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The following structure is called imidazolium. Which of the following statements about imidazolium are true? a. Both nitrogens are sp 2 hybridized, and the lone pair of electrons is in a 2 p orbital. b. The nitrogen on the right is sp 3 hybridized, while the nitrogen on the left is sp 2 hybridized. The lone pair of electrons is in an sp 3 hybrid orbital. c. The molecule has an equivalent contributing structure not shown. d. The molecule has no reasonable contributing structures. 1. Statements a and c are true. 2. Statements a and d are true. 3. Statements b and c are true. 4. Statements b and d are true.

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Organic Chemistry

8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350

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Section
BuyFindarrow_forward

Organic Chemistry

8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350
Chapter 1.9, Problem DQ
Textbook Problem
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The following structure is called imidazolium. Which of the following statements about imidazolium are true?

Chapter 1.9, Problem DQ, The following structure is called imidazolium. Which of the following statements about imidazolium

  1. a. Both nitrogens are sp2 hybridized, and the lone pair of electrons is in a 2p orbital.
  2. b. The nitrogen on the right is sp3 hybridized, while the nitrogen on the left is sp2 hybridized. The lone pair of electrons is in an sp3 hybrid orbital.
  3. c. The molecule has an equivalent contributing structure not shown.
  4. d. The molecule has no reasonable contributing structures.
    1. 1. Statements a and c are true.
    2. 2. Statements a and d are true.
    3. 3. Statements b and c are true.
    4. 4. Statements b and d are true.

Interpretation Introduction

Interpretation:

The correct statement has to be given according to the imidazolium structure.

Concept introduction:

Resonance:

The delocalization of electrons which is characterized as several structural changes.

Hybridization:

Hybridization is the process of combinations of atomic orbitals forms hybrid orbitals.

sp3 Hybrid orbital:

The combination of one s atomic orbital and three p atomic orbitals forms sp3 hybrid orbital.

sp2 Hybrid orbital:

The combination of one s atomic orbital and two p atomic orbitals forms sp2 hybrid orbital.

sp Hybrid orbital:

The combination of one s atomic orbital and one p atomic orbitals forms sp hybrid orbital.

According to VSPER theory the bond angle is depends on the valence electron of an atom. Valence electrons may be involved in the formation of single, double, or triple bonds or they may be unshared (lone pair) electrons.

According to VSPER theory,

Regions of electron density around the central atom is four, the geometry of the molecule may be tetrahedral and the bond angle is 109.5o.

Regions of electron density around the central atom is three, the geometry of the molecule may be trigonal planar and the bond angle is 120o.

Regions of electron density around the central atom is two, the geometry of the molecule may be linear and the bond angle is 180o.

Groups bonded to carbonOrbital hybridizationBond angleTypes of bond
4sp3109.5oFour σ bonds
3Sp2120 oThree σ bonds and one π bond
2sp180 oTwo σ bonds and two π bond

Explanation of Solution

The given imidazolium structure is shown below,

Reason for the correct answer:

Option 1 is correct answer.  Statement a and c are correct.

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Organic Chemistry
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