By Francis Carey, Neil Allison
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Extra resources for Student Solutions Manual to accompany Organic Chemistry, Seventh Edition
If A is axial as specified in the problem, X must therefore be equatorial. X A X and A are gauche. (c) For substituent X at C-1 to be anti to C-3, it must be equatorial. 3 X (d) A When X is axial at C-1, it is gauche to C-3. 5 (b) According to the numbering scheme given in the problem, a methyl group is axial when it is “up” at C-1 but is equatorial when it is up at C-4. Since substituents are more stable when they 48 CONFORMATIONS OF ALKANES AND CYCLOALKANES occupy equatorial rather than axial sites, a methyl group that is up at C-1 is less stable than one that is up at C-4.
2Ͼ1Ͼ3 2Ͼ3Ͼ1 2 (c) (d) 3 3Ͼ1Ͼ2 3Ͼ2Ͼ1 What is the total number of bonds present in the molecule shown? (a) 18 (b) 26 (c) 27 (d) 30 45 ALKANES B-8. B-9. Which of the following substances is not an isomer of 3-ethyl-2-methylpentane? (a) (c) (b) (d) None of these (all are isomers) Which alkane has the highest boiling point? (a) Hexane (d) 2,3-Dimethylbutane (b) 2,2-Dimethylbutane (e) 3-Methylpentane (c) 2-Methylpentane B-10. What is the correct IUPAC name of the alkyl group shown? CH2CH3 CHCH2CH(CH3)2 (a) (b) (c) (d) 1-Ethyl-3-methylbutyl 1-Ethyl-3,3-dimethylpropyl 4-Ethyl-2-methylbutyl 5-Methylhexyl B-11.
The substituents at C-4 are the same as those at C-3. The most stable conformation has the large tert-butyl groups anti to each other. H H C(CH3)3 H H C(CH3)3 Anti conformation of 2,2,5,5-tetramethylhexane (b) The zigzag conformation of 2,2,5,5-tetramethylhexane is an alternative way of expressing the same conformation implied in the Newman projection of part (a). It is more complete, 57 CONFORMATIONS OF ALKANES AND CYCLOALKANES however, in that it also shows the spatial arrangement of the substituents attached to the main chain.
Student Solutions Manual to accompany Organic Chemistry, Seventh Edition by Francis Carey, Neil Allison