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Aldehydes and ketones can be named in a systematic way by counting the number of carbon atoms (including the carbonyl carbon) that they contain. The name of the aldehyde or ketone is based on the hydrocarbon with the same number of carbon atoms. The ending -al for aldehyde or-one for ketone is added as appropriate. Draw the structural formulas for the following aldehydes or ketones: (a) 3-ethyl-2-pentanone, (b) 2,2 -diethylbutanal, (c) pentanal, (d) 1-bromo-3-heptanone.

Short Answer

Expert verified
The structural formulas for the given aldehydes and ketones are as follows: (a) 3-ethyl-2-pentanone: \( \text{CH}_3\text{C}(=O)\text{CH}_2\text{CH}(\text{C}_2\text{H}_5)\text{CH}_3\). (b) 2,2-diethylbutanal: \( \text{CH}_3\text{CH}(\text{C}_2\text{H}_5)_2\text{CH}_2\text{C}(=O)\text{H}\). (c) pentanal: \( \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{C}(=O)\text{H}\). (d) 1-bromo-3-heptanone: \( \text{CH}_2\text{Br}\text{CH}_2\text{C}(=O)\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_3\).

Step by step solution

01

(a) 3-ethyl-2-pentanone

: 1. Identify the parent chain: In this case, it is a pentanone (a ketone with a 5-carbon chain). 2. Write the structure of the parent chain: \( \text{CH}_3\text{C}(=O)\text{CH}_2\text{CH}_2\text{CH}_3\). 3. Identify the substituent: It is an ethyl group at the 3rd carbon. 4. Add the ethyl group to the parent chain: \( \text{CH}_3\text{C}(=O)\text{CH}_2\text{CH}(\text{C}_2\text{H}_5)\text{CH}_3\). The structural formula for 3-ethyl-2-pentanone is: \( \text{CH}_3\text{C}(=O)\text{CH}_2\text{CH}(\text{C}_2\text{H}_5)\text{CH}_3\).
02

(b) 2,2 -diethylbutanal

: 1. Identify the parent chain: In this case, it is butanal (an aldehyde with a 4-carbon chain). 2. Write the structure of the parent chain: \( \text{CH}_3\text{CH}_2\text{CH}_2\text{C}(=O)\text{H}\). 3. Identify the substituents: Two ethyl groups at the 2nd carbon. 4. Add the ethyl groups to the parent chain: \( \text{CH}_3\text{CH}(\text{C}_2\text{H}_5)_2\text{CH}_2\text{C}(=O)\text{H}\). The structural formula for 2,2-diethylbutanal is: \( \text{CH}_3\text{CH}(\text{C}_2\text{H}_5)_2\text{CH}_2\text{C}(=O)\text{H}\).
03

(c) pentanal

: 1. Identify the parent chain: In this case, it is pentanal (an aldehyde with a 5-carbon chain). 2. Write the structure of the parent chain: \( \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{C}(=O)\text{H}\). The structural formula for pentanal is: \( \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{C}(=O)\text{H}\).
04

(d) 1-bromo-3-heptanone

: 1. Identify the parent chain: In this case, it is a heptanone (a ketone with a 7-carbon chain). 2. Write the structure of the parent chain: \( \text{CH}_3\text{CH}_2\text{C}(=O)\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_3\). 3. Identify the substituent: A bromo group at the 1st carbon. 4. Add the bromo group to the parent chain: \( \text{CH}_2\text{Br}\text{CH}_2\text{C}(=O)\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_3\). The structural formula for 1-bromo-3-heptanone is: \( \text{CH}_2\text{Br}\text{CH}_2\text{C}(=O)\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_3\).

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Key Concepts

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

Naming Conventions in Organic Chemistry
Chemistry has its own language, and when it comes to organic molecules, naming conventions are like grammar rules. They ensure everyone understands the molecule being referenced. In organic chemistry, substances are often named based on their structure. This is crucial because it provides insight into the number of carbon atoms, their arrangement, and other groups attached to the molecule.

For ketones, the suffix "-one" is added. They are usually named by identifying the longest carbon chain containing the carbonyl group (\(C=O\)). For aldehydes, the suffix "-al" lets you know there's a carbonyl group at the end of a carbon chain.

  • Start by identifying the parent chain, the longest continuous chain of carbon atoms.
  • Look for functional groups; these are often added as prefixes or suffixes.
  • Substituents, like branches off the main chain, are noted as prefixes, specifying their position on the chain. For example, "ethyl" indicates a 2-carbon substituent.

Understanding these basics helps in effectively communicating the structure and nature of various organic compounds.
Aldehydes
Aldehydes are a class of organic compounds characterized by the presence of a carbonyl group (\(C=O\)) attached to at least one hydrogen atom. You can spot an aldehyde through its molecular formula, which usually ends with "-al."

Here are some key points about aldehydes:
  • The carbonyl group in an aldehyde is always located at the end of the carbon chain.
  • The simplest aldehyde is formaldehyde (\( ext{HCHO}\)).
  • Aldehydes are often more reactive compared to ketones because of the hydrogen atom linked to the carbonyl group.
  • When naming an aldehyde, locate the carbon chain, count the number of carbons, and add '-al' as the ending.

Familiar aldehydes include acetaldehyde and benzaldehyde, both important in industrial applications and in the formation of fragrances and flavors.
Ketones
Ketones are another class of organic compounds featuring the carbonyl group. Unlike aldehydes, this carbonyl group is located between two carbon atoms. They are generally less reactive than aldehydes due to this structural arrangement.

To identify and name ketones, follow these guidelines:
  • Find the longest carbon chain that includes the carbonyl group.
  • The suffix "-one" denotes a ketone in a compound's name.
  • Number the chain so that the carbonyl carbon gets the lowest number possible.
  • Identify any substituents, adding them as prefixes with the appropriate locants.

Molecules like propanone (commonly known as acetone) and butanone are typical examples of ketones, well-known for applications in solvents and chemical manufacturing processes.
Structural Formulas of Organic Compounds
Structural formulas are graphical representations of organic molecules that show how atoms are arranged and bonded. Knowing how to interpret and draw them is a fundamental skill in organic chemistry.

Here are critical aspects of structural formulas:
  • Each line represents a bond, with angles and line lengths often reflecting bond types.
  • Imagine the 3D structure for more complex molecules, as linear structural formulas can become unwieldy.
  • Arrange carbon atoms in a chain first, then add substituents and functional groups like hydroxyl (\(-OH\)) and carbonyl (\(C=O\)) groups.
  • Lastly, verify that you've respected the valency of atoms by ensuring each forms the correct number of bonds.

By mastering structural formulas, you build the ability to understand and predict the structure, properties, and reactivity of organic compounds. They are foundational in organic chemistry and crucial for communicating complex molecular information efficiently.

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Most popular questions from this chapter

The protein ribonuclease A in its native, or most stable, form is folded into a compact globular shape: (a) Does the native form have a lower or higher free energy than the denatured form, in which the protein is an extended chain? (b) What is the sign of the system's entropy change in going from the denatured to the folded form? (c) In the native form, the molecule hasfour \(-\mathrm{S}-\mathrm{S}-\) bonds that bridge parts of the chain. What effect do you predict these four linkages to have on the free energy and entropy of the native form relative to the free energy and entropy of a hypothetical folded structure that does not have any \(-\mathrm{S}-\mathrm{S}-\) linkages? Explain. (d) A gentle reducing agent converts the four \(-\mathrm{S}-\mathrm{S}-\) linkages in ribonuclease \(\mathrm{A}\) to eight \(-\mathrm{S}-\mathrm{H}\) bonds. What effect do you predict this conversion to have on the tertiary structure and entropy of the protein? (e) Which amino acid must be present for \(-\mathrm{SH}\) bonds to exist in ribonuclease \(\mathrm{A}\) ?

Indicate whether each statement is true or false. (a) Tryptophan is an aromatic amino acid. (b) Lysine is positively charged at pH 7. (c) Asparagine has two amide bonds. (d) Isoleucine and leucine are enantiomers. (e) Valine is probably more water-soluble than arginine.

Draw each molecule given its name and the following information. (a) Nitroglycerin, also known as 1,2,3-trinitroxypropane, the active ingredient in dynamite and a medication administered to people having a heart attack, (Hint: The nitroxy group is the conjugate base of nitric acid.) (b) Putrescine, also known as 1,4-diaminobutane, the compound responsible for the odor of putrefying fish, (c) Cyclohexanone, the precursor to Nylon, (d) 1,1,2,2 -tetrafluoroethene, the precursor to Teflon, (e) Oleic acid, also known as cis-9-octanedecenoic acid, a monounsaturated fatty acid found in many fats and oils. Draw the correct isomer.

Draw the condensed structure of the compounds formed by condensation reactions between (a) benzoic acid and ethanol, (b) ethanoic acid and methylamine, (c) acetic acid and phenol. Name the compound in each case.

Draw the molecular structure for \((\mathbf{a})\) a carboxylic acid that is an isomer of ethyl ethanoate, \((\mathbf{b})\) an alcohol that is an isomer of dimethylether.

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