Alkyne combustion reaction: 2 C 2 H 2 + 5 O 2 4 CO 2 + 2 H 2 O

1. Alkyne combustion reaction: 2 C2H2 + 5 O2 4 CO2 + 2 H2O The combustion reactions are all exothermic.

2. Substitution Reactions

3. Substitution Reactions Reaction with chlorine:

4. Substitution Reactions Reaction with chlorine: CH4 + Cl2 CH3Cl + HCl chloromethane

5. Substitution Reactions Reaction with chlorine: CH4 + Cl2 CH3Cl + HCl chloromethane CH3Cl + Cl2 CH2Cl2 + HCl dichloromethane

6. CH2Cl2 + Cl2 CHCl3 + HCl trichloromethane

7. CH2Cl2 + Cl2 CHCl3 + HCl trichloromethane CHCl3 + Cl2 CCl4 + HCl tetrachloromethane

8. For organic reactions it is common practice to indicate the reaction conditions. That is, for the reaction with chlorine:

9. For organic reactions it is common practice to indicate the reaction conditions. That is, for the reaction with chlorine: CH4 + Cl2 CH3Cl + HCl

10. For organic reactions it is common practice to indicate the reaction conditions. That is, for the reaction with chlorine: heat (300 oC) CH4 + Cl2 CH3Cl + HCl

11. For organic reactions it is common practice to indicate the reaction conditions. That is, for the reaction with chlorine: heat (300 oC) CH4 + Cl2 CH3Cl + HCl or uvirrad. room temp.

12. Addition Reactions

13. dark Cl2 + 25 oC 1,2- dichloroethane

14. CH3CCH+ 2 Cl2 CH3CCl2CHCl2 propyne 1,1,2,2-tetrachloropropane CH3CHCH2 + HBr CH3CHBrCH3 propene 2-bromopropane It turns out that when a hydrogen halide add to an alkene, the more electronegative halogen atom always tends to end up on the carbon atom of the double bond that has fewer hydrogen atoms (Markovnikov’s rule).

15. H2SO4 CH2CH2 + H2O CH3CH2OH

16. Hydrogenation The following reaction is an example of hydrogenation of an alkene, addition of H2 across a double bond.

17. + H2 ethene ethane

18. Functional Group Concept

19. Functional Group Concept A great many organic molecules have complex structures.

20. Functional Group Concept A great many organic molecules have complex structures. Trying to predict the properties and possible reactions of a complex structure can be very difficult.

21. Functional Group Concept A great many organic molecules have complex structures. Trying to predict the properties and possible reactions of a complex structure can be very difficult. Chemists have found it very useful to characterize certain well defined fragments of an organic molecule.

22. Functional Group Concept A great many organic molecules have complex structures. Trying to predict the properties and possible reactions of a complex structure can be very difficult. Chemists have found it very useful to characterize certain well defined fragments of an organic molecule. These fragments (in isolation) have well defined reactive capabilities.

23. When these units are found in complex structures, predictions can be made as to the likely properties and reactions of the complex structure.

24. When these units are found in complex structures, predictions can be made as to the likely properties and reactions of the complex structure. These fragment units are called functional groups.

25. Some common functional groups FunctionalNameExampleIUPACNameCommonName group formula

26. Some common functional groups FunctionalNameExampleIUPACNameCommonName group formula R O H alcohol CH3OH methanol methyl alcohol

27. Some common functional groups FunctionalNameExampleIUPACNameCommonName group formula R O H alcohol CH3OH methanol methyl alcohol R C carboxylicCH3CO2H ethanoicacid acetic acid acid

28. Some common functional groups FunctionalNameExampleIUPACNameCommonName group formula R O H alcohol CH3OH methanol methyl alcohol R C carboxylicCH3CO2H ethanoicacid acetic acid acid R C ketone CH3COCH3 propanone acetone

29. Some common functional groups FunctionalNameExampleIUPACNameCommonName group formula R O H alcohol CH3OH methanol methyl alcohol R C carboxylicCH3CO2H ethanoicacid acetic acid acid R C ketone CH3COCH3 propanone acetone R and are alkyl (or more complicated groups). cannot be H. R cannot be H for the alcohol (that would be water!), nor for the ketone (that would give an aldehyde).

30. FunctionalNameExampleIUPACNameCommonName group formula R C aldehyde HCHO methanal formaldehyde

31. FunctionalNameExampleIUPACNameCommonName group formula R C aldehyde HCHO methanal formaldehyde R C ester CH3CO2CH2CH3 ethyl ethanoate ethyl acetate

32. FunctionalNameExampleIUPACNameCommonName group formula R C aldehyde HCHO methanal formaldehyde R C ester CH3CO2CH2CH3 ethyl ethanoate ethyl acetate R NH2amine CH3NH2 aminomethane methylamine

33. FunctionalNameExampleIUPACNameCommonName group formula R C aldehyde HCHO methanal formaldehyde R C ester CH3CO2CH2CH3 ethyl ethanoate ethyl acetate R NH2amine CH3NH2 aminomethane methylamine R and are alkyl (or more complicated groups). cannot be H (that would give an acid). R cannot be H for the amine (that would be ammonia!).

34. FunctionalNameExampleIUPACNameCommonName group formula R O ether CH3OCH3methoxymethanedimethyl ether

35. FunctionalNameExampleIUPACNameCommonName group formula R O ether CH3OCH3methoxymethanedimethyl ether R C amide CH3CONH2ethanamide

36. FunctionalNameExampleIUPACNameCommonName group formula R O ether CH3OCH3methoxymethanedimethyl ether R C amide CH3CONH2ethanamide R and are alkyl (or more complicated groups). cannot be H (that would give an alcohol). R cannot be H for the ether (that would also give an alcohol).

37. Summary of name endings

38. Summary of name endings Functional group Parent alkane name ending

39. Summary of name endings Functional group Parent alkane name ending alcohol change e to ol

40. Summary of name endings Functional group Parent alkane name ending alcohol change e to ol carboxylic acid change e to oic acid

41. Summary of name endings Functional group Parent alkane name ending alcohol change e to ol carboxylic acid change e to oic acid ketone change e to one

42. Summary of name endings Functional group Parent alkane name ending alcohol change e to ol carboxylic acid change e to oic acid ketone change e to one aldehyde change e to al

43. Summary of name endings Functional group Parent alkane name ending alcohol change e to ol carboxylic acid change e to oic acid ketone change e to one aldehyde change e to al amide change e to amide

44. Summary of name endings Functional group Parent alkane name ending alcohol change e to ol carboxylic acid change e to oic acid ketone change e to one aldehyde change e to al amide change e to amide amine insert amino in front of alkane name

45. Summary of name endings Functional group Parent alkane name ending alcohol change e to ol carboxylic acid change e to oic acid ketone change e to one aldehyde change e to al amide change e to amide amine insert amino in front of alkane name ester insert alkyl name then change e to oate

46. Summary of name endings Functional group Parent alkane name ending alcohol change e to ol carboxylic acid change e to oic acid ketone change e to one aldehyde change e to al amide change e to amide amine insert amino in front of alkane name ester insert alkyl name then change e to oate ether change ane to oxy then add in second alkane name.

47. Key comment on a functional group The carboxylic acid is a combination of two functions groups: O O C C plus O H O H carboxylic acid ketone alcohol

48. Key comment on a functional group The carboxylic acid is a combination of two functions groups: O O C C plus O H O H carboxylic acid ketone alcohol HOWEVER, a compound such as

49. CH3CH2CCH2CH2 OH O would NOT function like a carboxylic acid, but as an alcohol in some reactions and a ketone in some other reactions.

50. Comparison of some properties