Reagents

Question 1

Reduction of everything

Answer 1

LiAlH4

OR NaBH4 (soft)

OR Na/NH3 (hard)

Question 2

Partial reduction of esters and nitriles at -78 degrees C

Answer 2

DIBAL-H

Question 3

Reduction of acids to alcohols

Answer 3

BH3

Question 4

Capping of carbonyls

Answer 4

Dithiane/BF3.OEt2

Question 5

Remove cap

Answer 5

MeI

OR

HgCl2

Question 6

Reduction of Imine to Amine

Answer 6

NaBH3CN

Question 7

Reduction of Allylic ketone to allylic alcohol

Answer 7

NaBH4.CeCl3/MeOH

Question 8

Oxidation of alcohols to ketones

Answer 8

(XCrO3)-

Question 9

Oxidation of ketone to Ester

Answer 9

mCPBA

Question 10

Mild oxidation of OH

Answer 10

DMSO/NEt3

Question 11

Mild oxidation of allylic/benzylic OH

Answer 11

MnO2

Question 12

Alkyne to E-Alkene

Answer 12

Na/NH3

Question 13

Alkyne to z-alkene to alkane

Answer 13

H2/Pd catalyst

Question 14

Alkene to Epoxide

Answer 14

Br2/H2O

OR mCPBA

Question 15

a-B unsaturated ketone to epoxide

Answer 15

H2O2/NaOH

Question 16

Alkene to diol

Answer 16

KMnO4

OR OsO4

Question 17

Diol to z-aldehydes

Answer 17

NaIO4

Question 18

Alkene cleavage

Answer 18

O3

To 2x alcohol - NaBH4
To 2x aldehyde - Ph3P/Zn
To 2x acid - H2O2

Question 19

Carbonyl to epoxide

Answer 19

(CH3)2SOCH2 (soft)

OR (CH3)2SCH2 (hard)

Question 20

Carbonyl to alkene

Answer 20

P-ylide

Question 21

Carbonyl to E-alkene

Answer 21

PhSO2(CH3)-
PhCOCl
Na

Question 22

Carbonyl to alkene

Answer 22

(CH3)3SiEt-

With H+ or OH-