Organic Chemistry,

16.1 Give the shape of benzene.

a.
b.
c.
d.

Tetrahedral
Bent
Trigonal pyramidal
Planar

16.1 Answer
a.
b.
c.
d.

Tetrahedral
Bent
Trigonal pyramidal
Planar

All six carbons and six hydrogens are in

the same plane.

16.2 Give the hybridization of

each carbon in benzene.
a.
b.
c.
d.

sp
sp2
sp3
sp4

16.2 Answer
a.
b.
c.
d.

sp
sp2
sp3
sp4

Each carbon in benzene is sp2 hybridized.

16.3 Give the bond angle of the

atoms in benzene.
a. 45
b. 60
c. 90

d. 109.5
e. 120

16.3 Answer
a. 45
b. 60
c. 90

d. 109.5
e. 120

The carbons are 120o apart in benzene.

16.4 Classify
a.
b.
c.
d.

Aromatic
Antiaromatic
Nonaromatic
Acyclic

16.4 Answer
a.
b.
c.
d.

Aromatic
Antiaromatic
Nonaromatic
Acyclic

The compound gives a whole number for

N in Hckels rule (4N + 2 = 6, N = 1).

16.5 Classify
a.
b.
c.
d.

Aromatic
Antiaromatic
Nonaromatic
Acyclic

16.5 Answer
a.
b.
c.
d.

Aromatic
Antiaromatic
Nonaromatic
Acyclic

The compound is cyclic and has

continuous delocalized electrons, but
does not give a whole number for
Hckels rule (4N + 2 = 8, N = 3/2).

16.6 Classify
a.
b.
c.
d.

Aromatic
Antiaromatic
Nonaromatic
Acyclic

16.6 Answer
a.
b.
c.
d.

Aromatic
Antiaromatic
Nonaromatic
Acyclic

This cyclic compound does not have a

continuous, overlapping ring of p
orbitals and is nonaromatic.

16.7 Name
a.
b.
c.
d.

Pyridine
Pyrrole
Pyrimidine
Imidazole

N
H

16.7 Answer
a.
b.
c.
d.

Pyridine
Pyrrole
Pyrimidine
Imidazole

Pyrrole is a heterocyclic aromatic

compound.

16.8 Name
a.
b.
c.
d.
e.

Imidazole
Pyrimidine
Pyridine
Purine
Furan

16.8 Answer
a.
b.
c.
d.
e.

Imidazole
Pyrimidine
Pyridine
Purine
Furan

Pyrimidine is an aromatic compound

with nitrogens in the 1 and 3 positions.

16.9 Name

.
O

a.
b.
c.
d.
e.

Pyrimidine
Imidazole
Purine
Furan
Thiophene

16.9 Answer
a.
b.
c.
d.
e.

Pyrimidine
Imidazole
Purine
Furan
Thiophene

Furan is a heterocyclic aromatic compound.

16.10 Name

.
S

a.
b.
c.
d.
e.

Pyrimidine
Imidazole
Purine
Furan
Thiophene

16.10 Answer
a.
b.
c.
d.
e.

Pyrimidine
Imidazole
Purine
Furan
Thiophene

Thiophene is a heterocyclic aromatic

compound.

16.11 Name
a.
b.
c.
d.

Anthracene
Naphthalene
Phenanthrene
Benzene

16.11 Answer
a.
b.
c.
d.

Anthracene
Naphthalene
Phenanthrene
Benzene

Naphthalene contains two benzene

rings fused together.

16.12 Name
a.
b.
c.
d.

Anthracene
Naphthalene
Phenanthrene
Benzene

16.12 Answer
a.
b.
c.
d.

Anthracene
Naphthalene
Phenanthrene
Benzene

Anthracene contains three benzene rings

fused together.

16.13 Identify how carbon,

diamond, and graphite are
related.
a.
b.
c.
d.

They are enantiomers of carbon.

They are diastereomers of carbon.
They are allotropes of carbon.
They have the same properties.

16.13 Answer
a.
b.
c.
d.

They are enantiomers of carbon.

They are diastereomers of carbon.
They are allotropes of carbon.
They have the same properties.

16.14 Name
a.
b.
c.
d.

Purine
Indole
Benzimidazole
Quinoline

N
H

16.14 Answer
a.
b.
c.
d.

Purine
Indole
Benzimidazole
Quinoline

Indole contains a benzene ring with a

five-membered ring fused to it.

16.15 Name
a.
b.
c.
d.

Purine
Indole
Benzimidazole
Quinoline

N
H

16.15 Answer
a.
b.
c.
d.

Purine
Indole
Benzimidazole
Quinoline

Benzimidazole contains a benzene ring

with an imidazole fused to it.

Cl

16.16 Name

NH2

.
Br

a. 4-Bromo-3chloroaniline
b. 4-Bromo-3chlorophenol
c. 4-Bromo-3chloroanisole

d. 1-Bromo-2chloro-4-aniline
e. 1-Bromo-2chloro-4-phenol

16.16 Answer
a. 4-Bromo-3chloroaniline
b. 4-Bromo-3chlorophenol
c. 4-Bromo-3chloroanisole

d. 1-Bromo-2chloro-4-aniline
e. 1-Bromo-2chloro-4-phenol

Aniline is the parent compound. The NH2 is

at position one.

CH3

16.17 Name

.
OH

a.
b.
c.
d.
e.

p-Methylphenol
m-Methylphenol
o-Methylphenol
4-Methylphenol
3-Methylphenol

16.17 Answer
a.
b.
c.
d.
e.

p-Methylphenol
m-Methylphenol
o-Methylphenol
4-Methylphenol
3-Methylphenol

The groups are on adjacent carbons,

which is ortho.

16.18 Name

O
C

NO2

a. 3-Amino-5benzaldehyde
b. 5-Amino-3benzaldehyde
c. 3-Aminobenzaldehyde

d. 5-Nitro-3benzaldehyde
e. 3-Nitrobenzaldehyde

16.18 Answer
a. 3-Amino-5benzaldehyde
b. 5-Amino-3benzaldehyde
c. 3-Aminobenzaldehyde

d. 5-Nitro-3benzaldehyde
e. 3-Nitrobenzaldehyde

Benzaldehyde is the parent compound.

16.19 Name

O
C

NO2

a. o-Aminobenzaldehyde
b. m-Aminobenzaldehyde
c. p-Aminobenzaldehyde

d. o-Nitrobenzaldehyde
e. m-Nitrobenzaldehyde

16.19 Answer
a. o-Aminobenzaldehyde
b. m-Aminobenzaldehyde
c. p-Aminobenzaldehyde

d. o-Nitrobenzaldehyde
e. m-Nitrobenzaldehyde

Benzaldehyde is the parent compound.

16.20 Name
C6H5CH2CH2CCCH3.
a.
b.
c.
d.
e.

1-Phenyl-3-pentyne
5-Phenyl-2-pentyne
4-Phenyl-2-pentyne
1-Phenyl-2-butyne
1-Phenyl-3-butyne

16.20 Answer
a.
b.
c.
d.
e.

1-Phenyl-3-pentyne
5-Phenyl-2-pentyne
4-Phenyl-2-pentyne
1-Phenyl-2-butyne
1-Phenyl-3-butyne