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OC1 Reagents Flashcards

1
Q

oxymerc. demerc.

  • Reagents
  • Regioselectivity
  • Stereospecificity
  • Products
A

Oxymerc. Demerc.

  1. Hg(OAc)2, H2O 2. NaBH4
    Mark
    —
    OH
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2
Q

Hydrobor. Ox.

  • Reagents
  • Regioselectivity
  • Stereospecificity
  • Products
A

Hydrobor. Oxid

  1. BH3*THF 2. ROOR, NaOH
    AM
    **Syn
    OH + En
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3
Q

det. Regioselectivities

A

Mark/Anti-Mark

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4
Q

det. Stereospecificities

A

Syn/Anti-Syn

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5
Q

Bromination

  • Reagents
  • Regioselectivity
  • Stereospecificity
  • Products
A

Bromination

AS
Br*2 + En

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6
Q
  • Reagents
  • Regioselectivity
  • Stereospecificity
  • Products
A

Catalytic Hydrogenation

Syn
H,H + En

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7
Q

Acid-Catalyzed Hydration

  • Reagents
  • Regioselectivity
  • Stereospecificity
  • Products
A

Acid-Catalyzed Hydration

diluted H2SO4
Mark
——
OH

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8
Q

Hydrohalogenation

  • Reagents
  • Regioselectivity
  • Stereospecificity
  • Products
A

Hydrohalogenation

HX (Cl=X), ROOR
AM
—-
X (Cl)

ONLY WHEN CARBOCAT NOT POSSIB.

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9
Q

Ozonolysis

  • Reagents
  • Regioselectivity
  • Stereospecificity
  • Products
A

Ozonolysis

  1. ## O3 2. DMScarboxyls 0.5 where the double bonds were
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10
Q

Syn Dihydroxylation (less toxic)

  • Reagents
  • Regioselectivity
  • Stereospecificity
  • Products
A

Syn Dihydroxylation

Syn
OH, OH + en

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11
Q

Syn Dihydroxylation (more toxic)

  • Reagents
  • Regioselectivity
  • Stereospecificity
  • Products
A

Syn Dihydroxylation

  1. ## OsO4 2. NaHSO3, H2OSyn
    OH, OH + en
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12
Q

H2, Lindlar

A

Alkyne—>Alkene (3-2)

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13
Q

H2, Pt (10)

A

Alkyne—->Alkane (3-1)

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14
Q

H2, Pt

A

Catalytic Hydrogenation

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15
Q

Catalytic Hydrogenation

  • Reagents
  • Regioselectivity
  • Stereospecificity
  • Products
A

Catalytic Hydrogenation

Syn
H2,H2

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16
Q

Hydrohalogenation

  • Reagents
  • Regioselectivity
  • Stereospecificity
  • Products
A

Hydrohalogenation

HX (& ROOR, possibly)
AM
—-
X

17
Q

HX (& ROOR, possibly)
AM
—-
X

A

Hydrohalogenation

18
Q

Syn
H2,H2

A

Catalytic Hydrogenation

19
Q
  1. ## OsO4 2. NaHSO3, H2OSyn
    OH, OH + en
A

Syn Dihydroxylation (more toxic)

  1. ## OsO4 2. NaHSO3, H2OSyn
    OH, OH + en
20
Q

Syn
OH, OH + en

A

Syn Dihydroxylation (less toxic)

Syn
OH, OH + en

21
Q
  1. ## O3 2. DMScarboxyls 0.5 where the double bonds were
A

Ozonolysis

  1. ## O3 2. DMScarboxyls 0.5 where the double bonds were
22
Q

Deprotonate Alkyne

A

NaNH2 ; XR

23
Q

Protect Alcohol

A

Protect

TMSCl, ET3N

24
Q

Deprotect Alcohol

A

Deprotect

TBAF

25
Grignard rxn * Reagents * Products
Grignard 1.Mg, Et2O 2.C=O grp 3.H2O Alcohol instead of carboxyl group
26
1* Alcohol * Reagents * Prod. * Stereochem
1* Alcohol 1. TsCl, pyr ; NaX Inversion
27
1*/2* Alcohol (Cl) * Reagents * Prod. * Stereochem
1*/2* Alcohol (SOCl2,pyr) SO2, Cl-, RCl Expect Inversion 2b happenin
28
1*/2* Alcohol (Br) * Reagents * Prod. * Stereochem
1*/2* Alcohol (Br) Pbr3 HOPBr2,RBr Expect Inversion 2b happenin

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