BROMINATION OF CYCLOHEXENES initially results in the formation of a diaxial product which usually isomerizes to the more stable diequatorial conformer. Shown is the bromination of (S)-4-(tert-butyl)cyclohex-1-ene where (1R,2R,4S)-1,2-dibromo-4-(tert-buty l)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.