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

Short Answer

Expert verified

Trans isomer of9-methyldecalin is more stable than cis isomer of 9-methyldecalin.

Step by step solution

01

Decalin

The most common example of a fused ring system is decalin. There are two geometric isomers of decalin. The isomer in which the rings are fused using two cis bonds is the cis-decalinand the isomer in which the rings are fused using two trans bonds is thetrans-decalin .

02

Drawing cis-decalinand trans-decalin

While drawing cis-decalin, if the left ring is considered, the bonds to the right ring are both directed in downward direction, where the attached hydrogens are directed upward. These bonds are cis, and this can be called a cis ring fusion. One of the bonds to the right ring must be in anaxial position, and the other is in an equatorial position.While drawing , one of the bonds to the right ring must be directed upward and the other in downward direction. These bonds are trans, and this can be called a trans ring fusion. Both of the bonds to the right ring are equatorial.

03

Identifying the stable isomer

The conformation ofcis-decalin is flexible while that of trans-decalinis quite rigid.

Cis isomer of 9-methyldecalinwill be less stable than trans isomer of 9-methyldecalinbecause ofa larger number of gauche interactions.

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Most popular questions from this chapter

Question: Which of the following cycloalkanes are capable of geometric (cis-trans) isomerism? Draw the cis and trans isomers

(a)3 - ethyl - 1,1 - dimethylcyclohexane

(b)1 - ethyl - 3 - methylcycloheptane

(c)1 - ethyl - 3 - methylcyclopentane

(d)1 - cyclopropyl - 2 - methylcyclohexane

(a) Draw the two chair conformations of cis-1,3-dimethylcyclohexane, and label all the positions as axial or equatorial.

(b) Label the higher-energy conformation and the lower-energy conformation.

(c) The energy difference in these two conformations has been measured to be about23 k´³â€‰(5.4 k³¦²¹±ô)per mole. How much of this energy difference is due to the torsional energy of gauche relationships?

(d) How much energy is due to the additional steric strain of the1,3-diaxial interaction?

Question: Draw a graph, similar to Figure 3-9, of the torsional strain of 2-methylpropane as it rotates about the bond between and . Show the dihedral angle and draw a Newman projection for each staggered and eclipsed conformation.

Each of the following descriptions applies to more than one alkane. In each case draw and name two structures that match the description.

(a)²¹²Ô â¶Ä‰i²õ´Ç±è°ù´Ç±è²â±ô³ó±ð±è³Ù²¹²Ô±ð

(b)²¹â€‰d¾±±ð³Ù³ó²â±ô»å±ð³¦²¹²Ô±ð

(c)acis −diethylcyclohexane

(d)atrans −dihalocyclopentane

(e)a(2,3-dimethylpentyl)cycloalkane

(f)²¹â€‰â¶Ä‰b¾±³¦²â³¦±ô´Ç²Ô´Ç²Ô²¹²Ô±ð


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

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