Reagents

Question 1

mCPBA

Answer 1

Creates epoxied in one step

With strong acid, forms diols

Question 2

OsO4, NMO

Answer 2

Creates diols

Question 3

Lindlar’s Catalyst, H2

Answer 3

Creates cis-alkene

Question 4

Li, NH3

Answer 4

Creates trans-alkene

Question 5

HgSO4, H2SO4

Answer 5

Creates enol from alkyne

Question 6

NaNH2, RX (R=carbons, X=leaving group)

Answer 6

Attaches ‘R’ to alkyne

Question 7

AlCl3, RCl

Answer 7

Attaches R to benzene ring (according to director)

Question 8

ALCL3, RC(=O)Cl

Answer 8

Attaches RC(=O) to benzene ring (according to director)

Question 9

NaIO4, H2SO4

Answer 9

Cleaves diols (forms ketone)

Question 10

Pd/C, H2

Answer 10

Completely reduces / breaks double bonds

Question 11

O3, PPh3

Answer 11

Breaks alkenes to from two ketones

Question 12

Br2, Et2O

Answer 12

Breaks alkenes to add Br to each carbon

Halogenation

Question 13

Br2, H2O

Answer 13

Adds OH to one carbon and Br to the other

Question 14

1) Hg(OAc)2, H2O

2) NaBH4

Answer 14

Breaks double bonds, adding oh to one carbon and two H to the other

Oxymercuration (like halohydration)

Question 15

1) BH3

2) H2O2, NaOH

Answer 15

Anti-Markovnikov addition of OH to alkenes

Question 16

HBr

Answer 16

HBr addition to alkene/ alkyne x2

Question 17

KMnO4, H2SO4

Answer 17

Oxidizing argent, causes double bond cleavage

cleaves alkenes to give carbonyl-containing products

Question 18

H2SO4, H2O

Answer 18

Strong acid, useful for elimination reactions

Question 19

NaH

Answer 19

Forms epoxides from enol

Question 20

FeX3, X2

Answer 20

Adds (X) to aromatic rings

Question 21

HNO3, H2SO4

Answer 21

Adds NO2 to aromatic ring

Question 22

Rh/C, H2

Answer 22

Strong reducing agent

Replaces all double bonds with hydrogens