The College at Old Westbury ORGANIC 11 Chapter 11: Arenes and Aromaticity 1)What is the IUPAC name of the following compound? ortho-ethyliodobenzene C) para-ethyliodobenzene para-ethylphenyl iodide D) 1-ethyl-4-iodo-1,3,5-cyclohexatriene How many isomeric dichlorobenzenes are there? no isomers - only a single compound B) 2 C) 3 D) 4 What is the IUPAC name of the following compound? 4-tert-butyl-3-chlorophenol C) ortho-tert-butylchlorophenol 4-tert-butyl-5-chlorophenol D) 2-tert-butyl-meta-chlorophenol What is the IUPAC name of the following compound? 6-phenylheptane C) 2-heptylbenzene 2-benzylheptane D) 2-phenylheptane Which of the following is 2-chloro-4-ethylphenol? A B) B C) C D) D What is the correct IUPAC name of the following compound? 1,4-dibromo-3-nitrobenzene C) 2-nitro-1,4-dibromobenzene 1,4-dibromo-2-nitrobenzene D) 1-nitro-2,5-dibromobenzene How many isomeric tribromobenzenes are possible? one B) two C) three D) four Which of the following is not true concerning the structure of benzene? All C-C-C bond angles are exactly 120o

Question

The College at Old Westbury

ORGANIC 11

Chapter 11: Arenes and Aromaticity

1)What is the IUPAC name of the following compound?

1. ortho-ethyliodobenzene C) para-ethyliodobenzene
2. para-ethylphenyl iodide D) 1-ethyl-4-iodo-1,3,5-cyclohexatriene

How many isomeric dichlorobenzenes are there?
1. no isomers - only a single compound B) 2 C) 3 D) 4

What is the IUPAC name of the following compound?

1. 4-tert-butyl-3-chlorophenol C) ortho-tert-butylchlorophenol
2. 4-tert-butyl-5-chlorophenol D) 2-tert-butyl-meta-chlorophenol

What is the IUPAC name of the following compound?

1. 6-phenylheptane C) 2-heptylbenzene
2. 2-benzylheptane D) 2-phenylheptane

Which of the following is 2-chloro-4-ethylphenol?

1. A B) B C) C D) D

What is the correct IUPAC name of the following compound?

1. 1,4-dibromo-3-nitrobenzene C) 2-nitro-1,4-dibromobenzene
2. 1,4-dibromo-2-nitrobenzene D) 1-nitro-2,5-dibromobenzene

How many isomeric tribromobenzenes are possible?
1. one B) two C) three D) four

Which of the following is not true concerning the structure of benzene?
1. All C-C-C bond angles are exactly 120^o.
2. The carbon-carbon bonds rapidly alternate between single and double bonds.
3. The six hydrogens are equivalent.
4. The ? bonds are completely conjugated.

What is the IUPAC name of the following compound?

1. 4,6-dichloro-2-benzoic acid C) 3,5-dichlorobenzoic acid
2. 2,4-dichlorobenzoic acid D) meta-dichlorobenzoic acid

The total number of resonance forms of the cyclopentadienide anion, C₅H₅¯, is
1. two. B) three. C) four. D) five.

Which of the following ions are aromatic species?

1. I and III B) II and III C) II and IV D) III and IV

Identify the aromatic compounds.

1. I and II B) III and IV C) I, II, and IV D) all of them

How many isomeric bromoanthracenes are there?

1. none, only one structure B) two C) three D) four

Which of the following reacts at the fastest rate when heated with N-bromosuccinimide (NBS) and benzoyl peroxide in carbon tetrachloride at 80^oC?
1. toluene C) isopropylbenzene (cumene)
2. ethylbenzene D) tert-butylbenzene

The Birch reduction of benzene with sodium in NH₃/CH₃OH goes by a four-step mechanism. The first step is the
1. transfer of a proton from CH₃OH to benzene.
2. transfer of an electron from Na to benzene.
3. transfer of an electron from benzene to NH₃.
4. transfer of a hydride ion, H¯, from NH₃ to benzene.

Which species is oxidized in the Birch reduction shown below?

1. benzene B) Na C) CH₃OH D) NH₃

The benzyl carbocation is shown below. Besides the benzylic carbon, identify any other carbon atoms which carry a partial positive charge based on resonance theory.

1. ortho and para carbon atoms C) meta and para carbon atoms
2. meta carbon atoms D) ortho and meta carbon atoms

Side chain oxidations of alkylbenzenes with Na₂Cr₂O₇ and H₂SO₄/H₂O will not work if the alkyl side chain has
1. only one carbon. C) benzylic hydrogens.
2. four or more carbons. D) no benzylic hydrogens.

Which of the following are consistent with the requirements for aromaticity?

A system with delocalized ? electrons in a ring.
4n ? electrons in the ring.
All the ring atoms must be carbons.
(4n + 2) ? electrons in the ring.

A) I and II B) I and IV C) I, II, and III D) I, III, and IV

Cyclopentadiene is unusually acidic for a hydrocarbon. Why?
1. Cyclopentadiene is aromatic.
2. The conjugate base of cyclopentadiene is aromatic.
3. Cyclopentadiene is an unstable diradical.
4. The conjugate base of cyclopentadiene is an unstable diradical.

Which of the following would most readily react with a strong base, such as NaNH₂, to form a carbanion?

1. A B) B C) C D) D

What is the value of n from Huckel's rule for the following aromatic compound?

A) n = 3 B) n = 4 C) n = 8 D) n = 9

The name of the following compound is

1. meta-bromoanisole. C) meta-bromoaniline.
2. meta-bromonitrobenzene. D) meta-bromophenol.

Which hydrogen atom would be most easily extracted by a bromine atom?

A) 1 B) 2 C) 3 D) 4

What is the product of the reaction shown below?

1. I B) II C) III D) IV

Propylbenzene is subjected to the sequence of reactions below. What is the final product?

1. A B) B C) C D) D

A compound X, C₈H₁₀, is oxidized to benzoic acid with potassium dichromate, K₂Cr₂O₇, in sulfuric acid. What is compound X?
1. para-xylene B) propylbenzene C) styrene D) ethylbenzene

Acid-catalyzed dehydration of cis-2-phenylcyclopentanol gives
1. 1-phenylcyclopentene. C) 4-phenylcyclopentene.
2. phenylcyclopentane. D) 1-phenylcyclopentanol.

Predict the major organic product in the following reaction.

1. A B) B C) C D) D

Which of the following has the fastest rate of S_N1 hydrolysis in aqueous acetone?

1. I B) II C) III D) IV

Select the best method to convert styrene, C₆H₅CH=CH₂, to 2-phenylethanol with minimal by-product formation.
1. H₂O, H₂SO₄
2. (1) BH₃-THF (2) H₂O₂, NaOH
3. (1) HBr (2) KOH, H₂O
4. (1) HBr, peroxides (2) NaOH, H₂O

Which of the following would be a correct number of ? electrons for a planar, monocyclic, completely conjugated polyene to be aromatic?

A) 3 B) 8 C) 18 D) 24

Which of the following is an aromatic hydrocarbon?

1. A B) B C) C D) D

Which of the following has the lowest heat of reaction on catalytic hydrogenation? (4 moles of H₂ per mole of hydrocarbon)

1. A B) B C) C D) D

In which of the following are carbon-carbon bond lengths arranged in the correct order?

1. A B) B C) C D) D
Benzene has ? molecular orbitals (bonding and antibonding), and the lowest

molecular orbitals are filled with electrons in the ground state.

1. three, three B) six, two C) six, three D) twelve, six

Which of the following ions has a ground state which is predicted to be a diradical by simple molecular orbital theory?

1. A B) B C) C D) D

Identify the site of protonation when one equivalent of HCl is added to the compound below.

1. N-1
2. N-2
3. both N-1 and N-2 (about 50% each)
4. neither N-1 or N-2, the compound is not basic

What is the hybridization of the nitrogen atom in pyrrole?

1. sp B) sp² C) sp³ D) 2p

Starting with toluene, which sequence of reactions below works best to prepare the following cyclohexadiene compound?

1. A B) B C) C D) D

Which of the following isomers would you predict has the highest heat of hydrogenation?
1. 1-ethyl-1,4-cyclohexadiene C) 1-ethyl-1,3-cyclohexadiene
2. 3-ethyl-1,4-cyclohexadiene D) 5-ethyl-1,3-cyclohexadiene

Which of the following is the product from the reaction sequence shown below?

1. I B) II C) III D) IV

Which one of following is not a resonance form of the benzyl free radical?

1. A B) B C) C D) D

Which one of the following compounds has the fastest S_N1 reaction rate with H₂O in acetone?

1. I B) II C) III D) IV

How many ? electrons are there in the following polycyclic aromatic hydrocarbon?

A) 6 B) 8 C) 10 D) 14

In the following conformation of styrene, the alignment of the -CH=CH₂ group results in

1. maximum conjugation and maximum steric hindrance with the C₆H₅ group.
2. maximum conjugation and minimal steric hindrance with the C₆H₅ group.
3. minimal conjugation and maximum steric hindrance with the C₆H₅ group.
4. minimal conjugation and minimal steric hindrance with the C₆H₅ group.

How many isomeric tetrachlorobenzenes are there?
1. two B) three C) four D) five

1,3-cyclopentadiene is known for
1. its unusually high acidity (pK_a ~ 16)
2. slowly dimerizing at room temperature
3. being a good Diels-Alder diene
4. all of the above.

Which of the resonance structures below is most important in explaining why this molecule has a relatively large dipole moment?

1. A B) B C) C D) D

Which of these would be most reactive with pure methanol?

1. A B) B C) C D) D

Considering aromaticity, which of these would be the most acidic?

1. A B) B C) C D) D

Which statement is true of the hydrogenation of benzene?
1. The ?H_{hydrogenation} of benzene is greater than three times that of cyclohexene.
2. The ?H_{hydrogenation} of benzene is equal to three times that of cyclohexene.
3. The ?H_{hydrogenation} of benzene is less than three times that of cyclohexene.
4. Benzene cannot be hydrogenated under any conditions.

From left to right, these two compounds are

1. aromatic and antiaromatic C) antiaromatic and aromatic
2. antiaromatic and non-aromatic D) both are antiaromatic

When a is on an atom directly attached to a benzene ring, the benzene ring will stabilize it by resonance.
1. negative charge C) unpaired electron (a radical)
2. positive charge D) all of the above