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Sn and Elimination
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Organic Chemistry
Undergraduate 2
11/18/2010

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Term
Sn2
Definition
favored by stronger nucleophiles, aproptic solvents, basic solvents
Term
Sn1
Definition
favored by weak nucleophiles, polar (protic) solvents, absence of base
Term
protic solvents
Definition
water, methanol, acetic acid, ethanol, trifluoroacetic acid
Term
aprotic solvents
Definition
DMSO, DMF, acetone
Term
E1
Definition
competes with Sn1, occurs under Sn2 conditions for tertiary compounds
Term
E2
Definition
competes with Sn2, occurs under SN1 conditions for primary solvents
Term
Sn2
Definition
A secondary substrate reacted with a nonbasic nucleophile will produce
Term
E2
Definition
A secondary substrate reacted with a strong base will produce
Term
Sn1 with some E1
Definition
A secondary substrate reacted in a polar solvent with the absence of a good nucleophile will produce
Term
alcohol
Definition
Under Sn1 conditions R-X + H20 =
Term
alcohol elimination
Definition
under Sn2 conditions with strong base R-X +OH-
Term
alcohol
Definition
Under Sn2 conditions with weak base R-X reacted with CH3CO2 over KOH, H2O
Term
ether elimination
Definition
Sn2 conditions, williamson synthesis, strong base
R-L + -OR
Term
ether
Definition
Sn1 synthesis (unless primary) R-L + HOR
Term
Ester
Definition
Sn2 conditions weak base R-L+ -O-CR
=O
Term
alkyl halide
Definition
Sn1 conditions (unless primary) R-OH + HCl or HBr or HI
Term
alkyl halide
Definition
Sn2 conditions R-OH + TsCl over X-
Term
Alkyl halide
Definition
R-OH + SOCl2 or PBr3 or PI3 Sn1 or Sn2 conditions, good one step process
Term
Alkyl halide
Definition
R-X + -X Sn2 conditions
Term
Amine
Definition
Sn2 conditions, multiple alkylation = bad R-L + NH3
Term
Amine
Definition
R-L + benzene ring pentene ring with two double bonded Os and a N - group over KOH, H20 Sn2 conditions Gabriel synthesis
Term
Hydrocarbon
Definition
R-L + LiALH4 or NaBH4 Sn2 conditions
Term
Carbon Cyanide
Definition
R-L + C=-N Sn2 conditions acceptable with secondary substrates
Term
alkyne
Definition
R-L + - C=-C-R Sn2 conditions primary substrates only
Term
alkyne ion
Definition
H-C=-C-R + -NH2
Term
Sulfide
Definition
R-L + -SH or -SR Sn2 conditions
Term
Phosphide
Definition
R-L +PPh3 Sn2 conditions
Term
Epoxide
Definition
O-triangle + Nu in base nucleophile bonds to less hindered carbon with inversion, in acid nucleophile bonds to more substituted carbon with inversion
Term
Alkene
Definition
C-C
-H -L + OH or OR E2 conditions
Term
Alkyne
Definition
-H-L
C-C
-H-L +OH or NH2 E2 conditions
Term
alkene
Definition
-H-OH
C-C + H2So4 or H3PO4 and heat E1 conditions
Term
Ketone, aldehyde
Definition
RCHR
-OH Na2Cr2O7 over H2SO4 converts secondary alcohols to ___ converts primary alcohols to ___
Term
Aldehydes
Definition
RCHR
-OH + CRO3and 2 benzene rings with nitrogen over CrO3CL +Benzene ring with N and H+ group
Term
carboxylic acid
Definition
R-C-H
=O + Cro3, H2SO4 or KMNO4 or Ag2O
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