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H2SO4 + R
ester
CH2N2
replaces -OH w/ -OMe
SOCl2
adds a Cl
heat
too hot for HOOC so it leaves
H2O/base
replace halogen w/ -OH
H2O
forms 2 HOOCR's
NaOH/H2O and heat
replace N-H group w/ O-
H3O+
makes double bond of 2,3 C w/o dropping -OH
H+/H2O and heat
break open cyclo, add -OH and -NH2
H+
reduces carbonyl to -OH
H2N-CH3
NH-CH3 replaces leaving group
NH3
ester leaves and NH2 replaces it
pyridine
forms an anhydride
R-MgBr
replaces LG with R group, forms -OH
(CH3)2 CULi
replaces LG w/ R group
LiAlH4/H2O
forms an NH2 or removes carbonyl
P4P10/heat
makes nitrile
acid anhydride/heat
makes nitrile
-OH
makes an O- on the carbonyl
X2/acid or base
adds "X" to the alpha carbon
Br2/OH-
forms an O- on empty carbon
LDA (strong base)
O becomes -, drops double bond to next carbon
NH2CH3
adds NCH3 to where R was
NaOH/R/H2O
R adds to alpha carbon
X-R/H3O+
R group leaves, attaches to ring, adds carbonyl group
KMnO4
carboxylic acid
DiBAL-H, -78/H2O
breaks open cyclo and adds -OH/ turns a nitrile into an aldehyde
NH2NH2/KOH
removes carbonyl group
(Ph)3P-CH2
removes O from carbonyl
HNO3/H2SO4
adds -NO2
LiAlH(OtBu)3, -78/H2O
remove -X and replace with H

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