Reagents Flashcards
HCl or HBr to an alkene
addition of an acid to an alkene- the halogen is added Markovnikov
addtion of a halogen Cl or Br
the Br and Br or Cl and Cl is added and breaks the double bond- Br is added syn
Hg(OAc)2, H2O/ NaBH4
addition of water- oxymercuration demurcuration
added markovnikov, nonstereospecific
BH3, THF/ H2O2, OH-
addition of water- hydroboration oxidation
added non markovnikov
CHCl3/ KOH
addition of a carbene to an alkene
this is stereospecific
H2/ Pd. to an alkene
halogenation
H’s are added syn
Br2/ H2O
epoxidation
via a halohydrin
RCOOOH to an alkene
epoxidation via peroxyacid
OsO4, pyr./ NaHSO3 (aq)
adding OH to a double bond- syn addition of OH
RCOOOH to a double bond
add OH trans
O3/ Zn, H+
ozonolysis of alkenes
KMnO4/ H+
cleaving a double bond- producing a carboxylic acid and CO2
OsO4, pyr./ NaHSO3
oxidation of glycols
adding H2 to a triple bond
add 2 molar equivalents
to reduce the bond to an alkane
H2/ lindlar’s catalyst
add this to a triple bond to get a CIS alkene
Na or Li/ NH3
add this to a triple bond to get a TRANS alkene
addition of a halogen to a triple bond
addition is anti
first product is trans
addition of an acid to a triple bond
add Cl or Br part of the acid markovnikov
H2O, H2SO4, HgSO4
oxymercuration demercuration to a triple bond to make a terminal alkyne
(addition of water)
- B2H6, THF
2. H2O2, OH- (aq)
hydroboration oxidation
addition of water
yields a terminal alkyne
how do you add a halogen to an alcohol?
PBr3 or SOCl2
4 ways to prepare alkyl halids
from alcohols, from alkenes (addition of HBr), from alkenes by radical halogenation, from alkenes by allylic bromination
NBS
allylic bromination
Mg + Br
creation of a Grignard
used to form an alcohol
water will eliminate a Grignard
2RLi+ CuI
gilman reagent
NaNH2
a base that will deprotonate a terminal hydrogen - you can add something once there is a negative charge there it will act as the nucleophile
