Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 3, Problem 8E

(a)

Interpretation Introduction

Interpretation: The hybridization state of each non-hydrogen atom in the below structures should be identified.

  Organic Chemistry: A Guided Inquiry, Chapter 3, Problem 8E , additional homework tip  1

Concept introduction: Two or more of orbitals undergo redistributions of their different energies so as to form mathematically averaged orbitals in terms of energy although they may differ in shape and orientation. This phenomenon is referred as hybridization.

The energy and orientation of the new hybrid orbital depends upon by the kind and number of orbitals used in the hybridization. The new hybrid orbitals are always equal in number to number of atomic orbitals that combine.

(b)

Interpretation Introduction

Interpretation: The number of p orbitals contributed by each non-hydrogen atom in the below structures should be identified.

  Organic Chemistry: A Guided Inquiry, Chapter 3, Problem 8E , additional homework tip  2

Concept introduction: Sequence that determines hybridization state of an atom is as follows:

  • A single bond is always associated with sigma bonds. Molecules that have all atoms connected by sigma bond exclusively are stated to be in sp3 hybridization.
  • A double bond is always associated with sp2 hybridization.
  • A triple bond is always associated with sp3 hybridization.

The table that shows the hybridization is as follows:

  Number of sigma bondnumber of pi bondHybridization40sp331sp222sp

(c)

Interpretation Introduction

Interpretation: For each p-orbital the “empty” or half-filled orbitals involved should be indicated.

Concept introduction: Sequence that determines hybridization state of an atom is as follows:

  • A single bond is always associated with sigma bonds. Molecules that have all atoms connected by sigma bond exclusively are stated to be in sp3 hybridization.
  • A double bond is always associated with sp2 hybridization.
  • A triple bond is always associated with sp3 hybridization.

(d)

Interpretation Introduction

Interpretation: The type of hybrid orbital that each lone pair resides in should be indicated.

Concept introduction:Sequence that determines hybridization state of an atom is as follows:

  • A single bond is always associated with sigma bonds. Molecules that have all atoms connected by sigma bond exclusively are stated to be in sp3 hybridization.
  • A double bond is always associated with sp2 hybridization.
  • A triple bond is always associated with sp3 hybridization.

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Represent the bonding in each molecule or ion by drawing the orbitals (hybridized and unhybridized) of each atom in the bond. Label the σ and π bonds and label each bond by the orbitals that it is made from. For instance, the C–H bond in CH4 would be made from the overlap of: C (sp3) – H (1 s). You may draw the hybridized sigma orbitals as sticks and the unhybridized p-orbitals as lobes for clairity and ease. a. HONO b. CH3 CCH c. C3 H4 d. C2 O4 2-
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