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E. Bromination of cyclohexenes initially results in the formation of a diaxial product which usually isomerizes to the more stable diequatorial conformer. Shown below is the bromination of (S)-4-(tert- butyl)cyclohex-1-ene where (1R,2R,4S)-1,2-dibromo-4-(tert-butyl)cyclohexane (diaxial) is formed as the MAJOR product. Show mechanistically how the product is formed and explain why the diequatorial product is not the major product. (Strain of one 1,3-diaxial interaction (kJ/mol): -C(CH3)3 = 11.4; Br = 1.0). Br Br2 CH,Cl2 Br (S)-4-(tert-butyl)cyclohex-1-ene (1R.2R,4S)-1.2-dibromo-4-(tert-butyl)cyclohexane

E. Bromination of cyclohexenes initially results in the formation of a diaxial product which usually isomerizes to the more stable diequatorial conformer. Shown below is the bromination of (S)-4-(tert- butyl)cyclohex-1-ene where (1R,2R,4S)-1,2-dibromo-4-(tert-butyl)cyclohexane (diaxial) is formed as the MAJOR product. Show mechanistically how the product is formed and explain why the diequatorial product is not the major product. (Strain of one 1,3-diaxial interaction (kJ/mol): -C(CH3)3 = 11.4; Br = 1.0). Br Br2 CH,Cl2 Br (S)-4-(tert-butyl)cyclohex-1-ene (1R.2R,4S)-1.2-dibromo-4-(tert-butyl)cyclohexane

Chemistry
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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III. E
E. Bromination of cyclohexenes initially results in the formation of a diaxial product which usually isomerizes to the more stable diequatorial conformer. Shown below is the bromination of (S)-4-(tert- butyl)cyclohex-1-ene where (1R,2R,4S)-1,2-dibromo-4-(tert-butyl)cyclohexane (diaxial) is formed as the MAJOR product. Show mechanistically how the product is formed and explain why the diequatorial product is not the major product. (Strain of one 1,3-diaxial interaction (kJ/mol): -C(CH3)3 = 11.4; Br = 1.0). Br Br2 CH,Cl2 Br (S)-4-(tert-butyl)cyclohex-1-ene (1R.2R,4S)-1,2-dibromo-4-(tert-butyl)cyclohexane
Transcribed Image Text:E. Bromination of cyclohexenes initially results in the formation of a diaxial product which usually isomerizes to the more stable diequatorial conformer. Shown below is the bromination of (S)-4-(tert- butyl)cyclohex-1-ene where (1R,2R,4S)-1,2-dibromo-4-(tert-butyl)cyclohexane (diaxial) is formed as the MAJOR product. Show mechanistically how the product is formed and explain why the diequatorial product is not the major product. (Strain of one 1,3-diaxial interaction (kJ/mol): -C(CH3)3 = 11.4; Br = 1.0). Br Br2 CH,Cl2 Br (S)-4-(tert-butyl)cyclohex-1-ene (1R.2R,4S)-1,2-dibromo-4-(tert-butyl)cyclohexane
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