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Unformatted text preview: to F . b. 13 C NMR: 22.7, t (2) 28.1, t (2) 35.6, t (2) 72.7, d a. E C 7 H 14 O F A B C D OH Bu 3 Sn-H AIBN Br gauche interaction destabilizes In both C and D, all substituents are equatorial in the more stable chair forms, but C has a destabilizing gauche interaction, so D is more stable. C D A B In the more stable chair forms of A and B, the isopropyl group is equatorial. That makes the methyl group axial in B, equatorial in A, so A is the more stable. OH Br R H-SnBu 3 Bu 3 Sn OH + Bu 3 Sn-Br OH H-SnBu 3 OH F + Bu 3 Sn 6. (20 points) Draw a detailed arrow-pushing mechanism for the transformation of G to H . AIBN G Bu 3 SnH H O O Br a b c d e f g h i j k l m R H-SnBu 3 Bu 3 Sn a b c m d l e k j i f g h bb bf Sn-H Sn-Br l-m c-d i-k a-Br c-k i-d a-m l-H O O O O O H-SnBu 3 O + Bu 3 Sn + Bu 3 Sn-Br...
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- Spring '08