Textbook Question
Draw the condensed structural formula for the alcohol formed when each of the following is reduced by hydrogen in the presence of a nickel catalyst:
c. hexanal
Ch.12 Alcohols, Thiols, Ethers, Aldehydes, and Ketones
Timberlake13th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9780134421353
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- Ch.1 Chemistry in Our Lives11
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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 34c
Timberlake 13th EditionCh.12 Alcohols, Thiols, Ethers, Aldehydes, and KetonesProblem 34cChapter 12, Problem 34c
Draw the condensed structural formula for the alcohol formed when each of the following is reduced by hydrogen in the presence of a nickel catalyst:
c. 3-chlorocyclopentanone
Verified step by step guidance1
Identify the functional group in the given compound, 3-chlorocyclopentanone. The compound contains a ketone group (C=O) attached to a cyclopentane ring and a chlorine atom at the 3rd position.
Understand the reduction process: When a ketone is reduced by hydrogen (H₂) in the presence of a nickel catalyst, the carbonyl group (C=O) is converted into a hydroxyl group (-OH), forming an alcohol.
Determine the location of the hydroxyl group: The ketone group in 3-chlorocyclopentanone is located on the cyclopentane ring. Reduction will convert this ketone group into an alcohol group (-OH) at the same position.
Account for the chlorine substituent: The chlorine atom at the 3rd position remains unchanged during the reduction process, as the reaction specifically targets the ketone group.
Write the condensed structural formula: Combine the cyclopentane ring with the hydroxyl group (-OH) replacing the ketone group and the chlorine atom at the 3rd position. The final condensed structural formula will represent the alcohol formed after reduction.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Reduction Reaction
Reduction is a chemical reaction that involves the gain of electrons or the decrease in oxidation state by a molecule, atom, or ion. In organic chemistry, this often refers to the conversion of carbonyl groups (like ketones and aldehydes) into alcohols. The process typically requires a reducing agent, such as hydrogen gas, and a catalyst, which in this case is nickel.
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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 provides a simplified view of the molecular structure, indicating how atoms are connected, which is particularly useful for visualizing organic compounds like alcohols derived from ketones.
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Cyclopentanone
Cyclopentanone is a cyclic ketone with the molecular formula C5H8O, characterized by a five-membered ring containing a carbonyl group (C=O). When reduced, cyclopentanone can be converted into cyclopentanol, an alcohol. Understanding the structure of cyclopentanone is essential for predicting the product of its reduction and drawing the correct condensed structural formula.
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Related Practice
Textbook Question
Draw the condensed structural formula for the alcohol formed when each of the following is reduced by hydrogen in the presence of a nickel catalyst:
d. 2-methyl-3-pentanone
Textbook Question
Draw the condensed structural formula for the alcohol formed when each of the following is reduced by hydrogen in the presence of a nickel catalyst:
a. ethyl propyl ketone
Textbook Question
Oxybenzone is an effective sunscreen whose structural formula is shown.
b. What is the molecular formula and molar mass of oxybenzone?
Textbook Question
Avobenzone is a common ingredient in sunscreen. Its structural formula is shown.
a. What functional groups are in avobenzone?
Textbook Question
Avobenzone is a common ingredient in sunscreen. Its structural formula is shown.
b. What is the molecular formula and molar mass of avobenzone?