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Chapter 2: Q14P (page 117)

Rank the following acids in decreasing order of their acid strength. In each case, explain why the previous compound should be a stronger acid than the one that follows it.

Short Answer

Expert verified

Stronger electron-withdrawing groups stabilize the anion of the conjugate base more than weaker groups do, leading to stronger acids. Chlorine is more electronegative and a stronger withdrawing group than bromine, making chloropentanoic acid a stronger acid than bromopentanoic acid.

Step by step solution

01

     Step 1

Stronger electron-withdrawing groups stabilize the anion of the conjugate base more than weaker groups do, leading to stronger acids. Chlorine is more electronegative and a stronger withdrawing group than bromine, making chloropentanoic acid a stronger acid than bromopentanoic acid.

02

Step 2

Adding a chlorine atom to pentanoic acid increases its acidity, and the effect is larger if the chlorine atom is closer to the acidic group.

03

Step 3

In case of bromopentanoic acid, acidic effect is larger if the bromine atom is closer to the acidic group. Therefore 2-bromopentanoic acid is more acidic than 4-bromopentanoic acid.

04

Step 4

Multiple electron-withdrawing groups stabilize the conjugate base and increase the acidity more than a single group does. Therefore 2,2 dichloropentanoic acid is more acidic than 2-chloropentanoic acid.

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Most popular questions from this chapter

Dimethyl ether and ethanol are isomers. Their boiling points are very different, however. Explain why these two compounds have dramatically different boiling points.

CH3-O-CH3 CH3CH2-OH

dimethyl ether, bp -24 掳C ethanol, bp 78 掳C

The following compound can become protonated on any of the three nitrogen atoms. One of these nitrogens is much more basic than the others, however.

  1. Draw the important resonance forms of the products of protonation on each of the three nitrogen atoms.
  2. Determine which nitrogen atom is the most basic.

The following compounds can all react as bases.

  1. For each compound, show its conjugate acid. Show any resonance forms if applicable.
  2. Rank the conjugate acids in the order you would predict, from most stable to least stable.
  3. Rank the original compounds in order from strongest base to weakest base.

Predict the products of the following acid-base reactions.

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

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

(a)
See all solutions

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