6. Answer ALL parts of this question: a) Draw all the molecular orbitals of ethene and buta-1,3-diene, indicating where applicable which are the HOMOS and which are the LUMOS in both the ground state and first excited state. b) Use relevant orbitals from those drawn above to explain why buta-1,3- diene reacts with ethene in a [4+2] cycloaddition reaction under thermal conditions, but if two molecules of ethene are to dimerise in a [2+2] cycloaddition reaction, then the reaction must be irradiated with ultraviolet light. c) Identify compound X in the following reaction (Scheme 4) and draw curly arrow mechanisms that lead to it and then lead from it to the final products. CO Me CO₂Me heat heat X CO₂Me CO,Me Scheme 4 d) The reaction shown below (Scheme 5) is another example of a cycloaddition reaction. Identify the number of electrons involved in it, draw a curly arrow mechanism leading to the product and suggest whether this reaction would take place under thermal or photochemical conditions. +
Reactions of Ethers
Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.
Epoxides
Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.
Williamson Ether Synthesis
An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.
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