Textbook Question
A compound with the formula C5H10O oxidizes to give 3-pentanone. Draw the condensed structural formula and give the IUPAC name for the compound.
Ch.12 Alcohols, Thiols, Ethers, Aldehydes, and Ketones
Timberlake13th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9780134421353
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Table of contents
- Ch.1 Chemistry in Our Lives11
- Ch.2 Chemistry and Measurements80
- Ch.3 Matter and Energy54
- Ch.4 Atoms and Elements51
- Ch.5 Nuclear Chemistry42
- Ch.6 Ionic and Molecular Compounds57
- Ch.7 Chemical Quantities and Reactions41
- Ch.8 Gases29
- Ch.9 Solutions51
- Ch.10 Acids and Bases and Equilibrium65
- Ch.11 Introduction to Organic Chemistry: Hydrocarbons78
- Ch.12 Alcohols, Thiols, Ethers, Aldehydes, and Ketones83
- Ch.13 Carbohydrates54
- Ch.14 Carboxylic Acids, Esters, Amines, and Amides90
- Ch.15 Lipids61
- Ch.16 Amino Acids, Proteins, and Enzymes84
- Ch.17 Nucleic Acids and Protein Synthesis83
- Ch.18 Metabolic Pathways and ATP Production67
Timberlake13th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9780134421353Not the one you use?Change textbook
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Timberlake 13th EditionCh.12 Alcohols, Thiols, Ethers, Aldehydes, and KetonesProblem 66
Timberlake 13th EditionCh.12 Alcohols, Thiols, Ethers, Aldehydes, and KetonesProblem 66Chapter 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 guidance1
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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1:53
Condensed Formula Concept 1
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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3:18IUPAC Naming Concept 3
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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1:32Alcohol Reactions Oxidation Reactions Example 1
Related Practice
Textbook Question
Draw the condensed structural formulas and give the IUPAC names for all the aldehydes and ketones that have the formula C5H10O. (12.3)
Textbook Question
Compound A is a primary alcohol whose formula is C3H8O. When compound A is heated with strong acid, it dehydrates to form compound B (C3H6). When compound A is oxidized, compound C (C3H6O) forms. Draw the condensed structural formulas and give the IUPAC names for compounds A, B, and C.
Textbook Question
Draw the condensed structural formulas and give the IUPAC names for all the alcohols that have the formula C5H12O.
Textbook Question
A compound with the formula C4H8O is synthesized from 2-methyl-1-propanol and oxidizes easily to give a carboxylic acid. Draw the condensed structural formula and give the IUPAC name for the compound.
Textbook Question
Compound X is a secondary alcohol whose formula is C3H8O. When compound X is heated with strong acid, it dehydrates to form compound Y (C3H6). When compound X is oxidized, compound Z (C3H6O) forms, which cannot be oxidized further. Draw the condensed structural formulas and give the IUPAC names for compounds X, Y, and Z.