Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 3, Problem 3.48P
Interpretation Introduction

(a)

Interpretation:

All non-hydrogen atoms that are required to be in the same plane for Adenine are to be identified.

Concept introduction:

According to the VSEPR theory, if an atom is surrounded by three electron groups, either three bonds or two bonds and one lone pair, then the geometry of such an atom is trigonal planar, and thus, it must be sp2 hybridized. When two atoms are connected by a double bond, those atoms, and any atoms to which they are directly bonded, prefer to lie in the same plane. In order to maintain this planar geometry, the atoms that are directly bonded to these doubly bonded atoms must lie in the same plane.

Interpretation Introduction

(b)

Interpretation:

All non-hydrogen atoms that are required to be in the same plane for Cytosine are to be identified.

Concept introduction:

According to the VSEPR theory, if an atom is surrounded by three electron groups, either three bonds or two bonds and one lone pair, then the geometry of such an atom is trigonal planar, and thus, it must be sp2 hybridized. When two atoms are connected by a double bond, those atoms, and any atoms to which they are directly bonded, prefer to lie in the same plane. In order to maintain this planar geometry, the atoms that are directly bonded to these doubly bonded atoms must lie in the same plane.

Interpretation Introduction

(c)

Interpretation:

All non-hydrogen atoms that are required to be in the same plane for Guanine are to be identified.

Concept introduction:

According to the VSEPR theory, if an atom is surrounded by three electron groups, either three bonds or two bonds and one lone pair, then the geometry of such an atom is trigonal planar, and thus, it must be sp2 hybridized. When two atoms are connected by a double bond, those atoms, and any atoms to which they are directly bonded, prefer to lie in the same plane. In order to maintain this planar geometry, the atoms that are directly bonded to these doubly bonded atoms must lie in the same plane.

Interpretation Introduction

(d)

Interpretation:

All non-hydrogen atoms that are required to be in the same plane for Thymine are to be identified.

Concept introduction:

According to the VSEPR theory, if an atom is surrounded by three electron groups, either three bonds or two bonds and one lone pair, then the geometry of such an atom is trigonal planar, and thus, it must be sp2 hybridized. When two atoms are connected by a double bond, those atoms, and any atoms to which they are directly bonded, prefer to lie in the same plane. In order to maintain this planar geometry, the atoms that are directly bonded to these doubly bonded atoms must lie in the same plane.

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2) a) Consider the following molecule . Given what you have learned about hybridization theory, draw an image or images explaining the bonding situation in this molecule. I want you to draw out all of the orbitals, hybrid orbitals and how they overlap to form the bonds in the molecule. Indicate the % s or p character in the given atomic and hybrid orbitals. Which C-C bond or bonds are the longest? In a paragraph or so explain the image or images you just drew. b) Lastly, consider the molecule below. Indicate the Molecular formula, the molar mass, label the hybridization of each atom except for hydrogen, indicate any chiral centers with a *, which bond or bonds are the shortest, identify by name of each functional group with an arrow pointing to the group.
Consider the T-system of the radical (a molecule with one unpaired electron) shown below. Note: the dot in this drawing represents an unpaired electron What is the best description of the following n molecular orbital (hint: consider the resonance structures of the radical)? ㅇ Note: each dot in this drawing represents a carbon nucleus bonding and filled with two electrons bonding and empty non-bonding and contains one electron antibonding and empty antibonding and filled with two electrons
Recall that for a lone pair to be involved in resonance, it must be in a p orbital, which requires the atom it is on to be sp² or sp hybridized. This means that for a situation with resonance, the actual hybridization of the atom is determined from the resonance structure where that atom has the lowest steric number (so it can use the required number of p orbitals to form pi bonds as shown in some of its resonance structures). This could be the situation in your initial drawing, or in one of the resonance structures you draw from it. All of the oxygens in the following molecules are sp² hybridized except one. Which of the following structures has an sp³ hybridized oxygen atom? НО. (A) (B) (D)
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