Problem 13 Why does the partial charge on t... [FREE SOLUTION]

Chapter 46: Problem 13

Why does the partial charge on the acidic hydrogen increase in the series \(\mathrm{CH}_{3} \mathrm{COOH}, \mathrm{CH}_{2} \mathrm{ClCOOH}, \mathrm{CHCl}_{2} \mathrm{COOH}, \mathrm{CCl}_{3} \mathrm{COOH} ?\)

Short Answer

Expert verified

The partial positive charge increase on the acidic hydrogen in the series CH3COOH, CH2ClCOOH, CHCl2COOH, CCl3COOH is due to the increasing presence of electron withdrawing groups (chlorine atoms). As more chlorine atoms replace hydrogen atoms in the series, the electron withdrawing effect becomes stronger. This results in an increase in the partial positive charge on the acidic hydrogen.

Step by step solution

Identify Electron Withdrawing Groups

First, identify the electron withdrawing group presence in each molecule. Electron withdrawing groups, as their name implies, trend to draw electrons in a molecule towards them by virtue of their high electronegativity. Chlorine (Cl) is an example of such as it has a significantly higher electronegativity than Carbon (C). In the series, chlorine atoms are sequentially replacing hydrogen atoms and therefore the electron withdrawing effects of chlorine increase in the series.

Understand the Effect of Electron Withdrawing Groups

An increased concentration of electron withdrawing groups means that the electrons in the covalent bonds will be more drawn towards those groups and away from the hydrogen atom in the carboxyl group. As the electron density around the acidic hydrogen decreases, the partial positive charge on this hydrogen increases.

Apply this Observation to the Given Series

Starting from acetic acid (CH3COOH), the hydrogen atoms in the methyl group (CH3) are sequentially replaced by chlorine atoms to form CH2ClCOOH, CHCl2COOH, and CCl3COOH. As the number of chloride atoms increases, the electron withdrawing effect becomes stronger. Therefore, the partial positive charge on the acidic hydrogen in the COOH group increases.

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

Recommended explanations on Chemistry Textbooks

View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

91影视

Why does the partial charge on the acidic hydrogen increase in the series \(\mathrm{CH}_{3} \mathrm{COOH}, \mathrm{CH}_{2} \mathrm{ClCOOH}, \mathrm{CHCl}_{2} \mathrm{COOH}, \mathrm{CCl}_{3} \mathrm{COOH} ?\)

Short Answer

Step by step solution

Identify Electron Withdrawing Groups

Understand the Effect of Electron Withdrawing Groups

Apply this Observation to the Given Series

One App. One Place for Learning.

Most popular questions from this chapter

Recommended explanations on Chemistry Textbooks

Chemical Analysis

Nuclear Chemistry

Chemical Reactions

Kinetics

The Earths Atmosphere

Inorganic Chemistry

Study anywhere. Anytime. Across all devices.