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Subreaction
Hydrohalogenation
Electrophilic Addition
Hydration
Halogenation
Bromohydrin formation
Catalytic Hydrogenation
REDOX
Cis Hydroxylation
Oxidative cleavage
Epoxide formation
Catalytic Hydrogenation
Catalytic Hydrogenation
Substitution
Sn1
Sn2
Elimination
E1
E2
Reduction
reactions of alcohols
oxidation
oxidation
oxidation
ether synthesis
E1, dehydration
reactions of ethers
ether cleavage
Synthesis of tosylates
hemiacetals/acetals formation
imine formation
Synthesis of amines
Imines
Alcohol Synthesis
Grignard
Grignard
Grignard
Grignard
Grignard
formation of anhydride
esterification
hydrolysis
hydrolysis
hydrolysis
esterification
formation of amide
reactions of esters
Hydrolysis
synthesis of alcohols
synthesis of alcohols
reactions of amides
Hydrolysis
Reduction
Synthesis of nitriles
SN2
Reactions of nitriles
hydrolysis
reduction
-Halogenation
synthesis of carboxylic acids
Reactions at the a-position of carbonyls
Haloform
Aldol
Claisen
Acetoacetic Ester Synth.
Malonic Ester Synth.
Michael reaction
Robinson Annulation
Acid/base chemistry
formation of enolate
formation of enols
oxidation chemistry
Electrophilic Aromatic Substitution
REDOX
Starting Material
Reagent
Product
Alkene
HX, ether
Alkyl halides
Alkene
H3O+
Alcohols
Alkene
Br2/CH2Cl2 or CCl4
trans-1,2 dibromides
Alkene
Br2/water
trans-1,2 bromohydrins
Alkene
H2, Pd/C
Alkanes
Alkene
OsO4
cis-1,2 diols
Alkene
KMnO4, H3O+
ketones or acids
Alkene
mcpba
epoxides
Alkynes
H2, Pd/C
alkanes
Alkynes
cis alkenes
Alkynes
NaNH2
Acetylide anion
2o or 3o alkyl halide
good nucleohile
Inversion of Configuration
2o or 3o alcohol
weak bases
alkyl halide
Aldehydes
1 Alcohol
Ketones
2 Alcohol
a. LAH b. H30+
1 Alcohol
1 Alcohol
PCC
Aldehydes
2 Alcohol
PCC or CrO3
Ketone
1 Alcohol
KMnO4 or CrO3
Carboxylic Acid
ethers
1o or 2o alcohol
t-butyl ether
H2SO4 or H3PO4
alkene
ether
HBr or HI (conc)
t-butyl ether
CF3CO2H
alcohols
Alcohols
PBr3
Alkyl Bromides
Alcohols
SOCl2
Alkyl Chlorides
Alcohols
tosyl chloride
tosylates
Aldehyde or Ketone
Alcohol, H+
Aldehyde or Ketone
1o amine, H+
imine
Amines
Ethylene Oxide
a. RMgBr/ether b. H30+
1 Alcohol w/ 2 C's
Aldehydes
a. RMgBr/ether b. H30+
2 Alcohol
Formaldehyde
a. RMgBr/ether b. H30+
1 Alcohol w/ 1 C
Ketones
a. RMgBr/ether b. H30+
3 Alcohol
CO2
a. RMgBr/ether b. H30+
Carboxylic Acid
Carboxylic Acid
SOCl2
Acid Chloride
Acid Chloride
Carboxylate Anion
Anhydride
acid catalyst
ester
Amide
Hydrolysis
Carboxylic Acid/Amine
Acid Chloride
Anhydride
acid chloride
Acid Chloride
H2O
H2O
Alcohol
Amine
Carboxylic Acid
Carboxylic Acid
ester
Amide
ester
ester
ester
acid or base
a. LAH b. H30+
a. RMgBr/ether b. H30+
amide
amide
acid or base
a. LAH b. H30+
NaCN
Nitrile
nitrile
nitrile
acid or base
a. LAH b. H30+
carboxylic acids
Amines
Ketone or aldehyde
methyl ketone
X2 /HX
I2, NaOH
base
acid
enolate
enol
alkene
a. mcpba, b. aqueous acid or base
Aromatics
X2, FeX3 OR AlX3
Aromatics
HNO3/H2SO4
Aromatics
H2SO4/SO3
Aromatics
3o alkyl halide, FeX3
Aromatics
RCOCl, FeCl3 OR AlCl3
Aromatics w/ at least 1 benzylic hydrogen KMnO4
nitroaromatics
H2, Pd/C OR iron and tin reagents
trans diol
halogenated aromatic
nitrated aromatic
sulfonated aromatic
alkylated aromatic
acylated aromatic
benzoic acids
Anilines
acidic
Conditions
Mechanism
yes
acidic
yes
neutral
yes
neutral
yes
neutral
no
basic
no
acidic
no
neutral
no
neutral
no
neutral
no
basic
yes
neutral or acidic
yes
neutral or basic
yes
neutral or acidic
yes
neutral or basic
yes
no
no
no
no
no
no
basic
yes
acidic
yes
acidic
yes
acidic
yes
acidic
yes
no
no
no
yes
yes
no
basic
yes
basic
yes
basic
yes
basic
yes
basic
yes
no
yes
acidic
yes
acidic or basic
yes
yes
yes
yes
yes
yes
no
yes
yes
no
yes
yes
no
Acidic
Basic
no
no
(enone or enal)
yes
yes
yes
yes
yes
basic
acidic
yes
yes
either
acidic
acidic
acidic
acidic
acidic
neutral
yes
yes
yes
yes
yes
no
no
Notes
Unimolecular; two step where RDS is formation of carbocation; substrate must be able to form cation (2 o or 3o)
Unimolecular; two step where RDS is formation of carbocation; substrate must be able to form cation (2 o or 3o)
selective oxidation
a specific E1 reaction
Water must be removed during the reaction; only cyclic hemiacetals are stable.
susceptible to hydrolysis
susceptible to hydrolysis
Fisher esterification
or
or
or
or
or
or