Predict the major products of the following reactions.
(a) toluene + excess Cl₂ (heat, pressure)

Verified step by step guidance

Step 1: Recognize the type of reaction. This is a halogenation reaction involving toluene (methylbenzene) and excess chlorine under conditions of heat and pressure. These conditions favor free radical halogenation rather than electrophilic aromatic substitution.

Step 2: Identify the reactive site. In free radical halogenation, the methyl group attached to the benzene ring is the most reactive site due to the hydrogen atoms on the methyl group being more susceptible to abstraction by radicals.

Step 3: Understand the mechanism. The reaction proceeds via a free radical chain mechanism: initiation (formation of chlorine radicals), propagation (abstraction of hydrogen atoms from the methyl group and formation of chloromethyl radicals), and termination (combination of radicals).

Step 4: Predict the product distribution. Since excess Cl2 is used, all three hydrogens on the methyl group are likely to be replaced by chlorine atoms, resulting in the formation of trichloromethylbenzene (C6H5CCl3) as the major product.

Step 5: Consider the role of heat and pressure. These conditions ensure the reaction proceeds efficiently and favor the complete substitution of the methyl hydrogens with chlorine atoms, minimizing side reactions or incomplete substitution.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.

Video duration:

Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In the case of toluene reacting with chlorine, the aromatic ring is activated by the methyl group, making it more reactive towards electrophiles. This process typically leads to the formation of chlorinated products, such as chlorotoluene.

Reactivity of Aromatic Compounds

Aromatic compounds, like toluene, exhibit unique reactivity due to their stable resonance structures. The presence of substituents, such as the methyl group in toluene, influences the reactivity and orientation of further substitutions. In this reaction, the excess chlorine and conditions of heat and pressure can lead to multiple substitutions, resulting in polysubstituted products.

Free Radical Chlorination

Free radical chlorination is a reaction mechanism that involves the substitution of hydrogen atoms with chlorine atoms through radical intermediates. Under heat and pressure, chlorine can generate free radicals that can react with toluene, leading to the formation of chlorinated products. This process can result in a mixture of products, including benzyl chloride and other chlorinated derivatives, depending on the reaction conditions.

Related Practice

Textbook Question

Propose mechanisms for the Birch reduction of anisole. Show why the observed orientation of reduction is favored in each case.

Textbook Question

Show how you would use Suzuki reactions to synthesize these products from the indicated starting materials. You may use any additional reagents you need.

(b)

views

Textbook Question

Predict the major products of the following reactions.

(b) benzamide (PhCONH₂) + Na (liquid NH₃, CH₃CH₂OH)

views

Textbook Question

Predict the major products of the following reactions.

(d) p-xylene + Na (liquid NH₃, CH₃CH₂OH)

(e)

views

Textbook Question