3.63 Quinapril (trade name Accupril) is a drug used to treat hypertension and congestive heart failure. a. Identify the functional groups in quinapril. HO´ b. Classify any alcohol, amide, or amine as 1°, 2°, or 3º. C. At which sites can quinapril hydrogen bond to water? d. At which sites can quinapril hydrogen bond to acetone [(CH3)½CO]? e. Label the most acidic hydrogen atom. f. Which site is most basic? quinapril

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### Quinapril (Accupril) Overview

Quinapril, known commercially as Accupril, is a medication primarily used to manage hypertension and congestive heart failure. Below is a representation of the chemical structure of quinapril, accompanied by related questions to explore its properties and interactions.

**Chemical Structure:**

- The provided diagram illustrates the molecular structure of quinapril. Key features include various functional groups, such as carbonyl (C=O), hydroxyl (OH), and amide (N-C=O) groups, as well as an aromatic ring.

**Discussion Points:**

a. **Identify the Functional Groups in Quinapril:**

   - Quinapril contains the following functional groups:
     - Carbonyl group (C=O)
     - Amide group (N-C=O)
     - Hydroxyl group (OH)
     - Aromatic ring

b. **Classification of Alcohol, Amide, or Amine:**

   - The hydroxyl group is an alcohol, which should be classified as primary (1°).
   - The amide group is typically classified under amides.

c. **Hydrogen Bonding with Water:**

   - The sites where quinapril can hydrogen bond with water include the hydroxyl group (OH) and the oxygen of the carbonyl group, as these are polar and can form hydrogen bonds with water molecules.

d. **Hydrogen Bonding with Acetone [(CH₃)₂CO]:**

   - Quinapril can hydrogen bond with acetone primarily through the hydroxyl group. The hydrogen from the hydroxyl group can interact with the oxygen of acetone.

e. **Most Acidic Hydrogen Atom:**

   - The most acidic hydrogen atom is typically found on the hydroxyl group (OH), as this hydrogen can dissociate in an aqueous solution.

f. **Most Basic Site:**

   - The most basic site is likely the nitrogen in the amide group, as nitrogen atoms in such structures can act as proton acceptors.

These insights provide a foundational understanding of quinapril’s chemical interactions, relevant to its pharmacological effects.
Transcribed Image Text:### Quinapril (Accupril) Overview Quinapril, known commercially as Accupril, is a medication primarily used to manage hypertension and congestive heart failure. Below is a representation of the chemical structure of quinapril, accompanied by related questions to explore its properties and interactions. **Chemical Structure:** - The provided diagram illustrates the molecular structure of quinapril. Key features include various functional groups, such as carbonyl (C=O), hydroxyl (OH), and amide (N-C=O) groups, as well as an aromatic ring. **Discussion Points:** a. **Identify the Functional Groups in Quinapril:** - Quinapril contains the following functional groups: - Carbonyl group (C=O) - Amide group (N-C=O) - Hydroxyl group (OH) - Aromatic ring b. **Classification of Alcohol, Amide, or Amine:** - The hydroxyl group is an alcohol, which should be classified as primary (1°). - The amide group is typically classified under amides. c. **Hydrogen Bonding with Water:** - The sites where quinapril can hydrogen bond with water include the hydroxyl group (OH) and the oxygen of the carbonyl group, as these are polar and can form hydrogen bonds with water molecules. d. **Hydrogen Bonding with Acetone [(CH₃)₂CO]:** - Quinapril can hydrogen bond with acetone primarily through the hydroxyl group. The hydrogen from the hydroxyl group can interact with the oxygen of acetone. e. **Most Acidic Hydrogen Atom:** - The most acidic hydrogen atom is typically found on the hydroxyl group (OH), as this hydrogen can dissociate in an aqueous solution. f. **Most Basic Site:** - The most basic site is likely the nitrogen in the amide group, as nitrogen atoms in such structures can act as proton acceptors. These insights provide a foundational understanding of quinapril’s chemical interactions, relevant to its pharmacological effects.
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