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 6, Problem 1E
Interpretation Introduction

Interpretation:The Newman projection of butane in its least favorable conformation is to be determined.

Concept introduction:

Newman Projection is useful for the alkaline stereochemistry. The confirmation of this projection is helpful to visualize the bond of the structure from front to back or rear.

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Compare the following conformers of butan-2-ol. Match each conformer to their corresponding relative energy. Recall, the more stable the conformer the lower the energy. 1. ОН CH3 CH3 H 2nd Highest Energy 2. HỌH CH3 2nd Lowest Energy H3C OH Highest Energy 3. H3C. CH3 Lowest Energy OH H. CH3 4. >
4. For the structure shown below, Part A) Draw the Newman projections and 3-D sawhorse structures corresponding to the lowest and highest energy conformations for rotation around the C2-C3 bond. Draw the Newman projections looking FROM THE C2 CARBON TO THE C3 CARBON (i.e. with the C2 carbon in the "front"). Part B) Determine the energy difference between the lowest and highest conformations, and be sure to clearly show each energy contribution that you are including in your calculation. Lowest Energy Conformation 3-D sawhorse Newman ECLIPSING Interactions Energy Difference: AB Energy kcal/mol H/H 1.0 H/Me 1.4 H/Et 1.5 H/Pr 1.6 H/1-Bu 3.0 Me / Me 2.6 Me/Et 2.7 Me/i-Pr 3.0 GAUCHE A Interactions Energy kcal/mol Me / Me 0.9 Me / Et 0.95 Me/i-Pr 1.1 Me/t-Bu 2.7 Et/Et 1.1 Et/i-Pr 1.6 Et/t-Bu 3.0 i-Pr/i-Pr 2.0 Highest Energy Conformation 3-D sawhorse Newman 1

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Organic Chemistry: A Guided Inquiry

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Organic Chemistry: A Guided Inquiry
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ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning