Chapter 13: Problem 6
What are the different products obtained by the treatment of ethanol with concentrated \(\mathrm{H}_{2} \mathrm{SO}_{4}\) at \(110^{\circ}, 140^{\circ}\), and \(170^{\circ} \mathrm{C}\) ?
Short Answer
Expert verified
Ethanol forms diethyl ether at 110°C, a mix of ether and alkene at 140°C, and ethylene at 170°C.
Step by step solution
01
Understanding Temperature Effects
When ethanol is treated with concentrated \( \mathrm{H}_{2}\mathrm{SO}_{4} \) at different temperatures, different reactions predominately occur. At slightly different temperatures, we will see different chemical reactions because \( \mathrm{H}_{2}\mathrm{SO}_{4} \) acts as both a dehydrating and esterifying agent.
02
Reaction at 110°C
When ethanol is treated with concentrated \( \mathrm{H}_{2}\mathrm{SO}_{4} \) at around \(110^{\circ} \mathrm{C}\), an etherification reaction takes place. Ethanol reacts to form diethyl ether (\( \mathrm{C}_{2}\mathrm{H}_{5}\mathrm{OC}_{2}\mathrm{H}_{5} \)), wherein two molecules of ethanol react to form the ether and release a molecule of water.
03
Reaction at 140°C
At around \(140^{\circ} \mathrm{C}\), an equilibrium mixture of the etherification product and some dehydration product can be observed. Although etherification to form diethyl ether (\( \mathrm{C}_{2}\mathrm{H}_{5}\mathrm{OC}_{2}\mathrm{H}_{5} \)) can still occur, there can also be a formation of some alkenes such as ethylene (\( \mathrm{C}_{2}\mathrm{H}_{4} \)) due to dehydration.
04
Reaction at 170°C
At a higher temperature of about \(170^{\circ} \mathrm{C}\), ethanol predominantly undergoes a dehydration reaction to form ethylene (\( \mathrm{C}_{2}\mathrm{H}_{4} \)). \( \mathrm{H}_{2}\mathrm{SO}_{4} \) facilitates the removal of a water molecule, yielding the alkene.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Etherification Reaction
Etherification is a key reaction when ethanol interacts with concentrated sulfuric acid (\( \mathrm{H}_{2} \mathrm{SO}_{4} \)). At approximately \(110^{\circ} \mathrm{C}\), the sulfuric acid catalyzes the transformation of ethanol into diethyl ether. This process involves the joining of two ethanol molecules to form a molecule of diethyl ether (\( \mathrm{C}_{2}\mathrm{H}_{5}\mathrm{OC}_{2}\mathrm{H}_{5} \)) along with the release of a water molecule.
This reaction is a type of condensation reaction where water is a byproduct. Etherification is useful in the industrial production of ethers, which are valuable solvents and intermediates in chemical processes.
This reaction is a type of condensation reaction where water is a byproduct. Etherification is useful in the industrial production of ethers, which are valuable solvents and intermediates in chemical processes.
- Diethyl ether is a common product.
- Water is released during the reaction.
- Concentrated \( \mathrm{H}_{2} \mathrm{SO}_{4} \) acts as a dehydration agent.
Temperature Effects on Chemical Reactions
Chemical reactions are highly sensitive to temperature, and this principle is particularly evident when ethanol is treated with concentrated \( \mathrm{H}_{2} \mathrm{SO}_{4} \). At different temperatures, different chemical pathways can dominate.
At \(110^{\circ} \mathrm{C}\), etherification leads to the production of diethyl ether. Meanwhile, as the temperature increases to \(140^{\circ} \mathrm{C}\), a mix of reactions can occur, creating both ethers and alkenes like ethylene.
Finally, when the temperature reaches \(170^{\circ} \mathrm{C}\), dehydration becomes the primary reaction, converting ethanol into ethylene.
At \(110^{\circ} \mathrm{C}\), etherification leads to the production of diethyl ether. Meanwhile, as the temperature increases to \(140^{\circ} \mathrm{C}\), a mix of reactions can occur, creating both ethers and alkenes like ethylene.
Finally, when the temperature reaches \(170^{\circ} \mathrm{C}\), dehydration becomes the primary reaction, converting ethanol into ethylene.
- The reaction type largely depends on temperature.
- Different products can form with slight temperature variations.
- Higher temperatures generally favor dehydration reactions.
Dehydration Reaction of Alcohols
Dehydration of alcohols involves removing a water molecule to form an alkene. In the case of ethanol treated with \( \mathrm{H}_{2} \mathrm{SO}_{4} \), dehydration becomes the main reaction at around \(170^{\circ} \mathrm{C}\).
The sulfuric acid acts as a catalyst, facilitating the removal of water, which results in the formation of ethylene (\( \mathrm{C}_{2}\mathrm{H}_{4} \)).
This reaction is key in producing alkenes, which are vital compounds in the production of polymers and other chemicals.
The sulfuric acid acts as a catalyst, facilitating the removal of water, which results in the formation of ethylene (\( \mathrm{C}_{2}\mathrm{H}_{4} \)).
This reaction is key in producing alkenes, which are vital compounds in the production of polymers and other chemicals.
- Dehydration typically requires higher temperatures.
- Alkenes like ethylene are commonly produced through this method.
- Sulfuric acid serves dual roles as dehydrating and catalyzing agent.