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Chemistry LibreTexts

22.11: Additional Exercises

  • Page ID
    183160
  • General Review

    20-1 Predict which amine is more basic and provide a reason for your answer.

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    20-2 Give the product of the following reaction.

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    20-3 Predict the final product of the following reaction chain and give its IUPAC name.

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    20-4 Propose a route of synthesis from nitrobenzene to the given product. Assume the given molecule is the major product, and for the purposes of this problem, ignore its isomers.

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    20-5 Choose the correct answer that describes the product of the following Cope elimination reaction.

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    a) N,N,2-trimethylpropan-1-iminium

    b) N,N,2-trimethylpropan-1-amine

    c) 2-methylprop-1-ene and N-hydroxy-N-methylmethanamine

    d) N-hydroxy-N,2-dimethylpropan-1-amine

    20-6 Explain why the following reaction might not be the best way to synthesize ethanamine.

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    Basicity and Effects of Amines

    20-7 Draw all possible resonance structures for aniline and cyclohexanamine.

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    20-8 Identify which of the following nitroaniline isomers is the most basic and give a reason for your answer.

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    20-9 For the following compounds, identify which substituents are pi-acceptors of the electrons from the amine group (if applicable) and if they are, draw their resonance structure to show the movement of electrons.

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    Aromatic Substitution of Arylamines and Pyridin

    20-10 Explain why the following arylamine needs to be turned into an amide before a Friedel-Crafts acylation and then predict the final product of the reaction.

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    20-11 Predict the products of the following reactions.

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    20-12 Predict the product of the following reaction and provide the correct IUPAC nomenclature.

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    Alkylation and Acylation of Amines

    20-13 Predict the product of the following acylation reaction.

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    20-14 Suggest a route of synthesis for the following compound, starting with benzoyl chloride.

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    20-15 Choose the correct product of the following reaction.

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    Formation of Sulfonamides

    20-16 Choose the correct structure of the product of the following reaction.

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    20-17 Provide the structure of the intermediate compound and final product of the following reaction.

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    20-18 Predict the product of the following reaction.

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    Amines as Leaving Groups: The Hofmann Elimination

    20-19 Predict the major alkene product of the following Hofmann elimination reaction and give the proper IUPAC nomenclature.

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    20-20 Choose the correct product of the following reaction.

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    20-21 Propose a route of synthesis from pentan-1-amine to pentanal (include a Hofmann elimination reaction).

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    Oxidation of Amines: The Cope Elimination

    20-22 Predict the structure and give the proper IUPAC nomenclature of the product of the following reaction.

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    20-23 Propose a route of synthesis for the following compound, starting with cyclohexanecarboxylic acid and include a Cope elimination reaction.

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    20-24 Predict the structure of the product of the following reaction.

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    Reactions of Amines with Nitrous Acid

    20-25 Predict the product of the following reaction and provide the correct IUPAC nomenclature.

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    20-26 Predict the products of the following reactions.

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    20-27 Suggest a route of synthesis for the following product, starting with aniline.

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    Synthesis of Amines by Reductive Amination and Acylation-Reduction

    20-28 Predict the product of the following reaction and provide its IUPAC nomenclature.

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    20-29 Identify which route of synthesis is the better way to make N-(cyclopentylmethyl)- -N-methylethanamine and then show the intermediate molecules for the correct path.

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    20-30 Choose the correct IUPAC nomenclature of the product of the following reaction.

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    a) N-propylbenzamide

    b) phenyl(propylamino)methanol

    c) N-benzylpropan-1-amine

    d) benzamide

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