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6TH Floor Dona Amparo Bldg., G.M. Tolentino St.


Brgy. 468 Zone 46, Sampaloc Manila

ORGANIC CHEMISTRY

A. Summary of Functional Groups


Common Name
Family Functional Group General Formula Example IUPAC Name

Hydrocarbons

Alkanes C-C CnH2n+2 CH3CH2CH3 Propane -


Alkenes C=C CnH2n CH2=CH2 Ethene Ethylene
Alkynes C≡C CnH2n-2 HC≡CH Ethyne Acetylene

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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6TH Floor Dona Amparo Bldg., G.M. Tolentino St.
Brgy. 468 Zone 46, Sampaloc Manila

Acid Ethanoic Acetic


-(C=O)-O-(C=O)- R-(C=O)-O-(C=O)-R CH3-(C=O)-O-(C=O)-CH3
Anhydrides anhydride anhydride
Nitrogen-Containing

-NH2 R-NH2
2-Phenyl Phenyl
Amines -NH-R R-NH-R
ethanamine ethylamine
-NR2 NR3
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6TH Floor Dona Amparo Bldg., G.M. Tolentino St.
Brgy. 468 Zone 46, Sampaloc Manila

-(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

Phenyl sulfonic Benzene


Sulfonic Acid -(O=S=O)-OH R-(O=S=O)-OH
acid sulfonic acid

Halogen-Containing
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6TH Floor Dona Amparo Bldg., G.M. Tolentino St.
Brgy. 468 Zone 46, Sampaloc Manila

Trichloroethanoic Trichloroacetic
Halides -X R-X CCl3-(C=O)-OH
acid acid

Reaction Example Type


Reaction of Alkanes

Substitution;
Halogenation
Radical reaction
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6TH Floor Dona Amparo Bldg., G.M. Tolentino St.
Brgy. 468 Zone 46, Sampaloc Manila

(isomers produced in long


chained alkanes)

A. Summary of Organic Reactions

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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6TH Floor Dona Amparo Bldg., G.M. Tolentino St.
Brgy. 468 Zone 46, Sampaloc Manila

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)

Halohydrin Formation Addition (Markovnikov


product)

Dihydroxylation Addition
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6TH Floor Dona Amparo Bldg., G.M. Tolentino St.
Brgy. 468 Zone 46, Sampaloc Manila

Oxidation
(forms carboxylic acids)

Ozonolysis
(forms ketones & aldehydes)

Reactions of Alkynes

H-C≡C-H + 2H2 → CH3-CH3


Hydrogenation
Addition
(forms alkanes)
Catalyst: Ni, Pt or Pd

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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6TH Floor Dona Amparo Bldg., G.M. Tolentino St.
Brgy. 468 Zone 46, Sampaloc Manila

Addition
Hydrohalogenation (Markovnikov product,
(forms dihalides) Geminal)

Addition
Hydration
(keto-enol tautomers
(keto-enol formation)
formed)
CH3-C≡C-H + H2O →

CH3-C≡C-H → CH3-(C=O)-OH + CO2


Oxidation
(forms carboxylic acids) Catalyst: KMnO4, -OH, ∆
then H+

CH3-C≡C-H → CH3-(C=O)-OH + H2CO3


Ozonolysis (forms
carboxylic acids) Catalyst: O3 then
Zn in H2O

Preparation of Alcohols

Reduction of Carbonyl
Aldehyde to 1˚ Alcohol CH3CH2-(C=O)-H → CH3CH2CH2-OH
Compounds
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6TH Floor Dona Amparo Bldg., G.M. Tolentino St.
Brgy. 468 Zone 46, Sampaloc Manila

Ketone to 2˚ Alcohol CH3CH2-(C=O)-CH3 → CH3CH2-(CH-OH)-CH3

Carboxylic Acid to 1˚ Alcohol CH3-(C=O)-OH → CH3CH2-OH

Ester to 1˚ Alcohol CH3-(C=O)-O-CH3 → CH3CH2-OH + CH3-OH

Catalyst: LiAlH4 or NaBH4

Hydration of Alkenes See Reaction of Alkenes

Preparation of Ethers

CH3CH2-OH → CH3CH2-O-CH2CH3
Dehydration of Alcohols
Catalyst: H2SO4, ∆

CH3CH2OH + CH3-X → CH2CH3-O-CH3


Williamson Synthesis
Catalyst: Na or NaH

Preparation of Carboxylic Acids

See Oxidation of Alkenes & Alkynes


Oxidation
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6TH Floor Dona Amparo Bldg., G.M. Tolentino St.
Brgy. 468 Zone 46, Sampaloc Manila

Aldehyde to Carboxylic Acid H-(C=O)-H → H-(C=O)-OH

Alcohol to Carboxylic Acid CH3CH2-OH → CH3CH2-(C=O)-OH

Catalyst: KMnO4, ∆, H+

Preparation of Esters

CH3-OH + CH3CH2-(C=O)-OH → CH3CH2-(C=O)-O-CH3


Esterification
Catalyst: ∆, H+

CH3CH2-(C=O)-O-CH3 + H-(C=O)-O-

Trans-esterification →

CH3CH2-(C=O)- + H-(C=O)-CH3

Reactions of Aromatic Compounds


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6TH Floor Dona Amparo Bldg., G.M. Tolentino St.
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Substitution

B. Nomenclature of Common Benzene Derivatives


Classification Structure

Halogenated Arenes
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6TH Floor Dona Amparo Bldg., G.M. Tolentino St.
Brgy. 468 Zone 46, Sampaloc Manila

Monosubstituted Arenes

Dimethyl Substituted
Arenes
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6TH Floor Dona Amparo Bldg., G.M. Tolentino St.
Brgy. 468 Zone 46, Sampaloc Manila

Polycyclic Benzenoids

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