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Chapter 5: Problem 35

The product obtained when benzene is treated with acetyl chloride in presence of anhydrous \(\mathrm{AlCl}_{2}\) is (a) benzophenone (b) benzoyl chloride (c) acetophenone (d) ethyl phenyl ketone

Short Answer

Expert verified
Answer: (c) Acetophenone

Step by step solution

01

Identify the Friedel-Crafts Acylation reagents

Acetyl chloride (CH\(_3\)COCl) and anhydrous \(\mathrm{AlCl}_{3}\) are reagents used in Friedel-Crafts Acylation reactions, which result in the formation of an acylium ion and its subsequent reaction with a benzene ring.
02

Generate the acylium ion

In a Friedel-Crafts Acylation, the Lewis acid (\(\mathrm{AlCl}_{3}\)) accepts a lone pair of electrons from the oxygen atom of the carbonyl group in acetyl chloride, forming a bond between the \(\mathrm{Al}^{3+}\) and the \(\mathrm{O}\) atoms. This makes the carbonyl carbon more electrophilic, allowing the chloride ion in acetyl chloride to be removed, which results in the formation of the acylium ion (CH\(_3\)CO\(^{+}\)) as shown: \(\mathrm{CH_{3}COCl + AlCl}_{3} \rightarrow \mathrm{CH_{3}CO}^{+} + (\mathrm{AlCl}_{4})^{-}\)
03

React benzene with the acylium ion

Now that the acylium ion (CH\(_3\)CO\(^{+}\)) has been generated, it can react with the benzene ring. One of the pi bonds in the benzene ring attacks the electrophilic acylium ion, forming a bond between the carbonyl carbon and the benzene ring. This process generates a carbocation named "Sigma Complex", temporarily disrupting the aromaticity of the benzene ring.
04

Restore aromaticity

Once the bond between the carbonyl carbon and the benzene ring has been formed (Sigma complex), a proton is removed from the benzene ring, causing the double bond to regenerate and restore the aromaticity of the benzene ring. The overall product of this reaction is acetophenone: Benzene + CH\(_3\)CO\(^{+}\) \(\rightarrow\) Acetophenone. Therefore, the correct answer is (c) acetophenone.

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Most popular questions from this chapter

Statement 1 2-methylpropanal undergoes Cannizzaro reaction when heated with \(50 \% \mathrm{NaOH}\) solution at about \(443-473 \mathrm{~K}\). and Statement 2 2-Methylpropanal contains an \(\alpha\) -hydrogen atom.

Column I Column II (a) \(\mathrm{p}-\mathrm{NO}_{2} \mathrm{C}_{6} \mathrm{H}_{4} \mathrm{CHO}\) (p) Friedel-Crafts reaction (b) \(\mathrm{CH}_{3} \mathrm{COOC}_{2} \mathrm{H}_{5}\) (q) Claisen Condensation (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCl}\) (r) Perkin reaction (d) \(\left(\mathrm{CH}_{3} \mathrm{CO}\right)_{2} \mathrm{O}\) (s) Benzoin condensation (t) Rosenmund's reduction

Which of the following halides will not give good yield of the corresponding acid by the conversion to cyanide, followed by hydrolysis? (a) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Br}\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CBr}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}\) (d) CC1CCCCC1

A compound, which is known as oil of bitter almonds is (a) acetaldehyde (b) acetone (c) acetophenone (d) benzaldehyde

The compound that forms a stable hemiacetal when treated with \(\mathrm{CH}_{3} \mathrm{OH}\) and dry \(\mathrm{HCl}\) is (a) benzaldehyde (b) cyclohexanone (c) cyclopropanone (d) propanone
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