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Chapter 3: Q22P (page 176)

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

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

Short Answer

Expert verified

(a)

(b)

Step by step solution

01

Step 1:

If we could freeze cyclohexane in a chair conformation, we would see that there are two different kinds of carbon–hydrogen bonds. Six of the bonds (one on each carbon atom) are directed up and down, parallel to the axis of the ring. These are called axial bonds. The other six bonds point out from the ring, along the “equator” of the ring. These are called equatorial bonds.

02

(a)

The axial bonds are drawn vertically to the ring connections for all methyl groups.

03

(b)

Equatorial bonds are drawn parallel to the ring connections for all methyl groups.

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Most popular questions from this chapter

Question: Using the general formula for alkanes

  1. Predict the molecular formula of theC27straight chain alkane.
  2. Predict the molecular formula of the alkanes containing 42 carbon atom with extensive branching.

Draw the structure that corresponds with each name.

(a)3-ethyloctane

(b)4-isopropyldecane

(c)sec-butylcycloheptane

(d)2,3-dimethyl-4-propylnonane

(e)2,2,4,4-tetramethylhexane

(f)trans-1,3-diethylcyclopentane

(g)cis-1-ethyl-4-methylcyclohexane

(h)isobutylcyclopentane

(i)tert-butylcyclohexane

(j)pentylcyclohexane

(k)cyclobutylcyclohexane

(l)cis-1-bromo-3-chlorocyclohexane

Question: This is a Newman projection of a substituted cyclohexane.

(a) Draw the equivalent chair form

(b)Draw the equivalent structure using wedge and dash notation on a cyclohexane hexagon.

(c) Give the IUPAC name.

Draw Newman projection, similar to Figure 3-25, down the C1-C6 bond in the equatorial conformation of methylcyclohexane. Show that the equatorial methyl group is also anti toC5. (Using your models will help.)

Draw the two chair conformations of each compound, and label the substituents as axial and equatorial. In each case, determine which conformation is more stable.

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

(b)trans-1-ethyl-2-isopropylcyclohexane

(c)cis-1-ethyl-3-methylcyclohexane

(d)trans-1-ethyl-3-methylcyclohexane

(e)cis-1-ethyl-4-methylcyclohexane

(f)trans-1-ethyl-4-methylcyclohexane
See all solutions

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