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
Timberlake14th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9781292472249
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Table of contents
- Ch.1 Chemistry in Our Lives19
- Ch.2 Chemistry and Measurements80
- Ch.3 Matter and Energy53
- Ch.4 Atoms and Elements58
- Ch.5 Nuclear Chemistry42
- Ch.6 Ionic and Molecular Compounds57
- Ch.7 Chemical Quantities and Reactions38
- Ch.8 Gases30
- Ch.9 Solutions50
- Ch.10 Acids and Bases and Equilibrium64
- Ch.11 Introduction to Organic Chemistry: Hydrocarbons77
- Ch.12 Alcohols, Thiols, Ethers, Aldehydes, and Ketones82
- Ch.13 Carbohydrates54
- Ch.14 Carboxylic Acids, Esters, Amines, and Amides91
- Ch.15 Lipids61
- Ch.16 Amino Acids, Proteins, and Enzymes84
- Ch.17 Nucleic Acids and Protein Synthesis86
- Ch.18 Metabolic Pathways and ATP Production73
Timberlake14th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9781292472249Not the one you use?Change textbook
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Timberlake 14th EditionCh.12 Alcohols, Thiols, Ethers, Aldehydes, and KetonesProblem 65
Timberlake 14th EditionCh.12 Alcohols, Thiols, Ethers, Aldehydes, and KetonesProblem 65Chapter 12, Problem 65
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.
Verified step by step guidance1
Identify the starting material: The problem states that the compound is synthesized from 2-methyl-1-propanol. This is an alcohol with the structure CH₃-CH(CH₃)-CH₂-OH.
Understand the reaction type: The problem mentions oxidation. Primary alcohols (like 2-methyl-1-propanol) oxidize first to aldehydes and then further to carboxylic acids. Since the compound oxidizes easily to a carboxylic acid, it must be an aldehyde.
Determine the structure of the aldehyde: Oxidation of 2-methyl-1-propanol removes two hydrogen atoms (one from the hydroxyl group and one from the carbon bonded to it) to form an aldehyde. The resulting structure is CH₃-CH(CH₃)-CHO.
Name the compound using IUPAC rules: The parent chain is the longest continuous chain containing the aldehyde group. This chain has three carbons, so the base name is 'propanal.' The methyl group on the second carbon makes the name 2-methylpropanal.
Verify the oxidation to a carboxylic acid: When 2-methylpropanal undergoes further oxidation, the aldehyde group (-CHO) is converted to a carboxylic acid group (-COOH), resulting in 2-methylpropanoic acid. This confirms the compound's ability to oxidize easily to a carboxylic acid.
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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 without depicting all the bonds explicitly. It typically groups atoms together to indicate how they are connected, making it easier to visualize the structure of the compound. For example, in the case of C₄H₈O, the condensed formula would reflect the specific arrangement of carbon, hydrogen, and oxygen atoms.
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Condensed Formula Concept 1
IUPAC Nomenclature
IUPAC nomenclature is a systematic method for naming chemical compounds based on their structure and functional groups. It provides a unique name that conveys information about the molecular structure, including the number of carbon atoms and the presence of functional groups like alcohols or carboxylic acids. Understanding IUPAC rules is essential for accurately naming compounds such as the one derived from 2-methyl-1-propanol.
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Oxidation of Alcohols
The oxidation of alcohols involves the conversion of alcohols into carbonyl compounds or carboxylic acids through the addition of oxygen or the removal of hydrogen. In this context, 2-methyl-1-propanol can be oxidized to form a carboxylic acid, which is a key aspect of understanding the reactivity of alcohols. This process is significant in organic chemistry as it helps in synthesizing various functional groups.
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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
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.
Textbook Question
Draw the condensed structural or line-angle formula for the ketone or carboxylic acid product when each of the following is oxidized:
d.