Chapter 18 Aromatic Substitution Reactions Test Bank Answers

Organic Chemistry, 4e (Klein)

Chapter 18 Aromatic Substitution Reactions

1) Which of the reagents shown could be used as the basis for a simple chemical test that would distinguish between ethylbenzene and styrene?

A) NaI/acetone

B) Br2/CCl4

C) NaOH/H2O

D) NaBH4/CH3OH

E) HCl/H2O

Diff: 1

Learning Objective: 18.1 Describe the difference between an addition reaction and an electrophilic aromatic substitution reaction

2) Why does benzene undergo a substitution reaction with bromine, whereas cyclohexene undergoes an addition reaction with bromine?

A) Benzene has delocalized π electrons not present in cyclohexene and adding bromine would result in a less stable, nonaromatic product.

B) Cyclohexene has delocalized π electrons that make it too stable to undergo an additional reaction.

C) Cyclohexene has a mix of localized and delocalized π electrons, so substitution would disrupt this pattern and make the ring less stable.

D) Benzene is highly unstable due to its lack of localized π electrons and this makes an addition reaction impossible.

E) Benzene has localized π electrons and this forms a structure that is stable and very unreactive, preventing an addition reaction from occurring.

Diff: 2

Learning Objective: 18.1 Describe the difference between an addition reaction and an electrophilic aromatic substitution reaction

3) What is the mechanism by which benzene reacts with bromine?

A) Unimolecular nucleophilic addition

B) Electrophilic aromatic addition

C) Electrophilic aromatic substitution

D) Biomolecular nucleophilic substitution

E) Aromatic nucleophilic substitution

Diff: 2

Learning Objective: 18.1 Describe the difference between an addition reaction and an electrophilic aromatic substitution reaction

4) Which illustration shows all of the resonance structures of the sigma complex that is formed when benzene reacts with an electrophile (E+)?

A) I, II, and III

B) I, III, and IV

C) I, II, and V

D) II, III, and IV

E) III, IV, and V

Diff: 2

Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction

5) What is the rate-determining step in the electrophilic aromatic substitution of benzene?

A) Formation of an electrophile

B) Formation of a sigma complex.

C) Loss of a proton from the sigma complex.

D) Addition of an electrophile & loss of a proton.

E) None of these

Diff: 1

Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction

6) The electrophilic bromination or chlorination of benzene requires ________ along with the halogen.

A) UV light

B) a Brønsted base

C) a Lewis base

D) a Lewis acid

E) none of these

Diff: 1

Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction

7) What is the electrophile in the bromination of benzene?

A) Br2

An iron atom carrying a negative charge is single-bonded to four bromine atoms. One of the bromine atoms carries a positive charge and is further bonded to another bromine atom.

C) FeBr3

D) FeBr2

E) B r carries a positive charge.

Diff: 1

Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction

8) What is the electrophile in the chlorination of benzene?

A) Cl2

An aluminum atom carrying a negative charge is single-bonded to four chlorine atoms. One of the chlorine atoms carries a positive charge and is further bonded to another chlorine atom.

C) AlCl3

D) AlCl2

E) C l carries a positive charge.

Diff: 1

Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction

9) What is the electrophile in the iodination of benzene?

A) I2

B) A copper atom carrying a negative charge is single-bonded to two iodine atoms. One of the iodine atoms carries a positive charge and is further bonded to another iodine atom.

C) CuI3

D) CuI2

E) I carries a positive charge.

Diff: 1

Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction

10) What reagents are used to carry out the chlorination of benzene?

A) Cl2/CCl4

B) Cl2/FeCl3

C) Cl2/AlCl3

D) NaCl/Fe

E) both B and C

Diff: 2

Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction

11) What reagents are used to carry out the iodination of benzene?

A) I2/CCl4

B) I2/FeCl3

C) I2/AlCl3

D) I2/CuCl2

E) NaI/Acetone

Diff: 2

Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction

12) In order, what are the major steps involved in an electrophilic aromatic substitution reaction?

A) 1) Reaction of an electrophile with an aromatic ring to form a sigma complex; 2) Deprotonation of the aromatic ring to form the aromatic product

B) 1) Deprotonation of the aromatic ring to increase its reactivity; 2) Addition of the electrophile to form the sigma product; 3) Loss of the leaving group to form the product

C) 1) Deprotonation of the aromatic ring to form a sigma complex; 2) Reaction of the sigma complex with the electrophile

D) 1) Formation of an electrophile; 2) Reaction of the electrophile with an aromatic ring to form the sigma complex; 3) Deprotonation of the sigma complex to restore aromaticity

E) 1) Polarization of a dihalide, yielding a nucleophile; 2) Reaction of the nucleophile with the aromatic ring to form an electrophile; 3) Loss of the leaving group to restore aromaticity

Diff: 2

Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction

13) What is the first step in the curved arrow mechanism for the chlorination of benzene in the presence of FeCl3?

A) I

B) II

C) III

D) IV

E) II or III

Diff: 2

Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction

14) Identify the electrophile in the sulfonation reaction of benzene.

A) SO2+

B) H2SO4

C) SO3+

D) H2SO3

E) SO3

Diff: 1

Learning Objective: 18.3 Draw the mechanism of sulfonation of an aromatic ring

15) Predict the product of reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 18.3 Draw the mechanism of sulfonation of an aromatic ring

16) What is the predicted product of the reaction shown?

A partial reaction shows the reactant that has a SMILES string of c1ccc(cc1)S(=O)(=O)O reacts with hydronium ion, H 3 O plus, in the presence of heat.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 18.3 Draw the mechanism of sulfonation of an aromatic ring

17) Predict the product for the reaction shown.

A partial reaction shows the reactant that has a SMILES string of CCc1cccc(c1)S(O)(=O)=O reacts with hydronium ion, H 3 O plus, in the presence of heat.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 18.3 Draw the mechanism of sulfonation of an aromatic ring

18) Which of the species shown acts as an electrophile in the nitration of benzene?

A) NO2+

B) HNO3

C) NO3+

D) H2SO4

E) NO2

Diff: 1

Learning Objective: 18.4 Draw the mechanism of nitration of an aromatic ring

19) Which of the species shown acts as an electrophile in the nitration of benzene?

A) sulfonium ion

B) nitrogen dioxide

C) nitronium ion

D) nitrous oxide

E) sulfur dioxide

Diff: 1

Learning Objective: 18.4 Draw the mechanism of nitration of an aromatic ring

20) Predict the product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.4 Draw the mechanism of nitration of an aromatic ring

21) What is the first step in the curved arrow mechanism of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 18.4 Draw the mechanism of nitration of an aromatic ring

22) What is the product from the reaction of nitrobenzene with iron and hydrochloric acid, followed with base?

A) nitrobenzene

B) benzene

C) aniline

D) 1,3-dinitrobenzene

E) 1,4-dinitrobenzene

Diff: 1

Learning Objective: 18.4 Draw the mechanism of nitration of an aromatic ring

23) What is the electrophile in a Friedel-Crafts alkylation?

A) aluminum chloride

B) carbocation

C) aluminum tetrachloride ion

D) carbanion

E) radical

Diff: 1

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

24) Predict the major product for the reaction shown.

A partial reaction shows the reactant that has a SMILES string of c1ccccc1 reacts with 1-chloro-2-methylpropane, (C H 3) 2 C H C H 2 C l and aluminum chloride, A l C l 3.

The bond-line structure of four compounds labeled 1 to 4 (in Roman Numerals) are as follows:
The first compound has a SMILES string of CC(C)Cc1ccccc1.
The second compound has a SMILES string of CCC(C)c1ccccc1.
The third compound has a SMILES string of CC(C)(C)c1ccccc1.
The fourth compound has a SMILES string of CCCCc1ccccc1.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

25) Which one of the reactions shown is most likely to give a polysubstituted product?

A) Friedel-Crafts alkylation

B) Friedel-Crafts acylation

C) nitration

D) sulfonation

E) halogenation

Diff: 2

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

26) Which one of the compounds shown does not undergo a Friedel-Crafts reaction?

A) benzene

B) chlorobenzene

C) nitrobenzene

D) toluene

E) t-butylbenzene

Diff: 2

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

27) Predict the major product for the reaction between benzene and 2-chlorobutane in the presence of AlCl3.

A) chlorobenzene

B) sec-butylbenzene

C) ethylbenzene

D) isopropylbenzene

E) t-butylbenzene

Diff: 2

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

28) Which of the halides shown cannot be used for a Friedel-Crafts alkylation reaction?

A) bromobenzene

B) vinylchloride

C) 2-chloropropane

D) chloroethane

E) both A and B

Diff: 2

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

29) Aryl and vinyl halides cannot be used in the Friedel-Crafts alkylation reaction, because they ________.

A) are exceptionally stable due to electron delocalization

B) do not have suitable leaving groups

C) are not very electrophilic

D) do not form stable cations

E) are not sufficiently nucleophilic

Diff: 3

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

30) Predict the major product for the reaction shown.

A partial reaction shows the reactant with SMILES string c1ccccc1 reacts with (1-Chloroethyl)cyclopentane, that has a SMILES string of CC(C1CCCC1)Cl, and aluminum chloride, A l C l 3.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

31) Predict the major product for the reaction shown.

A partial reaction shows the reactant with SMILES string c1ccccc1 reacts with (C H 3) thrice C C H 2 C l and aluminum chloride, A l C l 3.

The bond-line structure of five compounds labeled 1 through 5 (in Roman Numerals) are as follows:
The first compound has a SMILES string of CC(C)(C)Cc1ccccc1.
The second compound has a SMILES string of CCC(C)(C)c1ccccc1.
The third compound has a SMILES string of CCCC(C)c1ccccc1.
The fourth compound has a SMILES string of CCCCCc1ccccc1.
The fifth compound has a SMILES string of CC(C)CCc1ccccc1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

32) Provide the structures of the intermediate products and final product in the reaction sequence shown.

A) I

B) II

C) III

D) I and II

E) II and III

Diff: 3

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

33) Predict the major product for the reaction shown.

A partial reaction shows the reactant with the SMILES string c1ccccc1 reacts with three sets of reagents that are listed as follows:
Set 1:
Isobutyl chloride with SMILES string CC(C)CCl and aluminum chloride, A l C l 3.
Set 2:
C H 2 C H 2 C l and A l C l 3.
Set 3:
First with excess K M n O 4/N a O H/H 2 O and second with H 3 O plus.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

34) Predict the major product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

35) What is the first step of the stepwise, curved arrow mechanism for the reaction shown?

A reaction shows the reactant with SMILES string c1ccccc1 reacts with (1-Chloroethyl)cyclopentane, that has a SMILES string of CC(C1CCCC1)Cl, and aluminum chloride, A l C l 3 to form the product that has a benzene ring, in which C-1 is bonded to another cyclohexane ring. C 2 of the cyclohexane ring is further bonded to a methyl group.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

36) Predict the major product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

37) Predict the major product for the reaction shown.

A partial reaction shows the reactant with the SMILES string c1ccccc1 reacts with another reactant that has a SMILES string of CC(=CCCl)C in the presence of the reagent, aluminum chloride, A l C l 3.

The bond-line structure of five compounds labeled 1 through 5 (in Roman Numerals) are as follows:
The first compound has a SMILES string of C=CCc1ccccc1.
The second compound has a SMILES string of C/C=C/c1ccccc1.
The third compound has a SMILES string of CC(C)(C=C)c1ccccc1.
The fourth compound has a SMILES string of CC(C=C)c1ccccc1.
The fifth compound has a SMILES string of CCC(C)(C)c1ccccc1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

38) Predict the structure of the major product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

39) Which of the reactions shown would produce isopropylbenzene as the major product?

A) I

B) II

C) III

D) IV

E) all of these

Diff: 3

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

40) Which of the reactions shown would produce t-butylbenzene as the major product?

A) I

B) II

C) III

D) IV

E) all of these

Diff: 3

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents

41) Which of the choices is the electrophile for the Friedel-Crafts acylation of benzene?

A) aluminum tetrachloride anion

B) aluminum chloride

C) acylium ion

D) carbocation

E) carbanion

Diff: 1

Learning Objective: 18.6 Predict the products of a Friedel-Crafts acylation considering limitations on the choice of ring substituents, and describe the product that results from a subsequent reduction reaction

42) In a Clemmensen reduction, an aryl ketone is reduced to ________.

A) an aryl aldehyde

B) an aryl alkane

C) an aryl carboxylic acid

D) an aryl ester

E) an aryl anhydride

Diff: 1

43) Predict the structure of the major product for the reaction shown.

A partial reaction shows the reactant with the SMILES string c1ccccc1 reacts with Propanoyl chloride, with SMILES string CCC(=O)Cl and aluminum chloride, A l C l 3.

$The bond-line structure of five compounds labeled 1 through 5 (in Roman Numerals) are as follows: The first compound has a SMILES string of CCCc1ccccc1. The second compound has a SMILES string of C/C=C(\C)/c1ccccc1. The third compound has a SMILES string of c1ccc(cc1)C=O. The fourth compound has a SMILES string of CCC(=O)c1ccccc1. The fifth compound has a SMILES string of Cc1ccccc1.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

44) Predict the structure of the major product for the reaction shown.

A partial reaction shows the reactant with the SMILES string c1ccccc1 reacts with 3-Methylbutanoyl chloride, with SMILES string CC(C)CC(=O)Cl and aluminum chloride, A l C l 3.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

45) Predict the structure of the major product for the reaction shown.

A partial reaction shows the reactant with the SMILES string of c1ccccc1 reacts with a reagent with condensed formulas of C H 3 C H 2 C H 2 C (double-bonded to O) O C (double-bonded to O) C H 2 C H 2 C H 3 and aluminum chloride, A l C l 3.

The bond-line structure of five compounds labeled 1 through 4 (in Roman Numerals) are as follows:
The first compound has a SMILES string of CC(=O)CC(=O)c1ccccc1.
The second compound has a SMILES string of CCCCc1ccccc1.
The third compound has a SMILES string of CCCC(=O)c1ccccc1.
The fourth compound has a SMILES string of CCCC(c1ccccc1)O.

A) I

B) II

C) III

D) II and III

E) III and IV

Diff: 2

46) Provide the structure of the major products formed in each step of the reaction sequence shown.

A) I

B) II

C) III

D) I and II

E) III and IV

Diff: 2

47) What sequence of reagents could be used to carry out the conversion shown?

A reaction shows the reactant with the SMILES string c1ccccc1 reacts to form the product that has a SMILES string of CCCc1ccccc1.

A) 1. Fuming H2SO4; 2. Excess NBS

B) 1. Br2, 2. AlBr2; 2. Zn(Hg), HCl, heat

C) 1. The reagents are chloropropanol, with SMILES string CCC(Cl)O/aluminum chloride, A l C l 3.

D) 1. The reagents are propanoyl chloride, with SMILES string CCC(=O)Cl/aluminum chloride, A l C l 3. 2. Zn(Hg), HCl, heat

E) 1. The reagents are 1-chloropropane, with SMILES string CCCCl/aluminum chloride, A l C l 3. 2. Zn(Hg), HCl, heat

Diff: 3

48) Predict the structure of the product for the reaction shown.

A partial reaction shows the reactant with SMILES string c1ccccc1 reacts with another reactant that has a SMILES string of C1CC(=O)OC1=O. The reactants react first with aluminum chloride, A l C l 3, and second with hydronium ion, H 3 O plus.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

49) Predict the structure of the product for the reaction shown.

A partial reaction shows the reactant with SMILES string c1ccc(cc1)CCC(=O)Cl reacts with aluminum chloride, A l C l 3.

The bond-line structure of five compounds labeled 1 through 5 (in Roman Numerals) are as follows:
The first compound has a SMILES string of c1ccc2c(c1)CCC2=O.
The second compound has a SMILES string of c1ccc2c(c1)CCC2.
The third compound has a SMILES string of c1ccc2c(c1)CCC2O.
The fourth compound has a SMILES string of CC(=O)CCc1ccccc1.
The fifth compound has a SMILES string of CCCCc1ccccc1.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

50) Predict the structure of the product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

51) An alkyl group ________ the benzene ring to make it ________ reactive than benzene.

A) activates; less

B) blocks; less

C) deactivates; less

D) activates; more

E) deactivates; more

Diff: 1

Learning Objective: 18.7 Describe how the presence of an activator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction

52) Which of the substituents shown will not direct the incoming group to the ortho/para position during electrophilic aromatic substitution?

A) -CH2CH3

B) -CF3

C) -OCH3

D) -NHCH3

E) -Br

Diff: 1

Learning Objective: 18.7 Describe how the presence of an activator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction

53) Which of the substituents shown will direct the incoming group to the ortho/para position during electrophilic aromatic substitution?

A) -CH2CH3

B) -CF3

C) -OCH3

D) -COOCH3

E) both A and C

Diff: 2

Learning Objective: 18.7 Describe how the presence of an activator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction

54) Which one of the compounds shown will be most reactive towards an electrophilic aromatic bromination reaction?

A) nitrobenzene

B) anisole

C) acetanilide

D) benzene

E) benzaldehyde

Diff: 2

Learning Objective: 18.7 Describe how the presence of an activator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction

55) Which of the compounds shown will yield the ortho substituted compound as the major product for a nitration reaction?

A) toluene

B) ethylbenzene

C) cumene

D) t-butylbenzene

E) none of these

Diff: 2

Learning Objective: 18.7 Describe how the presence of an activator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction

56) Which of the structures shown are resonance structures of the sigma complex produced when aniline reacts with an electrophile (E+) to yield the para-substituted product?

A) I and II

B) II and III

C) II, III, and IV

D) I, III, IV, and V

E) I, II, IV, and V

Diff: 2

Learning Objective: 18.7 Describe how the presence of an activator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction

57) A nitro group ________ the benzene ring to make it ________ reactive than benzene.

A) activates; less

B) blocks; less

C) deactivates; less

D) activates; more

E) deactivates; more

Diff: 1

Learning Objective: 18.8 Describe how the presence of a deactivator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction

58) Which one of the substituents shown will direct the incoming group to the meta position during electrophilic aromatic substitution?

A) -NO2

B) -C≡N

C) -CCl3

D) -COOH

E) all of these

Diff: 1

Learning Objective: 18.8 Describe how the presence of a deactivator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction

59) Which one of the substituents shown will not direct the incoming group to the meta position during electrophilic aromatic substitution?

A) -NO2

B) -C≡N

C) -OCH3

D) -COOH

E) all of these

Diff: 1

Learning Objective: 18.8 Describe how the presence of a deactivator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction

60) Which one of the compounds shown will be least reactive towards a Friedel-Crafts reaction?

A) nitrobenzene

B) anisole

C) phenol

D) benzene

E) chlorobenzene

Diff: 2

Learning Objective: 18.8 Describe how the presence of a deactivator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction

61) Which of the structures shown are major resonance contributors when nitrobenzene reacts with an electrophile in electrophilic aromatic substitution at the meta position?

A) I

B) II

C) III

D) I, III, and IV

E) V

Diff: 1

Learning Objective: 18.8 Describe how the presence of a deactivator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction

62) A halogen ________ the benzene ring; the ring is ________ reactive than benzene.

A) activates; less

B) blocks; less

C) deactivates; less

D) activates; more

E) deactivates; more

Diff: 1

Learning Objective: 18.9 Describe how the presence of a halogen affects the rate and regiochemical outcome of an electrophilic aromatic substitution

63) What are the preferred products from the nitration of bromobenzene?

A) I and II

B) II and III

C) I and III

D) III and IV

E) II and IV

Diff: 1

Learning Objective: 18.9 Describe how the presence of a halogen affects the rate and regiochemical outcome of an electrophilic aromatic substitution

64) Which of the substituents shown directs the incoming group to the ortho/para position during electrophilic aromatic substitution?

A) -NO2

B) -CF3

C) -Br

D) -COOCH3

E) none of these

Diff: 1

Learning Objective: 18.9 Describe how the presence of a halogen affects the rate and regiochemical outcome of an electrophilic aromatic substitution

65) Which one of the compounds shown is the most reactive toward electrophilic aromatic substitution?

The bond-line structure of five compounds labeled 1 through 5 (in Roman Numerals) are as follows:
The first compound has a SMILES string of c1ccc(cc1)N.
The second compound has a SMILES string of Cc1ccccc1.
The third compound has a SMILES string of c1ccc(cc1)Cl.
The fourth compound has a SMILES string of CC(=O)c1ccccc1.
The fifth compound has a SMILES string of c1ccc(cc1)C(F)(F)F.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators

66) Which one of the compounds shown is the least reactive toward electrophilic aromatic substitution?

The bond-line structure of five compounds labeled 1 through 5 (in Roman Numerals) are as follows:
The first compound has a SMILES string of c1ccc(cc1)[N+](=O)[O-].
The second compound has a SMILES string of COc1ccccc1.
The third compound has a SMILES string of c1ccc(cc1)Cl.
The fourth compound has a SMILES string of CC(=O)c1ccccc1.
The fifth compound has a SMILES string of c1ccc(cc1)C(F)(F)F.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators

67) Arrange the compounds shown in order of decreasing reactivity towards electrophilic aromatic substitution.

A) V > II > I > III > IV

B) II > V > III > I > IV

C) IV > I > III > V > II

D) III > II > I > IV > V

E) IV > V > II > I > III

Diff: 2

Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators

68) Predict the major product for the reaction shown.

A partial reaction shows the reactant that has a SMILES string of CCc1ccccc1 reacts with dichlorine, C l 2/iron (3) chloride, F e C l 3.

The bond-line structure of five compounds labeled 1 through 5 (in Roman Numerals) are as follows:
The first compound has a SMILES string of CCc1ccc(cc1)Cl.
The second compound has a SMILES string of CCc1ccccc1Cl.
The third compound has a SMILES string of CC(c1ccccc1)Cl.
The fourth compound has a SMILES string of CCc1cccc(c1)Cl.
The fifth compound has a SMILES string of c1ccc(cc1)CCCl.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators

69) What reagent(s) are necessary to carry out the conversion shown?

t-butylbenzene → 1-t-butyl-4-chlorobenzene

A) Cl2, heat

B) Cl2, FeCl3

C) SOCl2, pyridine

D) HCl

E) PCl3

Diff: 2

Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators

70) What is the predicted major product for the reaction shown?

The bond-line structure of five compounds labeled 1 through 4 (in Roman Numerals) are as follows:
The first compound has a SMILES string of COc1ccccc1S(=O)(=O)O.
The second compound has a SMILES string of COc1ccc(cc1)S(=O)(=O)O.
The third compound has a SMILES string of COc1ccc(cc1S(=O)(=O)O)S(=O)(=O)O.
The fourth compound has a SMILES string of COc1cccc(c1)S(=O)(=O)O.

A) I

B) II

C) III

D) IV

E) I and II

Diff: 2

Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators

71) What is the predicted major product for the reaction shown?

A partial reaction shows the reactant that has a SMILES string of c1ccc(cc1)CC(=O)c2ccccc2 reacts with bromine, B r 2/aluminum bromide, A l B r 3.

The bond-line structure of five compounds labeled 1 through 5 (in Roman Numerals) are as follows:
The first compound has a SMILES string of c1ccc(cc1)CC(=O)c2ccc(cc2)Br.
The second compound has a SMILES string of c1ccc(cc1)C(=O)Cc2ccc(cc2)Br.

The third compound has a SMILES string of c1ccc(cc1)CC(=O)c2cccc(c2)Br.
The fourth compound has a SMILES string of c1ccc(cc1)C(=O)Cc2cccc(c2)Br.

The fifth compound has a SMILES string of C1=CC=C(C=C1)CC(=O)C2=CC=CC=C2Br.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators

72) What is the predicted major product for the reaction shown?

A partial reaction shows the reactant that has a SMILES string of CC(=O)Oc1ccccc1 reacts with bromine, B r 2/iron (III) bromide, F e B r 3.

The bond-line structure of five compounds labeled 1 through 4 (in Roman Numerals) are as follows:
The first compound has a SMILES string of CC(=O)Oc1ccccc1Br.
The second compound has a SMILES string of CC(=O)Oc1ccc(cc1Br)Br.
The third compound has a SMILES string of CC(=O)Oc1cccc(c1)Br.
The fourth compound has a SMILES string of CC(=O)Oc1ccc(cc1)Br.

A) I

B) II

C) III

D) IV

E) I & IV

Diff: 2

Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators

73) What is the predicted major product for reaction shown?

The bond-line structure of five compounds labeled 1 through 5 (in Roman Numerals) are as follows:
The first compound has a SMILES string of COC(=O)c1ccccc1[N+](=O)[O-].
The second compound has a SMILES string of COC(=O)c1ccc(cc1)[N+](=O)[O-].
The third compound has a SMILES string of COC(=O)c1cccc(c1)[N+](=O)[O-].

The fourth compound has a SMILES string of COC(=O)c1cccc(c1[N+](=O)[O-])[N+](=O)[O-].
The fifth compound has a SMILES string of COC(=O)c1cc(cc(c1)[N+](=O)[O-])[N+](=O)[O-].

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators

74) What is the predicted major product for the reaction shown?

A partial reaction shows the reactant with SMILES string CC(=O)c1cccc(c1)[N+](=O)[O-] reacts with chloromethane, C H 3 C l/aluminum chloride, A l C l 3.

The bond-line structure of five compounds labeled 1 through 4 (in Roman Numerals) are as follows:
The first compound has a SMILES string of Cc1cc(cc(c1)[N+](=O)[O-])C(=O)C.
The second compound has a SMILES string of Cc1c(cccc1[N+](=O)[O-])C(=O)C.
The third compound has a SMILES string of Cc1ccc(cc1[N+](=O)[O-])C(=O)C.
The fourth compound has a SMILES string of Cc1ccc(cc1C(=O)C)[N+](=O)[O-].

A) I

B) II

C) III

D) IV

E) no reaction

Diff: 2

Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators

75) What is the predicted major product for the reaction shown?

A partial reaction shows the reactant with SMILES string CCC(=O)c1cccc(c1)O reacts with chlorine, C l 2/aluminum chloride, A l C l 3.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators

76) What is the predicted major product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring

77) What is the predicted major product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring

78) What is the predicted major product for the reaction shown?

A partial reaction is as follows:
The reactant that has a benzene ring, in which C-1 is bonded to a carbonyl group, the carbonyl carbon is further bonded to an O C H 3 group, and C-4 is bonded to an O C H 3 group. The reactant reacts with the reagents that have the condensed formulas (C H 3) 3 C C l and A l C l 3.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring

79) Predict the major product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring

80) What are the predicted structures of the major intermediate (A) and product (B) of the reaction sequence shown?

A two-step reaction is as follows:
The first step shows the reactant that has a SMILES string of c1ccc2c(c1)OCCO2 reacts with bromine, B r 2/iron (III) bromide, F e B r 3 to form the intermediate compound A.
The second step shows the intermediate compound A reacts with chloroethane, C H 3 C H 2 C l, and aluminum chloride, A l C l 3 to form product B.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring

81) What is (are) the predicted major product(s) for the reaction shown?

A) I

B) II

C) III

D) II and III

E) IV and V

Diff: 3

Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring

82) What is the predicted major product for following reaction shown?

A partial reaction shows the reactant with the SMILES string c1ccc2c(c1)c3ccccc3[nH]c2=O reacts with bromine/iron(III)bromide, represented as B r 2/F e B r 3.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring

83) Predict the major product for the following reaction.

A partial reaction shows the reactant that has a SMILES string of CC(=O)Nc1ccc(cc1)c2ccccc2 reacts with C H 3 C l/A l C l 3.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring

84) What is the predicted major product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring

85) What is the predicted major product for the reaction shown?

A partial reaction shows the reactant that has a SMILES string of c1ccc(cc1)CC(=O)c2ccccc2 reacts with propanoyl chloride, with SMILES string CCC(=O)Cl/aluminum chloride, A l C l 3.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring

86) What is the predicted major product for the reaction shown?

A partial reaction shows the reactant with SMILES string c1ccc(cc1)Cc2ccc(cc2)[N+](=O)[O-] reacts with chloroethane, C H 3 C H 2 C l and aluminum chloride, A l C l 3.

A) I

B) II

C) III

D) IV

E) no reaction

Diff: 2

Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring

87) Which of the following series of reagents could be used to carry out the conversion shown?

A reaction shows the reactant that has a SMILES string of CC(C)(C)c1ccccc1 reacts to form the product that has a SMILES string of CC(C)(C)c1ccccc1Br.

A) 1. Fuming H2SO4; 2. Excess NBS

B) 1. Br2; 2. AlBr2; 2. Zn(Hg), HCl, heat

C) 1. Br2; 2. FeBr3

D) 1. Fuming H2SO4; 2. Br2/FeBr3; 3. Dilute H2SO4

E) 1. Br2; 2. AlBr3

Diff: 2

Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring

88) Which of following reagents or series of reagents could be used to carry out the conversion shown?

A) 1. Fuming H2SO4; 2. CH3CH2Cl/AlCl3; 3. H2O, heat

B) 1. CH3CH2Cl/AlCl3

C) 1. Cl2; 2. AlBr3; 1. CH3CH2Cl/AlCl3

D) 1. Dilute H2SO4; 2. CH3CH2Cl/AlCl3

E) 1. Dilute H2SO4; 2. CH3CH2CH2Cl/AlCl3

Diff: 2

Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring

89) Which of the following series of reagents could be used to carry out the conversion shown?

A reaction shows a reactant with SMILES string c1ccccc1 reacts to form the product that has a SMILES string of c1cc(cc(c1)Br)[N+](=O)[O-].

A) 1. HNO3/H2SO4; 2. Br2/FeBr3

B) 1. Br/AlBr3; 2. HNO3; 3. H3O+

C) 1. Br/AlBr; 2. Fuming H2SO4; 3. H2O, heat; 4. HNO3/H2SO4

D) 1. Br2/FeBr3; 2. HNO3, H3O+

E) 1. FeBr3; 2. HNO3; 3. H3O+

Diff: 1

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

90) Which of the following series of reagents could be used to carry out the conversion shown?

A reaction shows a reactant with SMILES string c1ccccc1 reacts to form the product that has a SMILES string of c1cc(ccc1[N+](=O)[O-])Cl.

A) 1. HNO3/H2SO4; 2. Fuming H2SO4; 3. Excess NBS; 4. Cl2/FeCl3

B) 1. Cl2; 2. HNO3; 3. H3O+

C) 1. HNO3, H2SO4; 2. Cl/FeCl3

D) 1. Cl2/FeCl3; 2. HNO3, H2SO4

E) 1. FeCl3; 2. HNO3; 3. H3O+

Diff: 1

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

91) What series of reagents necessary to carry out the following conversion?

A reaction shows a reactant with SMILES string c1ccccc1 reacts to form the product that has a SMILES string of CC(=O)c1cccc(c1)Br.

A) 1. An illustration shows two reagents used in a chemical reaction. The first reagent is C H 3 (C double bond O) C l and the second reagent is A l C l 3. ; 2. Br2/FeBr3

B) 1. Br2, FeBr3; 2. H3O+; 3. An illustration shows two reagents used in a chemical reaction. The first reagent is C H 3 (C double bond O) C l and the second reagent is A l C l 3.

C) 1. CH3CH2CH2Cl; 2. PCC, CH2Cl2; 3. Br2FeBr3

D) 1. An illustration shows two reagents used in a chemical reaction. The first reagent is C H 3 C H 2 C H 2 (C double bond O) C l and the second reagent is A l C l 3. /AlCl3; 2. Br2/FeBr3

E) 1. Br2/FeBr3; 2. Fuming H2SO4; 3. An illustration shows two reagents used in a chemical reaction. The first reagent is C H 3 (C double bond O) C l and the second reagent is A l C l 3. ; 4. H3O+

Diff: 2

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

92) What reagent or series of reagents could be used to carry out the conversion shown?

A reaction shows a reactant with SMILES string c1ccccc1 reacts to form the product that has a SMILES string of CCc1ccccc1Br.

A) 1. Br2/FeBr3; 2. H3O+, heat; 3. CH3CH2Cl/AlCl3

B) 1. Fuming H2SO4; 2. Br2/AlBr3; 3. H3O+, heat; 4. CH3CH2Cl/AlCl3

C) 1. Fuming H2SO4; 2. Br2/FeBr3; 3. H3O+, heat; 4. CH3CH2Cl/AlCl3

D) 1. CH3CH2Cl/AlCl3; 2. Fuming H2SO4; 3. Br2/ FeBr3; 4. H3O+, heat

E) 1. CH3CH2Cl/AlCl3; 2. Br2/ FeBr3; 3. H3O+, heat

Diff: 2

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

93) What series of reagents could be used to carry out the conversion shown?

A reaction shows a reactant with SMILES string c1ccccc1 reacts to form the product that has a SMILES string of c1cc(ccc1C(=O)O)Cl.

A) 1. CH3CH2Cl/AlCl3; 2. Cl2/FeCl3; 3. KMnO4, H2O, heat

B) 1. CH3CH2Cl/AlCl3; 2. Cl2/FeCl3; 3. PCC, CH2Cl2

C) 1. CH3CH2Cl/AlCl3; 2. Cl2/FeCl3; 3. Na2Cr2O7/H2O

D) 1. CH3CH2Cl/AlCl3; 2. KMnO4, H2O, heat; 3. Cl2/FeCl3

E) 1. CH3CH2Cl/AlCl3; 2. NaOH; 3. Cl2/FeCl3

Diff: 2

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

94) What series of reagents could be used to carry out the conversion shown?

A reaction shows a reactant with SMILES string c1ccccc1 reacts to form the product that has a SMILES string of CCCc1ccc(cc1)C(C)C.

A) 1. CH3CH2Cl/AlCl3; 2. Cl2/FeCl3; 3. KMnO4, H2O, heat

B) 1. CH3CH2Cl/AlCl3; 2. (CH3)2CHOH/AlCl3Cl2/FeCl3; 3. 3. H2O, heat

C) 1. (CH3)2CHCl/AlCl3; 2. An illustration shows two reagents used in a chemical reaction. The first reagent is C H 3 C H 2 (C double bond O) C l and the second reagent is A l C l 3. ; 3. Zn(Hg)/HCl, heat

D) 1. An illustration shows two reagents used in a chemical reaction. The first reagent is C H 3 C H 2 (C double bond O) C l and the second reagent is A l C l 3. ; 2. CH3CH2Cl/AlCl3; 3. H2O, heat

E) 1. The structure of the reagent used in a chemical reaction is C H 3 C H 2 C H 2 (C double bond O) C l. ; NaOH; 2. (CH3)2CHCl/AlCl3; 3. H2O, heat

Diff: 2

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

95) What series of reagents could be used to carry out the conversion shown?

A reaction shows a reactant with SMILES string c1ccccc1 reacts to form the product that has a SMILES string of CC(C#N)C1C=CC(=CC=1)S(O)(=O)=O.

A) 1. CH3CH2Cl/AlCl3; 2. NBS; 3. NaCN; 4. fuming H2SO4

B) 1. CH3CH2Cl/AlCl3; 2. fuming H2SO4, heat; 3. NBS, heat; 4. NaCN

C) 1. Fuming H2SO4; 2. NBS, heat; 3. NaCN; 4. CH3CH2Cl/AlCl3

D) 1. Fuming H2SO4; 2. NBS, heat; 3. CH3CH2Cl/AlCl3; 4. NaCN;

E) 1. CH3CH2Cl/AlCl3; 2. NBS; 3. fuming H2SO4; 4. NaCN

Diff: 2

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

96) What series of reagents could be used to carry out the conversion shown?

A reaction shows a s c1ccccc1 reacts to form the product that has a SMILES string of CC(C)c1c(cccc1Br)Br.

A) 1. (CH3)2CHCl/AlCl3; 2. NaOH; 3. excess Br2/FeBr3; 3. fuming H2SO4

B) 1. CH3CH2Cl/AlCl3; 2. Br2; 3. H2O, heat

C) 1. (CH3)2CHCl/AlCl3; 2. Zn(Hg)/HCl, heat; 3. excess Br2/FeBr3; 4. H3O+, heat

D) 1. excess Br2/FeBr3; 2. H3O+, heat; 3. (CH3)2CHCl/AlCl3; 4. fuming H2SO4

E) 1. (CH3)2CHCl/AlCl3; 2. fuming H2SO4; 3. excess Br2/FeBr3; 4. H3O+, heat

Diff: 2

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

97) What series of reagents could be used to carry out the conversion shown?

A reaction shows the reactant with SMILES string c1ccccc1 reacts to form the product that has a SMILES string of c1cc(c(c(c1)Br)C(=O)O)Br.

A) 1. excess Br2/FeBr3; 2. CH3CH2Cl/AlCl3; 3. fuming H2SO4; 4. dilute H2SO4, heat; 5. NaCr2O7/H2SO4/H2O

B) 1. CH3CH2Cl/AlCl3; 2. fuming H2SO4; 3. excess Br2/FeBr3; 4. dilute H2SO4, heat; 5. NaCr2O7/H2SO4/H2O

C) 1. excess Br2/FeBr3; 2. CH3CH2CH2Cl/AlCl3; 3. fuming H2SO4; 4. CH3CH2Cl/AlCl3; 5. fuming H2SO4;

D) 1. excess Br2/FeCl3; 2. H3O+, heat; 3. (CH3)2CHCl/AlCl3; 4. fuming H2SO4

E) 1. CH3CH2Cl/AlCl3; 2. fuming H2SO4; 3. excess Br2/FeBr3; 4. NaCr2O7/H2SO4/H2O

Diff: 2

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

98) What series of reagents could be used to carry out the conversion shown?

A reaction shows the reactant with SMILES string c1ccccc1 reacts to form the product that has a SMILES string of c1cc(ccc1C(Cl)(Cl)Cl)Cl.

A) 1. Cl2/FeCl3; 2. CH3Cl/AlCl3; 3. excess Cl2, heat

B) 1. CH3Cl/AlCl3; 2. Cl2/FeCl3; 3. excess Cl2, heat

C) 1. excess Cl2/FeCl3; 2. H3O+; 3. CH3Cl/AlCl3

D) 1. Excess Cl2; 2. CH3Cl/AlCl3

E) 1. Cl2/FeBr3; 2. CH3Cl/AlCl3; 3. H3O+, heat

Diff: 2

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

99) What series of reagents could be used to carry out the conversion shown?

A) 1. Cl2/FeBr3; 2. CH3Cl/AlCl3CH3MgBr/ether; 3. H2O

B) 1. Cl2/FeCl3; 2. CH3Cl/AlCl3CH3MgBr/ether; 3. H2O

C) 1. excess Cl2/FeCl3; 2. CH3MgBr/ether; 3. H2O, heat

D) 1. Cl2/FeCl3; 2. CH3MgBr/ether; 3. H2O; 4. H3PO4, heat

E) 1. CH3MgBr/ether; 2. Cl2/FeCl3; 3. H2O; 4. H3PO4, heat

Diff: 2

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

100) What reagents are necessary to prepare 1-bromo-3-isobutylbenzene from benzene?

A) 1. Excess Br2; 2. CH3CH2CH2CH2Cl; 3. Zn(Hg), HCl, heat

B) 1. Br2/FeBr3; 2. Zn(Hg), HCl, heat; 3. The condensed formulas for a set of reagents read, (C H 3) 2 C H (double-bonded to O) C C l/A l C l 3.

C) 1. The condensed formulas for a set of reagents read, (C H 3) 2 C H (double-bonded to O) C C l/A l C l 3. ; 2. Br2/FeBr3; 3. Zn(Hg), HCl, heat

D) 1. Br2/FeBr3; 2. The condensed formulas for a set of reagents read, (C H 3) 2 C H (double-bonded to O) C C l/A l C l 3. ; 3. Zn(Hg), HCl, heat

E) 1. Zn(Hg), HCl, heat; 2. Br2/FeBr3; 3. The condensed formulas for a set of reagents read, (C H 3) 2 C H (double-bonded to O) C C l/A l C l 3.

Diff: 2

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

101) What is the structure of the major product when anisole is treated with the reagents shown?

1. Br2, FeBr3

2. HNO3, H2SO4

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

102) What series of reagents could be used to carry out the conversion shown?

A reaction shows the reactant with SMILES string of c1ccccc1 that reacts to form the product that has a SMILES string of CC(C)(c1cccc(c1)Cl)O.

A) 1. The condensed formulas for a set of reagents read, C H 3 C (double-bonded to O) C l/A l C l 3. ; 2. Cl2/FeCl3; 3. CH3MgBr; 4. H2O

B) 1. Cl2/FeCl3; 2. CH3MgBr; 3. H2O; 4. The condensed formulas for a set of reagents read, C H 3 C (double-bonded to O) C l/A l C l 3.

C) 1. The condensed formulas for a set of reagents read, C H 3 C (double-bonded to O) C l/A l C l 3. ; 2. CH3CH2Cl/AlCl3; 3. excess Cl2; 4. H3O+, heat

D) 1. The condensed formulas for a set of reagents read, C H 3 C (double-bonded to O) C l/A l C l 3. ; 2. CH3CH2Cl/AlCl3; 3. H3O+, heat

E) 1. CH3COOH; 2. Cl2; 3. CH3MgBr; 4. H2O

Diff: 2

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

103) What series of reagents could be used to carry out the conversion shown?

A reaction shows the reactant with SMILES string c1ccccc1 reacts to form the product that has a SMILES string of COc1c(cc(cc1Br)[N+](=O)[O-])Br.

A) 1. HNO3/H2SO4; 2. Cl2/FeCl3; 3. CH3ONa; 4. excess Br2/FeBr3

B) 1. HNO3/H2SO4; 2. CH3ONa; 3. excess Br2/FeBr3; 4. Cl2/FeCl3

C) 1. Excess Cl2; 2. HNO3/H2SO4; 3. excess NBS

D) 1. Cl2/FeCl3; 2. HNO3/H2SO4; 3. CH3ONa; 4. excess Br2/FeBr3

E) 1. Cl2/FeCl3; 2. HNO3/H2SO4; 3. CH3ONa

Diff: 3

Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism

104) What series of reagents could be used to carry out the conversion shown?

A reaction shows the reactant with SMILES string c1ccccc1 reacts to form the product that has a SMILES string of c1cc(c(cc1[N+](=O)[O-])Cl)C(=O)O.

A) 1. CH3CH2Cl/AlCl3; 2. HNO3/H2SO4; 3. Cl2/FeCl3; 4. KMnO4/NaOH/H2O

B) 1. CH3CH2Cl/AlCl3; 2. HNO3/H2SO4; 3. KMnO4/NaOH/H2O; 4. H3O+

C) 1. HNO3/H2SO4; 2. CH3CH2Cl/AlCl3; 3. Cl2/FeCl3; 4. KMnO4/NaOH/H2O; 5. H3O+

D) 1. CH3CH2Cl/AlCl3; 2. Cl2/FeCl3; 3. KMnO4/NaOH/H2O; 4. HNO3/H2SO4; 5. H3O+

E) 1. CH3CH2Cl/AlCl3; 2. HNO3/H2SO4; 3. Cl2/FeCl3; 4. KMnO4/NaOH/H2O; 5. H3O+

Diff: 3

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

105) What reagent or series of reagents could be used to carry out the conversion shown?

A reaction shows the reactant with SMILES string c1ccccc1 reacts to form the product that has a SMILES string of c1c(cc(c(c1Br)O)Br)Br.

A) 1. Cl2/FeCl3; 2. H3O+ ; 3. excess Br2/FeBr3

B) 1. Cl2/FeCl3; 2. NaOH, heat; 3. H3O+ ; 4. excess Br2/FeBr3

C) 1. Br2/FeBr3; 2. NaOH, heat; 3. H3O+ ; 4. excess Br2/FeBr3

D) 1. Br2/FeBr3; 2. NaOH, heat; 3. H3O+

E) 1. excess Cl2/FeCl3; 2.H3O+ ; 3. excess Br2/FeBr3

Diff: 3

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

106) What would be an appropriate first step for a stepwise synthesis to convert benzene to the compound shown?

The bond-line structure of a compound has a benzene ring, in which C-1 is bonded to Bromo ethyl group, C H 2 C H 2 B r, C-3, and C-5 are bonded to N O 2 groups.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

107) What would be a good choice for the first reagent to begin a series of reactions to convert benzene to the product shown?

The bond-line structure of a compound has a SMILES string of c1cc(c(cc1[N+](=O)[O-])S(=O)(=O)O)O.

A) H3O+

B) HNO3/H2SO4

C) NaOH, heat

D) Cl2/FeCl3

E) fuming H2SO4

Diff: 3

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

108) What series of reagents could be used to carry out the conversion of benzene to the product shown?

An illustration shows a product and a series of reagents.
The bond-line structure of product has a SMILES string of c1cc(ccc1CCC#N)Br.

A) 1. CH3CH2Cl/AlCl3; 2. Br2FeBr3; 3. NBS, heat; 4. NaCN; 5. CH3CH2ONa; 6. HBr/CH3OOCH3

B) 1. CH3CH2Cl/AlCl3; 2. NBS, heat; 3. CH3CH2ONa; 4. HBr/CH3OOCH3; 5. NaCN

C) 1. CH3CH2Cl/AlCl3; 2. NBS, heat; 3. Br2FeBr3; 4. CH3CH2ONa; 5. HBr/CH3OOCH3; 6. NaCN

D) 1. Br2FeBr3; 2. CH3CH2Cl/AlCl3; 3. NBS, heat; 4. CH3CH2ONa; 5. HBr/CH3OOCH3; 6. NaCN

E) 1. Br2FeBr3; 2. NBS, heat; 3. CH3CH2ONa; 4. HBr/CH3OOCH3; 5. CH3CH2Cl/AlCl3; 6. NaCN

Diff: 3

Learning Objective: 18.12 Design a synthesis for a substituted benzene ring

109) Which of the criteria listed is necessary for a nucleophilic aromatic substitution reaction?

A) the ring must contain a very strong electron withdrawing group

B) the ring must contain a leaving group

C) the leaving group must be ortho or para to the electron withdrawing group

D) the leaving group must be meta to the electron withdrawing group

E) A, B and C

Diff: 1

Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism

110) Which of the compounds listed will not undergo nucleophilic aromatic substitution?

A) 1-chloro-2,4-dinitrobenzene

B) 1-bromo-4-nitrobenzene

C) o-chloronitrobenzene

D) m-chloronitrobenzene

E) p-chloronitrobenzene

Diff: 1

Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism

111) What is the predicted product of the following reaction?

A partial reaction shows the reactant that has a SMILES string of c1cc(ccc1[N+](=O)[O-])Cl reacts with sodium methoxide, C H 3 O N a.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism

112) What is the predicted product of the reaction shown?

A partial reaction shows the reactant that has a SMILES string of c1cc(ccc1[N+](=O)[O-])Cl reacts with ammonia, N H 3.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism

113) What is the predicted product for the reaction shown?

A partial reaction shows the reactant that has a SMILES string of c1cc(c(cc1[N+](=O)[O-])[N+](=O)[O-])Cl reacts with morpholine, with SMILES string C1COCCN1.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism

114) What is the predicted product for the reaction shown?

A partial reaction shows the reactant that has a SMILES string of c1cc(ccc1[N+](=O)[O-])Br reacts with methylamine, C H 3 N H 2.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism

115) What is the expected product of the reaction shown?

A partial reaction shows the reactant that has a SMILES string of c1cc(cc(c1)[N+](=O)[O-])[N+](=O)[O-] reacts with bromine/aluminum chloride, B r 2/A l C l 3.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism

116) Which structure(s) are major resonance contributors for the intermediate that results when p-chloronitrobenzene is treated with NaOH?

A) I and II

B) I and III

C) I, II, and IV

D) I, III, IV, and V

E) I, II, IV, and V

Diff: 3

Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism

117) What is the predicted product of the reaction shown?

A partial reaction shows the reactant that has a SMILES string of c1cc(ccc1[N+](=O)[O-])Cl reacts with sodium methoxide, C H 3 O N a.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism

118) What is(are) the predicted product(s) of the reaction shown?

A partial reaction shows the reactant that has a SMILES string of Cc1ccc(cc1)Cl reacts first with sodium hydroxide in the presence of heat, and second with hydronium ion, H 3 O plus.

The bond-line structure of five compounds labeled 1 through 5 (in Roman Numerals) are as follows:
The first compound has a SMILES string of Cc1ccc(c(c1)O)Cl.
The second compound has a SMILES string of Oc1c(C)ccc(Cl)c1C.
The third compound has a SMILES string of Cc1cccc(c1)O.
The fourth compound has a SMILES string of Cc1ccc(cc1)O.
The fifth compound has a SMILES string of c1cc(cc(c1)Cl)O.

A) I

B) II

C) I and III

D) I and IV

E) III and IV

Diff: 1

Learning Objective: 18.14 Predict the products of an elimination-addition reaction

119) What is(are) the predicted product(s) of the reaction shown?

A partial reaction shows the reactant that has a SMILES string of CCc1ccc(cc1)Cl reacts first with sodium amide, N a N H 2, ammonia, N H 3, and second with hydronium ion, H 3 O plus.

A) I

B) III

C) II and III

D) IV and V

E) II and V

Diff: 1

Learning Objective: 18.14 Predict the products of an elimination-addition reaction

120) What is the mechanism by which the following reaction occurs?

A reaction shows the reactant with SMILES string CCc1ccc(cc1)C reacts with chlorine, C l 2/ Iron (3) chloride, F e C l 3 to form the product that has a benzene ring, in which C-1 is bonded to a chlorine atom, C-3 is bonded to an ethyl group, and C-6 is bonded to a methyl group.

A) elimination-addition

B) nucleophilic aromatic substitution

C) electrophilic aromatic substitution

D) both B and C

Diff: 1

Learning Objective: 18.15 Predict the mechanism of an aromatic substitution reaction

121) What is the mechanism by which the following reaction occurs?

A reaction shows the reactant with SMILES string c1cc(ccc1[N+](=O)[O-])Br reacts with sodium methoxide, N a O C H 3 to form the product with the SMILES string COc1ccc(cc1)[N+](=O)[O-].

A) elimination-addition

B) nucleophilic aromatic substitution

C) electrophilic aromatic substitution

D) addition-elimination

E) both B and C

Diff: 2

Learning Objective: 18.15 Predict the mechanism of an aromatic substitution reaction

122) What is the mechanism by which the following reaction occurs?

A partial reaction shows the reactant that has a SMILES string of CCc1ccc(cc1)Cl reacts first with sodium amide, N A N H 2, and ammonia, N H 3, and second with hydronium ion, H 3 O plus.

A) elimination-addition

B) nucleophilic aromatic substitution

C) electrophilic aromatic substitution

D) addition-elimination

E) both B and C

Diff: 2

Learning Objective: 18.15 Predict the mechanism of an aromatic substitution reaction

© (2021) John Wiley & Sons, Inc. All rights reserved. Instructors who are authorized users of this course are permitted to download these materials and use them in connection with the course. Except as permitted herein or by law, no part of these materials should be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or otherwise.

Document Information

Document Type:

DOCX

Chapter Number:

Created Date:

Aug 21, 2025

Chapter Name:

Chapter 18 Aromatic Substitution Reactions

Author:

David R. Klein

Connected Book

Organic Chemistry 4e | Test Bank by Klein

By David R. Klein

Test Bank General

View Product →

Explore recommendations drawn directly from what you're reading

Chapter 16 Conjugated Pi Systems And Pericyclic Reactions

DOCX Ch. 16

Chapter 17 Aromatic Compounds

DOCX Ch. 17

Chapter 18 Aromatic Substitution Reactions

DOCX Ch. 18 Current

Chapter 19 Aldehydes And Ketones

DOCX Ch. 19

Chapter 20 Carboxylic Acids And Their Derivatives

DOCX Ch. 20

$24.99

100% satisfaction guarantee

Buy Full Test Bank

Quick Navigation

Preview Document Info Connected Book Recommendations

Benefits

Immediately available after payment

Answers are available after payment

ZIP file includes all related files

Files are in Word format (DOCX)

Check the description to see the contents of each ZIP file

We do not share your information with any third party

Chapter 18 Aromatic Substitution Reactions Test Bank Answers

Document Information

Connected Book

Organic Chemistry 4e | Test Bank by Klein

Explore recommendations drawn directly from what you're reading

$24.99

Quick Navigation

Benefits

Report Unauthorized Use

Added to Cart