21.12: Additional Exercises

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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.