Question

Which of the following products is obtained, when chloroethane reacts with silver oxide suspended in boiling water?
(A) \[C{H_3}C{H_2}C{H_2}C{H_3}\]
(B) \[C{H_3}C{H_3}\]
(C) \[C{H_3}C{H_2}OH\]
(D) \[C{H_3}C{H_2}OC{H_2}C{H_3}\]

Answer 1

Hint: In the given reaction, the leaving group is being eliminated to produce an unsaturated hydrocarbon as the main product and a salt as a side product. The base in this situation is silver oxide.

Complete Step by Step Solution:
The answer to the question is that silver oxide suspended in boiling water reacts with chloroethane.

As is well known, silver hydroxide is produced when silver oxide combines with water.
\[A{g_2}O + {H_2}O \to 2AgOH\]

The reaction of chloroethane with a silver oxide is shown below:
\[{C_2}{H_5}Cl{\text{ }} + {\text{ }}AgOH \to \;{C_2}{H_5}OH\; + {\text{ }}AgCl\]
In this process, silver oxide and chloroethane combine to generate ethanol with a double bond and silver chloride.

The following diagram illustrates the mechanism of chloroethane with a silver hydroxide:

In this reaction, the alcoholic \[AgOH\] acts as the base which will attack the hydrogen atom to form water. After the removal of hydrogen, the bond will shift to form an ethene and remove the chlorine. The chlorine acts as a nucleophile which will attack the positive silver ion to form silver chloride.

Anhydrous silver oxide is dissolved in ethanol to produce alcoholic silver hydroxide. It is utilised in water-sensitive elimination processes. An illustration of an elimination reaction is this one. A molecule with a saturated carbon (single bond) can become an unsaturated carbon through the elimination reaction (double bond).
In this reaction the leaving group from the reactant, which is removed to form an unsaturated carbon compound.
Therefore, the correct answer is: (C) \[C{H_3}C{H_2}OH\].

Note: Dehydrohalogenation is another name for this process. Make that the silver oxide being utilised in the reaction is of the alcoholic variety. When chloroethane and aqueous silver oxide combine, the major product that results after the silver chloride is removed is alcohol.