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48 Cards in this Set
- Front
- Back
reduction of an aldehyde or ketone to an alcohol
|
LiAlH4 or NaBH4
H3O H2O |
|
lithium dialkyl cuprate reagent from an alkyl halide
|
4 Li metal
CuI |
|
reduction of a nitro group to an amine
|
Zn(Hg) HCl
|
|
reduction of a benzyl carbonyl
|
H2/Pd or Zn(Hg) HCl
|
|
NAS
(normal condition must be 1 EWG ortho/para to leaving group) |
nucleophile (-OH, -OR, R3N)
|
|
benzyne reactions
|
1) NaOH
2) dilute acid |
|
benzyne reactions
|
NaNH2 NH3
|
|
changing an o/p to a m director
(NO2:NH2) |
Zn(Hg), HCl
|
|
changing an m to an o/p director
(CHR2:OCOH) |
KMnO4, H2O
|
|
acylation and de-acylation of ailines
|
OCCH3
NaOH |
|
sulfonation and de-sulfonation of aromatic rings
|
H2SO4 SO3
H3O+ H2O |
|
complete reduction of benzene
|
H2/Pt or H2/Rh
|
|
hydrate formation
|
H3O+
|
|
cyanohydrin formation
|
HCN -CN
|
|
acid halide reaction (nucleophilic acyl substitution)
|
nuc (HO-, RO-, NC-, R2N-, H-)
H-nuc (H2O, ROH, NR3) |
|
preparation of acid halides from carboxylic acids
|
SOCl2 X=Cl
PBr3 X=BR |
|
imine formation
|
R'-NH2 (NH3 or primary amine)
H (acid catalyst) |
|
enamine formation
|
R'-NH-R' (secondary amine)
H (acid catalyst) |
|
hemiacetal and acetal formation
|
H (acid catalyst)
R-OH (H acid catalyst) |
|
protection of a carbonyl against nuc
|
H catalyst
|
|
Williamson ether synthesis
|
NaH
R'-X (X=Cl, Br, I) |
|
1,4-addition to an alpha, beta-unsaturated carbonyl
|
1) nuc
2) dilute acid (H) |
|
1,4-addition of an amine to an alpha, beta-unsaturated carbonyl
|
H/R2NH
|
|
Wolf-Kishner
|
H2N/NH2
KOH |
|
Wittig Reactions
|
1) PPh3
2)/\/\Li |
|
reduction of carboxylic acid derivatives w/ hydride
|
1)LiAlH4
2) H3O primary alcohol |
|
reduction of carboxylic acid and derivatives w/ hydride (ketone)
|
1)LiAlH4 or NaBH4
2) H3O secondary alcohol |
|
reduction of carboxylic acid derivatives w/ hydride (amide)
|
1) LiAlH4
2) H3O amine |
|
acid-catalyzed ester synthesis
|
H
acidic conditions |
|
acid-catalyzed synthesis of a CA from an ester
|
H
acidic conditions |
|
ester saponification base catalyzed carboxylic acid synthesis
|
KOH
H acidify |
|
trans-esterification
|
H (acid-catalyzed)
or R''-ONa (base-catalyzed) |
|
acid-or-base-catalyzed hydrolysis of an amide
|
H (acid catalyzed)
or 1) OH (base catalyzed) 2) neutralize w/ dilute acid |
|
grignard/lithium reagent & CO2
|
1) O=C=O
2) H3O |
|
grignard/lithium reagent & nitrile
|
R'-MgBr
H/H2O |
|
formation of an ester from a 1 degree alkyl halide
|
R'-CH2-X (1 degree alkyl halide)
|
|
base-promoted alpha alkylation of carbonyl compounds
|
base (LDA)
R'-CH2-X (methyl of primary alkyl halide) |
|
acid catalyzed alpha-halogenation of carbonyl compounds
|
X-X/acetic acid
|
|
malonic ester synthesis of carboxylic acid
|
1)NaOR 2)R'CH2-X
H2O, H3O heat |
|
haloform reaction
|
NaOH/X2
|
|
alpha-bromination of carboxylic acids
|
1) PX3 or SOCl2
2) Br2 or NBS |
|
base-catalyzed aldol reactions
|
OH (low temp)
reaction stops at aldol |
|
base-catalyzed aldol reactions
|
OH (high temp)
OH (high temp dehydration) |
|
acid catalyzed aldol reaction
|
H
|
|
claisen reaction
|
OR (part a)
OR (part b) |
|
michael reaction
|
NaOr
|
|
gabriel synthesis of primary (1 degree) amines
|
NH3/heat (acid catalyst)
KOH Br-R KOH/H2O |
|
synthesis of amines via reduction of amides, aldehydes, ketones, or nitriles
|
LiAlH4
H2N-R' LiAlH4 or H2/metal catalyst |