Practice Exams › Organic Chemistry — Nucleophilic Substitution (SN1/SN2) › Question #25
Intro-College-Stem Organic-Chemistry
Which substrate undergoes SN2 substitution most rapidly with NaI in acetone?
1
Methyl bromide (CH3Br)
✓ Correct Answer

Explanation

SN2 reactivity decreases sharply with steric hindrance at the alpha carbon: methyl > primary > secondary >> tertiary. CH3Br (methyl) is unhindered and undergoes SN2 fastest. Tertiary substrates (e.g., t-BuBr) effectively do not undergo 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

Practice more questions like this

Organic Chemistry — Nucleophilic Substitution (SN1/SN2) — 5 questions available. No sign-up required.

Browse all questions