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Chapter 20: Q14P c. (page 1062)

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.

Short Answer

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Answer

(c) The intermediates formed in the protonation of carbonyl oxygen are more stable than the intermediate obtained from the protonation of the hydroxyl oxygen atom.

Step by step solution

01

Basicity

Basicity is the ability to accept hydrogen ions and forms a stable product. It mainly depends upon the availability of electron pairs. The greater number of electrons available, the more readily they can donate and form a new bond to a proton.

02

Carbonyl oxygen is more basic than hydroxy oxygen

(c) Carbonyl oxygen is more basic than hydroxyl oxygen because, as we know, it reacts more readily with a proton by the definition of basicity. The intermediates in the protonation of carbonyl oxygen are more stable than the intermediate in the protonation of the hydroxyl oxygen atom.

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Most popular questions from this chapter

In the presence of 18-crown-6, potassium permanganate dissolves inbenzene to give “purple benzene” a useful reagent for oxidizing alkenes in an aprotic environment. Use a drawing of the complex to show why dissolves in benzeneand why the reactivity of the permanganate ion is enhanced.

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

(a) Glycine isopropyl ester

(b) N-benzoylglycine

(c) N-benzyloxycarbonylglycine

(d) Tert-butyloxycarbonylglycine

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(a) isopentyl alcohol isopentyl acetate (banana oil)

(b) 3-ethylpentanoic acid3-ethylpentanenitrile

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(d) ethyl acetate3-methylpentan-3-ol

(e) cyclohexylamineN-cyclohexylacetamide

(f) bromocyclohexanedicyclohexylmethano

(g)

(h)

Show how you would use extractions with a separatory funnel to separate a mixture of the following compounds: benzoic acid, phenol, benzyl alcohol, aniline.

Show how you would synthesize the following compounds from the appropriate carboxylic acids or acid derivatives.

(a)

(b)

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