ACS Notes Flashcards
random reagents specific jobs
HBr
——->
Peroxides (R-O-O-R)
antimarkov- add to the least stable positions
BH3, THF
—->
NaOH H2O2
antimarkov-antimarkov- add to the least stable positions
Hg(OAc)2/H2O/NaBH4
does not cause a hydride shift, forms a epoxide intermediate
O3/Me/S
the ozone
always makes a ketone and aldehyde!!!!!!!
KMnO4/OH with heat
always make COOH and ketone!
NaBH4 not as strong, selective
converts ketones and aldehydes to alcohols
DiBAI-H
reduces esters to aldehyde
LiAlH4/THF
reduced ketones, COOH to alcohols
PCC
oxidizing agent makes 1* alcohols to aldehyde
and 2* into Ketone
CrO3/H2SO4/H2O
converts 1* alcohol to COOH
KMnO4/OH? H*
converts Alcohols to COOH or Ketone, but also 2x bonds to COOH
LiAIH(OBU)
COOH and dervi(COO) into amldehyde only!!!!!!AHHHAAHAHA
TsCl is used for
making OH a good leaving group and making esters! and works as a protecting group
KMnO4 , OH, heat can..
cleave the 2x bond
what type of additions are epoxides
they are syn addition, meaning same side
ClsiMe3 is also
a alcohol protecting group
sp3 for NMR
1ppm
H Bonded to a pie system (2x bond)
2ppm
H bonded to an O
3-4 ppm
Halogens
4 ppm
aldehyde
10 ppm
carboxylic acid
11-12 ppm
aromatic
1500
3x bonds and CN
2100
sp2 cx( single bonds)
3100-3000
what reagents is used to carry out diels alder
heat needs to be inovolved to drive the rxn forward
Zn(Hg) con do to cooh derv.
reduces( rids of 2x bonds)
what does HNO3/H2SO4 do
Makes NO2
NH2 undergo with NaNO2
N—N(3x bonds)
N—N(3xbonds) with H2PO2
Benzene
lindar
what is more stable 1,4 or 1,2 addition
1,4 - thermodynamic favored and stable due to charge stability
1,4 is conjugated and is attacked
at B positioning
1, 2 are direct and is attacked
a alpha positioning
Reversible reagents
OH, RO, H2N, R2N, Cl, Br, I, CN, COOH. LiCu
irreversible reagents
MgBr-R, R-Li, LiAlH4, NaH4, witting(C-P)
O3/H20
makes 3x bonds into 2 COOH
HCI/Zn rids of
COOH