Practice Exams › Organic Chemistry — Nucleophilic Substitution (SN1/SN2) › Question #29
Intro-College-Stem Organic-Chemistry
Tertiary substrates strongly favor SN1 over SN2 because:
1
The tertiary cation is stabilized and SN2 is sterically blocked
✓ Correct Answer

Explanation

Two reasons combined: (1) the tertiary carbocation intermediate is stabilized by three alkyl groups via hyperconjugation and induction, making ionization energetically feasible; (2) steric crowding around the tertiary alpha carbon physically blocks backside attack required for SN2.

📄 Source: https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Map%3A_Organic_Chemistry_(Vollhardt_and_Schore)/07._Further_Reactions_of_Haloalkanes/7.5%3A_The_Effects_of_Substrate_in_SN2_Reactions

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