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Chapter 19: Q42 (page 759)

Which carboxylic acid has the lower pKa, pyruvic acid (CH3COCOOH)or acetoacetic acid (CH3COCH2COOH) ? Explain your choice.

Short Answer

Expert verified

Pyruvic acid is the carboxylic acid that has a lower pKavalue.

Step by step solution

01

Meaning of  pKa

The pKa value is determines the acidic strength of the acids. Higher the value of pKa, lower will be the acidity of the compound.

The acidic strength increases due to the presence of the electron-withdrawing groups. The acidic strength also increases if the conjugate base is resonance stabilized.

02

Comparison of the acidic strength of pyruvic acid and acetoacetic acid

The structure of pyruvic acid is as follows:

Pyruvic acid

The structure of acetoacetic acid is as follows:

Acetoacetic acid

The acidic strength of acetoacetic acid is lower as compared to pyruvic acid. The pKa of acetoacetic acid is 3.58, whereas the pKa of pyruvic acid is 2.50. This implies that pyruvic acid is a stronger acid than acetoacetic acid.

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Most popular questions from this chapter

Question: Rank the following compounds in order of increasing boiling point. Which compound is the most water soluble? Which compound is the least water soluble?

Question: Draw the structure corresponding to each name.

  1. 3,3-dimethylpentanoic acid
  2. 4-chloro-3-phenylheptanoic acid
  3. (R)-2-chloropropanoic acid
  4. m-hydroxybenzoic acid
  5. potassium acetate
  6. sodium 伪-bromobutyrate
  7. 2,2-dichloropentanedioic acid
  8. 4-isopropyl-2-methyloctanedioic acid

The pKaof p-methylthiophenol(CH3SC6H4OH) is 9.53. Is p-methylthiophenol more or less reactive in electrophilic aromatic substitution than phenol?

For each amino acid [RCHNH2COOH], draw its neutral, positively charged, and negatively charged forms. Which form predominates at pH = 1, 6, and 11? What is the structure of each amino acid at its isoelectric point?

a. methionine (R=CH2CH2SCH3)

b. serine (R=CH2CH2OH)

Because phenol (C6H5OH)is less acidic than a carboxylic acid, it can be deprotonated by NaOH but not by the weaker base NaHCO3. Using this information, write out an extraction sequence that can be used to separate (C6H5OH) , benzoic acid, and cyclohexanol. Show what compound is present in each layer at each stage of the process, and if it is present in its neutral or ionic form.
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