Textbook Question
Draw the structures of the products formed when the following compounds react with a reducing agent.
a.
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15. Aldehydes and Ketones
Reduction of Aldehydes and Ketones
Problem 33a
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. butyraldehyde
Verified step by step guidance1
Understand the reaction: Reduction of an aldehyde involves the addition of hydrogen (H₂) in the presence of a catalyst, such as nickel, to convert the aldehyde group (-CHO) into an alcohol group (-CH₂OH).
Identify the structure of butyraldehyde: Butyraldehyde is a four-carbon aldehyde with the molecular formula C₄H₈O. Its condensed structural formula is CH₃CH₂CH₂CHO, where the aldehyde group (-CHO) is attached to the end of the carbon chain.
Determine the product of the reduction: During the reduction, the hydrogen atoms add to the carbonyl group (C=O) of the aldehyde, converting it into a hydroxyl group (-OH). The resulting alcohol will have the same carbon chain length as the original aldehyde.
Write the condensed structural formula for the alcohol: Replace the aldehyde group (-CHO) in butyraldehyde with a hydroxyl group (-CH₂OH) to form the alcohol. The condensed structural formula of the alcohol will be CH₃CH₂CH₂CH₂OH.
Verify the product: Ensure that the resulting alcohol is a primary alcohol, as the reduction of an aldehyde always produces a primary alcohol. In this case, the product is 1-butanol, which is consistent with the reduction of butyraldehyde.
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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 aldehydes and ketones, 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 connected. For example, the condensed formula for butanol, derived from butyraldehyde, would be written as CH3(CH2)2CH2OH, highlighting the functional groups and carbon chain.
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Aldehyde to Alcohol Conversion
The conversion of an aldehyde to an alcohol is a common transformation in organic chemistry. Aldehydes, characterized by the presence of a carbonyl group (C=O) at the end of a carbon chain, can be reduced to primary alcohols. In the case of butyraldehyde, the reduction process will yield butanol, where the carbonyl group is replaced by a hydroxyl group (–OH), resulting in a functional change from an aldehyde to an alcohol.
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