Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook

Bruice 8th Edition

Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Problem 85b

Chapter 16, Problem 85b

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.
b.

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Step 1: Identify the functional group transformation. The starting material is benzyl alcohol (C6H5CH2OH), and the target compound is phenylacetic acid (C6H5CH2COOH). This involves oxidation of the primary alcohol to a carboxylic acid.

Step 2: Choose an appropriate oxidizing agent. Common reagents for oxidizing primary alcohols to carboxylic acids include potassium permanganate (KMnO4) under acidic or basic conditions, or chromium-based reagents like Jones reagent (CrO3 in H2SO4).

Step 3: Set up the reaction conditions. For example, if using KMnO4, dissolve the alcohol in water or an appropriate solvent, add KMnO4, and heat the mixture gently to facilitate the oxidation reaction.

Step 4: Monitor the reaction progress. Use techniques like thin-layer chromatography (TLC) or infrared spectroscopy (IR) to confirm the disappearance of the alcohol functional group and the appearance of the carboxylic acid group.

Step 5: Purify the product. After the reaction is complete, isolate phenylacetic acid by acidifying the reaction mixture (if necessary), followed by extraction and recrystallization to obtain the pure compound.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the context of the question, the presence of hydroxyl (-OH) and carbonyl (C=O) groups indicates the transformation of alcohols to carboxylic acids or their derivatives, which is essential for understanding the reactivity and synthesis of the target compounds.

Oxidation Reactions

Oxidation reactions involve the loss of electrons or an increase in oxidation state by a molecule, atom, or ion. In organic chemistry, alcohols can be oxidized to aldehydes or carboxylic acids, depending on the conditions and reagents used. This concept is crucial for converting the starting alcohol into the desired carboxylic acid derivative in the question.

Reagents and Reaction Conditions

The choice of reagents and reaction conditions is vital in organic synthesis as they dictate the pathway and outcome of a reaction. Common reagents for oxidation include potassium dichromate, PCC, or even mild oxidants like silver oxide. Understanding how to select appropriate reagents based on the desired transformation is key to successfully preparing the target compounds from the given starting materials.

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Reagents

Related Practice

Textbook Question

The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, does not work with primary alcohols.

c. How does the Ritter reaction differ from the acid-catalyzed hydrolysis of a nitrile to form an amide?

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Textbook Question

What product do you expect to obtain from each of the following reactions?

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Textbook Question

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.

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Textbook Question

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.

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Textbook Question

The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, does not work with primary alcohols.

b. Why does the Ritter reaction not work with primary alcohols?

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Textbook Question

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.

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Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents. b.

Verified video answer for a similar problem:

Key Concepts

Functional Groups

Oxidation Reactions

Reagents and Reaction Conditions

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.
b.