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Ch. 18 - Ketones and Aldehydes
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Non è quello che usi tu?Cambia libro di testo
Tutti i libri di testoWade 9th EditionCh. 18 - Ketones and AldehydesProblema 60d
Capitolo 18, Problema 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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Reaction Mechanisms

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Functional Groups

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Synthesis Strategies

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