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Aromatic compound: Benzene, Carbonyl, Alkyl Halides, Carboxylic acid,…
Aromatic compound: Benzene
Friedel-Crafts reactions
Alkylation
CH3Cl/AlCl3
Acylation
CH3COCl/AlCl3
Electrophilic aromatic substitution reactions
Halogenation
Chlorination
Cl2/Fecl3
Bromination
Br2 /FeBr3
Nitration
Concentration HNO3/H2SO4
Reduction
1.Fe,H30+ 2.HO-
Sulfonation
SO3/H2SO4
Reduction
H2/PtO2
.
Carbonyl
Nucleophilic addition reactions of aldehydes and ketones
Addition of Grignard Reagent
Aldehyde
1.RMgX 2.H3O+
Secondary alcohol
Ketone
1.RMgX 2.H3O+
Tertiary alcohol
Addition of water: Hydrate formation
Aldehyde or ketone
+H2O
Reversible reaction
Nucleophilic addition of alcohols: acetal formation
Aldehyde or ketone
+2ROH
Reversible reaction
Synthesis
Oxidation of Alcohol
Aldehydes
Ketone
Ketone
Friedel-Crafts acylation
Refer to bezene group
Hydration of terminal alkyne
Oxidation of aldehydes
[O]
Carboxylic acid
.
Addition of amines to form imines
RNH2
Imine
+H2O
Aldehyde or ketone
.
Alkyl Halides
Preparing alkyl halides
Alkane
Methane +CL2
Sunlight
CH3Cl +HCl
Alkene
HX
X2
Alcohol
Reagent HX
1-Methylcyclohexanol
HCl(gas) Ether,0 Celsius
+H2O
1-Chloro-1-methylcyclohexane
Reagent SOCl2
Cyclopentanol
SOCl2
+SO2 + HCl
Chlorocyclopentane
Grignard Reagents
R-X
Mg Ether
R-Mg-X
Nucleophilic substitution reactions
R-X
+Nu:-
R-Nu + X:-
Elimination reaction
KOH Ethanol
+
Methylenecyclohexane (minor)
1-Methylcyclohexene (major)
1-Chloro-1-methyl-cyclohexane
.
Carboxylic acid
Reactions
Reduction
LiAlH4
Formation of ester
R-OH,H+
Formation of acid chlorides
SOCL2
Synthesis
Oxidation of alkylbenzenes
p-Nitrotoluene
KMnO4
p-Nitrobenzoic acid
Oxidation
Hydrolysis of nitriles
.
Alcohol
Synthesis
Reduction of aldehydes and ketones
Aldehyde
[H]
primary alcohol
Ketone
[H]
secondary alcohol
Reduction of ester and carboxylic acid
[H]
Primary alcohol
carboxylic acid or ester
Grignard Reactions of Carbonyl Compounds
Refer to amine group
.
.
Amines
Synthesis
Reduction of nitriles and amides
Sn2 alkylation reactions of alkyl halides
Ammonia
SN2
NaOH
RNH2
Reductive amination of aldehyde and ketones
.
.
+H2O
Acetal
Alkenes & alkyne
Alkenes
Addition of HX to alkenes: hydrohalogenation
2-Methylpropene
2-Chloro-2-methylpropane
+HCl
Orientation of alkene addition reactions: Markovnikov's rule
Ether
1-Bromo-1-methylcyclohexane
1-Methylcyclohexene
Addition of H2O to alkenes: hydration
H2O+
H3PO4(catalyst) 250 Celsius
Ethanol
Ethylene
Addition of X2 to alkenes: halogenation
Cl+
1,2-Dichloroethane
Ethylene
Addition of H2 to alkenes: hydrogenation
1,2-Dimethyl-cyclohexene
H2,PtO2 CH3CO2H(Solvent)
cis-1,2-Dimethyl-cyclohexane
Oxidation of alkenes
Hydroxylation
Cyclohexene
+KMnO4
H2O NaOH
cis-Cyclohexane-1,2-diol
Cleavage
+KMnO4
H3O+
+
1 more item...
Cyclohexanone
Isopropylidenecyclohexane
Alkynes
Addition of HX
HBr
HBr
2,2-Dibromohexane
2-Bromohex-1-ene
Hex-1-yne
Addition of X2
Br2 CH2Cl2
Br2 CH2Cl2
1,1,2,2-Tetrabromobutane
(E)-1,2-Dibromobut-1-ene
But-1-yne
Addition of H2
H2 / Lindlar catalyst
H2/ Pd/C catalyst
Octane
Addition of H2O
H2O,H2SO4 HgSO4
Hexan-2-one
An enol
Hex-1-yne
Formation of Acetylide Anions
NaNH2
RCH2Br
A terminal alkyne
Acetylene
.
Primary alcohols
CrO3,H3O+
4-Methylpentanoic acid
4-Methylpentan-1-ol
.
Hexanoic acid
Hexanal
CrO3, H3O+
Fenoprofen
Periodinane CH2Cl2
Citronellal
Citronellol
4-tert-Butylcyclohexanone
CrO3 H3O+
4-tert-Butylcyclohexanol
H3O+ HgSO4
Hexan-2-one
Hex-1-yne
Carbonyl hydrate (gem diol)
Toluene
Oxidation
KMnO4
NaCN
1.LiAlH4,ether 2.H2O
1.SOCl2 2.NH3
1.LiAlH,ether 2.H2O
NH3/H2
Propanoyl chloride
.
Ester
,
1.NaCN 2.NaOH,H2O 3.H3O+
.
Nitrobenzene
Chlorobenzene
Bromobenzene
Benzenesulfonic acid
Heat
Acetophenone
H2O
Benzoic acid
130 atm, 25 °C
Cyclohexane
Organic Functional Groups
Aniline
Primary alcohol
Acid
Catalyst
+HBr
