Textbook Question
In Chapter 13, we discuss the ring-opening reactions of epoxides, such as the one shown here.
(a) Based on the bonds formed and the bonds broken, calculate ∆H°.
10. Addition Reactions
Epoxide Reactions
2:40 minutesProblem 61a
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.
(a) 
Verified step by step guidance1
Step 1: Analyze the starting material and identify functional groups. The starting material contains an aldehyde group and a terminal alkene. These functional groups are reactive under acidic conditions.
Step 2: Recognize the reaction conditions. The presence of H2SO4 (sulfuric acid) and CH3OH (methanol) suggests an acid-catalyzed reaction, likely involving protonation and nucleophilic attack.
Step 3: Protonation of the aldehyde group. Under acidic conditions, the aldehyde oxygen is protonated, increasing the electrophilicity of the carbonyl carbon and making it more susceptible to nucleophilic attack.
Step 4: Intramolecular nucleophilic attack. The terminal alkene acts as a nucleophile, attacking the protonated aldehyde carbon. This forms a cyclic intermediate, likely a carbocation, stabilized by resonance or hyperconjugation.
Step 5: Methanol addition and deprotonation. Methanol acts as a nucleophile, attacking the carbocation formed in the previous step. Subsequent deprotonation leads to the formation of the final product, which includes a cyclic structure with hydroxyl and methoxy groups.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Biosynthesis Mechanisms
Biosynthesis mechanisms refer to the series of chemical reactions that occur in living organisms to produce complex molecules from simpler ones. In the context of lanosterol biosynthesis, these mechanisms often involve enzymatic reactions that facilitate the transformation of sterol precursors into more complex structures, highlighting the importance of understanding reaction pathways in organic chemistry.
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General Mechanism
Acid-Catalyzed Reactions
Acid-catalyzed reactions involve the use of an acid to increase the rate of a chemical reaction. In the provided reaction, sulfuric acid (H2SO4) acts as a catalyst in the presence of methanol (CH3OH), promoting the formation of the final product through protonation and subsequent nucleophilic attack. Understanding these mechanisms is crucial for predicting reaction outcomes in organic synthesis.
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Functional Group Transformations
Functional group transformations are chemical reactions that convert one functional group into another, altering the properties and reactivity of the molecule. In the reaction depicted, the transformation of an alcohol and the introduction of a methoxy group (OCH3) illustrate how functional groups can be modified to create more complex structures, which is a fundamental concept in organic chemistry.
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