Organic Chemistry Chapter 16 Test Questions

question

Alkene+______=diol
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KMnO4
question

Alkene+KMnO4=?

answer

Diol
question

Benzene+KMnO4=?
answer

No reaction
question

Alkene+Br2/CCl4=?

answer

Dibromide
question

Benzene+Br2/CCl4=?
answer

No Reaction
question

Alkene+Br2/?=Dibromide
answer

CCl4
question

Benzene+Br2, FeCl3/CCl4=?
answer

Bromobenzene (substitution reaction, byproduct HBr)

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Benzene+Br2, ?/CCl4=Bromobenzene
answer

FeBr3
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Hydrogenation of Alkene=? (energy)
answer

Exothermic

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Hydrogenation of 1 double bond in Benzene= ?(energy)
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Endothermic
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Aromatic requires that… (4 answers)

answer

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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4n (n=any whole number)
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non-aromatic= ? electrons
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odd number of-

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Aromatic= ? electrons
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4N+2

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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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Non-aromatic Properties
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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
question

[10]Annulene is ???

answer

Aromatic except for the non-planar isomers
question

Cyclopentadienyl ions are ???
answer

cation=anti-aromatic; anion=aromatic

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Cyclopentadiene is ____ (pH wise)
answer

Acidic (pKa= 16)
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Tropylium Ion is ?
answer

Aromatic
question

[image]
answer

Tropylium ion, Aromatic 6 pi electrons
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Dianion of [8]Annulene is ???
answer

Aromatic,;10 pi electrons
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Draw/visualize the reaction that forms the [8]annulene dianion
answer

[image]” align=”center”>
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Draw/visualize Pyridine
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[image]
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Draw/visualize the pyridinium ion
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[image]
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Pyridine’s 2 major properties
answer

Aromatic, weak base (pKb 8.8)
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Draw/visualize Pyrrole
answer

[image]
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Pyrrole (important properties)
answer

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?

answer

N with 3 bonds in a ring is basic, if NH then not

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Draw/visualize Pyrimidine

answer

[image]
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Draw/visualize Imidazole
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[image]
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Draw/visualize Purine
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[image]
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Draw/Visualize Furan
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[image]
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Draw/visualize Thiophene
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[image]
question

Draw/visualize Naphthalene

answer

[image]
question

Draw/visualize Anthracene
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[image]
question

Draw/visualize Phenanthrene
answer

[image]
question

Multi-ringed reactivity?

answer

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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[image]
question

Draw/visualize Pyrene and Benzo [a] Pyrene
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[image]” align=”center”>
question

What functional group is attached to Phenol?
answer

OH
question

What functional group is attached to Toluene?
answer

CH3
question

What functional group is attached to Aniline?
answer

NH2
question

What functional group is attached to Anisole?

answer

OCH3

question

What functional group is attached to;Styrene?
answer

HC=CH2

question

What functional group is attached to Acetophenone?
answer

O=C-CH3
question

What functional group is attached to Benzaldehyde?

answer

O=C-H
question

What functional group is attached to Benzoic Acid?
answer

O=C-O-H

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IUPAC of m-Xylene?

answer

Meta-dimethylbenzene
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Describe/draw Mesitylene
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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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describe/draw p-cresol
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A methyl group across para to an alcohol group on a benzene
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Phenyl vs. Benzyl
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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))
question

Describe the Physical properties of Aromatic rings (MP, BP, Density, and Solubility)
answer

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.
question

Draw/Visualize Idole
answer

[image]

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