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PCC
weak oxidizing agent; oxidizes alcohols to ketones or aldehydes
KMno4
performs similar to ozonolysis
oxidize the alkene as well as the alcohol (forms two products)
oxidizes alkenes to form ketones or carboxylic acid
Low/High Temperature Kmno4
low temp- forms a syn diol
high temp - bond cleavage
Oso4
Oxidation resulting in a syn diol
CrO3/H2So4/H2O
oxidizes first degree alcohol to make carboxylic acid
Reducing agents
DiBA1-H, LiAlH4/THF, and NaBH4/EtOH followed by H+
DiBAl-H
reduces carboxylic acids and esters to aldehydes
LiAlH4
strong and reduces ketones and carboxylic acids and esters to to alcohols
LiAlH(OBu)3
will convert ester to an aldehyde
NaBH4/EtOH
selectively - reduces ketones and aldehydes but not carboxylic acids or esters
Protecting an alcohol from reacting ...
ClSiMe3/2-methyl propene will convert the alcohol to an ether
Will protect alcohols from forming- use this if there’s an OH- group you do not want to react
Additions involving epoxide (after alkene transformation)
Is considered to be an anti addition
In acidic conditions, the nucleophile attacks the more substituted carbon
In acidic conditions, the oxygen will also attach to hydrogen as its first step
In basic conditions, the nucleophile attacks the less substituted carbon
TfCl/HCl/ZnCl2 reacting with an alcohol ...
wil NOT invert the product formed with chlorine
HNMR spectra shifts
sp3 c - 1
C in pi system - 2
c - o - 3-4
sp2 c - 5-6
aromatic c - 7-8
aldehyde c - 10
carboxylic acid c- 11,12
For HNMR spectroscopy hydrogens with more than one equivalent carbon ...
if there is more than two equivalent carbons for a hydrogen peak, divide the amount of splitting in half
CNMR spectra shifts
When resonance is given to a C=O bond ...
Less energy is required to stretch a C-O single bond than a C=O double bond, thus with resonance it will have a longer wavelength and lower frequency
IR spectroscopy values
Carboxylic acid stretch
Aldehyde Stretch
Ketone stretch
