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| Benzene+Br2, FeCl3/CCl4=? |
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Bromobenzene (substitution reaction, byproduct HBr) |
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| Benzene+Br2, ?/CCl4=Bromobenzene |
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| Hydrogenation of Alkene=? (energy) |
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| Hydrogenation of 1 double bond in Benzene= ?(energy) |
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Aromatic requires that... (4 answers) |
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1. Structure must by Cyclic with Conjugate Pi bonds 2. Each atom in the ring must have 1 unhybridized Pi orbital 3. The Pi orbitals must overlap continuously around the ring (planar!!!) 4. Compound is more stable than it's open chain counterpart |
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| Antiaromatic= ? electrons |
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| non-aromatic= ? electrons |
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Anti-aromatic= (key property) |
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Aromatic in nature but their energy is greater than their open chain counterpart. |
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Compounds do not have a continuous ring of P orbitals, and/or are non-planar. |
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| 4N rings greater than n=1 are ??? (and why) |
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| are non-aromatic because they are flexible |
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| Aromatic except for the non-planar isomers |
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| Cyclopentadienyl ions are ??? |
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cation=anti-aromatic; anion=aromatic |
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| Cyclopentadiene is ____ (pH wise) |
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| Tropylium ion, Aromatic 6 pi electrons |
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| Dianion of [8]Annulene is ??? |
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| Aromatic, 10 pi electrons |
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| Draw/visualize the reaction that forms the [8]annulene dianion |
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| Draw/visualize the pyridinium ion |
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| Pyridine's 2 major properties |
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| Aromatic, weak base (pKb 8.8) |
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| Pyrrole (important properties) |
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| Arromatic weak base (pKb=13.6), forms a non-arromatic strong acid when protonated (pKa=.4) |
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Nitrogens in rings, Basic or not? |
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N with 3 bonds in a ring is basic, if NH then not |
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Draw/visualize Pyrimidine |
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Draw/visualize Naphthalene |
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| Draw/visualize Anthracene |
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| Draw/visualize Phenanthrene |
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As the number of arromatic rings increases, so the ressonance energy per ring decreases, increasing the reactivity (will react with Br2) |
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| Draw/visualize the 2 products of bromination of Anthracene |
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| Draw/visualize Pyrene and Benzo [a] Pyrene |
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| What functional group is attached to Phenol? |
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| What functional group is attached to Toluene? |
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| What functional group is attached to Aniline? |
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What functional group is attached to Anisole? |
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| What functional group is attached to Styrene? |
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| What functional group is attached to Acetophenone? |
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What functional group is attached to Benzaldehyde? |
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| What functional group is attached to Benzoic Acid? |
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| 3 methyl groups spaced one apart on a benzene |
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Describe/draw o-toluic acid |
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| benzoic acid with a methyl group in ortho position |
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| A methyl group across para to an alcohol group on a benzene |
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| Phenyl means a functional group without a carbon is attached (I.E. Phenyl bromide), a benzyl has an extra carbon attached to the ring (I.E. Benzyl Bromide (CH2 group inbetween benzene and Br)) |
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| Describe the Physical properties of Aromatic rings (MP, BP, Density, and Solubility) |
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| Melting point is increased because crystals are more easily formed and are compact. Boiling point depends on the dipole moments (so for disubstituted benzenes, Ortho>meta>para). More dense than aromatics, but less dense than water. Generally, they are insoluble in water. |
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