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 9CTQ

(a)

Interpretation Introduction

Interpretation:

The most stable conformation of butane rotating around C2C3 bond in Newman projection should be drawn.

Concept Introduction:

The three-dimensional arrangement of atoms and molecules in space is known as stereochemistry.

(b)

Interpretation Introduction

Interpretation:

The explanation for most stable conformation names should be given.

Concept Introduction:

The three-dimensional arrangement of atoms and molecules in space is known as stereochemistry.

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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
2. Convert the line structure of 2,3-dimethylpentane into a Newman projection as viewed along the C2-C3 bond (C2 in front, C3 in back). Draw the most stable conformation. Two templates are given with one hydrogen atom drawn in place. Note that only one template leads to the correct answer, therefore use only one of the given templates. t Н. H.
b. Draw a Newman projection of the given compound H viewed from C-2 to C-3 orientated according to the first template. Then use the Newman projection to demonstrate the most stable conformation around the C2-C3 bond according to the second template. (Hint: Order of decreasing group size 'Pr > CH2CH3 > CH3 > OH > Br > H] NH2 Me Ме H 'Pr Given conformation Most stable conformation

Chapter 6 Solutions

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