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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鈥檚 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: Convert each Newman projection to the equivalent line-angle formula, and assign the IUPAC name.

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

Using what you know about the conformational energetics of substituted cyclohexanes, predict which of the two 9-methyldecalinisomers is more stable. Explain your reasoning.

Name the following compounds. Remember the two up bonds are cis; two down bonds are cis; one up and one down bond are trans.

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.
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