Show how you would synthesize the following alcohol from appropriate alkene.


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Verified step by step guidance

1. Step 1: Identify the target molecule. In this case, it's an alcohol. Look at the structure of the alcohol and identify the carbon that bears the hydroxyl group. This carbon was the site of the double bond in the alkene precursor.
2. Step 2: Identify the alkene that would be needed to synthesize this alcohol. This would be the alkene that, when subjected to an anti-Markovnikov hydration reaction, would yield the target alcohol.
3. Step 3: The anti-Markovnikov hydration reaction can be achieved using hydroboration-oxidation. In this reaction, borane (BH3) or a borane complex is added to the alkene in an anti-Markovnikov manner. This is followed by oxidation with hydrogen peroxide (H2O2) and a base (usually sodium hydroxide, NaOH) to yield the alcohol.
4. Step 4: Draw the mechanism of the hydroboration-oxidation reaction. This will help you understand how the reaction proceeds and how the alkene is converted into the alcohol.
5. Step 5: Finally, confirm that the alkene you identified in step 2, when subjected to hydroboration-oxidation, would indeed yield the target alcohol. If it does, then you have successfully shown how to synthesize the alcohol from the alkene.

Key Concepts

Alkene Reactivity

Alkenes are unsaturated hydrocarbons characterized by at least one carbon-carbon double bond. Their reactivity is primarily due to this double bond, which can undergo various reactions such as electrophilic addition. Understanding how alkenes react is crucial for synthesizing alcohols, as the addition of water (hydration) to an alkene can yield an alcohol.

Hydration Reactions

Hydration reactions involve the addition of water to an alkene, resulting in the formation of an alcohol. This process can occur through acid-catalyzed mechanisms, where the alkene is protonated to form a more stable carbocation intermediate, followed by nucleophilic attack by water. Recognizing the conditions and mechanisms of hydration is essential for synthesizing the desired alcohol from a specific alkene.

Markovnikov's Rule

Markovnikov's Rule states that when HX (where X is a halogen or OH) is added to an asymmetric alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This principle helps predict the major product of hydration reactions, guiding the synthesis of alcohols from alkenes by determining the regioselectivity of the reaction.