Using methylcyclohexane as a starting material, predict the final product based on the list of reagents given?

• A.
• B.
• C.
• D.

Answer: (D)

Verified step by step guidance

1. Step 1: Begin with the starting material, methylcyclohexane. The first reagent, Br2/hv, is used for radical bromination, which will replace a hydrogen atom with a bromine atom at the most substituted carbon, typically the tertiary carbon if available.
2. Step 2: The second reagent, tBuOK in tBuOH, is a strong base that will perform an elimination reaction (E2) on the bromoalkane formed in Step 1. This will result in the formation of an alkene, specifically a more substituted alkene due to Zaitsev's rule.
3. Step 3: The third reagent, BH3 in THF, is used for hydroboration-oxidation. This will add a hydroxyl group (OH) to the less substituted carbon of the alkene, resulting in an anti-Markovnikov alcohol.
4. Step 4: The fourth reagent, H2O2 in NaOH, completes the hydroboration-oxidation process by converting the borane intermediate to an alcohol.
5. Step 5: The fifth reagent, SOCl2, is used to convert the alcohol into an alkyl chloride. This step involves the substitution of the hydroxyl group with a chlorine atom, forming an alkyl chloride that can further react to form the final product.