Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 1, Problem 48P

(a)

Interpretation Introduction

Interpretation:Two resonance forms for ( CH3)2BN( CH3)2 , ( CH3)2BOCH3 and ( CH3)2BF should be formulated.

Concept introduction:When a certain Lewis structure proposed is not able to describe all the experimentally observed parameters of a molecule two or more Lewis structures that differ only in the location of multiple bonds are drawn. These are known as resonance structures. The actual molecule is essentially represented as the hybrid of each of such resonance structures. For instance, a molecule such as ozone O3 the resonance structure and hybrid are illustrated below.

  Organic Chemistry: Structure and Function, Chapter 1, Problem 48P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:Out of the two resonanceformsof ( CH3)2BN( CH3)2 , ( CH3)2BOCH3 and ( CH3)2BF , more important form should be formulated.

Concept introduction: When a certain Lewis structure proposed is not able to describe all the experimentally observed parameters of a molecule two or more Lewis structures that differ only in the location of multiple bonds are drawn. These are known as resonance structures. The actual molecule is essentially represented as the hybrid of each of such resonance structures. For instance, a molecule such as ozone O3 the resonance structure and hybrid are illustrated below.

  Organic Chemistry: Structure and Function, Chapter 1, Problem 48P , additional homework tip  2

(c)

Interpretation Introduction

Interpretation:The manner the relative importance of the resonance forms ( CH3)2BN( CH3)2 , ( CH3)2BOCH3 and ( CH3)2BF is affected by the electronegativity differences in nitrogen, oxygen, and fluorine should be determined.

Concept introduction: When a certain Lewis structure proposed is not able to describe all the experimentally observed parameters of a molecule two or more Lewis structures that differ only in the location of multiple bonds are drawn. These are known as resonance structures. The actual molecule is essentially represented as the hybrid of each of such resonance structures. For instance, a molecule such as ozone O3 the resonance structure and hybrid are illustrated below.

  Organic Chemistry: Structure and Function, Chapter 1, Problem 48P , additional homework tip  3

(d)

Interpretation Introduction

Interpretation: The hybridization of nitrogen in ( CH3)2BN( CH3)2 and oxygen in ( CH3)2BOCH3 should be predicted.

Concept introduction:The table that relates the steric number with hybridization is as follows:

  Steric NumberType of Hybridisation2sp3 sp24 sp35 sp3d6 sp3d2

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For each of the following covalent bonds: (a) use the symbols δ+ and δ- to indicate the direction of polarity (if any).(a) C-F; (b) N-Br; (c) B-C; (d) Si-H(b) Rank the following covalent bonds in order of increasing polarity. (i) C-H, O-H, N-H; (ii) C-N, C-O, B-O; (iii) C-P, C-S, C-N
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4) (a) For the following structure, using curved arOWs draw all resonance contributors (only those with an octet of electrons on all non-hydrogen atoms). Be sure to show all lone pairs and non-zero formal charge(s) where applicable. CH HC CH, CH2
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