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By Douglas Lloyd

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By Douglas Lloyd

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The cyclic compound has too many non-polar CH2 groups to dissolve. ) (d) H I H-C-C I H-C H (g) ' " H = I C-C-H / I (e) C-H H C-C I I 'H H H H H H H I I I I H, C C-C-C-H H - C � "C � I I I I I H C H H - C .. C I H' H C� I H H I H H (h) • (a) 0 H H I I " H-C-C-C-H I (d) I aldehyde H H H H H I I I I H-C-C-O-C-C-H I I I I H H H H (b) (e) ketone I I H H H " C .. H I , C - C :: C - C - H H-C� I I I H-C C .. H H " C � ... H H ' " H C=C-H I I H H H , 0 H H H H I I I I H -C-C-C-C-H I I I I H H H H alcohol 0 H" H H C ..

The t-butyl group, however, must point a methyl group toward the hydrogens on carbon s 3 and 5 , giving severe diaxial interactions, causing the energy of thi s conformer to j ump dramatic al l y . }JJ 5=H 3 C Hl i sopropylcyclohexane t-buty Icyclohexane 3-24 The most stable conformers have substituents equatori al. � CH3 H (b) CH] H 3-25 (a) cis - equatori al , axial (b) trans H H EQUAL ENERGY p:J H axi al , equatori al H � � H3C � CH 3 H equatorial , equatori al lower energy axi al , axial h igher energy (c) The trans i somer is more stable because BOTH substituents can be in the preferred equatori al positions.

Yours may be different from the ones shown . An easy w ay to compare is to n ame yours and see if the n ames match. � 2-meth y Iheptane Il-octane � 2 , 2,4-tri methylpentane 3-39 (a) � � ~ 2 , 3 ,4-tri methy Ipentane 2 , 3 -dimethylhexane T T * 3 -ethylhexane 3-ethyl-3 -methy l pentane 2,2,3,3-tetrameth y I butane (b) 4 4 6 correct name : 3 -methylhexane (longer chain) (c) correct n ame : 3 -ethyl-2-methy lhexane (more branching with this numbering) �I (d) CI correct name: 2 ,2-dimethylbutane (include a position number for each substituent, regardless of redundancies) correct name: 2-ch l oro-3 -methy l hexane (begin numbering at end c l osest to substi tuent) 54 3-39 continued (f) (e) c orrect name: sec-butylcyclohexane or ( I-methylpropyl)cyclohexane (the l onger chain or rin g is the base name) c orrect n ame: 1 ,2-diethylcyclopentane (position numbers are the l owest possible) 3 -40 (a) n-Octane has a h i gher boi l i n g point than 2,2,3 -trimethylpentane because linear molecules boil h igher than branched molecules of the s ame molecular weight (increased van der Waals interaction).

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