EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
2nd Edition
ISBN: 9780393630817
Author: KARTY
Publisher: W.W.NORTON+CO. (CC)
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Chapter 14, Problem 14.8YT
Interpretation Introduction

Interpretation:

Each MO shown in Figure 14-21 is to be labeled as bonding, antibonding, or nonbonding.

Concept introduction:

Overlap of atomic orbitals (AOs) can be thought of as wave interference. It can be destructive overlap or constructive overlap. Constructive interference increases the electron density between the two nuclei (an antinode) and results in a molecular orbital (MO) of lower energy. The phases of the overlapping orbitals are the same in this case. Destructive interference reduces the electron density between the two nuclei and results in an MO of higher energy. The phases of such AOs are opposite.

Non-bonding MOs are formed when there is neither constructive nor destructive interference between the AOs. The energy of the MO is the same as the contributing AOs.

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2. Please consider the two all 'cis' isomers of trimethylcyclohexane drawn below. Draw the two chair conformers of each stereoisomer below (1 and 2) and calculate their torsional interaction energies in order to identify the lower energy conformer for each stereoisomer. Based on your calculations, state which of the two stereoisomers 1 and 2 is less stable and which is more stable. [1,3-diaxial CH3 CH3 = 3.7kcal/mol; 1,3-diaxial CH3 H = 0.88kcal/mol; cis-1,2 (axial:equatorial) CH3 CH3 = 0.88kcal/mol; trans-1,2-diequatorial CH3 CH3 = 0.88kcal/mol) all-cis-1,2,3- 1 all-cis-1,2,4- 2
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EBK ORGANIC CHEMISTRY: PRINCIPLES AND M

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