Duration: 18 hours of lectures and 12 hours of seminars

Lecturer:

Aims: To introduce students to organic chemistry emphasising the importance of stereochemistry and mechanism in the reactions of simple mono-functional aliphatic compounds and, in seminar sessions, develop an understanding of the chemistry of alkanes, cycloalkanes, alkenes, alkynes, haloalkanes and alcohols.

Objectives:

1. Appreciate the scope of organic chemistry.

2. Appreciate the uniqueness of carbon in its ability to bond to other carbon atoms.

3. Using the VSEPR model, predict the tetrahedral shape of tetravalent carbon.

4. Use IUPAC nomenclature for alkanes and define constitutional isomerism and homologous series.

5. Understand the use of 1H and 13C nuclear magnetic resonance spectroscopy to distinguish constitutional isomers.

6. Appreciate the reactivity of alkanes towards free radicals, understand the steps involved in chlorination of simple alkanes.

7. Understand the conformations of ethane and of butane and relate these to conformations of cyclohexane and substituted cycloalkanes and be aware of the extension of these ideas to polycyclic molecules.

8. Appreciate the strain in, and therefore the reactivity of, cyclopropane.

9. Understand the structure and isomerism of alkenes.

10. Understand the stereoisomerism in but-2-ene and designate the stereoisomers of alkenes as E and Z using the Cahn-Ingold-Prelog rules.

11. Understand the reactivity of alkenes, especially the addition of electrophiles, and use of the "curved arrow" notation to show the movement of electrons in reactions.

12. Appreciate the relative stabilities of carbocations and so understand the orientation of addition of electrophiles such as HCl to propene and to other unsymmetrical alkenes.

13. Understand that, under different reaction conditions, addition of HBr to propene can result in the formation of either 2-bromopropane or
1-bromopropane.

14. Understand that addition of bromine to alkenes is trans whereas catalytic hydrogenation is a cis addition.

15. Understand polymerisation of alkenes.

16 Appreciate that the hydrogen on C-1 of alk-1-ynes is acidic, hence appreciate their application in synthesis, and know the result of addition of electrophiles to, and of catalytic hydrogenation of, alkynes.

17. Understand the concept of a functional group, list common groups,

, –C ? C–, Cl–, Br–, I–, HO–, –O–, HS, –S–, H2N–,

R2N–,  etc and appreciate the role of spectroscopy (NMR, IR, mass spectrometry) in structure determination.

18. Understand the mechanisms of nucleophilic substitution of haloalkanes, SN1, SN2.

19. Define the terms, chirality, stereogenic centre, and enantiomer and designate simple tetrahedral stereogenic centres as R or S.

20. Understand the consequences of having multiple stereogenic centres in a molecule and understand and define the term diastereomer.

21. Understand that elimination and substitution reactions can compete when nucleophiles react with haloalkanes and understand the stereochemical consequences of substitution and elimination reactions.

22. Appreciate that organometallic reagents are formed when metals such as Li or Mg react with haloalkanes.

23. Understand that amines are basic and react as nucleophiles.

24. Appreciate the consequences of hydrogen bonding on the physical properties of alcohols and know their acidity in relation to H2O and
RC ? CH.

25. Appreciate the reactions of alcohols – substitution, elimination, esterification, and oxidation and know how formation of derivatives can modify their reactivity in substitution and elimination reactions.

26. Appreciate the relative unreactivity of diethyl ether and the reactivity of ethylene oxide.

27. Understand the chemistry of thiols – acidity and oxidation.

28. Appreciate that thioethers can be oxidised to sulfoxides and sulfones.

29. Understand the nature of the carbonyl group and the reason for its reactivity.

30. Understand the relative reactivities of carbonyl compounds.

31. Know the physical and spectroscopic properties of aldehydes and ketones and be able to name simple examples.

32. Describe the reactions of aldehydes and ketones with oxygen, sulfur, nitrogen and carbon nucleophiles, giving full chemical mechanisms for these reactions and understanding the importance of the reversibility of the reactions with alcohols and nitrogen nucleophiles.

33. Describe the reduction and oxidation of aldehydes and ketones and the reagents employed for these transformations.

34. Understand the properties of carboxylic acids, be able to name simple examples, understand methods for their synthesis and know their chemical reactions.

35. Understand the role of resonance in acid strength of carboxylic acids

36. Understand the structures of esters and describe methods for the synthesis of esters, involving the chemical mechanisms.

37. Understand the hydrolysis of esters under acidic and basic conditions and know the chemical mechanisms.

38. Understand the reactions of nucleophiles with derivatives of carboxylic acids, particularly with reference to acyl halides, amides, anhydrides and esters.

39. Appreciate how structural features, including resonance, inductive effects and bond lengths, can affect the acid / base strength of organic molecules

40. Understand how trends in acidity / basicity relate to those in nucleophilicity / electrophilicity.