1. Chapter 17 Spring 2009

4. Larger aromatic hydrocarbons http://www.cem.msu.edu/~reusch/VirtualText/react3.htm

5. Pictures of Benzene Electrostatic potential surface Benzene molecular orbital In top picture notice a p orbital on each C atom. Bottom picture show the overlap of the p orbitals.

6. Orbital picture of benzene each carbon atom is sp 2 hybridized The resonance picture indicates why each C-C bond is the same length.

7. Electrostatic potential surface Electron-rich portion represents π electron cloud

9. Common names for aromatic compounds

12. Benzyl Benzyl substituent

13. Disubstituted benzenes 1,2-dimethylbenzene 1,3-dimethylbenzene 1,4-dimethylbenzene IUPAC names

14. Same substituent meta-dichlorobenzene or, 1,3-dichlorobenzene

15. Different substituents These two have common root names

16. Different substituents These two have common root names toluene analine

17. Different substituents These two have common root names meta-chlorotoluene ortho-chloroanaline

18. Different substituents These don’t have a common root name so alphabetize the name of the substituents.

19. Different substituents These don’t have a common root name so alphabetize the name of the substituents. ortho-bromochlorobenzene para-bromonitrobenzene

20. Heat of hydrogenation data The low heat of hydrogenation means that benzene is especially stable – this extra stability is characteristic of all aromatic compounds.

23. This molecule is non-aromatic It is cyclic, completely conjugated, non-planar, and contains 8 π electrons

24. This molecule is anti-aromatic Cyclic, planar, completely conjugated, and contain four π electrons.

26. Aromatic compounds can have more than one ring.

27. Aromatic rings can contain a single ring with lots of alternating single-double bonds

28. atomic orbitals molecular orbitals

29. Anti-aromatic

31. Label the cation, radical, and anion as aromatic, antiaromatic, or nonaromatic.

32. Heterocyclic aromatic compounds

34. Nucleic acids

35. Thymine

37. Aromatic Question Thiamin, or vitamin B1, contains a five-membered, nitrogen-sulfur heterocycle called a thiazalium ring. Explain why the thiazolium ring is aromatic.

38. Cycloheptatrienyl cation, radical and anion problem