1
Q
Characteristics of E2
A
Strong base Polar aprotic solvents faster Good LG Needs beta hydrogens Anti co-planar/trans diaxial 3 > 2 > 1 Bulky bases favor over SN2
2
Q
Characteristics of E1
A
Needs beta hydrogens Weak base okay, stronger base favors E2 Good LG Needs polar protic solvent 3 > 2 Resonance favored Rearrangements
3
Q
Name some polar protic solvents
A
H2O, CH3OH, CH3CH2OH, HCO2H, CH3CO2H
4
Q
Name some polar aprotic sovlents
A
DMSO,
5
Q
Characteristics of SN1
A
Racemization Polar protic solvent 3 > 2 Resonance favored Low temp Rearrangements Good LG that are weak bases, not bulky Weak nucleophiles favor SN1 over SN2
6
Q
Characteristics of SN2
A
Inversion Low temp Nonpolar solvents favor SN2 over SN1 CH3 > 1 > 2 Strong nucleophile weak base Good LG Good nucleophile
7
Q
Some strong bases
A
OH–, OR–, NH2–, CH3–, H–
8
Q
Some bulky bases but weak nucleophiles
A
KOC(CH3)3, DBU, DBN
9
Q
Some good nucleophiles that are weak bases
A
I-, Br-, HS-, -CN, CH3COO-
10
Q
Williamson ether synthesis
A
Alkoxide + (small, unhindered)alkyl halide = ether
11
Q
Alkoxide synthesis
A
Alcohol + strong base = alkoxide
12
Q
Cyclic ethers
A
Intermolecular chains: 4 or >= 7 membered rings
Intramolecular rings: 3, 5, 6
13
Q
Dehydration
A
alcohol + acid +heat = alkene
Primary through E2
2 and 3 through E1
use H2SO4 or TsOH
14
Q
Alcohols to alkyl halides
A
Use HI, HBr, HCl
Primary through SN2
2 and 3 through SN1
OChem 2
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