In fact, what would happen instead would likely be an E2 reaction elimination. And in the first step, you'd have to add a strong base, so we'll use sodium hydride here. Cumene hydroperoxide degradation. So this has an interesting smell to it. And we call that an alkoxide anion, which would interact with the positively charged sodium ion floating around.
Answer next time. Since alkoxide anions are strong bases, the possibility of a competing E2 elimination must always be considered. The oxygen is attached to tertiary carbons. So there's some electrostatic or ionic interaction between those opposite charges.
So a resonance-stabilized conjugate base stabilizes the conjugate base, which makes beta-naphthol a little bit better acid than other alcohols that we will talk about. How does this work? So since beta-naphthol is a little bit more acidic, that's why it's OK for us to use a weaker base for this example. In the next step, the free radical is attracted to an oxygen molecule.
Thus, reaction 1 gives a better and cleaner yield of benzyl isopropyl ether than does reaction 2, which generates considerable elimination product. In laboratory chemistry, in situ generation is most often accomplished by the use of a carbonate base or potassium hydroxide , while in industrial syntheses phase transfer catalysis is very common. Sulfuric acid is cheap. The mechanism of alkoxymercuration is similar to that of oxymercuration, with an initial anti-addition of the mercuric species and alcohol being followed by reductive demercuration. Partially positive carbon means that that carbon wants electrons. The mechanism of alkoxymercuration is similar to that of oxymercuration, with an initial anti-addition of the mercuric species and alcohol being followed by reductive demercuration.
So that's the second step.
So a lone pair of electrons on the oxygen attacks the carbon, kicks these electrons off onto the iodide, and we form our product. Finally, the hydroperoxide free radical abstracts a hydrogen free radical from a second molecule of cumene to form cumene hydroperoxide and a new tertiary free radical. And this alkoxide anion is resonance stabilized. Secondary alkylating agents also react, but tertiary ones are usually too prone to side reactions to be of practical use. And in the first step, you'd have to add a strong base, so we'll use sodium hydride here. Exercises Questions Q
In particular, some structures of alkylating agent can be particularly prone to elimination. We'll talk about why in a minute.