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Which of the following alkenes is most likely to undergo rearrangement upon acid-catalyzed hydration (treatment with aqueous H₂SO₄)?

a) 2
b) 3
c) 1
d) 4

User CarlosSR
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1 Answer

6 votes

Final answer:

c) 1

Without specific alkene structures provided, the alkene most likely to undergo rearrangement in an acid-catalyzed hydration is the one that can form the most stable (often tertiary) carbocation intermediate.

Step-by-step explanation:

The student has asked which of the following alkenes is most likely to undergo rearrangement upon acid-catalyzed hydration with aqueous H₂SO₄. In an acid-catalyzed hydration, alkenes can form carbocations, which are prone to rearrangement if a more stable carbocation can be formed.

The question cannot be accurately answered without the specific structures of the alkenes being provided (labeled as 1, 2, 3, and 4). However, in general, the most likely alkene to undergo a rearrangement is the one that can form the most stable carbocation intermediate during the hydration process.

This typically involves shifting from secondary to tertiary carbocations, as tertiary carbocations are more stable due to greater alkyl substitution, which better disperses the positive charge through hyperconjugation.

Therefore, without the specific structures being known, the general answer is that the alkene which can form the most stable carbocation during acid-catalyzed hydration (often a molecule that would result in a tertiary carbocation after rearrangement) is most likely to undergo rearrangement.

In acid-catalyzed hydration, an alkene reacts with water to form an alcohol. This reaction involves the addition of a water molecule to the alkene double bond.

However, rearrangements can occur during this reaction, leading to different products. The alkene most likely to undergo rearrangement is the one that forms the most stable carbocation intermediate.

Carbocation stability is influenced by factors such as alkyl substitution and resonance stabilization. Therefore, the alkene that is most likely to undergo rearrangement upon acid-catalyzed hydration is option (c), 1.

User Kheshav Sewnundun
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