Most popular questions from this chapter

(a) Give the products expected when acetic formic anhydride reacts with

(i) aniline and

(ii) benzyl alcohol

(b) Propose mechanisms for these reactions.

Question: A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.

  1. Draw the resonance forms of a carboxylic acid that is protonated on the hydroxy oxygen atom.
  2. Compare the resonance forms with those given previously for an acid protonated on the carbonyl oxygen atom.
  3. Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than the hydroxy oxygen.

The IR, NMR, and mass spectra are provided for an organic compound.

  1. Consider each spectrum individually, and tell what characteristics of the molecule are apparent from that spectrum.
  2. Propose a structure for the compound, and show how your structure fits the spectral data.
  3. Explain why an important signal is missing from the proton NMR spectrum.

Question:

  1. Why do most long-chain fatty acids show a large peak in the mass spectrum at m/z 60?
  2. Use equations to explain the prominent peaks at m/z 74 and m/z 87 in the mass spectrum of 2-methylpentanoic acid.
  3. Why doesn鈥檛 the mass spectrum of 2-methylpentanoic acid show a large peak at m/z 60?

Question: Show how you would synthesize the following carboxylic acids, using the indicated starting materials.

(a) hex-3-yne鈫�propanoicacid

(b) cis-cyclodecene鈫�decanedioicacid

(c ) iodobenzene鈫�phenylaceticacid

(d)pentan-3-ol鈫�2-ethylbutanoicacid

(e)o-xylene鈫�phthalicacid

(f) allylbromide鈫�but-3-enoicacid
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