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97 Cards in this Set
- Front
- Back
- 3rd side (hint)
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PCC (no water), CH2Cl2
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primary alcohol to aldehyde
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1. O3
2, CH3SCH3 |
alkene to two aldehydes
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MnO2
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allylic alchol to allylic aldehyde
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H20, H+
with Hg |
Markov addition to alkyne to enol and tautomerizes to ketone
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1. B - (dicyclohexyl)
2. H2O2, -OH |
anit-Markov addition to alkyne to enol and tautomerizes to aldehyde
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HOCH2CH2OH
H+/-OH catalyzed |
ketone to hemiacetal and acetal to ketone (reversible) - creates protecting group
with only H+ catalyzed - acetals |
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HSCH2CH2SH
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ketone to protected thioacetal
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H2O, HgCl2, CaCO3
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removes thioacetal protecting group
thioacetal to ketone |
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NH2R
H+ catalyzed |
ketone to imine (reversible)
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NHR'R"
H+ catalyzed |
ketone to enamine (reversible)
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1. Raney Ni
2. H2 |
thioacetal to alkane
(way to remove ketone) *do not use with alkene/alkyne groups present |
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H2N-NH2
acid catalyzed NaOH, CH3OCH3, heat |
Wolf-Kishner
ketone to hydrazone to alkane |
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Ph3-P(CR'R")
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Wittig reaction
ketone to alkene (E/Z conformation uncontrollable) |
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RCOOOH (peroxide)
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ketone to ester and carboyxlic acid
moving group stability tertiary>secondary=phenol>primary |
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McLafferty rearrangement
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*requires gamma carbon and gamma hydrogen
ketone with gamma hydrogen as molecular ion becomes enol that tautomerizes into ketone and an alkene |
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Br2 with base catalyzed
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ketone to uncontrolled addition of bromine at alpha carbon
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Br2 with acid catalyzed
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ketone to monosubstituted alpha carbon with bromine
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base, followed by CH3I
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ketone to ketone with one additional carbon added at alpha position
or multiple substituted to create secondary carbon |
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NHR2, acid catalyzed
followed by CH3I, and acid |
enamine - controlled
then added methyl group to alpha carbon remove NR2 group using acid to create ketone with additional carbon group at alpha carbon reversible reaction |
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OH-
H+ to ketone |
ketone to enolate
O- ketone to enols OH tautomerizes to ketone |
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2 ketones and a base
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aldol condensation
forms enolate attacks carbonyl of another ketone to form beta-hydroxy carbonyl reversible |
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beta-hydroxy carbonyl and heat
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aldol condesation continued
forms an alpha beta unsaturated carbonyl reversible delocalizes up and over carbonyl |
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Br-Br to alpha beta carbonyl
CH3Li, followed by acid |
1,2 addition of halogen
only touches one double bond strong nucleophile makes 1,2 addition |
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HCN to alpha beta unsaturated carbonyl
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adds 1,4 addition since strong weak nucleophile
tautomerizes to ketone with CN attached to beta carbon |
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CH3Li
followed by acid catalyst |
organilithium adds 1,2
creates alcohol and methyl at carbonyl carbon, leaves double bond |
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MgBr-CH3
followed by acid |
magnesium bromide
not selective mixtures of 1,2 and 1,4 |
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(R)2CuLi
followed by acid |
alpha beta carbonyl with cuprates
adds 1,4 enol that tautomerizes to ketone with R attached to beta carbon |
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alpha, beta - unsaturated carbonyl and enolate
followed by acid work-up |
Michael reactions
enolate attacks beta carbon of alpha beta unsaturated carbonyl to form a 1,5 dicarbonyl |
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1,5 dicarbonyl
with base and heat |
aldol condensation that removes OH for a cyclic alpha beta unsaturated carbonyl
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CrO3
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primary alcohol to carboxylic acid
or aldehyde to carboxylic acid |
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RMgBr or RLi to CO2
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carbon dioxide to carboxylic acid
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RCN, followed by aqueous work-up and heat
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CN to carboxylic acid
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hydrolysis of alkanoyl halides
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carboxylic acid
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aqueous work-up or alcohol to anhydride
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carboxylic acid
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esters with base and heat, followed by acid work-up
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ester to carboxylic acid
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amides with base and heat, followed by acid work-up
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amide to carboxylic acid
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carboxylic acid and SOCl2
or PBr3 |
alkanoyl halide with chlorine
alkanoyl halide with bromine |
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carboxylic acid with alkanoyl halide
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anhydride
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carboxylic acid with acid and alcohol
or alkanoyl halide or anhydride |
esters
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carboxylic acid w. acid and amine plus heat
or alkanoyl halide, anhydride, ester |
amide
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carboxylic acid with Br2 and trace P
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Hell-volhard-Zelinsky reaction
adds bromine to alpha carbon *use Br as good LG to other groups |
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ester with alcohol
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transesterification
alkane groups swap positions *only for with a different R group |
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amide with diatomic halogen and base
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Hoffman rearrangement
amine and carbon dioxide |
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alkanoyl halide
with RMgBr or RLi |
tertiary alcohol after aqueous work-up
*uncontrolled |
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alkanoyl halide with (R)2CuLi
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controlled organometallic addition to form ketone
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LiAlH4 to alkanoyl halide
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primary alcohol
uncontrolled hydride |
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alkanoyl halide with LiAl(O-trimethyl)3H
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soft hydride - controlled
alkanyol halide to aldehyde *only alkanoyl halides |
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DIBAL to esters, amides, or nitriles
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esters/amides or nitriles to aldehydes
*only the 3 types above |
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ester with another ester
followed by base alcohol with same ester alkane group and then acid work-up |
Claisen condensation
product is 1,3 dicarbonyl *must have an alpha hydrogen between carbonyls for acidity or reaction goes in reverse *can have different side chains on esters - mixed claisen forms mixtures of products can be limited with only enolizable location *Dieckman Condensation - intramolecular |
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1,3 dicarbonyl with -OR, followed by R-I
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alkylation of 1,3 dicarbonyl
mono-alkylated product between two carbonyl groups |
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1,3 dicarbonyl
1. -OR 2. alpha, beta unsaturated ketone 3. -OR |
Robinson annulation
with heat drives out -OH and creates double bond on ring |
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1,3 dicarbonyl with H+, H20 and heat
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decarboxylation
produces enols that tautomerize into ketones and CO2 |
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1,3 dicarbonyl esters
alkylate acid work-up with heat decarboxylate |
Malonic ester synthesis
creates carboxylic acid with 2 R groups on alpha carbon |
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RCN and hydrolysis
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RCN to carboxylic acid
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RCN with MgBrR
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organometallic addition to RCN forms ketone
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RCN with LiAlH4 followed by acid work-up
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RCN to amine
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aldehyde with ethyldithiol and acid
followed by butyl-lithium |
creates masked acyl anion
sulfur anion |
butyl lithium is a strong base
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ketone with sulfur anion
followed by acid work-up followed by CaCO3, H20, HgCl2 |
ketone to alcohol and sulfur attachement
ketone with alpha alcohol alpha hydroxy carbonyl |
HgCl2 and CaCO3 act as deprotection
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amine with haloalkane
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uncontrolled alkylation of amine
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CN with haloalkane
followed by LiAlH4 |
controlled alkylation
nitrile to amine |
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NH3 with heat, followed by K2CO3 and water
followed by haloalkane aqueous work-up and heat |
Gabriel Synthesis to form amines
both primary and secondary |
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ketone with amine
followed by NaCNBH3 |
reductive amination
creates secondary and tertiary amines |
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R-Br with Na N3
followed by LiAlH4 |
azide displacement
R-Br to primary amine R-NH2 N2 displaced as good LG |
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aldehyde plus amine
add enolate |
Mannich reaction
forms imminium ion that reacts with enolate to form beta amino carbonyl |
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alylic with NBS
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allylic bromination
*halogenation |
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allylic with H20
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hydrolysis
adds OH |
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allylic with butyl-li
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creates allylic stablized anion
deprotonated acidic allylic H |
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dienophile and diene
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Diels-Alder
endo/exo rules |
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Electrocylic reactions
using heat or light |
Woodward-Hoffman rules
con/dis |
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Br2 with FeBr3
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halogenation of benzene through EAS
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NO3H with H2SO4
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nitrotation of benzene using EAS
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fuming SO3
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sulfonation of benzene using EAS
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R-X with FeX3
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EAS
Friedel-Crafts alkylation of Benzene uncontolled never on a deactivated ring |
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R-OH with BF3
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uncontrolled alkylation of benzene by EAS
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benzene with alkene and carboxylic acid
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alkylation of benzene via EAS
but prone to rearrangements |
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alkanoyl halide with AlCl3
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acylation to benzene by EAS
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anhydride with AlCl3
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acylation to benzene by EAS
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benzene with alkanoyl halide with AlX3
followed by H2NNH2 and base |
controlled alkylation adds methyl-R
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P-Cl5
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adds Cl to SO3
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NH2R
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modification
replaces SO2Cl with SO2NH2R |
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Zn(Hg) HCl
or H2/Ni or Fr/HCl |
changes NO2 to NH2 in a benzene
modification |
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CF3COOOH
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changes NH2 to NO2 on a benzene modification
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Zn(Hg) HCl with heat
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removes benzylic carbonyl
*Wolff-Kishner also works |
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Br2, hv
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halogenation of benzylic position
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KMnO4, OH
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strong oxidation of all benzylic positions
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CrO2 with carboxylic acid followed by water
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weak oxidation of benzylic position
only does one does not over-oxidize |
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MnO2 with ketone
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selective oxidation of benzylic/allylic OH
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benzylic ether with H2, Pd-C
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hydrogenolysis creates methyl-benzene
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deactivated benzene ring with Cl
add Na2CO3, H20 and heat |
creates phenol
positions at deactivating groups matter (O/P) |
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halogenated ring with NaOH, H20, heat, high pressure
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benzyne intermediate to phenol
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phenol with anhydride
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ester with R group as benzene
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phenol with alkyl halide
base NaOH followed with R-X H-X and heat |
creates ester
removes alkane, to form phenol |
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amino-benzene with NaNO3, followed by H+
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formation of diazonium salts
N2 is a good leaving group |
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diazonium salt plus CuX or CuCN
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makes halo-benzene or benzene with CN substituent
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amine benzene with NaNO3, H+
followed by H3PO2 |
forms diazonium salt that has N2 LG
adds hydrogen to create benzene ring |
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halo-benzene with alkene
and Pd-(OAc)2 with P-Ph3, Et3N |
alkylates benzene
alkene must have at least 1 H |
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aldehyde and amine followed by H+, H20 heat'
followed by HCN and H+ |
Strecker synthesis
aldehyde to hydrozone with HCN to amine and CN H+ makes carboxylic acid with amine on alpha carbon |
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