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Chapter 3: Q49 (page 190)

Question: Draw Newman projections along the C3-C4bond to show the most stable and least stable conformations of 3 ethyl-2,4demethylheptane.

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01

Newman projection

Newman projections are often used in drawing conformations. In Newman’s projection, one views the C-C bond end on along the axis of connection. The front carbon is represented by the intersection of bonds, while the rear carbon appears as a circle.

02

Using Newman projections to draw the most stable conformer

The two bulky groups (propyl and isopropyl) are anti-periplanar in most stable conformations, while in the least stable, the two bulky groups (propyl and isopropyl) are syn-periplanar.

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Most popular questions from this chapter

Question: All of the following names are incorrect or incomplete. In each case, draw the structure ( or a possible structure) and name it correctly

Construct a graph, similar to Figure 3-11, of the torsional energy of 3-methylpentanealong theC2−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 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

Use your results from Problem 3-27 to complete the following table. Each entry shows the positions of two groups arranged as shown. For example, two groups that are trans on adjacent carbons must be equatorialor both axial.

List each set of compounds in order of increasing boiling point.

(a) hexane, octane, and decane

(b) octane, (CH3)3C-C(CH3)3, and CH3CH2C(CH3)2CH2CH2CH3
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