Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 21: Problem 13

Each molecule in this problem can be drawn as a hybrid of five contributing structures: two Kekulé structures and three that involve creation and separation of unlike charges. Draw these five contributing structures for each molecule. (a) Chlorobenzene (b) Phenol (c) Nitrobenzene

Short Answer

Expert verified
Question: Draw the five contributing structures (two Kekulé structures and three structures that involve creation and separation of unlike charges) for the following molecules: a) Chlorobenzene b) Phenol c) Nitrobenzene

Step by step solution

01

Understanding Kekulé structures

A Kekulé structure is a representation of a molecule that shows alternating single and double bonds in a resonance structure. Resonance structures are different ways of representing a molecule and contribute to the overall hybrid structure. In this exercise, we need to draw five contributing structures (including two Kekulé structures) for each molecule. Now let's draw the five contributing structures for each of the given molecules:
02

(a) Chlorobenzene: Kekulé structures

For chlorobenzene, the Kekulé structures will have alternating single and double bonds in the benzene ring, with the chlorine atom attached to one of the carbon atoms. Here are the two Kekulé structures for chlorobenzene: 1. Cl connected to a double bond: \chemfig{*6(=-=(-(-Cl)-=)-=-)} 2. Cl connected to a single bond: \chemfig{*6(=-(=(-Cl)-)-=-=)}
03

(a) Chlorobenzene: Structures with charge separation

We will now draw three structures with charge separation for chlorobenzene: 1. Positive charge on the carbon where Cl is attached, and negative charge on the adjacent carbon with double bond: \chemfig{*6((+)-(-Cl)-=(-(-))-=-)} 2. Positive charge on the carbon where Cl is attached, and negative charge on the other adjacent carbon with double bond: \chemfig{*6(=-=(-(-Cl)(+))-(-)=)} 3. Negative charge on the carbon where Cl is attached, and positive charge on the adjacent carbon with double bond: \chemfig{*6((+)-(-Cl(-))-=-=)}
04

(b) Phenol: Kekulé structures

For phenol, the Kekulé structures will have alternating single and double bonds in the benzene ring, with the hydroxyl group (OH) attached to one of the carbon atoms. Here are the two Kekulé structures for phenol: 1. OH connected to a double bond: \chemfig{*6(=-=(-(-OH)-=)-=-)} 2. OH connected to a single bond: \chemfig{*6(=-(=(-OH)-)-=-=)}
05

(b) Phenol: Structures with charge separation

We will now draw three structures with charge separation for phenol: 1. Positive charge on the carbon where OH is attached, and negative charge on the adjacent carbon with double bond: \chemfig{*6((+)-(-OH)-=(-(-))-=-)} 2. Positive charge on the carbon where OH is attached, and negative charge on the other adjacent carbon with double bond: \chemfig{*6(=-=(-(-OH)(+))-(-)=)} 3. Negative charge on the carbon where OH is attached, and positive charge on the adjacent carbon with double bond: \chemfig{*6((+)-(-OH(-))-=-=)}
06

(c) Nitrobenzene: Kekulé structures

For nitrobenzene, the Kekulé structures will have alternating single and double bonds in the benzene ring, with the nitro group (NO2) attached to one of the carbon atoms. Here are the two Kekulé structures for nitrobenzene: 1. NO2 connected to a double bond: \chemfig{*6(=-=(-(-NO_2)-=)-=-)} 2. NO2 connected to a single bond: \chemfig{*6(=-(=(-NO_2)-)-=-=)}
07

(c) Nitrobenzene: Structures with charge separation

We will now draw three structures with charge separation for nitrobenzene: 1. Positive charge on the carbon where NO2 is attached, and negative charge on the adjacent carbon with double bond: \chemfig{*6((+)-(-NO_2)-=(-(-))-=-)} 2. Positive charge on the carbon where NO2 is attached, and negative charge on the other adjacent carbon with double bond: \chemfig{*6(=-=(-(-NO_2)(+))-(-)=)} 3. Negative charge on the carbon where NO2 is attached, and positive charge on the adjacent carbon with double bond: \chemfig{*6((+)-(-NO_2(-))-=-=)}

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

Following each name is the number of Kekulé structures that can be drawn for it. Draw these Kekulé structures, and show, using curved arrows, how the first contributing structure for each molecule is converted to the second and so forth. (a) Naphthalene (3) (b) Phenanthrene (5)

Following are \({ }^{1} \mathrm{H}-\mathrm{NMR}\) and \({ }^{13} \mathrm{C}-\mathrm{NMR}\) spectral data for compound \(\mathrm{F}\left(\mathrm{C}_{12} \mathrm{H}_{16} \mathrm{O}\right)\). From this information, deduce the structure of compound \(F\). $$ \begin{array}{lll} \hline{ }^{1} \text { H-NMR } & \multicolumn{2}{c}{{ }^{13} \text { C-NMR }} \\\ \hline 0.83(\mathrm{~d}, 6 \mathrm{H}) & 207.82 & 50.88 \\ 2.11(\mathrm{~m}, 1 \mathrm{H}) & 134.24 & 50.57 \\ 2.30(\mathrm{~d}, 2 \mathrm{H}) & 129.36 & 24.43 \\ 3.64(\mathrm{~s}, 2 \mathrm{H}) & 128.60 & 22.48 \\ 7.2-7.4(\mathrm{~m}, 5 \mathrm{H}) & 126.86 & \\ \hline \end{array} $$

Describe the ground-state electron configuration of the cyclopentadienyl cation and radical. Assuming each species is planar, would you expect it to be aromatic or antiaromatic?

Arrange these compounds in order of increasing acidity: 2,4-dichlorophenol, phenol, cyclohexanol.

Molecules of \(6,6^{\prime}\)-dinitrobiphenyl-2,2'-dicarboxylic acid have no tetrahedral chiral center, and yet they can be resolved to a pair of enantiomers. Account for this chirality.
See all solutions

Recommended explanations on Chemistry Textbooks

Inorganic Chemistry

Read Explanation

Chemistry Branches

Read Explanation

Kinetics

Read Explanation

Organic Chemistry

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Physical Chemistry

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