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
Not the one you use?Change textbookSelect a different textbook
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
All textbooks
Timberlake 13th EditionCh.12 Alcohols, Thiols, Ethers, Aldehydes, and KetonesProblem 67
Timberlake 13th EditionCh.12 Alcohols, Thiols, Ethers, Aldehydes, and KetonesProblem 67Chapter 12, Problem 67
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.
Verified step by step guidance1
Step 1: Identify the structure of compound A. Since compound A is a primary alcohol with the formula C₃H₈O, it must have a hydroxyl group (-OH) attached to a primary carbon. The possible structure is CH₃CH₂CH₂OH (1-propanol).
Step 2: Determine the product of dehydration (compound B). When a primary alcohol like 1-propanol is heated with a strong acid, it undergoes a dehydration reaction, losing a water molecule. This forms an alkene. The double bond can form between the first and second carbons, resulting in CH₂=CHCH₃ (propene).
Step 3: Determine the product of oxidation (compound C). When a primary alcohol like 1-propanol is oxidized, it forms an aldehyde. The hydroxyl group (-OH) is converted into a carbonyl group (C=O) at the end of the chain. This results in CH₃CH₂CHO (propanal).
Step 4: Write the IUPAC names for the compounds. Compound A is 1-propanol, compound B is propene, and compound C is propanal.
Step 5: Summarize the condensed structural formulas and IUPAC names: Compound A: CH₃CH₂CH₂OH (1-propanol), Compound B: CH₂=CHCH₃ (propene), Compound C: CH₃CH₂CHO (propanal).
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Was this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alcohols and Their Properties
Alcohols are organic compounds characterized by the presence of one or more hydroxyl (-OH) groups. In this case, compound A is a primary alcohol, meaning the hydroxyl group is attached to a carbon atom that is connected to only one other carbon. Understanding the structure and reactivity of alcohols is essential for predicting their behavior during dehydration and oxidation reactions.
Recommended video:
Guided course
1:10
Alcohol Classification Concept 2
Dehydration Reaction
Dehydration is a chemical reaction that involves the removal of water (H₂O) from a compound. In the context of compound A, heating it with a strong acid facilitates the elimination of a water molecule, resulting in the formation of compound B, an alkene. This reaction is crucial for understanding how alcohols can convert to alkenes through the loss of water.
Recommended video:
Guided course
1:30Alcohol Reactions: Dehydration Reactions Concept 1
Oxidation of Alcohols
Oxidation refers to the process where a substance loses electrons, often involving the addition of oxygen or the removal of hydrogen. When compound A is oxidized, it transforms into compound C, which is an aldehyde in this case. Recognizing the oxidation states and the resulting functional groups is vital for determining the structure and IUPAC naming of the products formed from alcohols.
Recommended video:
Guided course
1:49Alcohol Reactions: Oxidation Concept 1
Related Practice
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.