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Ch.12 Alcohols, Thiols, Ethers, Aldehydes, and Ketones
Timberlake - Chemistry: An Introduction to General, Organic, and Biological Chemistry 13th Edition
Timberlake13th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9780134421353Not the one you use?Change textbook
Chapter 12, Problem 66

A compound with the formula C₅H₁₀O oxidizes to give 3-pentanone. Draw the condensed structural formula and give the IUPAC name for the compound. (12.3, 12.4)

Verified step by step guidance
1
Identify the functional group in 3-pentanone, which is a ketone with the carbonyl group (C=O) on the third carbon.
Recognize that the compound C₅H₁₀O must be an alcohol, as alcohols oxidize to form ketones.
Determine the structure of the alcohol that would oxidize to 3-pentanone. The alcohol must have the hydroxyl group (-OH) on the carbon that will become the carbonyl carbon in the ketone.
Draw the structure of the alcohol: CH₃CH₂CH(OH)CH₂CH₃, which places the hydroxyl group on the third carbon.
Name the alcohol using IUPAC nomenclature: 3-pentanol.

Key Concepts

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

Condensed Structural Formula

A condensed structural formula is a way of representing a chemical compound that shows the arrangement of atoms in a molecule while omitting some of the bonds. It typically lists the atoms in a linear format, indicating how they are connected. For example, in the case of C₅H₁₀O, the condensed formula would illustrate the connectivity of carbon, hydrogen, and oxygen atoms, providing insight into the molecular structure.
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IUPAC Naming

IUPAC naming refers to the systematic method of naming chemical compounds established by the International Union of Pure and Applied Chemistry. This nomenclature provides a unique name for each compound based on its structure, functional groups, and the number of carbon atoms. For the compound C₅H₁₀O, understanding IUPAC rules is essential to derive the correct name, which reflects its functional group and carbon chain length.
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Oxidation Reaction

An oxidation reaction involves the loss of electrons or an increase in oxidation state by a molecule, atom, or ion. In organic chemistry, this often refers to the conversion of alcohols to ketones or aldehydes. In the context of the question, the oxidation of the compound C₅H₁₀O to form 3-pentanone illustrates how functional groups change during chemical reactions, which is crucial for understanding the transformation of organic compounds.
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