Here is today’s Organic Chemistry Question of the Day from Dr. Romano.
A chemist wants to run an SN2 reaction using sodium ethoxide in ethanol. Six different halides are available — which one reacts the fastest?
Correct answer: D — 4-chloro-1-butanol
Why?
SN2 reactions require a backside attack, which works best with small, unhindered substrates.
Ethyl chloride is a strong primary substrate… but something is even better.
Intramolecular SN2.
4-chloro-1-butanol can form a favorable 5-membered ring, allowing a super-fast intramolecular SN2 reaction — faster than any standard primary halide.
Dr. Romano says you may just see this concept again one day!
More help available at Orgoman.com
DAT Destroyer | OAT Destroyer
A chemist wants to run an SN2 reaction using sodium ethoxide in ethanol. Six different halides are available — which one reacts the fastest?
Correct answer: D — 4-chloro-1-butanol
Why?
SN2 reactions require a backside attack, which works best with small, unhindered substrates.
Ethyl chloride is a strong primary substrate… but something is even better.
Intramolecular SN2.
4-chloro-1-butanol can form a favorable 5-membered ring, allowing a super-fast intramolecular SN2 reaction — faster than any standard primary halide.
Dr. Romano says you may just see this concept again one day!
More help available at Orgoman.com
DAT Destroyer | OAT Destroyer
