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17.13: Additional Exercises

  • Page ID
    183087
  • 18-1  Draw the resonance structures for benzaldehyde to show the electron-withdrawing group.

    18-2  Draw the resonance structures for methoxybenzene to show the electron-donating group.

    18-3  How would make the following compounds from benzene?

    A) m-bromonitrobenzene

    B) m-bromoethylbenzene

    18-4  There is something wrong with the following reaction, what is it?

    18-5 Choose the correct answer.

     

    a)  1-methyl-3-(2-methylprop-1-en-1-yl)benzene

    b)  2-chloro-4-methyl-1-(2-methylprop-1-en-1-yl)benzene

    c)  1-chloro-3-(2-methylprop-1-en-1-yl)benzene

    d)  1-(1-chloroethenyl)-3-methylbenzene

    18-6 Predict the final product of the following reaction chain.

    18-7 Provide the final product for the following reactions.

    18-8 For the following reaction chain, provide the intermediate and final product(s).

    18-9 Give the IUPAC name for the final product(s) of the previous problem, 18-8.

    18-10 For the following reaction chain, provide the intermediate and final product(s).

    18-11 Give the final product of the following reactions.

    Halogenation, Nitration, and Sulfonation of Benzene

    18-12 Predict the products of the following reactions.

    18-13 Give the IUPAC nomenclature and structure of the product of the following reaction.

    18-14 Choose the correct answer that describes the best route of synthesis of the following molecule.

    a)  Chlorination, sulfonation, nitration

    b)  Sulfonation, nitration, chlorination

    c)  Nitration, sulfonation, chlorination

    Activating, Ortho-, Para-Directing Substituents

    18-15 For the following compounds, point to the position(s) on the ring that are most likely to have a substituent added. 

    18-16 Predict the major product of the following reactions.

    18-17 Provide  the correct IUPAC nomenclature and structure of the product of the following reaction.

    Deactivating, Meta-Directing Substituents

    18-18 Predict the products of the following reactions.

    18-19 Predict the product of the following reaction.

    18-20 Choose the pathway that will lead to the product formed on the right.

    Halogen Substitutes: Deactivating, but Ortho, Para-Directing

    18-21 Choose the correct IUPAC nomenclature of one of the products of the following reaction.

     

    a)  3-bromobenzene-1-sulfonic acid

    b)  4-bromobenzene-1-sulfonic acid

    c)  5-bromobenzene-1,3-disulfonic acid

    d)  4-bromophenyl hydrogen sulfate

    18-22 Predict the products of the following reactions.

    18-23 Propose a route of synthesis for the following compound, starting with chlorobenzene (assume any desired intermediate compounds can be isolated for use in subsequent steps).

     

    Effects of Multiple Substituents on Electrophilic Aromatic Substitution

    18-24 For the following compounds, identify which substituent is the stronger activating group and predict the position(s) of a subsequent electrophilic aromatic substitution. 

    18-25 Predict all possible singly chlorinated products of the following reaction.

    18-26 Rank the following compounds in order from slowest to fastest to go through an electrophilic aromatic substituent reaction.

    Friedel-Crafts Alkylation/Acylation

    18-27 Predict the products of the following reactions.

    18-28 Explain whether or not the following reaction is the best way to synthesize propylbenzene and if not, propose a better route of synthesis.

    18-29 Choose the correct answer and if a product is formed, provide the structure of the product.

    a)  No reaction

    b)  4-amino-2-methylbenzonitrile

    c)  4-amino-2-ethylbenzonitrile

    d)  N-(4-cyano-2-ethylphenyl)acetamide

    Nucleophilic Aromatic Substitution

    18-30 Predict the product of the following reaction and provide the correct IUPAC nomenclature.

    18-31 Predict the product of the following reaction.

    18-32 Suggest a route of synthesis to make N-hydroxy-3,5-dimethylaniline from 1-bromo-4-nitrobenzene.

    Aromatic Substitutions Using Organometallic Reagents

    18-33 Provide the structure and IUPAC nomenclature of the product of the following reaction.

    18-34 Suggest a route of synthesis to make 2-bromo-4-chlorobenzoic acid from 4-nitrobenzoic acid.

    18-35 Choose the correct IUPAC nomenclature for the product of the following reaction.

    a)  2-bromo-5-nitrobenzoic acid

    b)  2-bromo-5-cyanobenzoic acid

    c)  3-cyano-5-nitrobenzoyl bromide

    d)  3-bromo-5-cyanobenzoic acid

    Side-Chain Reactions of Benzene Derivatives

    18-36 Predict the products of the following reactions.

    18-37 Choose the correct structure of the product of the following reaction.

    18-38 Provide the intermediate and final products of the following reactions.