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Level 204

E1, E2, SN1, SN2 & Addition Reactions

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Cl?, I?, Br?,
Strong Nucleophile Only
Strong Nucleophile Only
HS?, RS?, H2S, RSH
Strong Bases Only
HO?, MeO?, EtO?, (CH3)3O?
Strong Nucleophiles and Strong Base
Weak Nucleohiles and Weak Bases
SN1 & SN2
Strong Nucleophile (only) and 2°
Both mechanisms are sensitive to the nature of the leaving group but the _______ mechanism is more sensitive
1° Carbon (Strong Base, Hindered)
Strong Nuc/Strong Base and 1°
E2<SN2 (except when using a bulky base like tert-butoxide, when E2 dominates)
Strong Nuc/Strong Base and 2°
No Reactions
Weak Nuc/Weak Base and 1°
Weak Nuc/Weak Base and 2°
SN1 & E1 (resonnance and rearrangement)
Weak Nuc/Weak Base and 3°
SN1 & E1 (resonannce and rearrangement)
polar aprotic solvents
are incapable of of hydrogen bonding. they only solvate cations well.
Polar protic solvents
stabilize the anion in a solvation sphere lowering the energy of the reactant and rending it less reactive
SN2 Regiochemistry
Nucleophile attacks a position
SN2 Stereochemistry
Nucleophile replaces leaving group with inversion (stereospecific)
SN1 Regiochemistry
Nucleophile attacks carbocation at a position, unless carbocation rearrangement
SN1 Stereochemistry
The nucleophile replaces leaving group with racemic mixture (stereoselective)
E2 Regiochemistry
Zaitsev favored over Hofmann unless sterically hindered base is used
E2 Stereochemistry
Stereoselective and Stereospecfic; when applicable, trans disubstituted alkene will be favored over cis disubstituted alkene. When the ß position of the substrate has only one proton, the stereoisomeric alkene resulting from the anti-perpindicular elimination …
E1 Regiochemistry
Zaitsev product always favored (regiospecific)
E1 Stereochemistry
Stereoselective; when applicaple, trans is favored over cis
Addition of H and X
Hydration (3 ways)
Addition of H and OH
A reaction involving the addition of Hydrogen.
Addition of X and X
Halohydrin formation
Addition of OH and X
Dihydroxylation (2 ways)
Addition of OH and OH
(a)Acid Catalyzed Hydration
Markovinikov, Carbocation; Can form oxonium ion and require end proton tansfer; Dilute H3O+ pushes reaction forward (LaChateliers); Racemic; Gives H and OH
(b)Oxymercuration/Demercuration Hydration
No Rearrangement; Mercuinium Ion; Markovnikov; Hg(OAc)2, NaBH4, Nuc:-H; Gives H and OH, racemic!
(c) Hydroboration/Oxidation
Syn-Addition; Reagents=BH3/THF & H2O2.OH-; Gives H and OH; anti-markovnikov because concerted reaction and steric hindrance
Dihydroxylation (Anti)
Anti-addition; Reagents=peroxyacid (RCO3H) (or MCPBA) and H3O+; stepwise; makes a bridge between ring and Oxygen (epoxide), then Oxygen attacks acid (H+) and then water attacks, then deprotonation by another water results in last OH.
Dihydroxylation (Syn)
Stepwise; Reagents=OsO4 and NaHSO3 or Ni2SO3; double bond attacks oxygen and forms a bridge with the OsO4; then NaHSO3 or Ni2SO3 attacks and results in a syn-addition of OH and OH
Oxidative Cleavage
Reagents=O3 and DMS, break a bond wherever a double bond is and cap with an Oxygen