Question:

Ethyl chloride is converted into diethyl ether by:

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Alkyl halide on reaction with sodium alkoxide gives ether.

Updated On: Jan 15, 2024
  • Perkins reaction
  • Grignard reagent
  • Wurtz reaction
  • Williamsons synthesis
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The Correct Option is D

Approach Solution - 1

By Williamson synthesis, alkyl halide on reaction with sodium alkoxide gives ether

C2H5Cl + C2H5ONa → C2H5OC2H5 + NaCl

Ethyl chloride + Sodium Ethoxide → Diethyl ether + sodium chloride 

 Ethyl chloride is converted into diethyl ether by Williamson's synthesis.

Williamson's synthesis is a commonly used method to prepare ethers. In this reaction, an alkoxide ion (RO-) reacts with an alkyl halide to form an ether. The alkoxide ion is generated by treating an alcohol with a strong base.

In the case of converting ethyl chloride to diethyl ether, the reaction can be represented as follows:

CH3CH2Cl + CH3CH2O- → CH3CH2OCH2CH3 + Cl-

In this reaction, ethyl chloride (CH3CH2Cl) reacts with an alkoxide ion (CH3CH2O-) to produce diethyl ether (CH3CH2OCH2CH3) and a chloride ion (Cl-).

The other reactions mentioned, Perkins reaction, Grignard reagent, and Wurtz reaction, do not directly convert ethyl chloride into diethyl ether. Perkins reaction is used for the oxidation of aldehydes to corresponding carboxylic acids. Grignard reagent is used for the formation of carbon-carbon bonds, and the Wurtz reaction is used for the synthesis of alkyl halides with the formation of a carbon-carbon bond.

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Approach Solution -2

The conversion of ethyl chloride to diethyl ether is typically carried out using a process called dehydrohalogenation. This process involves the removal of a hydrogen halide (such as \(HCl\)) from the ethyl chloride molecule, which results in the formation of an alkene intermediate.

The alkene intermediate can then react with another molecule of ethyl chloride to form diethyl ether. This reaction is known as the Williamson ether synthesis, and it involves the use of a strong base (such as sodium or potassium hydroxide) to deprotonate the ethyl chloride and facilitate the ether formation reaction.

Overall, the reaction can be represented as follows:
\(2 C_2H_5Cl + 2 NaOH → C_2H_5OC_2H_5 + 2 NaCl + H_2O\)

In this reaction, two molecules of ethyl chloride (\(C_2H_5Cl\)) react with two molecules of sodium hydroxide (\(NaOH\)) to form one molecule of diethyl ether (\(C_2H_5OC_2H_5\)), two molecules of sodium chloride (\(NaCl\)), and one molecule of water (\(H_2O\)).

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Concepts Used:

Ethers

A class of organic compounds that mostly contain an ether group in which the oxygen atom is bonded to two alkyl or aryl groups are referred to as Ethers. For the same, C-O-C is the functional group.

Chemical Properties of Ether:

Ethers are less polar as well as less reactive, and they do not react with active metals (Na, K), cold dilute acid, oxidizing and reducing agents or other chemicals.

The reason is that they do not have an active functional group.

  • Because of the presence of a lone pair on the oxygen atom, ether has a basic nature and behaves like a Lewis base.  Formation of oxonium ion occurs when ethers react with cold conc. acid. Ethers, such as BF3, AICI3, and RMgX, form a dative bond with Lewis acid.
  • There is a significant difference between the boiling points of ethanol and dimethyl ether. Ethanol has very much higher boiling point of 78 degrees Celsius, whereas dimethyl ether has a negative 25 degrees boiling point. And this explains the molecules' state of matter.
  • Ethanol is, of course, a liquid at room temperature and pressure because its boiling point is higher than room temperature. On the other hand, Dimethyl ether already has turned into a gas due to its much lower boiling point.