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64 Cards in this Set
- Front
- Back
a |
a |
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b |
b |
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c |
c |
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cyclic product look to pos |
intramolecular rxn |
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form an ester reverse |
snks |
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ketone to alkane additional carbons |
wittig rxn djdkdkkr |
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carboxylic deriv to ketone |
nrjej |
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ketone to ester |
bayer villiger peroxi acid RCOOOH |
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reduce ketone to alkane basic |
wolff kishner reduction NH2NH2, NaOH, DMSO |
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reduce ketone to alkane acidic |
clemson reduction Zn(Hg), HCl |
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base halogenation of ketone Br replaces alpha hydrogen |
Br2 OH- |
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aldol condensation rxn (intramolecular) |
will favor a 5 or six membered ring |
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crossed aldol |
2 different different carbonyl compounds the alpha H will attach the carbonyl carbon |
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aldol initial product |
Beta hydroxy carbonyl |
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aldol condensation reaction final product |
Alpha Beta unsaturated carbonyl |
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iodoform test |
presence of methyl ketone |
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phenylhydrazine |
pg6 fnfkfk |
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why anhydride is more reactive than an ester |
better leaving group (acetate better than ethoxide) |
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acetic anhydride |
H3CC=O-O-C=OXH3
(CH3CO)2O O O || || CH3-C-O-C-CH3 |
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Ph-CH2Cl + NaCN |
forms cyano hydrin sn2 Ph-CH2CN |
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Ph-CH2CN H2SO4 reflux |
Ph-CH2COOH 11. |
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what will not undergo hydrolysis (in w/ acid or base present) |
ketone 12. |
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13 |
nmr review |
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acetoacetic ester Ch3C=OCH2C=O-O-CH2CH3 add r to alpha hydrogen |
1) NaOC2CH3 (same group limit competition) 2) RBr |
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dicaebonyl ester to CA |
1) NaOH 2) H3O+ (CA) 3) Heat (split at alpha carbon) |
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ester enolate |
deprotonated alpa carbon
2 resonense
15. |
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strength of acid |
melonic acid> di CA w/o the same resonance |
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nomenclature ester ketone aldehyde |
17 |
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tollens test 2,4-DNP distinguishes |
ketones and aldehydes 18. |
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C=N is called |
imine 18b. |
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initial product of aldol reaction |
Beta hydroxy carbonyl |
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only Carboxilic Acid derivitive with 2 carbonyl groups is |
anhydride RC=OOC=OR' |
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base promoted hydrolysis of ester called |
soponification |
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malonic ester synthesis is the synthetic equivolent used to make substituded |
Acetic acids |
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1° amine to Nitrile R-NH2 to R(trip)N |
P4O10 |
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propanamide |
CH3CH2C=O \ NH2 |
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5-oxo-4-propylhexanoic acid |
Carboxylic acid Carbonyl Carbon is 1 carbon 4 has prop group carbon 5 has carbonyl |
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enolate from acetalacetone pentane 2,4 dione |
deprotonat the alpha H first is the charged carbon 3 other resonance |
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hemi acetal mech |
protonate carbonyl nucleophile addition resonense addition regen
21. |
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long molecule with OH and CA group H2SO4 H2O |
intramolecular esterification (lactone) protonate carbonyl resonance deprotonate protonat leaving group (H2O) reform carbonyl deprotonate |
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intramolecular esterificarion mech |
·addition ·proton transfer ·reform/elimination ·deprotonate reform cat. |
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aldol exn alpha beta unsaturated carbonyl |
OH- Heat |
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alkyne to ketone
hydration of alkyne |
HgSO4 H2SO4 H2O heat |
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acid halide to ester |
R-OH pyridine |
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acid halide and amide group on one molecule
heat |
intramolecular reaction cyclic NH join at carbonyl carbon
wittig reaction |
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acid halide to add R group to carbonyl carbon |
(R)2CuLi cuprate |
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1 methylcyclohexane to 1methy1bromohexane |
Br2 hv (or heat) |
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1methy1bromocyclohexane
to 1methy1cyclohexene |
NaOH/heat |
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1methy1cyclohexene to 2methy 1cyclohexanol |
1)BH3, THF 2)H2O2, NaOH hydroboration |
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oxidate 2° alcohol to ketone |
oxidizer e.g. H2CrO4 |
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ketone to imine (C=N-R) |
(R)NH2 addition dehydration |
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CA to acid chloride |
PCl3 or SOCl2 |
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acid halid to amide at alpha carbon |
NH3 excess |
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amide to nitrile |
P4O10 heat |
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acid chloride add R group |
(R)2CuLi ether -78°C |
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ethyl actoacetate CH3COCH2COOC2H5 add R group to alpha carbon then form CA (split at alpha carbon) |
1)NaOCH2CH3 2) R-Br 3) NaOH 4) H3O+ 5) heat |
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Ketone to ester |
RCO3H |
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CA to 1° alcohol |
strong reduction 1)LiAlH4 2)H2O |
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primary alcohol to primary bromide |
PBr3 |
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ketone Ph-COCH3 with HONH2 H+ |
Ph-C=N-O \ CH3 |
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ketone replace all alpha hydrogens with Deuterium |
1)NaOD excess 2)D2O |
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primary alcohol to aldehyde |
PCC |
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diethyl melonate to 3 methylpentanoic acid |
1)NaOCH2CH3 (base same group) 2) CH3CHBrCH2CH3
3)NaOH (Soponification) 4)HCl (Acididication ,CA formes) 5) heat (decarboxylates) |
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compound with ketone and ester reduce ester keep ketone |
1)HOCH2CH2OH/H+ 2) LiAlH4 remove protecting group with acid at the end H+ |