Write equations for the following reactions and identify the product formed in each case (i) chlorobenzene + sodium \(\stackrel{\text { ether }}{\longrightarrow}\) (ii) chlorobenzene \(+\) chloral \(\stackrel{\text { con. } \mathrm{H}_{2} \mathrm{SO}_{4}}{\longrightarrow}\)

Short Answer

Expert verified
Answer: The products formed in the reactions are benzene (C6H6) in the first reaction and 2,2,2-trichloroethylbenzene (C6H5CCl3) in the second reaction.

Step by step solution

01

(Reaction 1: Identify the reactants)

The reactants for the first reaction are chlorobenzene and sodium.
02

(Reaction 1: Predict the product)

This reaction is a Wurtz-Fittig reaction that involves the reaction of an alkyl halide (chlorobenzene) with an alkali metal (sodium) in the presence of dry ether as a solvent. The product of this reaction is an alkane.
03

(Reaction 1: Write the balanced equation)

The balanced equation for this reaction: 2C\(_6\)H\(_5\)Cl + 2Na \(\stackrel{\text { ether }}{\longrightarrow}\) 2C\(_6\)H\(_6\) + 2NaCl The product formed is benzene (C\(_6\)H\(_6\)).
04

(Reaction 2: Identify the reactants)

The reactants for the second reaction are chlorobenzene and chloral.
05

(Reaction 2: Predict the product)

This reaction is a Friedel-Crafts alkylation action where the chlorobenzene reacts with the chloral in the presence of concentrated H\(_2\)SO\(_4\). The product of this reaction is the substituted benzene ring.
06

(Reaction 2: Write the balanced equation)

The balanced equation for this reaction is: C\(_6\)H\(_5\)Cl + Cl\(_3\)CCHO \(\stackrel{\text { con. H}_{2}\text{SO}_{4}}{\longrightarrow}\) C\(_6\)H\(_5\)CCl\(_3\) + HCl + H\(_2\)O The product formed is 2,2,2-trichloroethylbenzene (C\(_6\)H\(_5\)CCl\(_3\)).

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Key Concepts

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

Wurtz-Fittig Reaction
The Wurtz-Fittig reaction is an important chemical process used to synthesize alkanes from aryl halides and alkyl halides in the presence of an alkali metal.
In the reaction between chlorobenzene and sodium, dry ether is used as a solvent, creating an environment which allows the sodium metal to react and effectively remove the chlorine atoms from chlorobenzene.

The mechanism involves the formation of free radicals or organosodium compounds, which then combine to form a new carbon-carbon bond, yielding the desired alkane along with a byproduct of sodium chloride (salt). The reaction is as follows:
  • 2C6H5Cl + 2Na \( \stackrel{\text{ ether }}{\longrightarrow} \) 2C6H6 + 2NaCl
In this case, the product formed is benzene (C6H6). The Wurtz-Fittig reaction elegantly illustrates the concept of cross-coupling to form carbon-carbon bonds, a fundamental strategy in organic synthesis.
To further enhance understanding, visualization of the electron transfer during the process and the intermediate species involved can significantly aid students in grasping this reaction's concept.
Friedel-Crafts Alkylation
Friedel-Crafts alkylation is another classic reaction in organic chemistry where an alkyl group is added to an aromatic ring. This typically requires the use of a Lewis acid catalyst, such as AlCl3, FeCl3, or in the exercise example, concentrated H2SO4.

The reaction between chlorobenzene and chloral in the presence of concentrated H2SO4 leads to the formation of 2,2,2-trichloroethylbenzene. Here, chloral serves as the alkylating agent, undergoing a transformation to attach its carbon group to the benzene ring.
  • C6H5Cl + Cl3CCHO \( \stackrel{\text{ con. H}_{2}\text{SO}_{4}}{\longrightarrow} \) C6H5CCl3 + HCl + H2O
One should note that unlike Wurtz-Fittig, Friedel-Crafts alkylation may introduce side reactions such as carbocation rearrangements leading to product mixtures. Discussing potential side reactions and how they are suppressed or avoided can be highly educational for students to understand this complexity.
Reaction Mechanism
Understanding the reaction mechanism is critical for mastering organic chemistry. It details the step-by-step sequence of elementary reactions by which overall chemical change occurs. The mechanism includes details about molecular rearrangements, the order of bond breakage and formation, and the role of catalysts.

For example, in the Wurtz-Fittig reaction, understanding the role of free radicals or anions in the reaction, and how they come together to create the final product is key to grasping the overall process. In Friedel-Crafts alkylation, comprehending how the Lewis acid catalyst activates the alkyl halide and generates a carbocation intermediate which then attacks the aromatic ring, is crucial.

A thorough analysis of the reaction mechanism can reveal information such as reaction intermediates, transition states, and kinetic aspects such as reaction rate. This is not just about memorizing the steps, but about visualizing and understanding the dance of electrons that underpins the chemistry. For students, building this molecular insight develops a strong foundation for predicting the outcomes of reactions and for designing new syntheses in the laboratory.

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Most popular questions from this chapter

Reactions of Grignard reagents Organic compounds which contain atleast one carbon-metal bond are called organometallic compounds. Grignard reagents are very reactive organometallic compounds which are of great synthetic utility. They are used for the synthesis of alcohols, aldehydes, ketones, carboxylic acids, etc. They are however decomposed by compounds which have active hydrogen.

Write the steps involved in the conversion of the following (i) Ethanol to but-1-yne (ii) Ethyl bromide to butan- 2 - one (iii) 2 -chloropropane to propan-1-ol

In the preparation of \(\mathrm{CH}_{3}-\mathrm{O}-\mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}\), two methods, namely (i) and (ii) are suggested. Which method is preferable and why? (i) \(\mathrm{CH}_{3} \mathrm{ONa}+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{Br} \rightarrow \mathrm{CH}_{3}-\mathrm{O}-\mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}\) (ii) \(\mathrm{CH}_{3} \mathrm{Br}+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{ONa} \rightarrow \mathrm{CH}_{3}-\mathrm{O}-\mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}\)

Benzyl chloride and o-chlorotoluene can be distinguished using (a) alcoholic \(\mathrm{AgNO}_{3}\) (b) \(\mathrm{NaNO}_{2}\) and \(\mathrm{HCl}\) (c) hot alkaline \(\mathrm{KMnO}_{4}\) (d) both (a) and (c)

Primary, secondary and tertiary alcohols may be distinguished by converting them to the corresponding nitroalkanes and then treating with (a) \(\mathrm{NaNO}_{2}\) and dilute \(\mathrm{HCl}\) (b) \(\mathrm{con} \cdot \mathrm{H}_{2} \mathrm{SO}_{4}\) (c) Sn and hydrochloric acid (d) Ammonium hydroxide

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