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Chapter 21: Problem 64

Why is it preferable to produce chloroethane by the reaction of HCI(g) with ethene than by the reaction of \(\mathrm{Cl}_{2}(g)\) with ethane? (See Exercise 62.)

Short Answer

Expert verified
Producing chloroethane by the reaction of HCl(g) with ethene is more preferable because it has a faster one-step addition reaction mechanism, consumes less energy due to breaking weaker bonds, and doesn't produce additional by-products, simplifying the process and reducing costs compared to the substitution reaction of Cl\(_2\)(g) with ethane.

Step by step solution

01

Write down the chemical reactions

First, let's write down the two reactions mentioned in the exercise. Reaction 1: HCl(g) with ethene \[ C_2H_4 + HCl \rightarrow C_2H_5Cl \] Reaction 2: Cl\(_2\)(g) with ethane \[ C_2H_6 + Cl_2 \rightarrow C_2H_5Cl + HCl \]
02

Compare the reaction mechanisms

Now, let's compare the reaction mechanisms of the two reactions. For Reaction 1, it is an addition reaction where the HCl molecule adds across the double bond in ethene. This reaction is faster than Reaction 2 because it proceeds through a single step mechanism. For Reaction 2, it is a substitution reaction where one hydrogen atom in ethane is replaced by a chlorine atom from the Cl\(_2\) molecule. This reaction is slower than Reaction 1 because it proceeds through a two-step mechanism where first a chlorine radical attacks the ethane and then a hydrogen atom is replaced by a chlorine atom.
03

Compare energy requirements

We will also compare the energy requirements of the two reactions to produce chloroethane. Reaction 1 consumes less energy compared to Reaction 2 as it only involves breaking the strong π bond of ethene and a H-Cl bond. The breaking of the π bond requires less energy than breaking a σ bond, which is involved in Reaction 2. Reaction 2 requires more energy as it involves breaking two strong σ bonds in ethane and Cl\(_2\). Moreover, the reaction proceeds through an intermediate step with higher energy species, which further increases the energy requirement for the reaction.
04

Check for by-products

Both reactions produce chloroethane as the desired product but let's check for any additional by-products. Reaction 1 produces only chloroethane with no additional by-products. Reaction 2 produces chloroethane and also HCl as a by-product. This will require additional separation processes to obtain pure chloroethane, increasing the overall cost and complexity of the process.
05

Conclude the comparison

Based on the comparison of reaction mechanisms, energy requirements, and by-products: - Reaction 1 is faster, as it is an addition reaction requiring a single step mechanism - Reaction 1 consumes less energy because it involves relatively weaker bonds and fewer bond-breakings than Reaction 2 - Reaction 1 produces no additional by-products, simplifying the process and reducing costs Therefore, it is more preferable to produce chloroethane by the reaction of HCl(g) with ethene than by the reaction of Cl\(_2\)(g) with ethane.

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Most popular questions from this chapter

Draw the five structural isomers of hexane \(\left(\mathrm{C}_{6} \mathrm{H}_{14}\right).\)

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