EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260475685
Author: SMITH
Publisher: MCGRAW-HILL HIGHER EDUCATION
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Chapter 1, Problem 83P
Interpretation Introduction

(a)

Interpretation: The reason for difference in bond lengths of the bond [1] and bond [2] is to be stated.

Concept introduction: With an increase in the s character, bond strength increases and ultimately bond length decreases. This is because the electrons are held more tightly and closer to the nucleus by the hybrid orbitals.

Interpretation Introduction

(b)

Interpretation: The reason for equal bond length of bonds [3] and [4] and shorter bond length than bond [2] is to be stated.

Concept introduction: Resonance plays a significant role in stabililizing the molecule and it is responsible for properties exhibited by the molecule.

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Use the observed bond lengths to answer each question. (a) Why is bond [1] longer than bond [2] (143 pm versus 136 pm)? (b) Why are bonds [3] and [4] equal in length (127 pm), and shorter than bond [2]?
3. (a) Draw a resonance structure for Molecule 1 in Box B, which satisfies the octet for all non- hydrogen atoms. Hint you may want to use curved arrows to move electrons over the skeleton of Molecule 3 to help you find the resonance structure. H H H H Molecule 1 H H 3. (b) Fill in the table below for Molecule 1 Box B: Resonance Structure of Molecule 1 VSEPR electron pair geometry around atom Molecular geometry Approximate bond or shape around atom angles around atom N atom CH3 C atom CH C atoms 3. (c) Given the information that resonating electrons are delocalized and so are not used to determine VSEPR geometry, how will the table you filled in for 3.(b) change?
Use the observed bond lengths to answer each question. (a) Why is bond [1] longer than bond [2] (143 pm versus 136 pm)? (b) Why are bonds [3] and [4] equal in length (127 pm), and shorter than bond [2]?

Chapter 1 Solutions

EBK ORGANIC CHEMISTRY

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