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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

Table 3-6 shows that the axial-equatorial energy difference for methyl, ethyl, and isopropyl groups increases gradually: 7.6, 7.9 and 8.8 kJ/mol (1.8, 1.9, and 2.1 kcal/mol). The tert-butyl group jumps to an energy difference of 23 kJ/mol (5.4 kcal/mol), over twice the value for the isopropyl group. Draw pictures of the axial conformations of isopropylcyclohexane and tert-butylcyclohexane and explain why the tert-butyl substituent experiences such a large increase in axial energy over the isopropyl group.

There are eight different five-carbon alkyl groups.

(a) Draw them

(b) Give them systematic names.

(c) In each case, label the degree of substitution (primary, secondary, or tertiary) of the head carbon atom bonded to the main chain.

Question: The heat of combustion of cis-1,2-dimethylcyclopropane is larger than that of trans isomer. Which isomer is most stable? Use drawings to explain this difference in stability.

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

(a)

(b)

(c)

Question: The most stable form of 1,2,3,4,5,6-Cyclohexanehexolcontains a six-membered ring in the chair conformation with all the substituents equatorial. Draw this most stable conformation of cyclohexanehexol
See all solutions

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