orgchem

• Category of Organic Compounds based on the Structure

  Aliphatic Hydrocarbon

  Aromatic Hydrocarbon

  Alicyclic or Carbocyclic
• Aliphatic Hydrocarbon


  Single chain, no ring/s involved

  Saturated Hydrocarbon (Single bonds) Unsaturated Hydrocarbon (Double/Triple bonds)
• Aromatic Hydrocarbon


  Presence of ring/s, specifically benzene ring and its

  derivative.

  Benzene, naphthalene, Anthracene
• Alicyclic or Carbocyclic


  Chains that form a ring and behave like aliphatics. Cyclopropane

  Cyclobutane

  Cyclopentane
• Naphthalene


  With two benzene-like rings fused

  Mothballs

  Exposure: Hemolytic anemia, damage to liver and neurological system, cataracts and retinal hemorrhage.
• Anthracene


  With three rings

  AKA: Paranaphthalene or green oil.

  Use: production of dyes, smoke screen.

  Prolonged exposure: topical and systemic adverse reactions.
• Benzo[a]pyrene


  With five rings

  Benzopyrene - found in gasoline and diesel exhaust, cigarette smoke, charcoal- broiled food. (Carcinogenic)
• Benzopyrene


  found in gasoline and diesel exhaust, cigarette smoke, charcoal- broiled food. (Carcinogenic)
• Coronene


  With six rings
• Heterocycle


  A cyclic compound that contains atoms of two or more element in its ring, usually C along with N, O and S.
• Pyrimidine and Imidazole


  _________ and ___________ ring are important in

  biological chemistry.
• Pyrimidine


  Parent ring system in 3 of 5 heterocyclic amine bases in nucleic acid.
• Imidazole


  Present in histidine, 1 of 20 amino acid found in protein.
• Analog


  Differs structurally from the prototype drug only by one atom or group of atoms, generally isosteres of those borne by the parent drug.

  Owes its pharmacological activity to its own features, not to the drug which it derives.
• Heterocyclic Analog of Naphthalene

  Quinoline, Isoquinoline contain pyridine- like nitrogen (part of double bond and contribute 1 pi electron)

  
  

  Indole contain pyrrole-like nitrogen (NOT part of double bond and contribute 2 pi electron)

  
  

  Purine contain both type of nitrogen (part of double bond and not part of double bond
• Quinoline, Isoquinoline


  contain pyridine-like nitrogen (part of double bond and contribute 1 pi electron)
• Indole


  contain pyrrole-like nitrogen (NOT part of double bond and contribute 2 pi electron)
• Purine


  contain both type of nitrogen (part of double bond and not part of double bond
• Category of Organic Compounds based on the Composition

  Simple Hydrocarbons

  Organic compounds that only consist of H and C atom.

  
  

  Hydrocarbon Derivatives

  Hydrocarbons that bears other elements such as O, N, P, S, X
• Hydrocarbon Derivatives


  Oxygen-containing

  Alcohol/Phenol, Ether, Aldehyde, Ketone, Thioether

  Carboxylic acid & their derivatives (Ester, Amides, Anhydrides, Acid/Acyl chloride)

  
  

  Nitrogen-containing

  Amines, Imines, Nitriles, Nitro compounds, Amides Heterocyclic N-compounds

  
  

  Phosphorus-containing

  Organophosphates

  
  

  Sulfur-containing

  Thiols, Thioether, Thioester

  Sulfides, Disulfides, Sulfoxides

  
  

  Halogen-containing

  Alkyl Halides, Aryl Halides
• Oxygen-containing


  Alcohol/Phenol, Ether, Aldehyde, Ketone, Thioether

  Carboxylic acid & their derivatives (Ester, Amides, Anhydrides, Acid/Acyl chloride)
• Nitrogen-containing


  Amines, Imines, Nitriles, Nitro compounds, Amides Heterocyclic N-compounds
• Phosphorus-containing


  Organophosphates
• Sulfur-containing


  Thiols, Thioether, Thioester

  Sulfides, Disulfides, Sulfoxides
• Halogen-containing


  Alkyl Halides, Aryl Halides
• Alkanes


  All members of alkanes differ from each other by their molecular formula by the unit of CH2- and are called as member of "homologues series".

  Removal of one hydrogen from alkane yields an alkyl group (-R). General formula: CnH2n+1.

  Occurrence: petroleum or natural gas (80% met, 10% et, and 10 higher alkanes)
• homologues series


  All members of alkanes differ from each other by their molecular formula by the unit of CH2- and are called as member of ________________.
• Importance of Alkanes


  Important component of waxes.

  Exist as terpenes (bioactive compounds). Exhibit pharmacological activities.
• Straight-Chain Alkanes


  Carbons are connected in a row.
• Branched-Chain Alkanes


  Carbon are in branch chain.
• Alkyl Group (R)


  A substituent group derived from an alkane by the removal of a

  Alkyl groups are not stable compound themselves, they are simply parts of larger compound.

  They are named by replacing the '-ane' ending of the parent alkane with an '-yl' ending.
• Aryl Group (Ar)


  A substituent group derived from benzene by the removal of a hydrogen atom.
• Cycloalkanes


  Saturated Cyclic Hydrocarbons

  CnH2n

  Consist of rings of -CH2- units.
• Physical Properties of Alkanes

  C1 to C4: Colorless and odourless gas

  C5 to C17: Colorless and odourless liquid

  Other members: waxy solids

  Soluble in non-polar solvents

  Insoluble in polar solvents

  Lipophilic

  Less dense than water
• Physical Properties of Alkanes

  As ↑ MW = ↓ Solubility

  As ↑ MW, ↑ Density, BP and MP

  As ↑ branching, ↓ BP

  Normal or straight chain have higher boiling point and melting point than branched chain isomers.

  Example:

  n-pentane boils at 36.1 °C (no branch)

  isopentane (2-methylbutane) boils at 27.85 °C (1 branch) neopentane (2,2-dimethylpropane) boils at 9.5°C (2 branch)
• Chemical Properties of Alkanes

  1. Halogenation

  Reaction of alkanes with halogens.

  Chlorination

  Bromination

  Iodination

  Fluorination

  
  

  2. Nitration

  Nitration

  Substitution of hydrogen atom of alkanes with nitro

  (-NO2) group.

  The reaction between alkanes and nitric acid takes place in vapour phase at 400-500oC yields nitro alkanes.

  
  

  3. Sulfonation

  Occurs at a high temperature in the presence of

  oleum (H2S2O7).

  Substitution of hydrogen atom of alkanes with sulfonic acid (-SO3H group).

  Reaction does not take place at room temperature. Lower alkanes up to pentane cannot be sulfonated. Forms alkane sulfonic acid.

  
  

  4.Oxidation

  Combustion

  Oxidation of alkanes in presence of excess of oxygen

  forms carbon dioxide and water.

  If it is oxidized with insufficient oxygen it forms carbon monoxide and carbon.
• Halogenation


  Reaction of alkanes with halogens.

  
  

  Chlorination

  Bromination

  Iodination

  Fluorination
• Chlorination


  Reacts with chlorine ion in presence of UV light, heat or catalyst yields a mixture of product depending upon the amount of chlorine used.
• Bromination


  Methane —-> Methyl bromide
• Iodination


  Hydroiodic acid ————-> Iodine