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Chapter 19: Problem 27

A certain carboxylic acid \(\left(\mathrm{C}_{14} \mathrm{H}_{26} \mathrm{O}_{2}\right)\), which can be isolated from whale blubber or sardine oil. yields nonanal and \(\mathrm{O}=\mathrm{CH}\left(\mathrm{CH}_{2}\right)_{3} \mathrm{CO}_{2} \mathrm{H}\) on ozonolysis. What is the structure of this acid?

Short Answer

Expert verified
The structure is \( \mathrm{CH}_3(\mathrm{CH}_2)_7\mathrm{CH}=\mathrm{CH}(\mathrm{CH}_2)_3\mathrm{COOH} \).

Step by step solution

01

Write Down the Reaction

Identify the given compounds and the ozonolysis reaction. We know that a carboxylic acid \(\text{C}_{14}\text{H}_{26}\text{O}_{2}\) undergoes ozonolysis, producing nonanal \(\text{C}_{9}\text{H}_{18}\text{O}\) and \(\text{O}=\text{CH}(\text{CH}_2)_3\text{CO}_2\text{H}\).
02

Determine the Number of Carbons

The original molecule has 14 carbons, nonanal contributes 9 carbons, leaving 5 carbons for the other part since \(\text{O}=\text{CH}(\text{CH}_2)_3\text{CO}_2\text{H}\) has 5 carbons.
03

Identify the Position of the Double Bond

Since the carboxylic acid yields two fragments upon ozonolysis, it's implied that there was a double bond between the two fragments. Place the double bond at the end of the nonanal chain, creating a continuous chain when you combine the two pieces.
04

Construct the Complete Structure

Construct the carboxylic acid by linking nonanal's aldehyde carbon to the carbon next to the \(\text{CO}_2\text{H}\) group in the other fragment, resulting in: \[ \text{CH}_3(\text{CH}_2)_7\text{CH}=\text{CH}(\text{CH}_2)_3\text{COOH} \]
05

Verify the Structure

Check that the structure contains 14 carbons, 26 hydrogens, and 2 oxygens, matching the molecular formula \(\text{C}_{14}\text{H}_{26}\text{O}_{2}\). This confirms the correct structure of the original carboxylic acid.

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Key Concepts

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

Carboxylic Acids and Their Properties
Carboxylic acids are an important class of organic compounds characterized by the presence of a carboxyl group \((\text{-COOH})\). This functional group is highly polar, resulting in strong intermolecular hydrogen bonding. Consequently, carboxylic acids often have relatively high boiling points compared to other similar-sized organic compounds.
  • The carboxyl group consists of a carbonyl \((\text{C=O})\) and a hydroxyl \((\text{-OH})\) group connected to the same carbon.
  • Many carboxylic acids occur naturally and are often found in fats, oils, and waxes.
  • Considered weak acids, they can release a proton \((\text{H}^+)\) in solution, giving rise to a carboxylate ion \((\text{-COO}^-)\).
In the exercise, we are dealing with a carboxylic acid extracted from natural sources like whale blubber or sardine oil, which highlights its presence in marine organisms, often used to study natural fatty acids.
Ozonolysis Explained
Ozonolysis is an oxidative cleavage reaction where alkenes are broken down to form aldehydes, ketones, or carboxylic acids. In simpler terms, ozonolysis is a technique used to split unsaturated bonds like double bonds found in alkenes.
  • Ozone \((\text{O}_3)\) is the active compound used, which reacts with the double bonds in an alkene.
  • The initial intermediate formed is a molozonide, which rearranges to form a more stable ozonide.
  • The ozonide can be further reduced or oxidized to yield various products. In our specific case, the ozonolysis leads to nonanal and another carboxylic acid fragment.
For our exercise, the ozonolysis of the carboxylic acid \((\text{C}_{14}\text{H}_{26}\text{O}_2)\) results in the production of nonanal \((\text{C}_{9}\text{H}_{18}\text{O})\) and a smaller carboxylic acid fragment. This indicates there was a double bond in the middle of the original molecule.
Molecular Structure Determination Process
Molecular structure determination of organic compounds involves the identification and arrangement of atoms in a molecule. This determination can be essential for understanding the properties and reactivity of the molecule. By using techniques like ozonolysis, we can deduce the structure of complex organic compounds.
  • The exercise began with a known sum formula, \(\text{C}_{14}\text{H}_{26}\text{O}_2\), providing information about the atom count but not their arrangement.
  • By analyzing the products formed during ozonolysis, particularly nonanal and the other carboxylic acid, we identified two distinct segments.
  • The reconstructed molecular structure from these segments revealed a single double bond placement, allowing for the determination of the original molecular structure.
The practice of deducing molecular structures from reaction products is fundamental in organic chemistry, as it enables chemists to identify unknown compounds and understand their properties based on experimental evidence.

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Most popular questions from this chapter

(a) Lactic acid has a \(\mathrm{pK}_{\mathrm{a}}\) of \(3.9\). What is the [lactate]/[lactic acid] ratio at the \(\mathrm{pH}\) of blood (7.4)? (b) A \(0.1 M\) solution of lactic acid in water has a pH of \(2.5\). What is the [lactate] [lactic acid] ratio in this solution?

When levulinic acid \(\left(\mathrm{CH}_{3} \mathrm{CCH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}\right)\) was hydrogenated at high pressure over a nickel catalyst at \(220^{\circ} \mathrm{C}\), a single product, \(\mathrm{C}_{5} \mathrm{H}_{8} \mathrm{O}_{2}\), was isolated in \(94 \%\) yield. This compound lacks hydroxyl absorption in its IR spectrum. What is a reasonable structure for the compound?

Rank the compounds in each of the following groups in order of decreasing acidity: (a) Acetic acid, ethane, ethanol (b) Benzene, benzoic acid, benzyl alcohol (c) 1,3-Propanediol, propanedioic acid, propanoic acid (d) Acetic acid, ethanol, trifluoroacetic acid, \(2,2,2\) -trifluoroethanol, trifluoromethanesulfonic acid (CF_SOOH

What is the most acidic neutral molecule characterized by the formula \(\mathrm{C}_{3} \mathrm{H}_{x} \mathrm{O}_{2} ?\)

It is sometimes necessary to prepare isotopically labeled samples of organic substances for probing biological transformations and reaction mechanisms. Various sources of the radioactive mass- 14 carbon isotope are available. Describe synthetic procedures by which benzoic acid, labeled with \({ }^{14} \mathrm{C}\) at its carbonyl carbon, could be prepared from benzene and the following \({ }^{14} \mathrm{C}\) -labeled precursors. You may use any necessary organic or inorganic reagents. (a) \(\mathrm{CH}_{3} \mathrm{Cl}\) (b) \(\mathrm{HCH} \quad\) (c) \(\mathrm{CO}_{2}\)
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