OChem bases and nucleophiles

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50 Terms

1
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NaOH

Strong Base, Strong Nucleophile

2
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MeO⁻

Strong Base, Strong Nucleophile

3
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EtO⁻

Strong Base, Strong Nucleophile

4
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NH₃

Strong nucleophile, weak base

5
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NaCN

Strong nucleophile, weak base

6
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Ph₃P

Strong nucleophile, weak base

7
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I⁻, Br⁻, Cl⁻

Strong Nucleophile, weak base

8
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PhS⁻

Strong Nucleophile, weak base

9
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NaSH

Strong Nucleophile, weak base

10
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DBN

Weak Nucleophile, strong base

11
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DBU

Weak Nucleophile, strong base

12
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t-butoxide

Weak Nucleophile, strong base

13
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NaNH₂

Weak Nucleophile, strong base

14
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iPrOH

Weak nucleophile, weak base

15
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PhNH₂

Weak nucleophile, weak base

16
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H₂O

Weak Nucleophile, weak base

17
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MeOH

Weak Nucleophile, weak base

18
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EtOH

Weak Nucleophile, weak base

19
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Weak nucleophile, strong base, secondary carbon

E2

20
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Weak Nucleophile, Strong Base, Tertiary Carbon

E2

21
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Strong Nucleophile, Strong Base, Primary Carbon

Primarily SN2, some E2

22
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Strong Nucleophile, Strong Base, Secondary Carbon

Primarily E2, some SN2

23
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Strong Nucleophile, Strong Base, Tertiary Carbon

E2

24
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Strong Nucleophile, Weak Base, Primary Carbon

SN2

25
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Strong Nucleophile, Weak Base, Secondary Carbon

SN2

26
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Strong Nucleophile, Weak Base, Tertiary Carbon

SN1

27
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Weak Nucleophile, Weak Base, Secondary Carbon

No Reaction

28
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Weak Nucleophile, Weak Base, Tertiary Carbon

Half SN1, Half E1

29
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For weak nucleophiles and bases at 2° and 3° RX, with heat, major product favors?

E1

30
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For weak nucleophiles and bases at 2° and 3° RX, without heat, major product favors?

SN1

31
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For strong nucleophiles and/or good bases, with heat, major product favors?

E2

32
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3 ° + strong base ⁜

E2 ⁜

33
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3 ° + weak base ⁜

Sn1 and E1 ⁜

34
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1 ° + strong nu •

Sn2 •

35
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1 ° + Strong, sterically hindered base •

E2 •

36
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What pathway can a sterically hindered Nu or Base not go down? Sn or E?

Sn

37
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2 ° + Strong Nu/B △

Sn2 and E2 △

38
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2 ° + Strong, Bulky B  △

E2 △

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2 ° + weak Nu/B △

Sn1 and E1 △

40
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2 ° + Strong Nu, weak B △

Sn2 △

41
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A weak base cannot go down an elimination pathway with what of Carbon?

2 °

42
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CH3OH

Weak nucleophile/ base

43
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CH3SH

Weak base and nucleophile

44
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R-Li ℗

Strong Nu and B ℗

45
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R-MbBr ⌁

Strong B and Nu ⌁

46
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R3N »

Strong B and Nu »

47
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OH- ⌉

Strong Nu and B ⌉

48
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RO- ⌂

Strong Nu and B ⌂

49
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LDA

Bulky base

50
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N3 -

Strong Nu