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Chapter 20: Q25P (page 1038)

Explain why the acid-catalyzed condensation is a poor method for the synthesis of an unsymmetrical ether such as ethyl methyl ether, CH3CH2 - O - CH3.

Short Answer

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The acid-catalyzed condensation is a poor method for synthesizing unsymmetrical ethers as the unsymmetrical alcohols generate a mixture of products.

Step by step solution

01

Condensation reaction

Condensation reactions constitute an essential reaction in organic chemistry. An example of a condensation reaction is Claisen condensation.

02

Unsymmetrical ethers

Unsymmetrical ethers constitute ethers where the groups located on two sides of the oxygen atom are distinct. An example of an unsymmetrical ether is ethyl methyl ether ( CH3OC2H5).

03

Reason why the acid-catalyzed condensation is a poor method for the synthesis of an unsymmetrical ether

The sulphuric acid-catalyzed alcohol dehydration produces different products via unimolecular dehydration (E1 mechanism) and bimolecular dehydration (SN2 displacement reaction). The E1 mechanism produces an alkene, whereas the SN2 displacement mechanism generates an ether.

However, only symmetrical ethers are produced by SN2 displacement reaction from symmetrical alcohols. The unsymmetrical ethers generate a mixture of products. The reaction can be given as:

The combination of methanol and ethanol generates a mixture of products

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Most popular questions from this chapter

There are three dioxane isomers: 1,2-dioxane, 1,3- dioxane, and 1,4-dioxane. One of these acts like an ether and is an excellent solven for Grignard reactions. Another one is potentially explosive when heated. The third one quickly hydrolyzes in dilute acid. Show which isomer acts like a simple ether, and then explain why one of them is potentially explosive. Propose a mechanism for the acid hydrolysis of the third isomer.

Question: Draw the structures of the following compounds.

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The following reaction takes place under second-order conditions (strong nucleophile), yet the structure of the product shows rearrangement. Also, the rate of this reaction is several thousand times faster than the rate of substitution of hydroxide ion on 2-chlorobutane under similar conditions. Propose a mechanism to explain the enhanced rate and rearrangement observed in this unusual reaction. (鈥淓t鈥� is the abbreviation for ethyl.

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Question: Show the products you expect when each compound reacts with NBS with light shining on the reaction.

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