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

Most of the Fischer esterification mechanism is identical with the mechanism of acetal formation. The difference is in the final step, where a resonance-stabilized carbocation loses a proton to give the ester. Write mechanisms for the following reactions, with the comparable steps directly above and below each other. Explain why the final step of the esterification (proton loss) cannot occur in acetal formation, and show what happens instead.

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

(a) methyl salicylate

(b) methyl formate (bp 32°C)

(c) ethyl phenylacetate

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(a) isopentyl alcohol isopentyl acetate (banana oil)

(b) 3-ethylpentanoic acid3-ethylpentanenitrile

(c) isobutylamineN-isobutylformamide

(d) ethyl acetate3-methylpentan-3-ol

(e) cyclohexylamineN-cyclohexylacetamide

(f) bromocyclohexanedicyclohexylmethano

(g)

(h)

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.

(a)

(b)

(c)

Question:

  1. The Key Mechanism for Fischer esterification omitted some important resonance forms of the intermediates shown in brackets. Complete the mechanism by drawing all the resonance forms of these two intermediates.
  2. Propose a mechanism for the acid-catalyzed reaction of acetic acid with ethanol to give ethyl acetate.
  3. The Principle of Microscopic Reversibility states that a forward reaction and a reverse reaction taking place under the same conditions (as in equilibrium) must follow the same reaction pathway in microscopic detail. The reverse of the Fischer esterification is the acid-catalyzed hydrolysis of an ester. Propose a mechanism for the acid-catalyzed hydrolysis of ethyl benzoate, PhCOOCH2CH3.
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