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C 10 J Organic Chemistry

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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C 10 J Organic Chemistry

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  1. C 10 J Organic Chemistry Dr. W. Gallimore winklet.gallimore@uwimona.edu.jm

  2. Organic ChemistryThe chemistry of compounds of Carbon • Almost all reactions in living matter involve Organic Chemistry • Major constituents of living matter • Protein, DNA, carbohydrates

  3. Other Organic substances of importance include: • Gasoline • Clothes (e.g. cotton, synthetic fibres) • Medicines e.g. aspirin

  4. Research in Organic Chemistry • Making Molecules (Synthesis) • Changing the Structures of Molecules (Transformations – Biotransformations) • Discovering New Molecules (Natural Products Chemistry)

  5. 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.

  6. Lecture Outline • Bonding in Organic Compounds • Ionic and covalent bonding • Structure and bonding in alkanes, alkenes and alkynes • Hybridization in carbon

  7. Bonding in Compounds Ionic and Covalent Bonding • Ionic bond - Formed by electron transfer • Covalent bond • Involves the sharing of electrons

  8. 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

  9. 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

  10. 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

  11. Bonding in Methane • Each orbital is as far away as possible from the other orbitals • Minimizes repulsion • Angle = 109.5o

  12. Bonding in Ethane • Contains two sp3 hybridized carbon atoms - Each carbon atom is tetrahedral

  13. Structure/Bonding in Ethene ( H2C=CH2, an alkene)

  14. Bonding in Ethene • The sp2 hybridized carbon is trigonal

  15. What type of overlap is present in each bond of CH3CH=CH2?

  16. Bonding in Ethyne (an alkyne) • The sp orbitals form two equivalent and linear sigma bonds

  17. Types of bonds in ethyne • Sigma and pi bonds are formed

  18. 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

  19. Effect of hybridization on bond lengths

  20. 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.

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