Reagents Reverse

Question 1

LiAlH4

Answer 1

Reduces everything

Question 2

NaBH4

Answer 2

Reduces everything (soft)

Question 3

DIBAL-H

Answer 3

Partial reduction at -78 degrees C

Ester to aldehyde) (nitrile to imine

Question 4

BH3

Answer 4

Acids to alcohols

Question 5

Thiol/BF3OEt2

Answer 5

Caps carbonyls

Question 6

MeI or HgCl2

Answer 6

Removes cap

Question 7

Na/NH3 (general)

Answer 7

Reduces everything (hard)

Question 8

NaBH3CN

Answer 8

Imine to amine

Question 9

NaBH4.CeCl3/MeOH

Answer 9

Allylic ketone to allylic alcohol

Question 10

CrO3X-

Answer 10

Alcohols to ketones

Question 11

mCPBA (ketone)

Answer 11

Ketone to Ester

Question 12

SeO2

Answer 12

Alkene to allylic alcohol

Question 13

Singlet Oxygen

Answer 13

Alkene to allylic alcohol (flipped)

Question 14

DMSO/NEt3

Answer 14

Mild oxidation of OH

Question 15

MnO2

Answer 15

Mild oxidation of allylic/benzylic OH

Question 16

Na/NH3 (alkyne)

Answer 16

Alkyne to e-alkene

Question 17

H2/Pd c

Answer 17

Alkyne to z-alkene to alkane

Question 18

Br2/H20

Answer 18

Alkene to epoxide

Question 19

mCPBA (Alkene)

Answer 19

Alkene to epoxide

Question 20

H2O2/NaOH

Answer 20

a-B unsaturated ketone to epoxide

Question 21

KMnO4

Answer 21

Alkene to diol

Question 22

OsO4

Answer 22

Alkene to diol

Question 23

NaIO4

Answer 23

Diol to z-aldehydes

Question 24

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

Answer 24

Alkene cleavage

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

Question 25

(CH3)2S+(CH2)-

Answer 25

Carbonyl to epoxide (hard)

Question 26

(CH3)2S+O(CH2)-

Answer 26

Carbonyl to epoxide (soft)

Question 27

P-ylide

Answer 27

Carbonyl to alkene

Question 28

PhSO2(CH2)-/PhCOCl/Na

Answer 28

Carbonyl to E-alkene

Question 29

(CH3)3Si(CH2CH3)-

Followed by H+ or OH-

Answer 29

Carbonyl to alkene