Organic Chem Synthetic Transformations

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41 Terms

1
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Anti-Markovnikov Addition of H & OH

  1. BHR, THF

  2. H202m NaOH

2
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Anti-Markovnikov Addition of H & Br

HBr peroxides (ROOR), heat + light

3
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Anti-Markovnikov Epokide Ring Opening - Basic Conditions

Strong Base

4
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Anti-Markovnikov Addition of H20 to Alkyne

  1. BH3, THF

  2. H202, NaOH, H20

5
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Markovnikov Addition of H & X

HX, cold + dark, no peroxides

6
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Markovnikov Epoxide Ring Opening - Acidic Conditions

H+, HOR

7
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Markovnikov Addition of Br & OR to Alkene

Br2, HOR

8
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Markovnikov Addition of H & X

HX

9
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Markovnikov Addition of H2O to Alkyne

H2SO4, H2O, HgSO4

10
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Oxidation of 1° Alcohol to Aldehyde

PCC

11
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Oxidation of 2° Alcohol to Keton

KMnO4, CrO3, PCC, Na2Cr2O7

12
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Oxidation of a 1° Alcohol/Aldehyde to Carboxylic Acid

  1. PCC

  2. KMnO4, CrO3, Na2Cr2O7

13
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Halogenation of Alcohol using HX

HX

14
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Halogenation of Alcohol using SOCl2

SOCl2

15
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Halogenation of Alcohol using Pbr3

PBr3

16
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Addition of Br2 to Alkene

Br2

17
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Syn Addition of 2 OH groups to Pi Bond

  1. Oso4

  1. H2O2, NaHSO3

18
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Addition of X2

X2

19
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Oxymercuration-Demurcuration

  1. Hg(OAc)2, THF, H2O

  2. 2.) NaBH4

20
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Alkoxymercuration-Demurcuration

  1. Hg(OAc)2, THF, HOR

  2. NaBH4

21
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Oxidation of Alkene to Epoxide

mCPBA

22
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Cyclopropane Ring from Alkene

KOH or CH2I2, Zn(Cu)

23
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Hydroboration-Oxidation

  1. BH3, THF

  2. H2O2, NaOH

24
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Catalytic-Hydrogenation

Pt Pd, H2

25
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Alkyne Reaction

Pt° Pd°, H2

NiB2/Lindlar Catalyst

Na°, NH3

26
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Ozonolysis

  1. O3

  2. Zn, acetic acid

27
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Permanganate (MnO4-)

  1. KMnO4 (heat)

  2. H3O+/H2O

28
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Tautomerization

No reagents, ketone
29
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Deprotonation of Alkyne

NaNH2

30
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Nitrile Hdrolysis

H2O2, H2SO4

31
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Zatisev/Hofmann

No reagents.

Zatisev - most-substituted

Hofmann - violates Zaitsev's Rule

32
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C-H Bond

50 pka

33
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H-H

40 pka

34
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N-H w/ less R groups

35 pka

35
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O-H w/ less R groups

16 pka

36
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N-H w/ more R groups

9 pka

37
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H-F

3 pka

38
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H-Cl (or any strong acid)

0 pka

39
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O-H bond with alcohol and R-group

5 pka

40
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Ethyne C-H bond

25 pka

41
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Benzylic Ring with O-H alcohol bond

10 pka