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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 33d

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

Verified step by step guidance
1
Identify the functional group in the given compound, 2-methyl-3-pentanone. The compound contains a ketone functional group (-C=O) located at the third carbon of the pentane chain.
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 structure of the alcohol: The reduction of 2-methyl-3-pentanone will result in the addition of hydrogen atoms to the carbonyl group, converting it into a secondary alcohol. The hydroxyl group (-OH) will be attached to the third carbon of the pentane chain.
Write the condensed structural formula for the alcohol: Start with the pentane backbone, include the methyl group at the second carbon, and place the hydroxyl group (-OH) at the third carbon. Ensure the formula reflects the correct connectivity of atoms.
Verify the structure: Double-check that the condensed structural formula accurately represents the alcohol formed after the reduction of 2-methyl-3-pentanone, ensuring all bonds and groups are correctly placed.

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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 compounds, like ketones and aldehydes, into alcohols. The process typically requires a reducing agent, such as hydrogen gas, and a catalyst, like nickel, to facilitate the reaction.
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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 grouped together. For example, in alcohols, the hydroxyl (-OH) group is often highlighted to show its presence in the structure.
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Nickel Catalyst

A nickel catalyst is a substance that accelerates the rate of a chemical reaction without being consumed in the process. In the context of hydrogenation reactions, nickel is commonly used to facilitate the addition of hydrogen to unsaturated compounds, such as ketones. Its role is crucial in ensuring that the reduction occurs efficiently, leading to the formation of the desired alcohol.
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