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21.12: Additional Exercises

  • Page ID
    183147
  • General Review

    23-1 For each of the following reactions, predict the product. Then identify which one gives the kinetic product and which one gives the thermodynamic product. Explain your reasoning.

    23-2 Predict the final product of the following reaction.

    23-3 Explain why we obtain the products shown below as a result of the base catalyzed α-halogenation reaction, instead of a single or double halogenated product. 

    23-4 Identify the starting molecule of the aldol addition-condensation reaction that resulted in the final product below. 

    23-5 The following reaction is an example of an intramolecular aldol addition-condensation reaction. Given the aldol product, identify the starting molecule and the condensation product.

    23-6 Provide the final product of the following reaction (for now, ignore any stereochemistry).

     

    23-7 Predict the final product of the following reaction.

    Enols and Enolate Ions

    23-8 Choose the correct IUPAC nomenclature of the product of the following reaction and provide its structure.

    a)  dibromo(4-methylphenyl)methanol

    b)  4-methylbenzoic acid

    c)  4-methylbenzoyl bromide

    d)  bromo(4-methylphenyl)methanol

    23-9 Draw the mechanism for the following self-catalyzed halogenation reaction.

            

    23-10 Predict the product of the following reaction.

    Formation and Alkylation of Enamines

    23-11 Choose the correct IUPAC nomenclature for the product of the following reaction.

    a)  (2Z)-N,N-diethylpent-2-en-3-amine

    b)  N,N-diethylpentan-3-amine

    c)  3-(diethylamino)pentan-3-ol

    d)  Tetraethylhydrazine

    23-12 Predict the major products of the following reactions.

    23-13 Predict the product of the following reaction.

    Alpha Halogenation of Ketones

    23-14 Predict the product of the following reaction.

     

    23-15 Draw the mechanism for the α-halogenation step of the ketone in problem 23-14.

    23-16 Provide the structures of the products of the following reactions.

    Alpha Bromination of Acids: The HVZ Reaction

    23-17 Give the product of the following reaction.

     

    23-18 Choose the correct IUPAC nomenclature of the product of the following reaction.

    a)  1-chlorocyclohexane-1-carboxylic acid

    b)  1-bromocyclohexane-1-carbonyl chloride

    c)  1-chlorocyclohexane-1-carbonyl chloride

    d)  1-hydroxycyclohexane-1-carbonyl bromide

    23-19 Provide the structure and IUPAC nomenclature of the product of the following reaction.

     

    The Aldol Condensation of Ketones and Aldehydes

    23-20 Give the structure of the product of the following aldol condensation reaction.

    23-21 Predict the structure of the product of the following reaction.

    23-22 Provide the structure of the product of the following reaction.

     

    Dehydration of Aldol Products

    23-23 Choose the correct IUPAC nomenclature for the product of the following aldol condensation reaction.

    a)  5-ethyl-4-methylheptan-3-one

    b)  5-ethyl-4-methylhept-4-en-3-one

    c)  5-ethyl-5-hydroxy-4-methylheptan-3-one

    d)  (5Z)-5-ethyl-4-methylhept-5-en-3-one

    23-24 Provide the mechanism for the reaction to the answer for the previous question.

    23-25 For the following compounds, draw a possible product of the condensation step.

    Crossed Aldol Condensations

    23-26 Provide the structure of the product of the following  reaction.

    23-27 Suggest the structures of the starting compounds that were reacted to create this final crossed aldol condensation product.

    23-28 Provide the structures of all possible products of the following crossed aldol condensation reaction.

    Aldol Cyclizations

    23-29 Provide the IUPAC name for the product of the following intramolecular aldol condensation reaction.

    23-30 Identify the starting material used to create the following products of aldol cyclization.

    23-31 Starting with a single diketone molecule, propose a method of synthesis for the following compound that includes an aldol cyclization step.

     

         

    Claisen Condensations

    23-32 Predict the product of the following Claisen condensation reaction.

    23-33 Predict the final product of the following reaction.

    23-34 Provide the structure of the products of the following crossed Claisen condensation reactions.

    Syntheses Using β-Dicarbonyl Compounds

    23-35 Give the structure and IUPAC nomenclature of the product of the following reaction.

    23-36 Choose the correct IUPAC nomenclature of the product of the following reaction.

    a_  2,2,4,4-tetramethylpentan-3-one

    b)  2,2,4-trimethylpentan-3-one

    c)  2,4,4-trimethylpent-1-en-3-one

    d)  2,4,4-trimethyl-3-oxopentanoic acid

    23-37 Suggest a way to make (5-methylhexyl)benzene from 3-hydroxy-5-methylhexanoic acid.

    Conjugate Additions: The Michael Reaction

    23-38 For the following pairs of compounds, identify the Michael acceptor and the Michael donor.

    23-39 Predict the product of the following reaction chain.

    23-40 Pick the answer that correctly names the product of the following Michael addition reaction.

    a)  3-(ethylamino)butan-2-one

    b)  2-(ethylamino)butan-2-ol

    c)  4-(ethylamino)butan-2-one

    d)  4-(methylamino)butan-2-one

    The Robinson Annulation

    23-41 Predict a possible product of the following reactions.

    23-42 Given the following compound, predict the Michael acceptor and donor that initially reacted to allow for the aldol condensation to occur.

    23-43 Given the following Robinson annulation product, identify the intermediate compound that results from the Michael addition and exists before the aldol condensation.