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    AK - Practice Problems Chapter 15 Organic Chemistry

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    angeline
    This document contains 20 practice problems about electrophilic aromatic substitution reactions and Friedel-Crafts reactions. The problems test understanding of concepts like resonance stabilization of carbocations, directing effects of substituents, suitable reaction conditions, and predicting products of multi-step synthesis problems. The key takes students through example reactions and asks them to identify structures, reaction intermediates, and major products.

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    © All Rights Reserved
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    AK - Practice Problems Chapter 15 Organic Chemistry

    Uploaded by

    angeline
    149 views10 pages
    This document contains 20 practice problems about electrophilic aromatic substitution reactions and Friedel-Crafts reactions. The problems test understanding of concepts like resonance stabilization of carbocations, directing effects of substituents, suitable reaction conditions, and predicting products of multi-step synthesis problems. The key takes students through example reactions and asks them to identify structures, reaction intermediates, and major products.

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    AK_Practice problems chapter 15 Organic Chemistry

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    This document contains 20 practice problems about electrophilic aromatic substitution reactions and Friedel-Crafts reactions. The problems test understanding of concepts like resonance stabilization of carbocations, directing effects of substituents, suitable reaction conditions, and predicting products of multi-step synthesis problems. The key takes students through example reactions and asks them to identify structures, reaction intermediates, and major products.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    149 views10 pages

    AK - Practice Problems Chapter 15 Organic Chemistry

    Uploaded by

    angeline
    This document contains 20 practice problems about electrophilic aromatic substitution reactions and Friedel-Crafts reactions. The problems test understanding of concepts like resonance stabilization of carbocations, directing effects of substituents, suitable reaction conditions, and predicting products of multi-step synthesis problems. The key takes students through example reactions and asks them to identify structures, reaction intermediates, and major products.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 10

    Practice problems chapter 15

    1) Which of the following structures contribute(s) to the resonance hybrid of the intermediate
    formed when acetanilide undergoes para-bromination?

    a) I
    b) II
    c) III
    d) IV
    e) All of these choices.

    Answer: E

    2) Which of the following contributors to the resonance stabilized hybrid formed when aniline
    undergoes para-chlorination would be exceptionally stable?

    a) I
    b) II
    c) III
    d) IV
    e) None of these choices.

    Answer: B

    3) Which of these liquids would be unsuitable as an inert solvent for a Friedel-Crafts reaction?

    a) Chlorobenzene
    b) Nitrobenzene
    c) Acetophenone
    d) (Trifluoromethyl) benzene
    e) All of these choices could be used.

    Answer: A
    4) This substituent deactivates the benzene ring towards electrophilic substitution but directs the
    incoming group chiefly to the ortho and para positions.

    a) -OCH​2​CH​3
    b) -NO​2
    c) -F
    d) -CF​3
    e) -NHCOCH​3

    Answer: C

    5) This molecule ​does not normally​ participate as a reactant in a Friedel-Crafts reaction.

    a) Benzene
    b) Chlorobenzene
    c) Nitrobenzene
    d) Toluene
    e) ​tert​-Butylbenzene

    Answer: C

    6) What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and HF?

    a) butylbenzene
    b) 2-phenylbutane
    c) 2-methyl-1-phenylpropane
    d) ​t-​butylbenzene
    e) 2,2-diphenylbutane

    Answer: B

    7) A mixture of chlorobenzene (1 mol) and anisole (1mol) is allowed to react with Br​2​ (0.5 mol)
    in the presence of trace amounts of FeBr​3​. What is the principal product of the competing
    reactions?

    a) 1-bromo-4-chlorobenzene
    b) 1-bromo-2-chlorobenzene
    c) 1-bromo-3-chlorobenzene
    d) 4-bromoanisole
    e) 3-bromoanisole

    Answer: D

    8) Which of the following reactions could be used to synthesize ​tert​-butylbenzene?

    a)

    b)

    c)
    d) All of these choices.
    e) None of these choices.

    Answer: D

    9) Consider the following reaction: what is the expected product?

    a) I
    b) II
    c) III
    d) IV
    e) V

    Answer: B
    10) Which of the following reactions would produce isopropylbenzene?

    a)

    b)

    c)

    d)
    e) All of these choices.

    Answer: E

    11) Which of the following reactions would give the product(s) indicated in substantial amounts
    (i.e., in greater than 50% yield)?
    IV. None

    Ans D

    12) The major product(s) of the following reaction,

    would be:

    a) I
    b) II
    c) III
    d) IV
    e) V

    Answer: E

    13) What would be the product of the following reaction sequence?


    a) I
    b) II
    c) III
    d) IV
    e) V

    Answer: E

    14) What would you expect to be the major product obtained from the following reaction?

    a) I
    b) II
    c) III
    d) IV
    e) V

    Answer: E

    15) The major product(s), A, of the following reaction,

    would be:

    a) I
    b) II
    c) A mixture of I and II.
    d) III
    e) IV

    Answer: E

    16) What would you expect to be the major product obtained from the following reaction?
    a) I
    b) II
    c) III
    d) IV
    e) V

    Answer: E

    17) Toluene is subjected to the action of the following reagents in the order given: (1)
    KMnO​4​,OH​-​, heat; then H​3​O​+​ (2) HNO​3​, H​2​SO​4​ (3) Br​2​, FeBr​3
    What is the final product of this sequence?

    a) I
    b) II
    c) III
    d) IV
    e) V

    Answer: A

    18) What product would result from the following series of reactions,

    a) I
    b) II
    c) III
    d) IV
    e) V

    Answer: D

    19) Arrange the following compounds in order of ​decreasing​ reactivity in electrophilic


    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

    Answer: B

    20) Which of the following carbocations would be most stable?

    a)

    b)

    c)

    d)

    e)

    Answer: E

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