Organic

• Organic Chemistry


  Study of compounds containing carbon, hydrogen, halogen, oxygen, nitrogen, sulfur, and phosphorus
• Organic Compounds


  • Hydrocarbons
  • Hydrocarbon Derivatives
• Hydrocarbons

  • Composed of carbon and hydrogen
  • Backbone of organic compounds
• Aliphatic Hydrocarbons


  • Saturated (alkanes)
  • Unsaturated (alkenes, alkynes)
• Aromatic Hydrocarbons


  • Benzene and its derivatives
  • Polycyclic benzenoids (Polyaromatic hydrocarbons)
• Polycyclic Benzenoids


  • Naphthalene
  • Anthracene
  • Phenanthrene
  • Chrysene
  • Pyrene
• Aryl groups


  Ar or Ph
• Hydrocarbon Derivatives


  • Halogen
  • Oxygen
  • Nitrogen
  • Sulfur
  • Phosphorus
• Alkyl halides


  R - X
• Aryl halides


  Ar - X
• Alcohol


  R - OH
• Phenol


  Ph - OH
• Ethers


  R1 - O - R
• Amines


  • Primary Amines (R1 - NH2)
  • Secondary Amines
  • Tertiary Amines
  • Quaternary Amines
• Thiols


  R - SH
• Thioethers


  R1 - S - R2
• Phosphorus Compounds


  • ATP
  • Organophosphates
  • Glucose - 6 - PO43-
• Carbon


  • Octet rule
  • Catenation
  • Hybrid orbitals
• Hybrid Orbitals


  • sp (linear, AB2)
  • sp2 (trigonal planar, AB3)
  • sp3 (tetrahedral, AB4)
• Isomerism


  Existence of two or more compounds having the same molecular formula but different structural formula or structures
• Types of Isomerism


  • Structural / Constitutional Isomerism (chain, positional, functional)
  • Stereoisomerism (geometric, conformational, configurational)
• Chain Isomerism


  • Butane
  • Pentane
• Positional Isomerism


  • Butene
  • Bromopropane
  • Dibromobenzene
• Functional Isomerism


  • C2H6O
  • C3H6O
  • C3H6O2
• Index of Hydrogen Deficiency (IHD)


  Formula to calculate degree of unsaturation
• IHD Calculations


  • C5H12 (IHD = 0, alkane)
  • C4H8 (IHD = 1, alkene or cycloalkene)
  • C3H6O (IHD = 1, double bond with oxygen or cyclic ether)
• Geometric Isomers


  • Exhibited by alkenes and cyclic alkanes
  • Cis/Trans Isomerism
  • E/Z Isomerism
• Cis/Trans Isomerism


  Used for double bonds with approximately similar substituents around it
• E/Z Isomerism


  Used for double bonds with different substituents around it
• Conformational Isomers


  • Rotation along single bonds
  • Acyclics (ethane, Newman projection)
  • Cyclics (ring flipping)
• Torsional Energy


  Energy needed to resist rotation, higher torsional energy results in decreased stability
• Steric Effect


  Crowding of bulky groups, results in decreased stability
• Configurational Isomers


  • Exhibit optical activity
  • Dextrorotatory (d/+)
  • Levorotatory (l/-)
  • Require asymmetric carbon or chiral center
• Fischer Projection


  Structures using two perpendicular lines with the intersection representing the chiral center
• Stereoisomer Types


  • Meso Compounds
  • Diastereomers
  • Enantiomers
• Dextrorotatory


  Rotates plane polarized light to the right
• Levorotatory


  Rotates plane polarized light to the left
• Optical rotations of a compound can only be determined using polarimeter
• Compound must have an asymmetric carbon or chiral center


  • sp3 hybridized carbon with four different groups attached
• Tartaric acid


  No. of Stereoisomers = 2n = 4, n = # of chiral centers