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Chem 2nd Midterm

QuestionAnswer
Protic Solvents Acetic acid (AcOH), tert-butyl alcohol (t-BuOH), ethanol (EtOH), isopropanol (iProOH), methanol, water
Aprotic Solvents acetone, acetonitrile (MeCN), ether (Et2O), dimethoxyethane (DME), dimethylformamide (DMF), dimethylsulfoxide (DMSO), tetrahydroturan (THF), pyridine (Pyr)
Polar, protic solvent SN1 and E1
Prolar, aprotic solvent SN2 and E2
If 1 Alkyl Halide or Sulfonate Ester Weak Base, Good Nucleophile = Sn2 Moderate Base, Good Nucleophile = Sn2 Strong Base = Sn2 with good nucleophiles, E2 with poor nucleophiles
If 2 Alkyl Halide or Sulfonate Ester Weak Base, Good Nucleophile = Sn1 or Sn2 (Some E1 at higher temps) Moderate Base, Good Nucleophile = Sn2, E2 at higher temps Strong Base = E2
If 3 Alkyl Halide or Sulfonate Ester Weak Base, Good Nucleophile = Sn1 and E1 (E1 predominates at higher temps) Moderate Base, Good Nucleophile = E2 Strong Base = E2 (like with HO- or RO-)
If 1 Alcohol... Weak Base, Poor Nucleophile = E2 at high temp Weak Base, Good Nucleophile = Sn2 Moderate or Strong Base = No rxn
If 2 Alcohol... Weak Base, Poor Nucleophile = E1 Weak Base, Good Nucleophile = Sn1 and E1 Moderate or Strong Base = No rxn
If 3 Alcohol... Weak Base, Poor Nucleophile = E1 Weak Base, Good Nucleophile = Sn1 and E1 Moderate or Strong Base = No rxn
Common Weak Base, Poor Nucleophile (pKa of CA less than 5) HSO4-, H2PO4- (both occur in E1), F-
Common Weak Base, Good Nucleophile (pKa of CA less than 5) R3P, Cl-, Br-, I- (occurs under SN2), H2O, RCOOH, H2S
Common Moderate Base, Poor Nucleophile (pka of CA is 5-12) RCOO-, R3N
Common Moderate Base, Good Nucleophile (pka of CA is 5-12) N3-, CN-, ArS-, RS-, NH3-, RNH2, R2NH, ARO- (all occur under SN2)
Common Strong Base, Poor Nucleophile (pKa of CA > 15) (CH3)3 CO-, LDA, Potassium tert-butoxide (all occur under E2)
Common Strong Base, Good Nucleophile (pKa of CA > 15) OH-, RO-, H- (from LiAlH4), NH2 - (all occur under SN2)
Common Bad Leaving Groups, Strong Bases tend to be bad leaving groups OH-, RO-, NH2-, H-, R-, F-, CN-
Sn1 vs Sn2 Sn1 includes carbocation, benzylic, allylic, all 3, all 2. It is weakly basic, protic, and includes racimization. SN2 includes methyl 1, 2, strong bases, polar, aprotic, and invasion of configuration.
Common EWGs (increase acidity) -NO2, -CN, -COOH, -CF3, -CHO
Common EDGs (decrease acidity) -O, -OH, -NH2, -NR
SN1 Stability of Carbocations: 3 Benzylic, allylic > 3 - 2 benzyli, allylic > 2 - 1 benzylic, allylic >> (1>methyl>vinyl, phenyl)
Created by: smurtab
 

 



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