Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
bartleby

Concept explainers

Question
Book Icon
Chapter 2.SE, Problem 20VC
Interpretation Introduction

Interpretation:

A model of naphthalene is given. The position of multiple bonds in it is to be shown. The number of possible resonance structures for naphthalene is to be stated and their structures are to be drawn.

Concept introduction:

Hydrogen is monovalent. Carbon is tetravalent and it can form four bonds. The position of double bonds can be identified by looking for carbons in the model having only three bonds. Resonance forms differ only in the placement of their π and nonbonding valence electrons. Neither the position nor the hybridization of any atom changes from one resonance form to another. The shift of electrons to give another resonance structure is represented by a curved arrow.

To determine:

The position of multiple bonds in the given model of naphthalene, C10H8. The number and structures of possible resonance structures for naphthalene are to be drawn

Expert Solution & Answer
Check Mark

Answer to Problem 20VC

The positions of multiple bonds in naphthalene are shown in the structure given below.

Organic Chemistry, Chapter 2.SE, Problem 20VC , additional homework tip  1

Naphthalene has three resonance forms as shown.

Organic Chemistry, Chapter 2.SE, Problem 20VC , additional homework tip  2

Explanation of Solution

In the model of naphthalene shown all the carbons have formed only three bonds and all the carbons require one more bond to satisfy their fourth valence. This fourth valence of each carbon can be satisfied by placing five double bonds between adjacent carbons as shown.

By shifting the position of double bonds, in total, three resonance structures can be drawn.

Conclusion

The positions of multiple bonds in naphthalene are shown in the structure given below.

Organic Chemistry, Chapter 2.SE, Problem 20VC , additional homework tip  3

Naphthalene has three resonance forms as shown.

Organic Chemistry, Chapter 2.SE, Problem 20VC , additional homework tip  4

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
03:12
Students have asked these similar questions
Fill in the multiple bonds in the following model of naphthalene, C10H8 (gravy = C, ivory = H). How many resonance structures does naphthalene have? Draw them.
Three major contributing resonance structures are possible for the following cation. One is given below. Draw the remaining structures (in any order), including nonbonding electrons and formal charges. Omit curved arrows. н н CH3З Which contributes most to the hybrid? The structure with the positive charge on sulfur. All contribute equally. O The structures with the positive charge on carbon.
Diazomethane (CH2N2) is an important reagent for the methylation of some organic molecules. Complete Parts 1 and 2 below about this unique reagent.  Draw the Lewis structure of diazomethane (CH2N2) that contains a formal charge on carbon and nitrogen. Be sure to include all lone pairs of electrons and formal charges.

Chapter 2 Solutions

Organic Chemistry

Ch. 2.7 - Nitric acid (HNO3) reacts with ammonia (NH3) to...Ch. 2.8 - Prob. 12PCh. 2.8 - Amide ion, H2N-, is a much stronger base than...Ch. 2.9 - Prob. 14PCh. 2.9 - Prob. 15PCh. 2.9 - Prob. 16PCh. 2.11 - Using curved arrows, show how the species in part...Ch. 2.11 - Prob. 18PCh. 2.12 - Of the two vitamins A and C, one is hydrophilic...Ch. 2.SE - Prob. 20VCCh. 2.SE - The following model is a representation of...Ch. 2.SE - cis-l, 2-Dichloroethylene and trans-1,...Ch. 2.SE - The following molecular models are representations...Ch. 2.SE - Predict the product(s) of the acid/base reactions...Ch. 2.SE - Use curved arrows to draw the protonated form of...Ch. 2.SE - Prob. 26MPCh. 2.SE - Double bonds can also act like Lewis bases,...Ch. 2.SE - Prob. 28APCh. 2.SE - Use the electronegativity table given in Figure...Ch. 2.SE - Which of the following molecules has a dipole...Ch. 2.SE - Prob. 31APCh. 2.SE - Phosgene, C12C=O, has a smaller dipole moment than...Ch. 2.SE - Prob. 33APCh. 2.SE - Methanethiol, CH3SH, has a substantial dipole...Ch. 2.SE - Calculate the formal charges on the atoms shown in...Ch. 2.SE - Assign formal charges to the atoms in each of the...Ch. 2.SE - Which of the following pairs of structures...Ch. 2.SE - Prob. 38APCh. 2.SE - 1, 3-Cyclobutadiene is a rectangular molecule with...Ch. 2.SE - Alcohols can act either as weak acids or as weak...Ch. 2.SE - The O-H hydrogen in acetic acid is more acidic...Ch. 2.SE - Draw electron-dot structures for the following...Ch. 2.SE - Write the products of the following acid-base...Ch. 2.SE - Rank the following substances in order of...Ch. 2.SE - Which, if any, of the substances in Problem 2-44...Ch. 2.SE - The ammonium ion (NH4+, pKa = 9.25) has a lower...Ch. 2.SE - Prob. 47APCh. 2.SE - Prob. 48APCh. 2.SE - Calculate Ka values from the following pka’s:...Ch. 2.SE - Calculate pKa values from the following Ka’s:...Ch. 2.SE - What is the pH of a 0.050 M solution of formic...Ch. 2.SE - Prob. 52APCh. 2.SE - Maleic acid has a dipole moment, but the closely...Ch. 2.SE - Assume that you have two unlabeled bottles, one of...Ch. 2.SE - Identify the acids and bases in the following...Ch. 2.SE - Which of the following pairs represent resonance...Ch. 2.SE - Draw as many resonance structures as you can for...Ch. 2.SE - Carbocations, which contain a trivalent,...Ch. 2.SE - We’ll see in the next chapter that organic...Ch. 2.SE - The azide functional group, which occurs in...Ch. 2.SE - Phenol, C6H5OH, is a stronger acid than methanol,...Ch. 2.SE - Thiamin diphosphate (TPP), a derivative of vitamin...Ch. 2.SE - Determine if each compound or ion below has a...Ch. 2.SE - Prob. 64APCh. 2.SE - Prob. 65APCh. 2.SE - Draw the conjugate base for each compound below...Ch. 2.SE - 1, 1, 1-Trichloroethanol is an acid more than 1000...
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Chemistry: The Molecular Science
    Chemistry
    ISBN:9781285199047
    Author:John W. Moore, Conrad L. Stanitski
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
Text book image
Chemistry: The Molecular Science
Chemistry
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning