/*! 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} Q15-15-27 Look at the five resonance struc... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 15: Q15-15-27 (page 477)

Look at the five resonance structures for phenanthrene (Problem 15-26), and predict which of its carbon-carbon bonds is the shortest.

Short Answer

Expert verified

Shorter bond at 6 and 7 carbon

Step by step solution

01

Characteristic of shorter bond

The carbon-carbon double bond that is present in most of the resonance structures of phenanthrene is the bond that shows more double bond character. This bond corresponds to a shorter bond compared to other double bonds.

02

Shorter bond in Phenanthrene

As mentioned in the diagram, the double bond between carbon 6 and 7 is present in four resonance structures out of five. Thus, this bond has a more double-bond character and is shorter than the other carbon bonds of phenanthrene. Therefore, the resonance structures showing the shorter bond is depicted as follows:

Shorter bond at 6 and 7 carbon

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

Give IUPAC names for the following compounds

b)

Look at the three resonance structures of naphthalene shown in Section 15-6, and account for the fact that not all carbon-carbon bonds have the same length. The C1鈥揅2 bond is 136 pm long, whereas the C2鈥揅3 bond is 139 pm long

The substitution reaction of toluene with Br2 can, in principle, lead to the formation of three isomeric Bromo toluene products. In practice, however, only o- and p-Bromo toluene are formed in substantial amounts. The meta isomer is not formed. Draw the structures of the three possible carbocation intermediates (Problem 15-51), and explain why ortho and para products predominate over meta products.

Draw structures corresponding to the following names:

(a) 3-Methyl-1,2-benzenediamine

(b) 1,3,5-Benzenetriol

(c) 3-Methyl-2-phenylhexane

(d) o-Aminobenzoic acid

(e) m-Bromophenol

(f) 2,4,6-Trinitrophenol (picric acid)

Calicene, like azulene (Problem 15-17), has an unusually large dipole moment for a hydrocarbon. Explain, using resonance structures.

Calicene
See all solutions

Recommended explanations on Chemistry Textbooks

Nuclear Chemistry

Read Explanation

Chemical Reactions

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Kinetics

Read Explanation

Making Measurements

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.