O Chem 2 Reactions

Question 1

Br2 and hv (light)

Answer 1

Adds Br to more sub or allylic carbon

“Radical Bromination”

Question 2

Cl2 and hv

Answer 2

Adds Cl to more sub or allylic carbon

Question 3

NBS and hv

Answer 3

Adds Br to more sub or allylic carbon

*Best way to add Br

Question 4

Conjugated DB: HBr @ -78 degrees

Answer 4

Adds Br to allylic C+ intermediates

Question 5

Conjugated DB: HBr @ 40 degrees

Answer 5

Adds Br to allylic C+ intermediates after resonance that is the most sub

Question 6

Benzene Ring: Br2, FeBr3

Answer 6

Adds Br

Question 7

Benzene Ring: Cl2, FeBr3

Answer 7

Adds Cl

Question 8

Benzene Ring: HNO3, H2SO4

Answer 8

Adds NO2

Question 9

Sn, HCl

Answer 9

Turns NO2 into NH2

Question 10

Benzene Ring: SO3, H2SO4

Answer 10

Adds SO3H

Question 11

Benzene Ring: R-C, AlCl3

Answer 11

Adds R

• Not preferred, Hydride shifts

Question 12

Benzene Ring: R-acid chloride, AlCl3

Answer 12

Adds R-ketone (Cl forms bond with benzene)

*Does NOT work with EWG on benzene

Question 13

NH2NH2, KOH

Answer 13

Removes carbonyl

Question 14

Benzene Ring: KMnO4

Answer 14

Turns any R group on ring into Carboxylic acid as long as there’s a H on R

Question 15

TBDMS

Answer 15

Turns OH into OTBDMS

*Protecting group

Question 16

TBAF

Answer 16

Turns protecting group into OH

Question 17

Carbonyls: LAH, H2O

Answer 17

Turns carbonly into OH

Question 18

Carbonyls: NaBH4, CH3OH

Answer 18

Turns carbonyl into OH

Question 19

Carbonyls: R-MgBr, H2O

Answer 19

Turns carbonly into OH and adds R at same carbon

Question 20

Esters and Acid Chlorides: R-MgBr, H2O

Answer 20

Turns carbonyl into OH and R adds twice!

Question 21

Carbonyls: H2O

Answer 21

Carbonly leaves and 2 OH’s add

“Acetal reaction”

Question 22

Carbonyls: R-NH2

Answer 22

N-R replaces O but keeps the double bond

“Amine reaction”

Question 23

Carbonyls: R2-NH

Answer 23

NR2 replaces O but DB is one carbon away

Question 24

Carbonyls: Ph3P=R2

Answer 24

Turns carbonyl into >=R2

Question 25

LDA, -78 degrees, R-Br

Answer 25

Adds R to less hindered carbon adjacent to carbonyl

Question 26

NaOET, RT, R-Br

Answer 26

Adds R to most hindered carbon adjacent to carbonyl

Question 27

Carboxylic acid: SOCl2

Answer 27

Turns carboxylic acid into an acid chloride

*SOCl2 turns OH into Cl

Question 28

R-NH2

Answer 28

Turns OH into N-R