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Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook
All textbooksBruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 81a
Chapter 16, Problem 81a

Cardura, a drug used to treat hypertension, is synthesized as shown here.
Chemical reaction diagram illustrating the synthesis of Cardura, highlighting intermediate A and the reaction mechanism.
a. Identify the intermediate (A) and show the mechanism for its formation.

Verified step by step guidance
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Step 1: Analyze the reaction sequence. The first step involves the use of potassium carbonate (K₂CO₃), which is a base. This suggests that the reaction may involve deprotonation or nucleophilic substitution.
Step 2: Identify the starting materials and their functional groups. Look for reactive sites such as halides, hydroxyl groups, or acidic hydrogens that could interact with K₂CO₃.
Step 3: Propose the mechanism for the formation of intermediate A. If the starting material contains an acidic hydrogen (e.g., an alcohol or phenol group), K₂CO₃ can deprotonate it to form an alkoxide ion. Represent this step using the equation: ROH+K2CO3→RO-+K2HCO3
Step 4: Consider the role of the alkoxide ion formed. Alkoxide ions are strong nucleophiles and can participate in substitution reactions if an electrophilic site (e.g., an alkyl halide) is present in the starting material. This would lead to the formation of intermediate A.
Step 5: Write the structure of intermediate A based on the substitution reaction. Ensure that the mechanism accounts for the formation of A and aligns with the subsequent steps in the synthesis of Cardura.

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Key Concepts

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

Reaction Mechanism

A reaction mechanism is a step-by-step description of how reactants transform into products in a chemical reaction. It outlines the individual steps, including bond breaking and forming, and the intermediates involved. Understanding the mechanism is crucial for predicting the outcome of reactions and for identifying intermediates like compound A in the synthesis of Cardura.
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Heck Reaction Mechanism

Intermediates

Intermediates are species that are formed during the course of a chemical reaction but are not present in the final products. They are often unstable and exist only for a short duration. Identifying intermediates is essential for understanding the overall reaction pathway and for elucidating the mechanism of synthesis, as seen in the formation of compound A in the synthesis of Cardura.
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Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction type in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. This process is key in the formation of many organic compounds, including intermediates. In the context of Cardura's synthesis, understanding nucleophilic substitution helps explain how compound A is formed and subsequently transformed into the final product.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
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.

a. Propose a mechanism for the Ritter reaction.

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Textbook Question

Cardura, a drug used to treat hypertension, is synthesized as shown here.

b. Show the mechanism for conversion of A to B. Which is formed more rapidly, A or B?

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Textbook Question

a. A student did not obtain any ester when he added 2,4,6-trimethylbenzoic acid to an acidic solution of ethanol. Why? (HINT: Build models.)

b. Would he have encountered the same problem if he had tried to synthesize the methyl ester of 4-methylbenzoic acid in the same way?

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Textbook Question

Identify the major and minor products of the following reaction:

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Textbook Question

When a compound with molecular formula C11H14O2 undergoes acid-catalyzed hydrolysis, one of the products that is isolated gives the following 1H NMR spectrum. Identify the compound.

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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?