2. (30 pts) By using the same alkene, how do you synthesize the following alcohols? Give the alkene and show the mechanisms for each product formation.

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∻Solution∻ ‖ 1 ⋮ **Identify the starting alkene**: To synthesize the given alcohols from the same alkene, we must first identify a suitable alkene that can be transformed into all three alcohols. The molecular formula for the alcohols is $C_4H_{10}O$, which suggests that the alkene should have four carbon atoms and be able to form alcohols at different positions. The suitable starting alkene is but-2-ene, which has the formula $C_4H_8$. ‖ ‖ 2 ⋮ **Synthesize the first alcohol**: The first alcohol is a tertiary alcohol, which can be synthesized from but-2-ene using acid-catalyzed hydration. This reaction follows Markovnikov's rule, where the $OH$ group attaches to the more substituted carbon atom. The mechanism involves the formation of a carbocation intermediate at the tertiary carbon, followed by the attack of a water molecule and deprotonation to form the tertiary alcohol. ‖ ‖ 3 ⋮ **Synthesize the second alcohol**: The second alcohol is a primary alcohol, which can be synthesized from but-2-ene using hydroboration-oxidation. This anti-Markovnikov reaction involves the addition of borane ($BH_3$) to the less substituted carbon of the alkene, followed by oxidation with hydrogen peroxide ($H_2O_2$) to replace the boron atom with a hydroxyl group, yielding the primary alcohol. ‖ ‖ 4 ⋮ **Synthesize the third alcohol**: The third alcohol can be synthesized by first converting but-2-ene into a secondary alcohol using acid-catalyzed hydration, similar to the first alcohol, but with a different regioselectivity. This can be achieved by using a different reaction condition or catalyst that favors the formation of the secondary carbocation intermediate. The water molecule then attacks the secondary carbocation, followed by deprotonation to form the secondary alcohol. ‖ ∻Answer∻ ⚹ The starting alkene for the synthesis of all three alcohols is but-2-ene. The first tertiary alcohol is synthesized via acid-catalyzed hydration following Markovnikov's rule. The second primary alcohol is synthesized via hydroboration-oxidation following anti-Markovnikov's rule. The third secondary alcohol is synthesized via acid-catalyzed hydration with different regioselectivity. ⚹ ∻Key Concept∻ ⚹ Synthesis of alcohols from alkenes ⚹ ∻Explanation∻ ⚹ Alcohols can be synthesized from alkenes using different reactions such as acid-catalyzed hydration and hydroboration-oxidation, which follow Markovnikov's and anti-Markovnikov's rules, respectively, to determine the position of the hydroxyl group. ⚹◊What is the general mechanism for the hydration of alkenes to form alcohols?⍭ Generate me a similar question◊

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