Organic Chemistry Chapter 16 Test Questions – Flashcards
Unlock all answers in this set
Unlock answers| Alkene+______=diol |
| KMnO4 |
Alkene+KMnO4=? |
| Diol |
| Benzene+KMnO4=? |
| No reaction |
Alkene+Br2/CCl4=? |
| Dibromide |
| Benzene+Br2/CCl4=? |
| No Reaction |
| Alkene+Br2/?=Dibromide |
| CCl4 |
| Benzene+Br2, FeCl3/CCl4=? |
Bromobenzene (substitution reaction, byproduct HBr) |
| Benzene+Br2, ?/CCl4=Bromobenzene |
| FeBr3 |
| Hydrogenation of Alkene=? (energy) |
Exothermic |
| Hydrogenation of 1 double bond in Benzene= ?(energy) |
| Endothermic |
Aromatic requires that... (4 answers) |
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 |
| Antiaromatic= ? electrons |
| 4n (n=any whole number) |
| non-aromatic= ? electrons |
odd number of- |
| Aromatic= ? electrons |
4N+2 |
Anti-aromatic= (key property) |
Aromatic in nature but their energy is greater than their open chain counterpart. |
| Non-aromatic Properties |
Compounds do not have a continuous ring of P orbitals, and/or are non-planar. |
| 4N rings greater than n=1 are ??? (and why) |
| are non-aromatic because they are flexible |
[10]Annulene is ??? |
| Aromatic except for the non-planar isomers |
| Cyclopentadienyl ions are ??? |
cation=anti-aromatic; anion=aromatic |
| Cyclopentadiene is ____ (pH wise) |
| Acidic (pKa= 16) |
| Tropylium Ion is ? |
| Aromatic |
| [image] |
| Tropylium ion, Aromatic 6 pi electrons |
| Dianion of [8]Annulene is ??? |
| Aromatic,;10 pi electrons |
| Draw/visualize the reaction that forms the [8]annulene dianion |
| [image]" align="center"> |
| Draw/visualize Pyridine |
| [image] |
| Draw/visualize the pyridinium ion |
| [image] |
| Pyridine's 2 major properties |
| Aromatic, weak base (pKb 8.8) |
| Draw/visualize Pyrrole |
| [image] |
| Pyrrole (important properties) |
| Arromatic weak base (pKb=13.6), forms a non-arromatic strong acid when protonated (pKa=.4) |
Nitrogens in rings, Basic or not? |
N with 3 bonds in a ring is basic, if NH then not |
Draw/visualize Pyrimidine |
| [image] |
| Draw/visualize Imidazole |
| [image] |
| Draw/visualize Purine |
| [image] |
| Draw/Visualize Furan |
| [image] |
| Draw/visualize Thiophene |
| [image] |
Draw/visualize Naphthalene |
| [image] |
| Draw/visualize Anthracene |
| [image] |
| Draw/visualize Phenanthrene |
| [image] |
Multi-ringed reactivity? |
As the number of arromatic rings increases, so the ressonance energy per ring decreases, increasing the reactivity (will react with Br2) |
| Draw/visualize the 2 products of bromination of Anthracene |
| [image] |
| Draw/visualize Pyrene and Benzo [a] Pyrene |
| [image]" align="center"> |
| What functional group is attached to Phenol? |
| OH |
| What functional group is attached to Toluene? |
| CH3 |
| What functional group is attached to Aniline? |
| NH2 |
What functional group is attached to Anisole? |
OCH3 |
| What functional group is attached to;Styrene? |
HC=CH2 |
| What functional group is attached to Acetophenone? |
| O=C-CH3 |
What functional group is attached to Benzaldehyde? |
| O=C-H |
| What functional group is attached to Benzoic Acid? |
O=C-O-H |
IUPAC of m-Xylene? |
| Meta-dimethylbenzene |
| Describe/draw Mesitylene |
| 3 methyl groups spaced one apart on a benzene |
Describe/draw o-toluic acid |
| benzoic acid with a methyl group in ortho position |
| describe/draw p-cresol |
| A methyl group across para to an alcohol group on a benzene |
| Phenyl vs. Benzyl |
| 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)) |
| Describe the Physical properties of Aromatic rings (MP, BP, Density, and Solubility) |
| 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. |
| Draw/Visualize Idole |
| [image] |
