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What is the major product obtained from the acid-catalyzed hydration of #CH_3CH_2CH_2CH=CHCH_3#?

Answer 1

Hexan-2-ol is presumably the main product.

CH₃CH₂CH₂CH⁺-CH₂CH₃ and CH₃CH₂CH₂CH₂CH⁺-CH₃ are the cations that are produced.

Given that both are 2° carbocations, the stability differences are negligible.

However, the second structure has five β hydrogens, while the first structure has four β hydrogens to stabilize the carbocation.

Therefore, the second structure might be a little bit more stable.

Though not by much, I would anticipate hexan-2-ol to be the main product rather than hexan-3-ol.

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Answer 2

Christian Anderson

The major product obtained from the acid-catalyzed hydration of CH3CH2CH2CH=CHCH3 is 2-methyl-2-butanol.

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Answer from HIX Tutor

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.