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24 Cards in this Set
- Front
- Back
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aromatic hallogenation
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X2 FeX3
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aromatic nitration
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h2so4, HNO3
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aromatic sulfonation
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SO3, H2SO4
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Friedel crafts alkylation
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R-Cl, AlCl3
no deactivating groups |
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Friedel Crafts Acylation
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RCO-Cl, AlCl3
no deactivating groups |
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strongly deactivating groups
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-NO2, -NR3(+), -CF3, -C-Cl3
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Moderate & weak deactivating groups
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-CN, -SO3H, -CO2H, -CO2R, -CHO, -COR
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clemmenson reduction
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Zn HCl
carbonyl to CH2 |
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protecting groups 1
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acid chloride can be added to aromatic -NH2 to make it moderately activating. remove with acid
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Formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde
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starting with formaldehyde, add a carbon link to the chain for each
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acetyl, benzoyl, formyl
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the r group in the aldehyde is: methyl, phenyl, a hydrogen atom
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Aldehyde synthesis
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1 alcohols - PCC oxidation
Acid Chlorides (DIBAH -78) esters (DIBAH -78) alkyl hallides + KCN --> nitrile (DIBAH -78) ---> |
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Ketone Synthesis
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2 alcohols - PCC oxidation
Friedel-Crafts Acylation Carboxyllic acids + SOCl2 ---> Acid chlorides + R2CuLi Ozonolysis of alkenes Alkynes (HgSO4, H2SO4) Nitriles (grignard) |
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CrO3
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Jones reagent- oxidizes aldehydes only
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Ag(NH3)2
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Tollens reagent - oxidizes aldehydes only - silver precip. AgO2 does the same.
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I2
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iodoform test - turns yellow precip for methyl ketones only
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standard nucleophillic addition
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H2O, NH3, HCN, RNH2, R2NH, R-OH (and deprotonated forms)
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addition of alcohols
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gives hemiacetals and hemiketals. excess gives the fully substituted acetal
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protecting groups 2
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cyclic acetal/ketal is created is created with ethyl diol to "replace" the O in the carbonyl to protect it. this reverts immediately in acid.
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thioacetals/thioketals
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form the same way as hemi ketals/acetals, but with sulfur instead. can be cleaved with Raney Ni and H2 to form the alkane.
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Amine addition
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RNH2, OHNH2, H2N-CO-NHNH2, and DNPH (benzyl) all lose their H2, the carbonyl loses its =O, and is replaced with =N. elements of water lost. derivatives useful for melting pt identification.
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NH2-NH2, KOH
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reduces in cleaving and forming the alkane as does Zn H2.
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-CN
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once bonded, it can be oxidized with acid to carboxyllic acid, forming a hydroxyacid. with more acid + heat, dehydration elimination. Or, -CN can be reduced to -CH2NH2 with LiAlH4
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SOCl2
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forms acid chlorides from carboxyllic acids.
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