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Chapter 3: 37P (page 189)

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

(a)an  isopropylheptane

(b)a diethyldecane

(c)acis −diethylcyclohexane

(d)atrans −dihalocyclopentane

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

(f)a  bicyclononane


Short Answer

Expert verified

(a)

(b)

(c)

(d)

(e)

(f)

Step by step solution

01

Cis and transisomers

Cis and transisomerism can be used only for the compounds in which two doubly bonded carbon atoms have similar atoms or groups. When similar atoms or groups lie on the same side, it is called a cis-isomer, and when similar atoms or groups lie on the opposite sides, it is called a trans-isomer. These two geometric isomers cannot interconvert without breaking and forming the bonds again

02

Alkanes

Alkanes are hydrocarbon containing only single bonds. The general formula for analkane is ,where number of carbon atoms.

03

Dr

(a) The structures matching the description are 2,3-dimethyloctaneand 3-ethyl-2-methylheptane.

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Most popular questions from this chapter

Draw the structures of the following compounds.

(a) 4-(1,1-dimethylethyl)nonane

(b) 5-(1,2,2-trimethylpropyl)decane

(c) 3,3-diethyl-4-(2,2-dimethylpropyl)nonane

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.

Question: Draw a graph, similar to Figure 3-11, of the torsional energy of 2-methylbutane as it rotates about theC2-C3 bond.

(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 kJ (5.4 kcal)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?

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