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Chapter 22: Problem 54

Name all the aldehydes and ketones that have the formula \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}\).

Short Answer

Expert verified
The aldehydes and ketones with the molecular formula C₅H₁₀O are: Aldehydes: 1. Pentanal (H - (CH₂)₃ - CHO) Ketones: 1. Pentan-2-one (H - \(\mathrm{CO}\) - (CH₂)₃ - H) 2. Pentan-3-one (H - CH₂ - \(\mathrm{CO}\) - (CH₂)₂ - H) 3. 3-Methylbutan-2-one (CH₃ - C (CH₃) - \(\mathrm{CO}\) - CH₂ - CH₃)

Step by step solution

01

Identify the possible linear aldehydes with the given molecular formula

To find linear aldehydes with the molecular formula C₅H₁₀O, we need to consider that the aldehydes will have a terminal carbonyl group (\(\mathrm{-CHO}\)). Since there are 5 carbon atoms in total, the linear structures can be as follows: 1. H - (CH₂)₃ - CHO We have only one possible linear aldehyde structure.
02

Identify the possible linear ketones with the given molecular formula

To find linear ketones with the molecular formula C₅H₁₀O, we need to consider the ketone functional group, \(\mathrm{C=O}\), which must be present at an internal carbon position. The possible linear ketone structures include: 1. H - \(\mathrm{CO}\) - (CH₂)₃ - H 2. H - CH₂ - \(\mathrm{CO}\) - (CH₂)₂ - H These are the two possible linear ketone structures.
03

Identify the possible branched aldehydes with the given molecular formula

For the given molecular formula, aldehydes must always be at the terminal carbon atom and cannot be present at the branching position. Therefore, there are no additional branched aldehydes apart from the one we found in step 1.
04

Identify the possible branched ketones with the given molecular formula

To find branched ketones with the molecular formula C₅H₁₀O, we need to consider that the \(\mathrm{C=O}\) group can be present at an internal carbon position, and we need to find all possible arrangements for the hydrocarbon chain for five carbon atoms. The branched structure for five carbon atoms would be isopropyl, with central carbon as a branch point. The possible branched ketone structures include: 1. CH₃ - C (CH₃) - \(\mathrm{CO}\) - CH₂ - CH₃ This is the only possible branched ketone structure.
05

Compile the list of aldehydes and ketones with the given molecular formula

Based on steps 1-4, we can conclude that the aldehydes and ketones with the molecular formula C₅H₁₀O are: Aldehydes: 1. Pentanal (H - (CH₂)₃ - CHO) Ketones: 1. Pentan-2-one (H - \(\mathrm{CO}\) - (CH₂)₃ - H) 2. Pentan-3-one (H - CH₂ - \(\mathrm{CO}\) - (CH₂)₂ - H) 3. 3-Methylbutan-2-one (CH₃ - C (CH₃) - \(\mathrm{CO}\) - CH₂ - CH₃)

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