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Level 203

SN1, SN2, E1 & E2 Mechanism


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SN1 Substrate
Controlled by electronics. Tertiary>Secondary>Primary>Methyl
SN2 Substrate
Controlled by sterics.
SN1 Nucleophile
Any nucleophile (Can be weak)
SN2 Nucleophile
Only good nucleophiles
SN1 Leaving Groups
Good leaving groups
SN2 Leaving Groups
Good leaving groups
SN1 Solvent
Must stabilize the carbocation. Requires protic, polar solvents.
SN2 Solvent
Less sterics needed. Requires polar, aprotic solvents.
SN1 Temperature
High energy for carbocation (high temp)
SN2 Temperature
Not needed.
Tertiary>secondary>primary
E1 Substrate
E2 Substrate
Any carbon with beta hydrogens
E1 Leaving Group
Contains a leaving group
E2 Leaving Group
Contains a leaving group
E1 Base
Weak base
E2 Base
Strong, bulky base
E1 Solvent
Protic, polar solvents
E2 Solvent
Aprotic or protic solvents
High
E1 Temp
E2 Temp
High (slows down SN2)
Weak Bases
H2O, ROH, PR3, Halides, RS, N3, NC, RCOO
Strong bases
Bases that dissociate completely into metal ions and hydroxide ions and aqueous solutions
Good Nucleophiles
I, Br, Cl, HS, H2S, RSH, OH, RO, NC
Bad Nucleophiles
F, H2O, ROH
Good Leaving Groups
Conjugate bases of strong acids.
Bad Leaving Groups
Conjugate bases of weak acids.
Common Leaving Groups
Halids and Sulfonate Ions (S double bonded to 2 Oxygen)
Protic Solvents
Solvents not listed as aprotic
Aprotic Solvents
Acetone, DMSO, DME, DMF