Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
2nd Edition
ISBN: 9780393655551
Author: KARTY, Joel
Publisher: W. W. Norton & Company
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Chapter 14, Problem 14.7P
Interpretation Introduction

Interpretation:

The complete MO energy diagram for butadienyl dication [CH2-CH=CH-CH2]2+ similar to the one shown in Figure 14-12 is to be drawn.

Concept introduction:

MOs arise from interacting AOs on different atoms. The number of MOs formed must equal the number of contributing AOs. MO energies differ as a result of constructive and destructive interference among contributing AOs. For a linear system of conjugated p orbitals, all nodal planes in a resulting π MO must be positioned symmetrically about the centre of that set of p orbitals. The energy of the MO with only bonding interactions is the lowest. As the number of antibonding interactions increases, so does the energy of the resulting MO. The MO with only antibonding interactions has the highest energy.

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Answer the questions below for 2,4-hexadiene. Before you begin, construct a molecular orbital (MO) diagram for the conjugated system. Number the MOs consecutively in order of increasing energy starting with 1 for the MO at lowest energy. a How many p atomic orbitals are in the conjugated system?
44a) Draw the bond-line structure of 1,4-dimethyl-cyclohexa-1,3-diene here: STRUCTURE: b) Circle all the sp²-hybridized carbons in your drawing of the structure. c) In the spaces below, draw two potential products from a chlorination reaction (addition of Cl2) with your first structure Product 1: Product 2:
Product ?

Chapter 14 Solutions

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)

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