Draw the principal resonance forms of the nitronium ion.

Short Answer

Expert verified
The nitronium ion (NO₂⁺) has two principal resonance forms. In the first resonance structure, nitrogen is double bonded to one of the oxygen atoms and single bonded to the other. In the second resonance structure, the positions of the double and single bonds are reversed. Both structures show a positive charge on the central nitrogen atom. These resonance forms represent the resonance-stabilized distribution of electrons between the nitrogen and oxygen atoms.

Step by step solution

01

Determine Lewis Structure of Nitronium Ion

First, we need to draw the Lewis Structure of the nitronium ion (NO₂⁺). To do that, we will count the valence electrons of each atom and connect them with single bonds. Nitrogen has 5 valence electrons, and each oxygen atom has 6 valence electrons. Since the molecule has a positive charge, we will remove one electron. In total, there will be (5 + 6 + 6 - 1) = 16 valence electrons in the molecule.
02

Distribute the Remaining Electrons

Now, we need to distribute the remaining valence electrons as lone pairs around each atom to satisfy the octet rule (except for the central nitrogen atom in this case). Each oxygen atom is connected to the nitrogen atom with a single bond, which accounts for 4 electrons. We have 12 remaining electrons to distribute as lone pairs. Each oxygen atom will receive 3 lone pairs (6 electrons in total). This accounts for all 16 valence electrons.
03

Identify π Electrons and Bonding Atoms

Next, we need to identify the π electrons that can be involved in resonance and the atoms they are shared between. The π electrons are the lone pair electrons on oxygen atoms that are not being used for the single bond to nitrogen. The π electrons can be shared between the two oxygen atoms and the central nitrogen atom.
04

Draw Resonance Forms

To draw the resonance forms, we will show the alternate position of the π electrons being shared in the form of double bonds. The first resonance structure will have a double bond between nitrogen and one of the oxygen atoms, with the other oxygen atom having a single bond. The second resonance structure is formed by moving the double bond to the other oxygen atom, with the first oxygen atom now having a single bond. Make sure to include the positive charge on nitrogen atom. Here are the resonance structures for NO₂⁺ ion: ``` O O \\ // N⁺ N⁺ // \\ O O ``` The nitronium ion has two principal resonance forms, which represent the resonance-stabilized distribution of electrons between the nitrogen and oxygen atoms.

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 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

How do you account for the fact that benzene in the presence of \(\mathrm{ALCl}_{3}\) reacts: (a) with n-propyl bromide to give isopropylbenzene; (b) with isobutyl bromide to yield tert-butylbenzene; (c) with neopentyl bromide to yield tert-pentylbenzene? (d) By which of the alternative mechanisms for the Friedel-Crafts reaction are these products probably formed?

Is \(\mathrm{BH}_{3}\) a nucleophile or an electrophile? Explain.

Explain the following observations: (1) The ortho-para ratio of the products obtained by sulfonation of toluene is lower than that of nitration; (2) The ortho-para ratio of the products obtained by nitration of isopropylbenzene is lower than that of nitration of toluene.

Give structures and names of the principal organic products expected from the monosulfonation of: (a) cyclohexylbenzene (d) m-nitrophenol (b) benzenesulfonic acid (e) o-fluoroanisole (c) salicylaldehyde (f) o-nitroacetanilide \(\left(\mathrm{O}-\mathrm{HOC}_{6} \mathrm{H}_{4} \mathrm{CHO}\right) \quad\left(\mathrm{o}-\mathrm{O}_{2} \mathrm{NC}_{6} \mathrm{H}_{4} \mathrm{NHCOCH}_{3}\right)\) (g) o-xylene

Even though \(1,3,5-\) trinitrobenzene (TNB) has more shattering power (more brisance) and is no more dangerous to handle, \(2,4,6-\) trinitrotoluene (TNT) has always been the high explosive in more general use. Can you suggest a reason (connected with manufacture) for the popularity of TNT? (Benzene and toluene are both readily available materials; for many years benzene was cheaper.)

See all solutions

Recommended explanations on Chemistry Textbooks

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