EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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A common illicit synthesis of methamphetamine involves an interesting variation of the Birch reduction. A solution of ephedrine in alcohol is added to liquid ammonia, followed by several pieces of lithium metal. The Birch reduction usually reduces the aromatic ring, but in this case it eliminates the hydroxy group of ephedrine to give methamphetamine. Propose a mechanism, similar to that for the Birch reduction, to explain this unusual course of the reaction.
The (R)-isomer of a-terpineol is a component of perfumes and flavorings and has a lilac-like floral odor. The (S)-isomer has a pine-like odor. Propose two methods of producing a-terpineol using Grignard reactions. [Ignore stereochemistry in your synthesises.]
Arrange the compounds in order of INCREASING reactivity towards bromination.
Toluene, Nitrobenzene, Anisole, Aniline
Acetophenone, Bromobenzene, Aniline, Phenol
Acetanilide, Benzaldehyde, Toluene, Iodobenzene
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- The compound eutypine is an antibacterial agent isolated from the fungus Eutypa lata. This fungus results in a disease common to vineyards called eutyposis. Give a sequence of reactions that will take the following reactant and give eutypine when the other reactants used in the sequence are acetylene and acetone.arrow_forwardBenzene underwent a Friedel–Crafts acylation followed by a Wolff–Kishner reduction. The product gave the following 1H NMR spectrum. What acylchloride was used in the Friedel–Crafts acylation?arrow_forwardThe following compound may be synthesized through alkylation of an appropriate enamine with an alkyl bromide, followed by hydrolysis of the resulting immonium ion. Using this strategy, provide the necessary starting materials for the synthesis.arrow_forward
- The Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between acetophenone and 3-buten-2-one. Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine. Draw the structure of the Michael addition product. Draw the structure of the final product.arrow_forwardBenzene underwent a Friedel–Crafts acylation followed by a Wolff–Kishner reduction. The product gave the following 1H NMR spectrum. What acyl chloride was used in the Friedel–Crafts acylation?arrow_forwardThe Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between cyclohexanone and propenal Draw the structure of the product of the enamine formed between cyclohexanone and dimethylamine. - Michael addition to an α,β-unsaturated carbonyl compound, and - hydrolysis of the enamine in dilute acid to regenerate the ketone.arrow_forward
- Explain how benzaldehyde and dimedone reacts with each other, and then with the aminotriazole to form compound 1a in the presence of an acid catalyst. Provide a detailed reaction mechanism and explanation.arrow_forwardWhich of the reaction conditions could afford the following transformation?arrow_forwardCompound A undergoes an acid-catalyzed hydrolysis. One of the products (B) that is isolated gives the following 1H NMR spectrum. Identify the compounds A and Carrow_forward
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