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OCHEM II

Substitution and Elimination Chart

QuestionAnswer
Zaitsev's Rule The β hydrogen that is MOST substituted is removed
Expceptions to Zaitsev's Rule 1) If Fluorine is the leaving group 2) If a bulky base (tert-butoxide) is used in the elimination 3) If the more substituted beta-hydrogen CANNOT adopt anti-periplanar conformation (E2 on cyclic rings)
What makes a base bulky? If the molecule is big and attached to multiple atoms
What happens if the beta-hydrogen has the same stereochemistry as the leaving group? The reaction becomes anti-zaitsev and it is the LEAST substituted beta-hydrogen that is eliminated
Sn1 3°>>>2°>1°
Strong Nucleophiles 1. Negatively Charged 2. Not Bulky
Strong Bases 1. Negatively Charged 2. C,H,O,N unless pi-bonds are present
1°/WN/SB E2
1°/SN/SB Sn2
1°/SN/WB Sn2
2°/WN/SB E2
2°/SN/SB E2
2°/SN/WB Sn2
3°/WN/SB E2
3°/SN/SB E2
3°/SN/WB Sn1 &/or E1 (heat)
3°/WN/WB Sn1 &/or E1 (heat)
Created by: emily.zegarra
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