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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

Expert verified

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

Question: Rank the compounds in each set in order of increasing acid strength.

(a)CH3CH2COOH,CH3CHBrCOOH,CH3CBr2COOH

(b) CH3CH2CH2CHBrCOOH,CH3CH2CHBrCH2COOH,CH3CHBrCH2CH2COOH

(c)

,CH3CH2COOH,

Question: Oxidation of primary alcohol to an aldehyde usually gives some over-oxidation to the carboxylic acid. Assume you have used PCC to oxidize pentan-1-ol to pentanal.

  1. Show how you would use acid-base extraction to purify the pentanal.
  2. Which of the expected impurities cannot be removed from pentanal by acid-base extractions? How would you remove this impurity?

Question: Oxidation of a primary alcohol to an aldehyde usually gives some over-oxidation to the carboxylic acid. Assume you have used PCC to oxidize pentan-1-ol to pentanal.

(b). Which of the expected impurities cannot be removed from pentanal by acid-base extractions? How would you remove this impurity?

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.

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?
See all solutions

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