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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