Textbook Question
Suggest mechanisms for the following reactions, which are similar to the mechanism we saw for lanosterol biosynthesis at the end of Chapter 8.
(b)
10. Addition Reactions
Epoxide Reactions
3:57 minutesProblem 41d
Textbook Question
Three arene oxides can be obtained from phenanthrene.
d. Which of the three phenanthrene oxides is most likely to be carcinogenic?
Verified step by step guidance1
Identify the structure of phenanthrene and locate the positions where epoxidation can occur to form arene oxides. Phenanthrene is a polycyclic aromatic hydrocarbon with three fused benzene rings.
Understand that arene oxides are formed by the addition of an oxygen atom across a double bond in the aromatic ring, creating an epoxide group. In phenanthrene, this can occur at different positions, leading to different arene oxides.
Consider the stability and reactivity of each arene oxide. The most stable arene oxide is typically less reactive, while less stable ones may be more reactive and potentially more harmful.
Evaluate the potential for each arene oxide to form a reactive intermediate that can interact with biological molecules, such as DNA. This interaction is often a key factor in carcinogenicity.
Determine which arene oxide is most likely to form a stable carbocation or other reactive species that can lead to DNA adduct formation, a common mechanism for carcinogenicity. This typically involves analyzing the electronic and steric effects at each epoxidation site.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Arene Oxides
Arene oxides are reactive intermediates formed from the oxidation of aromatic compounds, such as phenanthrene. They typically contain an epoxide functional group, which can undergo further reactions, including rearrangements and hydrolysis. Understanding the structure and reactivity of arene oxides is crucial for assessing their biological activity and potential toxicity.
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Carcinogenicity
Carcinogenicity refers to the ability of a substance to cause cancer in living tissue. This property is often linked to the formation of DNA adducts, where reactive metabolites bind to DNA, leading to mutations. Evaluating the carcinogenic potential of compounds, such as phenanthrene oxides, involves understanding their metabolic pathways and the stability of their reactive intermediates.
Phenanthrene Metabolism
The metabolism of phenanthrene involves its biotransformation into various metabolites, including arene oxides, through enzymatic processes primarily in the liver. Cytochrome P450 enzymes play a significant role in this conversion, and the resulting metabolites can exhibit different levels of toxicity and carcinogenicity. Knowledge of these metabolic pathways is essential for predicting the health risks associated with phenanthrene and its derivatives.
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