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Chapter 3: Problem 42

$$ \begin{array}{l} \text { The organic product (X) formed in the following reaction is }\\\ \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Cl}+\mathrm{C}_{6} \mathrm{H}_{5} \stackrel{\mathrm{AICl}_{3}}{\longrightarrow} \mathrm{X} \end{array} $$

Short Answer

Expert verified
Answer: The organic product (X) formed is C6H5C6H5CH2, where both benzene rings are connected via a -CH2- group.

Step by step solution

01

Identify the Reaction

The given reaction involves an aromatic benzene ring (C6H5) and an alkyl halide (C6H5CH2Cl). The catalyst used is AlCl3. This is a classic example of a Friedel-Crafts Alkylation reaction.
02

Generate the Electrophile

In a Friedel-Crafts Alkylation reaction, the first step is to generate the electrophile. The Lewis acid AlCl3 coordinates with the chlorine atom in the alkyl halide (C6H5CH2Cl) to create a positively charged carbon atom (an electrophile) and an AlCl4- ion. The electrophile formed is C6H5CH2+.
03

Aromatic Ring Attacks the Electrophile

The next step involves the attack of the aromatic ring (C6H5) on the electrophile (C6H5CH2+). The pi electrons of the benzene ring act as a nucleophile and form a bond with the electrophilic carbon atom, resulting in the formation of a carbocation intermediate.
04

Deprotonation and Regeneration of Aromatic Character

Finally, a base (most likely an AlCl4- ion) removes a proton from the carbon atom adjacent to the carbocation, and the electrons in the C-H bond move into the ring, restoring the aromatic character. This step leads to the formation of the final product (X).
05

Write the Final Product

The product (X) formed after the completion of the Friedel-Crafts Alkylation reaction is: $$\mathrm{X}= \mathrm{C}_6 \mathrm{H}_5 \mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}_2$$ where both benzene rings are connected via a -CH2- group.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Understanding Organic Chemistry
Organic chemistry is the study of carbon-containing compounds, which includes a vast array of substances that constitute the basis of all life. Most organic compounds are structured around chains or rings of carbon atoms with various functional groups attached.

In organic reactions, these carbon-based molecules can react with each other or with different elements to perform complex transformations, one of which is the Friedel-Crafts Alkylation that involves aromatic compounds. Organic chemistry is fundamental in developing pharmaceuticals, plastics, and many other chemical products that are integral to modern life.
Deciphering Electrophilic Aromatic Substitution
Electrophilic Aromatic Substitution (EAS) is a core reaction mechanism in organic chemistry where an electrophile reacts with an aromatic compound. The stability of the aromatic ring drives this reaction. The ring, containing delocalized pi electrons, acts as a nucleophile and can attract electrophiles.

The Steps of Electrophilic Aromatic Substitution

  • Generation of the electrophile, which can be a positively charged ion or a neutral atom with a positive polarity.
  • Attack of the aromatic ring on the electrophile to form a non-aromatic carbocation intermediate.
  • Restoration of aromaticity by loss of a proton, which regenerates the stable aromatic ring system.
The Friedel-Crafts Alkylation is a classic example of an EAS where an alkyl group is introduced to the aromatic ring.
Aromatic Compounds and Their Chemical Behavior
Aromatic compounds, like benzene, are cyclic molecules with a unique stability due to their resonance structures. The electron cloud above and below the plane of the molecule can be described as delocalized pi electrons.

Characteristics of Aromatic Compounds

  • They have a high degree of unsaturation.
  • They follow Huckel's rule, having 4n+2 pi electrons, where n is a non-negative integer.
  • Aromatic molecules tend to undergo substitution reactions rather than addition ones, preserving the aromatic framework.
In the context of a Friedel-Crafts Alkylation, the aromatic compound acts as a nucleophile and attacks an electrophile, keeping its aromaticity intact—which is essential for understanding how and why these reactions occur.

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Most popular questions from this chapter

o-Nitrophenol has lower \(\mathrm{pK}\) than (a) p-nitrophenol (b) o-cresol (c) o-fluorophenol (d) \(\mathrm{p}\) -methoxyphenol

The reaction (s) which give tert-butyl benzene among the following is/are (a) \(\mathrm{C}_{6} \mathrm{H}_{6}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Cl} \stackrel{\mathrm{AlCl}_{3}}{\longrightarrow}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{6}+\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2} \mathrm{OH} \stackrel{\mathrm{BF}_{3}}{\longrightarrow}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{6}+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CH} \stackrel{\mathrm{BF}_{3}}{\longrightarrow}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{6}+\mathrm{Me}_{2} \mathrm{C}=\mathrm{CH}_{2} \stackrel{\mathrm{HF}}{\longrightarrow}\)

Column I \(\quad\) Column II (a) Salicylic acid (p) characteristic colour with neutral \(\mathrm{FeCl}_{3}\) solution (b) \(\mathrm{p}\) -Hydroxy acetophenone (q) Kolbe's reaction (c) Quinol (r) Fries rearrangement (d) picric acid (s) Elbs persulphate oxidation (t) Decomposes \(\mathrm{NaHCO}_{3}\) solution

The product P formed in the following reaction is \(\mathrm{C}_{6} \mathrm{H}_{6}+\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}_{2} \stackrel{\mathrm{HF}}{\stackrel{0^{\circ} \mathrm{C}}}{\longrightarrow} \mathrm{P}\) (a) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{2}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}_{3}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}=\mathrm{CH}_{2}\) (c) CC=C(C)CCC (d) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}=\mathrm{CH}_{2}\)

Sodium phenoxide when heated with \(\mathrm{CO}_{2}\) under pressure gives sodium salicylate. This reaction is known as (a) Reimer-Tiemann reaction (b) Schotten-Baumann reaction (c) Williamson's synthesis (d) Kolbe's reaction
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