The stereoelectronic requirement of an E2 process is that the groups to be eliminated should be anti-periplanar (conformationally Trans to one another, with a dihedral angle of 180o ) and not syn-periplanar (conformationally Cis to one another, with a dihedral angle of 0o ).
The stereoelectronic requirement of anti-periplanarity exists because of the following reasons
(i) Coplanarity of the sigma orbitals of the departing groups cause maximum overlap of the developing
p-orbitals (minimum energy of the transition state).
(ii) The anti geometry allows the bonding electrons of beta substituent to displace the leaving group from
back side(back side attack is energetically favourable)
(iii) The attacking base and the leaving group remain far apart from each other(steric interactions are
minimum).
The stereoelectronic requirement of anti-periplanarity exists because of the following reasons
(i) Coplanarity of the sigma orbitals of the departing groups cause maximum overlap of the developing
p-orbitals (minimum energy of the transition state).
(ii) The anti geometry allows the bonding electrons of beta substituent to displace the leaving group from
back side(back side attack is energetically favourable)
(iii) The attacking base and the leaving group remain far apart from each other(steric interactions are
minimum).
No comments:
Post a Comment