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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.

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    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.

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

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

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    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).

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

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    Halogenation, Nitration, and Sulfonation of Benzene

    18-12 Predict the products of the following reactions.

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

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

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    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.

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

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

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    Deactivating, Meta-Directing Substituents

    18-18 Predict the products of the following reactions.

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    18-19 Predict the product of the following reaction.

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

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    Halogen Substitutes: Deactivating, but Ortho, Para-Directing

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

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    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.

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    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).

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    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.

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

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

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    Friedel-Crafts Alkylation/Acylation

    18-27 Predict the products of the following reactions.

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    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.

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

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    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.

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    18-31 Predict the product of the following reaction.

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

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    Aromatic Substitutions Using Organometallic Reagents

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

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

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

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    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.

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

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

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