Organic chemistry - Alkenes (3)
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1.
State the conditions required for the cracking of alkanes and explain why a catalyst is necessary.
The cracking of alkanes requires high temperatures, typically in the range of 400-600 °C. High pressure is also often used, although not always essential. A catalyst is necessary because the cracking reaction is endothermic, meaning it requires heat to proceed. Without a catalyst, the reaction rate would be too slow to be commercially useful.
Why a catalyst is necessary:
- Lower Activation Energy: A catalyst provides an alternative reaction pathway with a lower activation energy. This means that a smaller proportion of molecules have sufficient energy to react at a given temperature.
- Increased Reaction Rate: By lowering the activation energy, the rate of the reaction increases significantly. This allows the cracking process to occur at a practical rate.
- Product Selectivity: Some catalysts can also influence the distribution of products, favouring the formation of certain types of alkanes or alkenes.
2.
Describe the process by which larger alkane molecules are converted into smaller, more useful products (alkenes and hydrogen) through thermal cracking. Your answer should include details of the conditions required and the role of a catalyst.
Thermal cracking is a chemical process used to break down large alkane molecules into smaller, more valuable products such as alkenes and hydrogen. This process occurs at very high temperatures, typically between 500°C and 600°C. A catalyst is essential to lower the activation energy required for the reaction and improve the yield of the desired products.
Conditions Required:
- High Temperature: Temperatures of 500-600°C are necessary to provide the energy required to break the strong carbon-carbon and carbon-hydrogen bonds in the large alkane molecules.
- Inert Atmosphere: An inert atmosphere, such as nitrogen, is used to prevent unwanted side reactions like oxidation of the hydrocarbons.
- Catalyst: A catalyst is used to lower the activation energy of the reaction, allowing it to proceed at a lower temperature and with a higher yield of the desired products.
Role of a Catalyst:
A catalyst, typically a solid acid catalyst like aluminium oxide (Al2O3) or silica gel (SiO2), provides a surface for the alkane molecules to adsorb. This weakens the bonds within the alkane molecule, making them more susceptible to breaking. The catalyst does not get consumed in the reaction; it simply speeds up the rate.
Products: The main products of thermal cracking are alkenes (like ethene, propene) and hydrogen. Smaller alkanes and other hydrocarbons are also formed as by-products.
3.
A student carries out the cracking of n-butane using a high temperature and a catalyst. Draw a reaction equation for the cracking of n-butane into ethene and hydrogen. Explain the mechanism by which the catalyst facilitates this reaction.
Reaction Equation:
C4H10 (n-butane) → C2H4 (ethene) + H2 (hydrogen)
Mechanism of Catalyst Action:
The cracking reaction facilitated by a solid acid catalyst like Al2O3 or SiO2 proceeds through a surface reaction. Here's a simplified explanation:
- Adsorption: The n-butane molecule adsorbs onto the surface of the catalyst. The catalyst's acidic sites (e.g., hydroxyl groups on silica) interact with the alkane molecule.
- Bond Weakening: The interaction between the alkane and the catalyst weakens the carbon-hydrogen and carbon-carbon bonds within the n-butane molecule. This is due to the polarized nature of the catalyst surface.
- Bond Breaking: The weakened bonds break, leading to the formation of a carbenium ion (C4H9+). This is a highly reactive intermediate.
- Ethene Formation: The carbenium ion loses a proton (H+) from a neighboring carbon atom to form ethene (C2H4). This proton is abstracted by another catalyst site.
- Hydrogen Formation: The carbenium ion can also lose a proton to form hydrogen (H2).
- Desorption: The ethene and hydrogen molecules desorb from the catalyst surface, freeing up the active sites for further reactions.
The catalyst provides a surface where the reaction can occur more easily than in the gas phase. The acidic sites on the catalyst surface promote the formation of the carbenium ion, which is a crucial step in the cracking mechanism. The catalyst also helps to stabilize the intermediates and products, increasing the overall reaction rate.