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Chapter 2: Q21P (page 121)

Choose the more acidic member of each pair of isomers, and show why the acid you chose is more acidic.

(a)

Short Answer

Expert verified

The more acidic among the given pair is

Step by step solution

01

Step 1

The acidic strength of the compound is depending upon the stability of its conjugate base.

02

Step 2

Here among the given pair the compound on left is more acidic as deprotonation gives resonance stabilized anion. The resulting anion has delocalization of the negative charge on the carbonyl group.

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Most popular questions from this chapter

Classify the following hydrocarbons, and draw a lewis structure for each one. A compound may fit into more than one of the following classifications:

Alkane, alkene, alkyne, cycloalkane, cycloalkene, cycloalkyne, aromatic hydrocarbon.

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Ozone has a dipole moment of 0.53 D. Carbon dioxide has a dipole moment of zero, even though C-O bonds are more polar than O-O bonds. Explain this apparent contradiction.

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CH3-O-CH3 CH3CH2-OH

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Question: The pKa of ascorbic acid (vitamin C, page 9) is 4.17 , showing that it is lightly more acidic than acetic acid (CH3COOH, pKa = 4.74).

(a)Show four different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid.

(b) Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic.

(c) Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group

Like nitrogen and carbon, oxygen also shows this same hybridization effect on acidity. Both of the following compounds can lose a proton from a positively charged oxygen with three bonds to give a conjugate base containing a neutral oxygen with two bonds. One of these structures has pKa = -2.4 , while the other has pKa = -8.0.

  1. Show the reaction of each compound with water.
  2. Match each structure with its pKa , and explain your choice.
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