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 7, Problem 11CTQ
Interpretation Introduction

Interpretation: The relationship between given two structures needs to be explained.

Concept Introduction: The possible relationship between two structures depends on the molecular formula and structural arrangement of atoms in the molecules.

The possible relations are as follows:

Identical: Two molecular structures are identical if they have same molecular formula as well as same arrangement of atoms. The bonding substituent and their positions are same in the identical molecules.

Conformers: Two molecules are said to be conformer if they have different orientation of atoms by rotation around a single bond. They are also known as conformational isomer. For example, eclipse and staggered conformation.

Configurational isomer: They cannot be converted into one another due to the rotation around a single bond. For example, geometric and optical isomers. They can be interconverted after breaking of old bonds and making of new bonds.

Constitutional isomer: They are also known as structural isomers. They have same molecular formula, but the bonding of groups is different. For example, n-pentane and isopentane.

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Build a model of 2,2,5,5-tetramethylhexane. Orient the model so that you are looking at the carbon with the arrow pointing to it in Figure 3. Align the bond to the next carbon in the chain so that it is directly behind the first carbon to match a Newman projection view. (See Figure MM.3 in the lab manual) Spin the carbons on either side of the bond you're looking down to cycle through all three staggered and all three eclipsed positions of the substituents. Draw all six positions as Newman projections on the data sheet and identify the position with the highest energy. Draw the six Newman projections of all of the different energy levels. Label each as staggered or eclipsed and rank in order from lowest energy to highest.
H3C H. NHCH3 NHCH3 H H
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Organic Chemistry: A Guided Inquiry
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ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning