Wiley Chp. 17: Aromatic Compounds

Aromatic compounds include _____ and its derivatives.

Benzene

What is the usually the parent name of monosubstituted aromatic rings?

Benzene

Toluene is a benzene ring with what substituent?

Methyl

Phenol is a benzene ring with what substituent?

Hydroxyl

Anisole is a benzene ring with what substituent?

Methoxy

Aniline is a benzene ring with what substituent?

Primary amine

Benzoic acid is a benzene ring with what substituent?

Carboxylic acid

Benzaldehyde is a benzene ring with what substituent?

Aldehyde

Acetophenone is a benzene ring with what substituent?

Ketone

Styrene is a benzene ring with what substituent?

Ethene

If the parent chain is _____ than the benzene ring it's attached to, then it becomes the parent name.

Larger

When benzene rings are named as substituents, they are called _____.

Phenyl

Common name for dimethyl benzene derivatives

Xylene

Ortho, meta, and para are used to describe substitutents on ______ rings.

Disubstituted

Ortho means two substituents are in the _____ positions.

1,2

Meta means two substituents are in the _____ positions.

1,3

Para means two substituents are in the _____ positions.

1,4

Aromatic rings _____ undergo addition reactions.

Do not

Aromatic rings are ____ stable than cyclic dienes.

More

The first criterion for a compound to be aromatic is to be _____, fully conjugated, and planar.

Cyclic

The first criterion for a compound to be aromatic is to be cyclic, _____, and planar.

Fully conjugated

The first criterion for a compound to be aromatic is to be cyclic, fully conjugated, and _____.

Planar

For a compound to be aromatic, it must meet _____ rule.

Huckel's

Huckel's rule says that an aromatic compound must have _____ pi electrons.

4n+2

Huckel's rule says that an aromatic compound must have an _____ number of pairs of pi electrons.

Odd

Fully conjugated rings with _____ or more carbons adopt non planar conformations.

8

Fully conjugated rings with 8 or more carbons are nonplanar and _____.

Nonaromatic

Compounds that fail the first aromatic critrion (conjugated, cyclic, planar) are _____.

Nonaromatic

Compounds that fail the second aromatc criterion/Huckel's rule are _____.

Antiaromatic

Antiaromatic compounds are _____ in energy than aromatic compounds.

Higher

Antiaromatic compounds are _____ in energy than nonaromatic compounds.

Higher

Nonaromatic compounds are _____ in energy than aromatic compounds.

Higher

Nonaromatic compounds are _____ in energy than antiaromatic compounds.

Lower

Aromatic compounds are _____ in energy than nonaromatic compounds.

Lower

Aromatic compounds are _____ in energy than antiromatic compounds.

Lower

_____ can be used to predict the shapes and energies of molecular orbitals.

Frost circles

Rings that are fully conjugated are known as _____.

Annuelenes

Rings containing carbanions and carbocations can be _____.

Aromatic

The cyclopentadienyl anion is an example of a _____ anion.

Aromatic

The tropylium cation is an example of an _____ cation.

Aromatic

Aromatic rings can also contain atoms other than C and H, called _____.

Heteroatoms

Pyridine and pyrrole are examples of aromatic rings containing _____.

Heteroatoms

If a heteroatom's lone pair is necessary for aromaticity, it is included in the calculation for _____.

Huckel's rule

If a lone pair is necessary for aromaticity, it is ____ basic than other lone pairs.

Less

A carbon attached directly to a benzene ring is in the _____ position.

Benzylic

Benzylic positions are readily _____ by chromic acid/Jone's reagent.

Oxidized

_____ positions are readily oxidized by chromic acid/Jone's reagent.

Benzylic

A benzylic position must have at least one _____ to undergo oxidation.

Hydrogen

Benzylic positions can be oxidized by chromic acid/Jone's reagent or what reagent(s)?

Permanganate (KMnO4)

Benzylic position readily undergo free radical _____.

Bromination

When benzylic positions undergo free radical bromination, they form _____.

Benzylic bromides

Benzylic _____ readily undergo substitution and elimination reactions.

Bromides

Benzene can be forcely reduced to _____.

Cyclohexane

Reagents/conditions for the reduction of benzene to cyclohexane under forceful conditions

H2, Ni, 100 atm, 150C

In the presence of a benzene ring, _____ will be selectively hydrogenated.

Alkenes

Benzene can be reduced to _____ via Birch reduction.

1,4-cyclohexadiene

Benzene can be reduced to 1,4-cyclohexadiene via _____ reduction.

Birch

Reagents for Birch reduction

Na, MeOH, NH3

The mechanism of birch reduction is similar to the _____ reduction of an alkyne.

Dissolving metal

Birch reduction involves a _____ intermediate.

Radical anion

Substituents on the benzene ring affect the _____ of Birch reduction.

Regioselectivity

If there is an electron-donating substituent during Birch reduction, the product will have the EDG in a _____ position.

Vinylic

If there is an electron-withdrawing substituent during Birch reduction, the product will have the EDG in a _____ position.

Allyic

If there is an _____ during Birch reduction, the product will have the _____ in a vinylic position.

Electron-donating group

If there is an _____ during Birch reduction, the product will have the _____ in a allylic position.

Electron-withdrawing group

In H NMR, a Para-disubstituted benzene ring with identical substituents will produce a _____ with an integration of 4.

Singlet

In H NMR, a Para-disubstituted benzene ring with identical substituents will produce a singlet with an integration of _____.

4

In H NMR, a Para-disubstituted benzene ring with two different substituents will produce two_____ each with an integration of 2.

Doublets

In H NMR, a Para-disubstituted benzene ring with two different substituents will produce two doublets each with an integration of _____.

2

In 13C NMR, Benzene carbons typically appear at _____ ppm.

100-150

Graphite consists of layers of sheets of fused _____.

Aromatic rings

Buckyballs are C60 spheres made of interlocking _____.

Aromatic rings

Buckyballs are also known as

Buckminster fullerenes

Buckyballs can also be made into _____.

Nanotubes

_____ is the main soure of aromatic compounds used for energy.

Petroleum