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Chapter 3: Q14P (page 165)

Draw a perspective representation of the most stable conformation of 3-methylhexane.

Short Answer

Expert verified

The most stable conformation of 3-methylhexane is;

Step by step solution

01

The Conformation.

The conformation is a process of rotating the compound about the sigma bonds to get a different conformational isomer.

02

The skeletal conformer of 3-methylhexane converted to Newman projection.

The given compound consists of 7 carbon atoms, out of which; one carbon atom (methyl group) is attached to the 3rd carbon of the hexane chain.

In the flying wedge projectionof the given compound; the 3rd and 4th carbon are brought in front of each other.

There is one H-atom in 3rd carbon and two H-atoms on 4th carbon.

03

The most stable conformation of 3-methylhexane.

This is the anti-conformation of 3-methylhexane in Newman Projection;

Here, the two bulky ethyl groups are at anti-position and one methyl is in gauche interaction with one of the ethyl groups; making it the most stable conformer.

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Most popular questions from this chapter

Construct a graph, similar to Figure 3-11, of the torsional energy of 3-methylpentanealong theC2鈭�C3.PlaceC2in front, represented by three bonds coming together in a Y shape, andC3in back, represented by a circle with three bonds pointing out from it. Define the dihedral angle as the angle between the methyl group on the front carbon and ethyl group on the back carbon. Begin your graph at 00thedihedral angle and begin to turn the front carbon. Show the Newman projection and the approximate energy at each600of rotation. Indicate which conformations are the most stable (lowest energy) and the least stable (highest energy).

Draw the both chair conformations of each of the following substituted cyclohexanes. In each case, label the more stable conformation.

(a) cis-1-ethyl-2-methylcyclohexane

(b)trans-1,2-diethylcyclohexane

(c) cis-1-ethyl-4-isopropylcyclohexane

(d)trans-1-ethyl-4-methylcyclohexane

Draw 1,2,3,4,5,6-hexamethylcyclohexane with all the methyl groups

(a) in axial positions. (b) in equatorial positions.

Draw Newman projections of the following molecules viewed from the direction of the arrows.

(a)

(b)

(c)

(a) Draw and name the five cycloalkane structures of formulaC5H10. Can any of these structures give rise to geometric (cis-trans) isomerism? If so, show the cis and trans stereoisomers.

(b) Draw and name the eight cycloalkane structures of formulaC6H12that do not show geometric isomerism.

(c) Draw and name the four cycloalkanes of formulaC6H12that do have cis-trans isomerism.
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