OCHEM table chpt 11

1° RX + weak nucleophile/base (H2O, MeOH, or MeSH) in protic solvent → ?

No reaction

2° RX + weak nucleophile/base (H2O, MeOH, or MeSH) in protic solvent → ?

Both: SN1 (major) + E1 (minor)

Allylic/benzylic RX + weak nucleophile/base (H2O, MeOH, or MeSH) in protic solvent → ?

Both: SN1 (major) + E1 (minor)

3° RX + weak nucleophile/base (H2O, MeOH, or MeSH) in protic solvent → ?

Both: SN1 (major) + E1 (minor)

1° RX + moderate nucleophile (Cl−, Br−, I−, CH3S−, CH3COO−, CN−, or N3−) → ?

Substitution: SN2

2° RX + moderate nucleophile (Cl−, Br−, I−, CH3S−, CH3COO−, CN−, or N3−) in DMSO or DMF → ?

Substitution: SN2

2° RX + moderate nucleophile/base under the table's protic conditions (CH3COOH, CH3SH, or CH3OH) → ?

Both: SN1 (major) + E1 (minor)

Allylic/benzylic RX + moderate nucleophile (Cl−, Br−, I−, CH3S−, CH3COO−, CN−, or N3−) in DMSO or DMF → ?

Substitution: SN2

Allylic/benzylic RX + moderate nucleophile/base under the table's protic conditions (CH3COOH, CH3SH, or CH3OH) → ?

Both: SN1 (major) + E1 (minor)

3° RX + Cl−, Br−, I−, CH3COO−, or N3− → ?

Both: SN1 (major) + E1 (minor)

3° RX + CH3CH2S− or CN− → ?

Elimination: E2

1° RX + NaOH in H2O → ?

Substitution: SN2

2° RX + NaOH in H2O at room temperature → ?

Both: SN2 (major) + E2 (minor)

2° RX + NaOH in H2O with heat → ?

Elimination: E2

Allylic/benzylic RX + NaOH in H2O at room temperature → ?

Both: SN2 (major) + E2 (minor)

Allylic/benzylic RX + NaOH in H2O with heat → ?

Elimination: E2

3° RX + NaOH in H2O → ?

Elimination: E2

1° RX + KOH/MeOH (CH3O−) → ?

Substitution: SN2

2° RX + KOH/MeOH (CH3O−) → ?

Elimination: E2

Allylic/benzylic RX + KOH/MeOH (CH3O−) → ?

Elimination: E2

3° RX + KOH/MeOH (CH3O−) → ?

Elimination: E2

1° RX + bulky base t-BuO− [(CH3)3CO−] in t-BuOH → ?

Elimination: E2

2° RX + bulky base t-BuO− [(CH3)3CO−] in t-BuOH → ?

Elimination: E2

Allylic/benzylic RX + bulky base t-BuO− [(CH3)3CO−] in t-BuOH → ?

Elimination: E2

3° RX + bulky base t-BuO− [(CH3)3CO−] in t-BuOH → ?

Elimination: E2