/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Q14P Rank the following acids in decr... [FREE SOLUTION] | 91影视

91影视

Log out

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.

Over 30 million students worldwide already upgrade their learning with 91影视!

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 N-F bond is more polar than N-H bond, but NF3 has smaller dipole moment than NH3. Explain the curious result.

NH3: 碌= 1.5 D, NF3: 碌= 0.2D

Predict the products of the following acid-base reactions.

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

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.

Circle the functional groups in the following structures. State to which class (or classes) of compounds the structure belongs.

(a)

(b)


(c)

(d)

(e)

(f)

(g)

(h)


(i)

Write equations for the following acid-base reactions. Label the conjugate acids and bases and show any inductive stabilization. Predict whether the equilibrium favors the reactants or products. Try to do this without using a table of pKa values, but if you need a hint, you can consult Appendix 4.
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Reactions

Read Explanation

Inorganic Chemistry

Read Explanation

Kinetics

Read Explanation

Organic Chemistry

Read Explanation

Nuclear Chemistry

Read Explanation

The Earths Atmosphere

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.