Hw 4: Aromatic Compounds

The structure of chlorobenzene is correctly represented by:

B

Which of the following structures accurately represents phenol?

C

The name of the following molecule is: 

A) toluene

B) ethylbenzene

C) cumene

D) styrene

E) anisole

Anisole 

Which dibromobenzene can form only one tribromobenzene?

A) o-dibromobenzene

B) m-dibromobenzene

C) p-dibromobenzene

D) cumene

E) styrene

p-dibromobenzene 

Using the following monosubstituted benzene, which position would be meta to X?

A) 1,4

B) 2,6

C) 3,5

D) 2,3

E) 5,6

3,5

Which of the following molecules is o-nitrophenol?

C

What is the name of the following molecule?

PhCH₂CH₂CH=CH₂

A) styrene

B) 4-phenyl-1-butene

C) 1-phenyl-3-butene

D) 3-benzyl-1-propene

E) allylbenzene

4-phenyl-1-butene

Which position would be para to X? 

A) 1

B) 2

C) 3

D) 4

E) 6

4

The correct name for

A) 2-chloro-4-bromotoluene.

B) o-chlorobromotoluene.

C) 1-bromo-3-chloro-4-methylbenzene.

D) 4-bromo-2-chlorotoluene.

E) p-chlorobromotoluene.

4-bromo-2-chlorotoluene.

The structural formula for p-chlorobenzoic acid is:

A

Which of the following statements about benzene is FALSE?

A) the molecule is planar and each carbon is at a corner of regular hexagon

B) there are two resonance structures of equivalent energy

C) the bond angles at each carbon center is equal, 120º

D) the typical mechanism by which reactions occur is by addition

E) The bond lengths between each two carbons of the rings are equal

The typical mechanism by which reactions occur is by addition

Which statement about benzene is true?

A) All six hydrogens in benzene are chemically equivalent.

B) Benzene decolorizes bromine solutions.

C) The molecule is planar, and each carbon is at the corner of a regular hexagon.

D) Both a and c are true.

E) Both b and c are true.

Both a and c are true

Which of the following is NOT an electrophile in an electrophilic aromatic substitution

reaction?

A) NO₂+

B) (CH₃)₃C +

C) SO₃

D) Cl -

E) all are

Cl -

Which of the following groups is a nucleophile?

A) NO₂+

B) (CH₃)₃C +

C) SO₃

D) Cl -

E) all are

Cl -

Which heterocyclic compound is commonly found in DNA and RNA bases?

A) Pyridine

B) Furan

C) pyrol

D) Pyrimidine

E) Thiophene

Pyrimidine

Which heterocyclic compound is commonly found in vitamin B6?

A) Pyridine

B) Furan

C) pyrol

D) Pyrimidine

E) Thiophene

Pyridine  

What is the name of the following compound?

Benzyl Alcohol

Nitrobenzene can be prepared by treating benzene with:

A) nitrous acid

B) nitric acid

C) Nitrogen molecule

D) Nitrate acid

E) nitrogen

Nitric Acid

What is a heterocyclic compound?

A) A compound containing only carbon and hydrogen in a ring

B) A compound with a ring that includes atoms other than carbon

C) A compound with an open-chain structure containing atoms other than carbon

D) A compound with only aromatic rings

E) A compound with only fused rings

A compound with a ring that includes atoms other than carbon

If p-nitrophenol is treated with chlorine in the presence of AlCl₃ , the only trisubstituted product

observed is:

A) 2-chloro-4-nitrophenol

B) 3-chloro-4-nitrophenol

C) 3-chloro-5-nitrophenol

D) 4-chloro-2-nitrophenol

E) 4-chloro-3-nitrophenol

2-chloro-4-nitrophenol 

What is the structural formula for benzaldehyde?

D

The name of the product of the following reaction is:

Benzene + HNO₃ in presence of sulfuric acid

A) benzenesulfonic acid

B) aniline

C) benzoic acid

D) nitrobenzene

E) anisole

Nitrobenzene 

What is the name of the following compound?

A) aniline

B) anisole

C) benzoic acid

D) phenol

E) toluene

Benzoic acid

Why is benzene more stable than expected based on its structure?

A) It undergoes addition reactions

B) It contains alternating single and double bonds

C) It has localized π bonds

D) It has delocalized π electrons over the ring (aromaticity)

E) It undergoes substitution reactions

It has delocalized π electrons over the ring (aromaticity)

The polycyclic aromatic hydrocarbon benzo[a]pyrene is a known carcinogen found in soot and tobacco smoke. How many benzene rings are there in its structure?

A) 1

B) 2

C) 3

D) 4

E) 5

5

What is the name of the following compounds?

A) Benzene 

B) fluorobenzene

C) hexafluorobenzene

D) o-fluorobenzene

E) p-fluorobenzene

Hexafluorobenzene

What type of product is formed in a Friedel–Crafts acylation of benzene?

A) carboxylic acid

B) An alcohol

C) A ketone

D) An aldehyde

E) HNO₃

A ketone 

What is the name of the following compound?

PhCH₂Cl

A) Phenyl chloride

B) Benzyl chloride

C) benzoic acid

D) chlorobenzene

E) chloromethylphenol

Benzyl Chloride 

Write the 3 criteria for aromaticity.

1. Be Cyclic 

2. Be Planar 

3. Have a continuous ring of p orbitals on each atom of the ring (Fully conjugated: alternate single and bond)