Determine the major product(s) of the following alkane reaction. (Assume monosubstitution.)

• A.
• B.
• C.
• D.

Answer: (D)

Verified step by step guidance

1. Identify the type of reaction: The reaction shown is a halogenation of an alkane, specifically a bromination, which typically proceeds via a free radical mechanism.
2. Determine the most stable radical intermediate: In free radical halogenation, the most stable radical intermediate will form preferentially. Tertiary radicals are more stable than secondary, which are more stable than primary radicals.
3. Locate the hydrogen atoms: Examine the structure of the alkane to identify the different types of hydrogen atoms (primary, secondary, tertiary) that can be abstracted by the bromine radical.
4. Predict the major product: The major product will result from the substitution of a hydrogen atom with a bromine atom at the position where the most stable radical was formed. This is typically at the tertiary carbon if available.
5. Consider regioselectivity: Bromination is highly regioselective, favoring substitution at the most substituted carbon due to the stability of the resulting radical. Therefore, the major product will be the one where bromine is attached to the carbon that forms the most stable radical.