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Ch.5 Chemical Reactions
Frost - General, Organic and Biological Chemistry 4th Edition
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696Not the one you use?Change textbook
Chapter 2, Problem 70

Epinephrine is the active ingredient in the EpiPen® used to treat severe allergic reactions. EpiPens expire due to the oxidation of the epinephrine. One of these reactions is shown below. Circle the groups in the product that were oxidized.

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1
Examine the chemical structure of epinephrine in the provided image and identify the functional groups present (e.g., hydroxyl groups, amine groups, etc.).
Review the chemical reaction shown in the image to determine which functional groups undergo oxidation. Oxidation typically involves the loss of electrons, often resulting in the addition of oxygen or the removal of hydrogen.
Focus on the changes in the molecular structure between the reactant (epinephrine) and the product. Look for new bonds to oxygen or changes in the oxidation state of specific atoms.
Circle the functional groups in the product that have been altered due to oxidation. Commonly oxidized groups include hydroxyl groups converting to ketones or aldehydes.
Verify your identification by ensuring the circled groups align with the chemical principles of oxidation and the reaction mechanism depicted in the image.

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Key Concepts

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

Epinephrine Structure

Epinephrine, also known as adrenaline, is a catecholamine with a specific chemical structure that includes a benzene ring, two hydroxyl groups, and an amine group. Understanding its structure is crucial for identifying which parts of the molecule are susceptible to oxidation, particularly the hydroxyl groups and the amine.
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Oxidation Reaction

Oxidation is a chemical reaction that involves the loss of electrons or an increase in oxidation state by a molecule. In the context of epinephrine, oxidation can lead to the formation of different products, which may alter its effectiveness. Recognizing the specific groups that undergo oxidation helps in understanding the stability and shelf life of EpiPens.
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Chemical Stability and Expiration

Chemical stability refers to the tendency of a compound to maintain its original chemical structure over time. In the case of EpiPens, the oxidation of epinephrine reduces its potency, leading to expiration. Awareness of factors that affect chemical stability, such as light, temperature, and oxygen exposure, is essential for proper storage and usage of these medical devices.
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