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What do aspirin, Tylenol, ibuprofen, almonds, vanilla, and mothballs have in common?

What do aspirin, Tylenol, ibuprofen, almonds, vanilla, and mothballs have in common?. aspirin. Tylenol. ibuprofen. almonds. vanilla. mothballs. Structural Properties: Planar All C atoms sp 2 hybridized All C-C bonds equal length. Aromatic ring.  electrons “smeared out”.

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What do aspirin, Tylenol, ibuprofen, almonds, vanilla, and mothballs have in common?

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  1. What do aspirin, Tylenol, ibuprofen, almonds, vanilla, and mothballs have in common? aspirin Tylenol ibuprofen almonds vanilla mothballs Structural Properties: Planar All C atoms sp2 hybridized All C-C bonds equal length Aromatic ring  electrons “smeared out” Resonance structures

  2. Structure of Benzene H H H H C C C C H H C C H H C C C C C C H H H H Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212

  3. Benzene 3-D • VSEPR Diagram Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212

  4. Aromatic Compounds Benzene, C6H6 Toluene Phenol Chemical Properties Special Stability (aromaticity) No addition reactions Hf Aniline -156 kJ/mol Aromatic substituents: + 118 kJ/mol -38 kJ/mol phenyl + 113 kJ/mol 75 kJ/mol - 26 kJ/mol benzyl 49 kJ/mol

  5. Benzene • C6H6 • Uses: styrene; phenol; synthetic detergents; cyclohexane for nylon; DDT; insecticides; fumigants; solvent; paint removers; rubber cement; antiknock gasoline

  6. Names of monosubstituted benzene rings Chlorobenzene Toluene Bromobenzene Styrene Phenol Nitrobenzene

  7. Phenol, (carbolic acid) • C6H5OH • Uses:solvent for refining lubricating oils; salicylic acid; phenoltpthalein; germicidal paints; pharmaceuticals; laboratory reagent; slimicide

  8. Benzene Nitrobenzene NO3- Mark Wirtz, Edward Ehrat, David L. Cedeno*

  9. Aromatic Hydrocarbons Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 430

  10. Cholesterol Compounds

  11. CH3 6 C C 1 ortho C C 2 5 C C 3 4 meta para position numbername 1, 2 ortho- (o-) 1,3 meta- (m-) 1,4 para- (p-)

  12. CH3 H C C CH3 H C C C C H H 6 1 2 5 3 4 ortho-dimethylbenzene or 1, 2 - dimethylbenzene

  13. CH3 H C C H H C C C C H CH3 6 1 2 5 3 4 meta-dimethylbenzene or 1, 3 - dimethylbenzene

  14. CH3 H C C H H C C C C CH3 H 6 1 2 5 3 4 para-dimethylbenzene or 1, 4 - dimethylbenzene

  15. MD H C C H H C C C C MD H 6 1 2 5 3 4 para-docs or paradox

  16. MD H C C MD H C C C C H H 6 1 2 5 3 4 ortho-docs or orthodox

  17. Fe2+ Fe2+ C C Fe2+ Fe2+ C C C C Fe2+ Fe2+ 6 1 2 5 3 4 ferrous wheel or ferris wheel

  18. NO2 H C C NO2 H C C C C H H o - dinitrobenzene or 1, 2 - dinitrobenzene

  19. NO2 CH3 C C H O2N C C C C H NO2 Toluene 2,4,6 - trinitrotoluene or TNT

  20. 2,4,6 -Trinitrotoluene • CH3C6H2(NO2) 3 • Uses:Explosives; intermediate in dyestuffs and photographic chemicals • Will detonate only if vigorously shocked or heated to 450oF

  21. CH3 Cl C C Cl H C C C C Cl H Toluene 2, 4, 6 - trichlorotoluene or 2, 4, 6 -trichloromethylbenzene

  22. O O C CH3 H C C COOH H C C C C H H 2-acetyloxybenzoic acid or (acetylsalicylic acid or aspirin)

  23. Cl Cl Cl H H H H C C C C H C Cl C C C C Cl CCl3 C C C C C H H H H dichlorodiphenyltrichloroethane or DDT

  24. CH CH2 H C C H H C C C C H H n phenyl ethene or styrene a.k.a. (styrofoam) poly

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