Textbook Question
Which alkyne should be used for the synthesis of each of the following ketones?
a.
b.
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10. Addition Reactions
Alkyne Hydration
3:47 minutesProblem 20f
Textbook Question
What are products of the following reactions?
f. 
Verified step by step guidance1
Step 1: Identify the type of reaction. The given reaction involves an alkyne reacting with water in the presence of sulfuric acid (H₂SO₄). This is an example of an acid-catalyzed hydration of an alkyne.
Step 2: Understand the mechanism. In acid-catalyzed hydration, the alkyne undergoes electrophilic addition of water, facilitated by the acid catalyst. The reaction typically proceeds via the formation of an enol intermediate, which then tautomerizes to form a ketone.
Step 3: Analyze the structure of the alkyne. The alkyne shown is terminal, meaning the triple bond is at the end of the carbon chain. Terminal alkynes typically form methyl ketones as the major product in acid-catalyzed hydration reactions.
Step 4: Predict the intermediate. The addition of water across the triple bond forms an enol intermediate. The enol has a hydroxyl group (-OH) attached to one of the carbons of the former triple bond, and a double bond between the two carbons.
Step 5: Tautomerization to the final product. The enol intermediate undergoes tautomerization, a process where the hydroxyl group and the double bond rearrange to form a ketone. For this reaction, the final product will be a methyl ketone with the carbonyl group (C=O) on the second carbon of the chain.
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3mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
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