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Medical College Admission Test
Chemical and Physical Foundations of Biological Systems

2-Bromopropane Reactivity: Substitution vs. Elimination

Very Hard Organic Chemistry Nucleophilic Substitution And Elimination Reactions

Consider the following reaction of 2-bromopropane with a nucleophile in a polar solvent:

2-bromopropane (C3H7Br) reacts to form either propene (C3H6) through elimination or a substitution product by displacing the bromide ion. Analyze the reaction conditions and the structure of 2-bromopropane to determine which type of mechanism predominantly occurs, along with the expected product if the reaction proceeds via a nucleophilic substitution pathway.

In particular, consider whether the reaction conditions favor an SN1, SN2, E1, or E2 mechanism. Which product is the major product formed when 2-bromopropane is treated with a strong nucleophile in a protic solvent?

Hint

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