Practice Exams › Organic Chemistry — Nucleophilic Substitution (SN1/SN2) › Question #28
Intro-College-Stem Organic-Chemistry
Polar protic solvents (e.g., methanol, water) generally favor:
1
SN1 over SN2
✓ Correct Answer

Explanation

Polar protic solvents stabilize the developing cation in the SN1 transition state through ion-dipole and hydrogen-bonding interactions. They also hydrogen-bond to nucleophiles, reducing their reactivity, which suppresses SN2. Polar aprotic solvents (DMSO, DMF, acetone) favor SN2.

📄 Source: https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Map%3A_Organic_Chemistry_(Vollhardt_and_Schore)/07._Further_Reactions_of_Haloalkanes/7.6%3A_The_Effects_of_Solvent_on_SN1_and_SN2_Reactions

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