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Chapter 15: Problem 62

Draw all aldehydes and ketones with the formula \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}\)

Short Answer

Expert verified
Pentanal, 3-methylbutanal, pentan-2-one, pentan-3-one, 2-methylbutan-2-one.

Step by step solution

01

Identify the molecular formula components

The molecular formula \(\text{C}_5 \text{H}_{10} \text{O}\) contains carbon (C), hydrogen (H), and oxygen (O). Aldehydes and ketones typically have a carbonyl group (C=O). Since the formula needs to fit into the structure of either an aldehyde or a ketone, we will consider all possible structures.
02

Draw possible aldehyde structures

Aldehydes have the general structure \(\text{R-CHO}\), where \(\text{R}\) is an alkyl group. Given the formula, we can have CHO as a part of the molecule and the remaining carbons forming alkyl chains. Possible structures are: (1) \(\text{CH}_3-\text{CH}_2-\text{CH}_2-\text{CH}_2-\text{CHO}\) (pentanal), (2) \(\text{CH}_3-\text{CH}_2-\text{CH(CH}_3\text{)-CHO}\) (3-methylbutanal).
03

Draw possible ketone structures

Ketones have the general structure \(\text{R-CO-R'}\), where \(\text{R}\) and \(\text{R'}\) are alkyl groups. Given the formula, possible structures are: (1) \(\text{CH}_3-\text{CO}-\text{CH}_2-\text{CH}_2-\text{CH}_3\) (pentan-2-one), (2) \(\text{CH}_3-\text{CH}_2-\text{CO}-\text{CH}_2-\text{CH}_3\) (pentan-3-one), (3) \(\text{CH}_3-\text{CO}-\text{CH}(\text{CH}_3)-\text{CH}_3\) (2-methylbutan-2-one).

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Molecular Formula
A molecular formula represents the types and numbers of atoms in a molecule. In the given problem, \(\text{C}_5 \text{H}_{10} \text{O}\), we have 5 carbons (C), 10 hydrogens (H), and 1 oxygen (O). This molecular formula can correspond to different structures. Here, we focus on aldehydes and ketones. Both types have a carbonyl group (C=O). The specific arrangement of atoms will differentiate aldehydes from ketones.
Aldehyde Structures
Aldehydes contain the formyl group (\text{CHO}), where the carbonyl group (C=O) is attached to at least one hydrogen atom. This can be symbolized as \text{R-CHO}, with \text{R} representing an alkyl group. For \(\text{C}_5\text{H}_{10}\text{O}\), potential aldehyde structures include:
\begin{itemize}
  • \(\text{CH}_3-\text{CH}_2-\text{CH}_2-\text{CH}_2-\text{CHO}\) (pentanal)
  • \(\text{CH}_3-\text{CH}_2-\text{CH}(\text{CH}_3)-\text{CHO}\) (3-methylbutanal)
    • these structures consist of the formyl group bonded to a chain of carbons (alkyl groups).
    Ketone Structures
    Ketones feature the carbonyl group (C=O) bonded to two alkyl groups, symbolized as \text{R-CO-R'}. Unlike aldehydes, the carbonyl carbon is not at the end of the carbon chain. With the molecular formula \(\text{C}_5\text{H}_{10}\text{O}\), possible ketone structures are:
    • \(\text{CH}_3-\text{CO}-\text{CH}_2-\text{CH}_2-\text{CH}_3\) (pentan-2-one)
    • \(\text{CH}_3-\text{CH}_2-\text{CO}-\text{CH}_2-\text{CH}_3\) (pentan-3-one)
    • \(\text{CH}_3-\text{CO}-\text{CH}(\text{CH}_3) -\text{CH}_3\) (2-methylbutan-2-one)
    Carbonyl Group
    The carbonyl group (C=O) is a fundamental functional group in organic chemistry. It's characterized by a carbon double-bonded to an oxygen. This group defines both aldehydes and ketones but in distinct contexts.
    • Aldehydes: Here, the carbonyl carbon is bonded to at least one hydrogen atom. This makes the carbonyl group terminal in the structure.
    • Ketones: In ketones, the carbonyl carbon is bonded to two carbon atoms, making it more internal in the structure.
    Understanding the behavior and reactivity of the carbonyl group is key to mastering organic chemistry.

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    Most popular questions from this chapter

    2-Butanone is reduced by hydride ion donors, such as sodium borohydride \(\left(\mathrm{NaBH}_{4}\right),\) to the alcohol 2 -butanol. Even though the alcohol has a chiral center, the product isolated from the redox reaction is not optically active. Explain.

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