Textbook Question
Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iv) H2SO4 , H2O
(g)
10. Addition Reactions
Acid-Catalyzed Hydration
2:42 minutesProblem 52a
Textbook Question
Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.
a. 1-methylcyclohexanol
Verified step by step guidance1
Step 1: Begin by identifying the functional group transformation required. The target compound, 1-methylcyclohexanol, contains an alcohol (-OH) group at the 1-position and a methyl group at the same position. Methylenecyclohexane is an alkene, so the synthesis will involve both an alkene hydration and methylation.
Step 2: Perform hydroboration-oxidation to convert the alkene in methylenecyclohexane into an alcohol. Use BH₃·THF (borane-tetrahydrofuran complex) for hydroboration, followed by oxidation with H₂O₂ (hydrogen peroxide) in a basic solution (NaOH). This reaction will yield cyclohexanol with the hydroxyl group at the less substituted carbon due to anti-Markovnikov addition.
Step 3: Protect the hydroxyl group if necessary to prevent side reactions during methylation. This can be done by converting the alcohol into a silyl ether using a reagent like TMSCl (trimethylsilyl chloride) in the presence of a base such as Et₃N (triethylamine).
Step 4: Introduce the methyl group at the 1-position using a strong base like NaH (sodium hydride) to deprotonate the cyclohexanol derivative, followed by reaction with a methylating agent such as CH₃I (methyl iodide). This will result in the formation of 1-methylcyclohexanol.
Step 5: If the hydroxyl group was protected in Step 3, remove the protecting group by treating the compound with an acid (e.g., HCl) or fluoride ion (e.g., TBAF, tetrabutylammonium fluoride) to regenerate the free alcohol group, yielding the final product, 1-methylcyclohexanol.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Synthesis in Organic Chemistry
Synthesis in organic chemistry refers to the process of constructing complex organic compounds from simpler ones through a series of chemical reactions. Understanding the synthesis pathway is crucial for determining the necessary reagents and conditions required to transform starting materials into the desired product. This involves knowledge of reaction mechanisms, functional group transformations, and the reactivity of different compounds.
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Reagents and Reaction Conditions
Reagents are substances used in chemical reactions to facilitate the transformation of reactants into products. Each reagent has specific properties that influence the reaction's outcome, such as its ability to donate or accept electrons. Additionally, reaction conditions, including temperature, pressure, and solvent choice, play a significant role in determining the efficiency and selectivity of the synthesis process.
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Functional Group Interconversion
Functional group interconversion involves the transformation of one functional group into another within a molecule. This concept is essential for synthesizing compounds like 1-methylcyclohexanol from methylenecyclohexane, as it may require the introduction of hydroxyl (-OH) groups or the modification of existing groups. Mastery of functional group chemistry allows chemists to design effective synthetic routes and predict the behavior of organic molecules.
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