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C 10 J Organic Chemistry Dr. W. Gallimore winklet.gallimore@uwimona.edu.jm Organic Chemistry The chemistry of compounds of Carbon Almost all reactions in living matter involve Organic Chemistry Major constituents of living matter Protein, DNA, carbohydrates

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slide1

C 10 J

Organic Chemistry

Dr. W. Gallimore

winklet.gallimore@uwimona.edu.jm

organic chemistry the chemistry of compounds of carbon
Organic ChemistryThe chemistry of compounds of Carbon
  • Almost all reactions in living matter involve

Organic Chemistry

    • Major constituents of living matter
      • Protein, DNA, carbohydrates
slide3
Other Organic substances of importance include:
    • Gasoline
    • Clothes (e.g. cotton, synthetic fibres)
    • Medicines e.g. aspirin
research in organic chemistry
Research in Organic Chemistry
  • Making Molecules (Synthesis)
  • Changing the Structures of Molecules (Transformations – Biotransformations)
  • Discovering New Molecules (Natural Products Chemistry)
part 1 course outline
Part 1 Course Outline
  • Describe the structure and bonding in alkanes, alkenes and alkynes in terms of the hybridization states of carbon
  • Represent alkanes, alkenes and alkynes as dash formulae, condensed formulae, and bond-line drawings.
  • Name acyclic and cyclic alkanes, alkenes and alkynes using the IUPAC system of nomenclature.
  • Represent constitutional isomers of hydrocarbons.
  • Represent and name geometric isomers of alkenes using the cis/trans and E/Z systems.
  • Carry out conformational analysis of simple alkanes with the aid of sawhorse and Newman projections.
  • Devise syntheses of alkanes, alkenes and alkynes using the methods described in the syllabus.
lecture outline
Lecture Outline
  • Bonding in Organic Compounds
    • Ionic and covalent bonding
  • Structure and bonding in alkanes, alkenes and alkynes
  • Hybridization in carbon
bonding in compounds
Bonding in Compounds

Ionic and Covalent Bonding

  • Ionic bond - Formed by electron transfer
  • Covalent bond
    • Involves the sharing of electrons
bonding in organic compounds
Bonding in Organic Compounds
  • Carbon atoms are able to share electrons not only with different elements but also with other carbon atoms – it is possible for millions of organic compounds to exist
    • forms covalent bonds with other atoms (electrons shared)

Bonding pairs are represented by lines

structure and bonding
Structure and Bonding
  • Electrons are concentrated in certain regions of space around the nucleus and are called orbitals. Each orbital contains a maximum of two electrons
  • Orbitals differ in shape (s, p) and are grouped in shells – 1, 2, 3
  • P-orbitals are oriented along three axes
hybridization structure bonding in methane ch 4 an alk ane
HybridizationStructure/ Bonding in Methane (CH4, an alkane)
  • Carbon is bonded to four hydrogen atoms
  • One s-orbital is combined with three p orbitals
  • The resultant sp3 hybridized carbon is tetrahedral
bonding in methane
Bonding in Methane
  • Each orbital is as far away as possible from the other orbitals
    • Minimizes repulsion
    • Angle = 109.5o
bonding in ethane
Bonding in Ethane
  • Contains two

sp3 hybridized

carbon atoms

- Each carbon

atom is tetrahedral

bonding in ethene
Bonding in Ethene
  • The sp2 hybridized carbon is trigonal
bonding in ethyne an alk yne
Bonding in Ethyne (an alkyne)
  • The sp orbitals form two equivalent and linear sigma bonds
types of bonds in ethyne
Types of bonds in ethyne
  • Sigma and pi bonds are formed
effect of hybridization on bond lengths
Effect of hybridization on bond lengths
  • 2s electrons are generally found closer to the nucleus than 2p electrons
    • A hybrid orbital with a greater proportion of s character is of lower energy and is closer to the nucleus
  • sp orbitals contain more s-character
    • It forms shorter and stronger bonds
c 10 j course outline
C 10 J Course Outline

At the end of this course you should be able to:

  • Describe the structure and bonding in alkanes, alkenes and alkynes in terms of the hybridization states of carbon.
  • Represent alkanes, alkenes and alkynes as dash formulae, condensed formulae, and bond-line drawings.
  • Name acyclic and cyclic alkanes, alkenes and alkynes using the IUPAC system of nomenclature.
  • Represent constitutional isomers of hydrocarbons.
  • Represent and name geometric isomers of alkenes using the cis/trans and E/Z systems.
  • Carry out conformational analysis of simple alkanes with the aid of sawhorse and Newman projections.
  • Devise syntheses of alkanes, alkenes and alkynes using the methods described in the syllabus.
  • Explain the production and stability of alkyl radicals and carbocations.
  • Provide detailed mechanisms for the halogenation of alkanes, alkenes and alkynes.
  • Describe, with the aid of structural diagrams and curly arrows, the ionic mechanism and stereochemical outcome of the addition of electrophiles to alkenes and alkynes.
  • Predict the products of the reaction of any given alkene and alkyne with the following oxidizing agents: OsO4, KMnO4, O3.
  • Explain the basis of the acidity of terminal alkynes and show their usefulness in synthesis.
  • Define the terms: chiral, enantiomer, racemic, optical activity.
  • Make perspective drawings of the enantiomers and name them using the R-S system.