Solutions_Manual_for_Organic_Chemistry_6th_Ed 59

Solutions_Manual_for_Organic_Chemistry_6th_Ed 59 - 3-23 The...

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Unformatted text preview: 3-23 The isopropyl group can rotate so that i ts hydrogen i s near the axial hydrogen s on c arbons 3 a nd 5, s i milar to a methyl group's hydrogen, and therefore simi l ar to a methyl group i n energy. The t-butyl group, however, must point a methyl group toward the hydrogens on carbon s 3 a nd 5 , giving severe diaxial interactions, causing the energy of thi s conformer to j ump dramatic al l y . }JJ 5=H 3 CHl i sopropylcyclohexane t-buty Icyclohexane 3-24 T he most stable conformers have substituents equatori al. (b) � H - CH3 CH] H 3-25 ( a) cis H H axi al , equatori al equatori al , axial (b) t rans EQUAL ENERGY H p:J CH 3 axi al , axial h igher energy Positions 1,2 1,3 H � � � H 3C H equatorial , equatori al lower energy (c) The trans i somer is more stable because BOTH substituents can be in the preferred equatori al positions. 3-26 cis trans ( e,a) or (a,e) ( e,e) or (a,a) ( e,a) or (a,e) (e,e) or (a,a) (e,a) or (a,e) (e,e) or (a,a) 1 ,4 50 ...
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