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Draw Newman projections along the C3-C4 bond to show the

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 47SP Chapter 3

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 47SP

Draw Newman projections along the C3-C4 bond to show the most stable and least stable conformations of 3-ethyl-2,4,4-trimethylheptane

Step-by-Step Solution:

Solution 47SP :

Step 1:

A Newman projection is a way to look at the conformation of a noncyclical molecule. It visualizes chemical conformations of a carbon-carbon chemical bond from front to back of the compound. The front carbon atom is represented by a dot and the carbon atom at the back is represented as a circle. The front carbon atom is called as proximal and the back carbon atom is called distal.

Sometimes there can be various newman projections for a molecule or compound as  carbon atoms in the compound are linked by single bonds and the bonds are able to freely rotate,    allowing for various conformations.

There are mainly 2 conformations for newman projection - eclipsed conformation and staggered conformation.

Among these 2 conformations, staggered conformation is most stable than the eclipsed conformation.

Step 2:

The compound, 3-ethyl-2,4,4-trimethylheptane has molecular formula of C12H26. The structure of the compound would look as shown below :

        

The staggered conformation of the Newman projections along the C3-C4 bonds is shown below :

The above conformation is the most stable conformation as the 2 larger groups -the methyl(CH3) and the ethyl(CH3CH2) group are anti placed because of which there is very less torsional strain and gauge strain.

Step 3 of 3

Chapter 3, Problem 47SP is Solved
Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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