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Chapter 18: Q4P (page 877)

Show the mechanism for the generation of the acylium ion if an acid anhydride is used instead of an acyl chloride for the source of the acylium ion.

Short Answer

Expert verified

The answer is,

Mechanism

Step by step solution

01

Acid anhydride

The acid anhydride reacts with lewis acid-like Aluminium chloride to generate the electrophile acylium ion.

Aluminum chloride is a lewis acid that can accept the lone pair of electrons from the acid anhydride.

02

Explanation

The mechanism for generating the acylium ion from an acid anhydride is shown below.

Mechanism

The lone pair on the oxygen atom attacks the Aluminium chloride and donate the lone pair electrons to it. The intermediate generated then undergoes electron rearrangement to give the acylium ion.

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Most popular questions from this chapter

Question: The pKa values of a few ortho-, meta-, and para-substituted benzoic acids are shown below:

The relative pKa values depend on the substituent. For chloro-substituted benzoic acids, the ortho isomer is the most acidic and the para isomer is the least

acidic; for nitro-substituted benzoic acids, the ortho isomer is the most acidic and the meta isomer is the least acidic; and for amino-substituted benzoic acids, the meta isomer is the most acidic and the ortho isomer is the least acidic. Explain these relative acidities.

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