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Organic Chemistry Aromatics

H. H. C. C. H. C. H. C. C. C. H. H. Organic Chemistry Aromatics ( Arenes ). OUTCOME QUESTION(S):. C11-5-14 NAMING AND DRAWING Name and draw structural models of simple and branched alkanes.

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Organic Chemistry Aromatics

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  1. H H C C H C H C C C H H Organic Chemistry Aromatics (Arenes)

  2. OUTCOME QUESTION(S): C11-5-14 NAMING AND DRAWING • Name and draw structural models of simple and branched alkanes. Include: complete structural formula, molecular formula, general formula, isomers • Name and draw structural models of simple and branched alkenes and alkynes. • Compare and contrast the structure and uses of aromatic and aliphatic hydrocarbons. Vocabulary & Concepts arene resonance

  3. Aromatic Compounds Cyclical hydrocarbons with delocalized electron sharing acrosssingle/ double bonds. • Unsaturated • Originally named because of their smell/odour This way of representing organic compounds is called a “line structure” Benzene is the most common aromatic compound.

  4. Electrons participating in the double bonds are actually sharedby all carbons – delocalized. H H H H H C C C C C C H The shifting electrons create two correct representations Resonance: When one or more correct structures can be drawn for a compound.

  5. H C C C H H H C C H C The moving electrons create 1½ bonds everywhere instead of double bonds H Benzene(C6H6): • naturally occurring in crude oil • a known carcinogen • colorless, highly flammable liquid • importantindustrial solvent and precursor

  6. Benzene and all modified compounds of benzene are called arenes modified benzene compounds

  7. Common aromatic smells: These two are called optical isomers Citrus fruits Limonene C10H16 Almonds Benzaldehyde C7H6O Spearmint / Caraway Carvone C10H14O

  8. Common aromatic smells: Licorice Glycyrrhizin C42H62O16

  9. Common aromatic compounds: Adrenaline 4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol C9H13NO3 Caffeine 1,3,7-Trimethylpurine-2,6-dione C8H10N4O2 Now you know why these have common names Testosterone 17β-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17- tetradecahydrocyclopenta[a]phenanthren-3-oneC19H28O2

  10. CH2 - CH2 - CH3 Naming Arenes • Benzene is ONLY theparentchainwhen the ring is off an end(1st)carbon of alinear alkane. • As a branchthe benzene ring is called a phenylgroup. • Branches named as per the rules for alphatics 1 CH3 - CH2 - CH - CH3 4 2 3 1 butylbenzene 2-phenylbutane

  11. CH2 - CH2 - CH2 - CH3 CH3 CH2 - CH = CH2 CH3 - CH2 - CH - CH3 3-phenylpropene 2-phenylbutane methylbenzene or "toluene" butylbenzene This is such a commonly used compound that it has a “slang” name - toluene

  12. Name this compound: CH3 - CH2 - CH2 - CH - CH3 4 2 3 1 3-methyl-1-phenylbutane

  13. Double substituted benzene compounds use special prefixes to denote the location: 1,2 – ortho 1,3 – meta 1,4 – para CH3 CH3 CH3 CH3 CH3 o-dimethylbenzene m-dimethylbenzene CH3 p-dimethylbenzene This is another common compound called xylene

  14. Name these compounds: CH2CH3 Br CH2CH3 p-bromomethylbenzene p-bromotoluene o-diethylbenzene CH2CH3 CH3 CH3 m-ethylmethylbenzene m-ethyltoluene

  15. CAN YOU / HAVE YOU? C11-5-14 NAMING AND DRAWING • Name and draw structural models of simple and branched alkanes. Include: complete structural formula, molecular formula, general formula, isomers • Name and draw structural models of simple and branched alkenes and alkynes. • Compare and contrast the structure and uses of aromatic and aliphatic hydrocarbons. Vocabulary & Concepts arene resonance

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