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Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Non è quello che usi tu?Cambia libro di testo
Capitolo 12, Problema 51c

Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.
(c)

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Identify the carbonyl compound in the image. The structure shown is a ketone, specifically a phenyl-2-propanone.
Recall that ketones are typically formed by the oxidation of secondary alcohols. Therefore, the alcohol precursor must be a secondary alcohol.
Examine the structure of the ketone. The carbonyl group is attached to a phenyl group and a propyl group, indicating that the secondary alcohol must have a hydroxyl group on the carbon that is bonded to both the phenyl and propyl groups.
Determine the structure of the alcohol. The secondary alcohol that would oxidize to form this ketone is 1-phenyl-2-propanol, where the hydroxyl group is on the second carbon of the propyl chain.
Understand the oxidation process. During oxidation, the hydroxyl group of the secondary alcohol is converted into a carbonyl group, resulting in the formation of the ketone shown in the image.

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Alcohol Classification

Alcohols are classified into three categories: primary, secondary, and tertiary, based on the number of carbon atoms attached to the carbon bearing the hydroxyl (-OH) group. Primary alcohols can be oxidized to aldehydes, secondary alcohols to ketones, and tertiary alcohols generally do not oxidize to carbonyl compounds due to the lack of a hydrogen atom on the carbon bearing the -OH group.
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Structural Classification

Oxidation Reactions

Oxidation in organic chemistry refers to the process of increasing the oxidation state of a molecule, often involving the addition of oxygen or the removal of hydrogen. In the case of alcohols, oxidation typically converts them into carbonyl compounds, such as aldehydes or ketones, depending on the type of alcohol being oxidized.
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Benzylic Oxidation

Reagents for Oxidation

Common reagents used for the oxidation of alcohols include potassium dichromate (K2Cr2O7), chromium trioxide (CrO3), and pyridinium chlorochromate (PCC). The choice of reagent can influence the extent of oxidation, with some reagents selectively oxidizing primary alcohols to aldehydes while others may further oxidize them to carboxylic acids.
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Reagents used to oxidize Sulfides.