O Chem 2 Reactions Flashcards
Br2 and hv (light)
Adds Br to more sub or allylic carbon
“Radical Bromination”
Cl2 and hv
Adds Cl to more sub or allylic carbon
NBS and hv
Adds Br to more sub or allylic carbon
*Best way to add Br
Conjugated DB: HBr @ -78 degrees
Adds Br to allylic C+ intermediates
Conjugated DB: HBr @ 40 degrees
Adds Br to allylic C+ intermediates after resonance that is the most sub
Benzene Ring: Br2, FeBr3
Adds Br
Benzene Ring: Cl2, FeBr3
Adds Cl
Benzene Ring: HNO3, H2SO4
Adds NO2
Sn, HCl
Turns NO2 into NH2
Benzene Ring: SO3, H2SO4
Adds SO3H
Benzene Ring: R-C, AlCl3
Adds R
- Not preferred, Hydride shifts
Benzene Ring: R-acid chloride, AlCl3
Adds R-ketone (Cl forms bond with benzene)
*Does NOT work with EWG on benzene
NH2NH2, KOH
Removes carbonyl
Benzene Ring: KMnO4
Turns any R group on ring into Carboxylic acid as long as there’s a H on R
TBDMS
Turns OH into OTBDMS
*Protecting group
TBAF
Turns protecting group into OH
Carbonyls: LAH, H2O
Turns carbonly into OH
Carbonyls: NaBH4, CH3OH
Turns carbonyl into OH
Carbonyls: R-MgBr, H2O
Turns carbonly into OH and adds R at same carbon
Esters and Acid Chlorides: R-MgBr, H2O
Turns carbonyl into OH and R adds twice!
Carbonyls: H2O
Carbonly leaves and 2 OH’s add
“Acetal reaction”
Carbonyls: R-NH2
N-R replaces O but keeps the double bond
“Amine reaction”
Carbonyls: R2-NH
NR2 replaces O but DB is one carbon away
Carbonyls: Ph3P=R2
Turns carbonyl into >=R2
LDA, -78 degrees, R-Br
Adds R to less hindered carbon adjacent to carbonyl
NaOET, RT, R-Br
Adds R to most hindered carbon adjacent to carbonyl
Carboxylic acid: SOCl2
Turns carboxylic acid into an acid chloride
*SOCl2 turns OH into Cl
R-NH2
Turns OH into N-R
