Mechanisms Chapter 9
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20 Terms
Dehydration Reaction
3° and 2° = E1
Methyl and 1° = E2
Dehydration Reaction
3° and 2° = E1
Methyl and 1° = E2
Dehydration Reaction
ONLY E2
E1 or SN1
E2 or SN2
Alcohol to Alkyl Halide
3° and 2° = SN1
Methyl and 1° = SN2
SN2 ONLY. 1° and 2° Alcohols ONLY
SN2 ONLY. 1° and 2° Alcohols ONLY
Forms a good leaving group
Ether Cleavage : SN2
Ether Synthesis
Epoxide Limitations
Unsymmetrical Epoxides: Acid - Attacks MORE substituted carbon
Unsymmetrical Epoxides: Strong Nucleophile - Attacks LESS substituted carbon
Symmetrical Epoxides attack from either carbon. Forms RACEMIC mixture
Epoxide Synthesis
Cyclic Ether Cleavage: SN2
Tosylate - A Good Leaving Group, does NOT affect stereochemistry when formed
1,2 - Alkyl Shift
E1 and SN1 ONLY
Converts a lesser substituted carbocation into a more substituted carbocation.
Occurs before a pi bond is formed in dehydration (E1) or before the substitution (SN1).
1,2 - Hydride Shift
E1 and SN1 ONLY
Converts a lesser substituted carbocation into a more substituted carbocation.
Occurs before a pi bond is formed in dehydration (E1) or before the substitution (SN1).