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Multiple Choice
Using methylcyclohexane as a starting material, predict the final product based on the list of reagents given?
A
B
C
D
Verified step by step guidance
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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.
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.
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.
Step 4: The fourth reagent, H2O2 in NaOH, completes the hydroboration-oxidation process by converting the borane intermediate to an alcohol.
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.