Organic chemistry chapter 16

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
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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
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