Chapter 3: Problem 35

The wrong statement relating to the influence of substituents on aromatic electrophilic substitution reactions is (a) The rate determining step in an electrophilic substitution is the one which leads to the formation of an arenium ion. (b) Electron releasing groups make the transition state more stable and the transition state resembles the arenium ion. (c) The arenium ion is a highly energetic intermediate and the step that leads to it is a highly exothermic step. (d) An electron withdrawing substituent makes the arenium ion less stable and the transition state leading to such an arenium ion is less stable.

Short Answer

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Answer: The incorrect statement is (c): The arenium ion is a highly energetic intermediate, and the step leading to it is a highly exothermic step.

Step by step solution

Statement (a)

The rate-determining step in an electrophilic substitution is the one which leads to the formation of an arenium ion. This statement is true, as the rate-determining step in these reactions is indeed the formation of the arenium ion, which is the intermediate that forms when an electrophile attacks the aromatic system.

Statement (b)

Electron-releasing groups make the transition state more stable, and the transition state resembles the arenium ion. This statement is true because electron-releasing groups donate electron density, which stabilizes the transition state. In turn, this increases the rate of electrophilic substitution reactions.

Statement (c)

The arenium ion is a highly energetic intermediate, and the step leading to it is a highly exothermic step. This statement is false. The arenium ion is indeed a highly energetic intermediate, but the step leading to its formation is actually endothermic, not exothermic. This is due to the breaking of aromaticity, which requires energy input.

Statement (d)

An electron-withdrawing substituent makes the arenium ion less stable, and the transition state leading to such an arenium ion is less stable. This statement is true because electron-withdrawing groups pull electron density away from the aromatic system, making the arenium ion less stable. Consequently, the transition state leading to this arenium ion is also less stable, leading to a slower electrophilic substitution reaction. The wrong statement related to the influence of substituents on aromatic electrophilic substitution reactions is statement (c).

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Short Answer

Step by step solution

Statement (a)

Statement (b)

Statement (c)

Statement (d)

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