Chem Nucleophile and bases

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28 Terms

1
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H2O

Weak Nucleophile

Weak Base

2
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MeOH

Weak Nucleophile

Weak base

3
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EtOH

Weak Nucleophile

Weak base

4
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iPrO-H

Weak Nucleophile

Weak base

5
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NaOH

Strong Nucleophile

Strong base

6
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NaOMe

Strong Nucleophile

Strong base

7
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NaOET

Strong Nucleophile

Strong base

8
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NaOiPr

Strong Nucleophile

Strong base

9
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NaOtBu

Weak Nucleophile

Strong base

10
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LDA

Lithium Diisopropylamide

  • Weak Nucleophile

  • Strong Base

11
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DBU

1,8-diazabicyclo[5.4.0]undecene

  • Weak Nucleophile

  • Strong Base

12
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NaCN

Strong nucleophile

Weak base

13
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F-

Poor leaving group

14
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HS-

Poor leaving group

15
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MeS-

Poor leaving group

16
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OH-

Poor leaving group

17
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MeO-

Poor leaving group

18
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CN-

Poor leaving group

19
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I-

Good leaving group

20
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ROSO2-

Good leaving group

21
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I-

Good leaving group

22
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Br-

Good leaving group

23
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Cl-

Good leaving group

24
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H2O

Good leaving group

25
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Conc. HBr, HCl on R-OH 1°

SN2

26
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Conc. HBr, HCl on R-OH 2+3°

SN1 like at rt or 0°C

27
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Conc. H2SO4 on R-OH 1°

not practical

28
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Conc. H2SO4 on R-OH 2+3°

E1-like temp (at Δ)

Conditions: Heat + non-nucleophilic acid (H2SO4, H3PO4)