3.27 Determine whether the two structures in each of the following pairs represent constitutional isomers, different conformations of the same compound, or stereoisomers that cannot be interconverted by rotation about single bonds. cn, cHy H 4 » HC cI H ~— O) ans d . \ u HAC. CH HAC. H ) and HAC ‘CH, Hc H H @ cis-1,2-Dimethyleyclopentane and trans-1,3-dimethyleyclopentane CHACHs at HTT en, ” cam, 2) “ope 3.28 Select the compounds in each group that are isomers and specify whether they are constitutional isomers or stereoisomers. (@) (CHy:CCH.CH,CH, —(CH)),CCH,CH,CHCH——_(CH,),CHCHCH.CHs CH © eet cele fe O Nae CHs Hc He H cH 5 Hye HC ee © fer ye ects 7 (zee Pape 3.31 Draw (a) a Newman projection of the most stable conformation sighting down the C-3—C-4 bond and (b) a bond-line depiction of 2,2,5,5-tetramethylhexane.3.34 Onecf the staggered conformations of 2-methylbutane in Problem 3.33b is more stable than the other. Which one is more stable? Why’? 3.37 Evea though the methyl group occupies an equat the most stable one for methyleyelohexane. Explain. torial site, the conformation shown is nt 4.38 Which do you expect to be the mor stable conformation of cis-1 3-dimethyleyclabutane, orB? Why? cH eS = we h K A B Identify the more stable stereoisomer in each ofthe following pairs, and give the reason for your choice: (4) cls- oF trans-Isopropy!-2-methyleyelohexane () cis: or rans: (© cis- or rrans-1-Isopropyl-4-methyleyctohexane HC, CH We, Hy i eS i 5 "CH HAC, CH HAC, CH, © or co “CHS "CH, 340 3.43 _Incach of the following groups of compounds, identify the one with the largest heat of ‘combustion and the one with the smallest. In which cases can a comparison of heats of combustion be used to assess relative stability? (@) Cyclopropane, cyclobutane, eyelopentane (©) cis-12-Dimethyleyclopentane, methyleyclohexane, |,,2,2-tetramethyleyclopropane obd DID “CP CD Ck a H 1 3.44 The heats of combustion of the more and less stable stereoisomers of the 1,2 1, and 1.4-dimethyleyclohexanes are given here. The values are higher for the 1, dimethyleyclohexanes than forthe 1,3- and 1-isomers. Suse? an explanation. Dimethyleyclohexane 12 13 14 Heats of combustion (kI/mol): ‘More stable stereoisomer 5217 9212 5212 Less stable stereoisomer 5223 5219 5219 3.47 Which one of the dichlorocyclohexane isomers has the smallest dipole moment?