Log out Go to App
Go to App

Learning Materials

Features

Discover

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.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

The following compounds can all react as acids.

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

Question: The C ≡ Ntriple bond in acetonitrile has a dipole moment of about 3.6 Dand a bond length of about 1.16 Å. Calculate the amount of charge separation in this bond. How important is the charge separated resonance form in the structure of acetonitrile?

TheKa of phenylacetic acid is5.2 × 10-5, and thepKaof propionic acid is4.87.

(a)Calculate thepKaof phenylacetic acid and theKaof propionic acid.

(b) Which one of these is the stronger acid? Calculate how much stronger an acid it is.

(c) Predict whether the following equilibrium will favor the reactants or the products.

N-Methylpyrrolidine has a boiling point of81οC, and piperidine has a boiling point of106οC.

  1. Explain the large difference (25οC) in boiling point for these two isomers.
  2. Tetrahydropyran has a boiling point of 88οC, and cyclopentanol has a boiling point of 141οC. These two isomers have a boiling point difference of 53οC.Explain why the two oxygen-containing isomers have a much larger boiling point difference than two amine isomers.
  3. N,N-Dimethylformamide has a boiling point of 150οC, and N-methylacetamide has a boiling point of 206οC, for a difference of 56οC.Explain why these two nitrogen-containing isomers have a much larger boiling point difference than the two amine isomers. Also explain why these two amides have higher boiling points than any of the other four compounds shown (two amines, an ether, and an alcohol).

The following compounds can all react as acids.

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

Recommended explanations on Chemistry Textbooks

Inorganic Chemistry

Read Explanation

Chemistry Branches

Read Explanation

Chemical Analysis

Read Explanation

Chemical Reactions

Read Explanation

Making Measurements

Read Explanation

Ionic and Molecular Compounds

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free