Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 9: Problem 51

Write three resonance structures for hydrazoic acid, \(\mathrm{HN}_{3}\). The atomic arrangement is HNNN. Show formal charges.

Short Answer

Expert verified
The resonance structures of hydrazoic acid (HN3) are three: \[ \mathrm{H-N=N=N}, \mathrm{H=N-N\:^{-}-N\:^{+}}, \mathrm{H\:^{-}-N\:^{+}-N=N} \] The formal charges on Nitrogen atoms in these structures are respectively: \[ \{(0, 0, 0), (-1, 0, +1), (+1, 0, -1)\} \]

Step by step solution

01

Draw a valid Lewis structure

Initially, start by drawing a valid Lewis structure for hydrazoic acid. In this structure, the Hydrogen is bonded to the first Nitrogen, and Nitrogen atoms are connected consecutively. Each Nitrogen atom must have 5 valence electrons (as per the periodic table), and hydrogen must have one valence electron. Use these rules to position the other electrons around the atoms.
02

Draw Resonance Structures

Based on the initial Lewis representation, make changes where the double bond can flip between Nitrogen atoms, thereby creating resonance structures. This leads to redistribution but not total count of electrons. Add a double bond between 2nd and 3rd Nitrogen atoms and remove one from 1st and 2nd. This will form the second resonance structure. Similarly, make the third resonance by forming double bond between 1st and 2nd Nitrogen again but this time remove lone pair of electron from 1st Nitrogen and put it as lone pair to third. This satisfies the octet rule where each Nitrogen atom is surrounded by 8 electrons and hydrogen by 2 electrons.
03

Establish Formal Charges

Formal charges for each atom in all three structures will be determined. The formal charge of any atom can be found using the equation: Formal charge = (number of valence electrons) - (non-bonding valence electrons + number of bonds). Apply this formula to each atom in your resonance structures. This ensures that the overall charge of each structure is consistent with the actual molecule.

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

Write three reasonable resonance structures of the azide ion \(\mathrm{N}_{3}^{-}\) in which the atoms are arranged as NNN. Show formal charges.

What is Lewis's contribution to our understanding of the covalent bond?

Using this information: $$ \begin{array}{rr} \mathrm{C}(s) \longrightarrow \mathrm{C}(g) & \Delta H_{\mathrm{rxn}}^{\circ}=716 \mathrm{~kJ} / \mathrm{mol} \\ 2 \mathrm{H}_{2}(g) \longrightarrow 4 \mathrm{H}(g) & \Delta H_{\mathrm{rxn}}^{\circ}=872.8 \mathrm{~kJ} / \mathrm{mol} \end{array} $$ and the fact that the average \(\mathrm{C}-\mathrm{H}\) bond enthalpy is \(414 \mathrm{~kJ} / \mathrm{mol}\), estimate the standard enthalpy of formation of methane \(\left(\mathrm{CH}_{4}\right)\).

Which of these molecules has the shortest nitrogento-nitrogen bond? Explain. $$ \begin{array}{llll} \mathrm{N}_{2} \mathrm{H}_{4} & \mathrm{~N}_{2} \mathrm{O} & \mathrm{N}_{2} & \mathrm{~N}_{2} \mathrm{O}_{4} \end{array} $$

The amide ion, \(\mathrm{NH}_{2}^{-}\), is a Bronsted base. Represent the reaction between the amide ion and water in terms of Lewis structures.
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Reactions

Read Explanation

Organic Chemistry

Read Explanation

Making Measurements

Read Explanation

Physical Chemistry

Read Explanation

Chemical Analysis

Read Explanation

Nuclear 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