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Organic > Reagents Reverse > Flashcards

Reagents Reverse Flashcards

1
Q

LiAlH4

A

Reduces everything

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2
Q

NaBH4

A

Reduces everything (soft)

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3
Q

DIBAL-H

A

Partial reduction at -78 degrees C

Ester to aldehyde) (nitrile to imine

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4
Q

BH3

A

Acids to alcohols

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5
Q

Thiol/BF3OEt2

A

Caps carbonyls

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6
Q

MeI or HgCl2

A

Removes cap

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7
Q

Na/NH3 (general)

A

Reduces everything (hard)

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8
Q

NaBH3CN

A

Imine to amine

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9
Q

NaBH4.CeCl3/MeOH

A

Allylic ketone to allylic alcohol

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10
Q

CrO3X-

A

Alcohols to ketones

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11
Q

mCPBA (ketone)

A

Ketone to Ester

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12
Q

SeO2

A

Alkene to allylic alcohol

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13
Q

Singlet Oxygen

A

Alkene to allylic alcohol (flipped)

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14
Q

DMSO/NEt3

A

Mild oxidation of OH

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15
Q

MnO2

A

Mild oxidation of allylic/benzylic OH

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16
Q

Na/NH3 (alkyne)

A

Alkyne to e-alkene

17
Q

H2/Pd c

A

Alkyne to z-alkene to alkane

18
Q

Br2/H20

A

Alkene to epoxide

19
Q

mCPBA (Alkene)

A

Alkene to epoxide

20
Q

H2O2/NaOH

A

a-B unsaturated ketone to epoxide

21
Q

KMnO4

A

Alkene to diol

22
Q

OsO4

A

Alkene to diol

23
Q

NaIO4

A

Diol to z-aldehydes

24
Q 
O3
Followed by:
1. NaBH4
2. Ph3P/Zn
3. H2O2
A

Alkene cleavage

  1. 2x alcohol
  2. 2x aldehyde
  3. 2x acid
25
Q

(CH3)2S+(CH2)-

A

Carbonyl to epoxide (hard)

26
Q

(CH3)2S+O(CH2)-

A

Carbonyl to epoxide (soft)

27
Q

P-ylide

A

Carbonyl to alkene

28
Q

PhSO2(CH2)-/PhCOCl/Na

A

Carbonyl to E-alkene

29
Q

(CH3)3Si(CH2CH3)-

Followed by H+ or OH-

A

Carbonyl to alkene

Organic (2 decks)

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