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Chapter 2: Problem 88

Which of the following alkenes will undergo acid catalysed hydration most readily? (a) (b) Cis-2-butene (c) trans-2-butene (d) 1 -butene

Short Answer

Expert verified
(a) unspecified, (b) cis-2-butene, (c) trans-2-butene, or (d) 1-butene? Answer: Both (b) cis-2-butene and (c) trans-2-butene will undergo acid-catalyzed hydration more readily than (d) 1-butene. However, as option (a) is unspecified, it cannot be compared to the other options.

Step by step solution

01

Draw the alkenes

Draw the structures of the four alkenes listed in the exercise. (a) is unspecified, so we can't analyze it. (b) Cis-2-butene: H2C=C(H)-CH2-CH3 (c) trans-2-butene: H2C=C(-H)-CH2-CH3 (d) 1-butene: H2C=CH-CH2-CH3
02

Determine the carbocations formed from each alkene

Determine the carbocations formed from each of these alkenes upon the addition of water across the double bond. (b) Cis-2-butene: H3C-C^(+)(-H)-CH2-CH3 (c) trans-2-butene: H3C-C^(+)(-H)-CH2-CH3 (d) 1-butene: H3C-CH2-C^(+)-CH3
03

Determine the intermediate carbocation stability

Now, compare the stability of the intermediate carbocations. Carbocation stability is generally in the order: 3°>2°>1° (b) Cis-2-butene: A 2° carbocation (c) trans-2-butene: A 2° carbocation (d) 1-butene: A 1° carbocation
04

Compare the reactivity of the alkenes

Since both cis-2-butene and trans-2-butene form a 2° carbocation during acid-catalyzed hydration, they will undergo the reaction more readily than 1-butene, which forms a less stable 1° carbocation. While cis and trans isomers can have different properties, the reaction rate does not significantly vary between them for this specific case. So the final answer is: Both (b) Cis-2-butene and (c) trans-2-butene will undergo acid-catalyzed hydration more readily than (d) 1-butene. However, as option (a) is unspecified, it cannot be compared to the other options.

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