Unpaired electrons FIGURE 14-21 Energy diagram for the MOs of square cyclobutadiene (a) Four unhybridized p atomic orbitals on the C atoms of cyclobutadiene. (b) Energy diagram of the four T MOs of cyclobutadiene. The dashed line represents the energy of the unhybridized p AOs. AO energies Four p AOs Four T MOs (a) (b) HC CH HC. CH АO energies TT2 TT3 6 p AOs 6 п MOs (a) (b) (с) FIGURE 14-19 ↑ Energy
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.
Repeat Problem 14.36 for [8]annulene.
Draw the π MO energy diagram for [10]annulene, similar to those in Figures 14-19 and 14-21. Fill up the orbitals with the appropriate number of π electrons. Based on this diagram, should [10]annulene
be
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