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Ch. 18 - Ketones and Aldehydes
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh. 18 - Ketones and AldehydesProblem 60d
Chapter 18, Problem 60d

Show how you would accomplish the following syntheses.
(d) Chemical reaction showing the conversion of a phenyl alcohol to tetralone with an arrow indicating the synthesis process.

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1
Step 1: Begin by oxidizing the primary alcohol group (-CH2OH) in the starting material, Ph-(CH2)4-OH, to an aldehyde (-CHO). This can be achieved using an oxidizing agent such as PCC (Pyridinium Chlorochromate). The product will be Ph-(CH2)3-CHO.
Step 2: Perform an intramolecular aldol condensation. Under basic conditions (e.g., NaOH or KOH), the aldehyde group (-CHO) will react with the alpha-hydrogen of the adjacent methylene group (-CH2-) to form a cyclic intermediate. This step creates the six-membered ring structure.
Step 3: Dehydrate the aldol intermediate to form the conjugated enone. This step involves the elimination of water, typically under acidic or basic conditions, resulting in the formation of the double bond in the ring structure.
Step 4: Hydrogenate the double bond in the enone selectively to form the saturated ketone. This can be achieved using a catalyst such as palladium on carbon (Pd/C) under hydrogen gas (H2). The product will be tetralone.
Step 5: Verify the structure of tetralone by analyzing its chemical properties or using spectroscopic techniques such as NMR or IR to confirm the presence of the ketone group and the cyclic structure.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Reaction Mechanisms

Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. A clear grasp of mechanisms helps predict the outcomes of reactions and the conditions required for successful synthesis.
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Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups is essential for predicting reactivity and understanding how different compounds can be synthesized or transformed. Each functional group has unique properties that influence the overall behavior of the molecule.
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Synthesis Strategies

Synthesis strategies involve planning a series of chemical reactions to construct a desired compound from simpler starting materials. This includes selecting appropriate reagents, reaction conditions, and understanding the order of reactions. Effective synthesis requires knowledge of various reactions and the ability to foresee potential challenges and side reactions.
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Related Practice
Textbook Question

There are three dioxane isomers: 1,2-dioxane, 1,3-dioxane, and 1,4-dioxane. One of these acts like an ether and is an excellent solvent for Grignard reactions. Another one is potentially explosive when heated. The third one quickly hydrolyzes in dilute acid. Show which isomer acts like a simple ether, and then explain why one of them is potentially explosive.

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Textbook Question

There are three dioxane isomers: 1,2-dioxane, 1,3-dioxane, and 1,4-dioxane. One of these acts like an ether and is an excellent solvent for Grignard reactions. Another one is potentially explosive when heated. The third one quickly hydrolyzes in dilute acid. Propose a mechanism for the acid hydrolysis of the third isomer.

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Textbook Question

Show how you would accomplish the following syntheses.

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Textbook Question

Show how you would accomplish the following syntheses.

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Show how you would accomplish the following syntheses.

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Textbook Question

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