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). %3D Br Br2 CH2CI2 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). %3D Br Br2 CH2CI2 Br (S)-4-(tert-butyl)cyclohex-1-ene (1R,2R,4S)-1,2-dibromo-4-(tert-butyl)cyclohexane
Chemistry
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Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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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
CH2CI2
Br
(S)-4-(tert-butyl)cyclohex-1-ene
(1R,2R,4S)-1,2-dibromo-4-(tert-butyl)cyclohexane
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