Textbook Question
How could the following compounds be prepared using an alkene as one of the starting materials?
c.
10. Addition Reactions
Acid-Catalyzed Hydration
6:46 minutesProblem 101
Textbook Question
Propose a mechanism for the following reaction:
Verified step by step guidance1
Step 1: Identify the reaction type. This is an acid-catalyzed hydration of an alkene. The alkene reacts with water in the presence of sulfuric acid (H₂SO₄) to form an alcohol.
Step 2: Protonation of the alkene. The sulfuric acid donates a proton (H⁺) to the double bond of the alkene, forming a carbocation intermediate. The more stable carbocation will form, so consider the rearrangement of the carbocation if necessary.
Step 3: Nucleophilic attack by water. The water molecule acts as a nucleophile and attacks the carbocation, forming an oxonium ion (a positively charged oxygen species).
Step 4: Deprotonation of the oxonium ion. A water molecule or another base removes a proton from the oxonium ion, resulting in the formation of the alcohol product.
Step 5: Analyze the product structure. The final product is a tertiary alcohol, indicating that the carbocation formed during the reaction underwent rearrangement to achieve maximum stability before the nucleophilic attack by water.
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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 a chemical reaction occurs at the molecular level. It outlines the sequence of elementary steps, including bond breaking and formation, and the intermediates formed during the reaction. Understanding the mechanism helps predict the products and the conditions under which the reaction occurs.
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Nucleophiles and Electrophiles
Nucleophiles are species that donate an electron pair to form a chemical bond, while electrophiles are electron-deficient species that accept an electron pair. Identifying these species in a reaction is crucial for proposing a mechanism, as it determines how reactants interact and the direction of electron flow during the reaction.
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Transition States and Intermediates
Transition states are high-energy states that occur during the transformation of reactants to products, representing the point of maximum energy along the reaction pathway. Intermediates are species that are formed and consumed during the reaction but are not present in the final products. Understanding these concepts is essential for accurately depicting the mechanism and energy changes throughout the reaction.
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