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ORGANIC CHEMISTRY
Hydrocarbons
Arenes
Methylbenzene Toluene
(Aromatics)
R- -CH3
Oxygen-Containing
Isopropyl
Alcohols -OH R-OH CH3(CH-OH)-CH3 2-Propanol
alcohol
Ethyl methyl
Ethers -O- R-O-R CH3OCH2CH3 Methoxyethane
ether
Aldehydes R-(C=O)-H H-(C=O)-H Methanal Formaldehyde
-(C=O)-
Ketones R-(C=O)-R CH3-(C=O)-CH3 Propanone Acetone
Carboxylic
-(C=O)-OH R-(C=O)-OH CH3-(C=O)-OH Ethanoic acid Acetic acid
Acids
Methyl ethanoate Methyl acetate
Esters -(C=O)-O- R-(C=O)-O-R CH3-(C=O)-OCH3
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-NH2 R-NH2
2-Phenyl Phenyl
Amines -NH-R R-NH-R
ethanamine ethylamine
-NR2 NR3
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-(C=O)-NH2 R-(C=O)-NH2
Amides -(C=O)-NH-R R-(C=O)-NH-R CH3-(C=O)-NH2 Ethanamide Acetamide
-(C=O)-NR2 R-(C=O)-NR2
Nitriles -C≡N R-C≡N CH3CH2-C≡N Propanenitrile Cyanoethane
Sulfur-Containing
Thiols Methyl
-SH R-SH CH3-SH Methanethiol
(Mercaptans) mercaptan
Sulfides & -S- R-S-R R-Sn-R Methyldisulfanyl Dimethyl
CH3-S-S-CH3
Polysulfides -Sn- methane disulfide
Thio
Thioaldehydes R-(C=S)-H H-(C=S)-H Methanethial
-(C=S)- formaldehyde
Thioketones R-(C=S)-R CH3-(C=S)-CH3 2-Propanethione Thioacetone
Thiocarboxylic Ethanethioic acid Thioacetic acid
-(C=O)-SH R-(C=O)-SH CH3-(C=O)-SH
Acids
Halogen-Containing
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Trichloroethanoic Trichloroacetic
Halides -X R-X CCl3-(C=O)-OH
acid acid
Substitution;
Halogenation
Radical reaction
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Reactions of Alkenes
CH2=CH2 + H2 → CH3-CH3
Hydrogenation Addition
(forms alkanes)
Catalyst: Ni, Pt or Pd
Halogenation Addition
(forms dihalides) (Vicinal product)
Addition
Hydrohalogenation
(Markovnikov
(forms haloalkanes)
product)
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Hydration, Addition
Acid-Catalyzed (Markovnikov
(forms 2˚ or 3˚ alcohol) product)
Hydration, Addition
OxymercurationDemercuration (Markovnikov
(forms 2˚ or 3˚ alcohol) product)
Hydration, Addition
Hydroboration-Oxidation (Anti-Markovnikov
(forms 1˚ or 2˚ alcohol) product)
Dihydroxylation Addition
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Oxidation
(forms carboxylic acids)
Ozonolysis
(forms ketones & aldehydes)
Reactions of Alkynes
H-C≡C-CH3 + H2 → CH2=CHCH3
Addition
Hydrogenation Catalyst: Cis, Lindlar Catalyst
(cis or trans isomer
(forms alkenes) depending on catalyst
Trans, Na or Li in NH3
used)
Halogenation
CH3-C≡C-CH3 + 2Cl2 → CH3-CCl2-CCl2-CH3 Addition
(forms tetrahalides)
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Addition
Hydrohalogenation (Markovnikov product,
(forms dihalides) Geminal)
Addition
Hydration
(keto-enol tautomers
(keto-enol formation)
formed)
CH3-C≡C-H + H2O →
Preparation of Alcohols
Reduction of Carbonyl
Aldehyde to 1˚ Alcohol CH3CH2-(C=O)-H → CH3CH2CH2-OH
Compounds
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Preparation of Ethers
CH3CH2-OH → CH3CH2-O-CH2CH3
Dehydration of Alcohols
Catalyst: H2SO4, ∆
Catalyst: KMnO4, ∆, H+
Preparation of Esters
CH3CH2-(C=O)-O-CH3 + H-(C=O)-O-
Trans-esterification →
CH3CH2-(C=O)- + H-(C=O)-CH3
Substitution
Halogenated Arenes
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Monosubstituted Arenes
Dimethyl Substituted
Arenes
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Polycyclic Benzenoids