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CSS Organic and Environmental Chemistry P-II QUESTION #1444
Question 1
Which reaction is most likely to occur with a bulky base like tert-butoxide?
  • SN1
  • SN2
  • E2✔️
  • None of these
Correct Answer Explanation
Bulky bases like potassium tert-butoxide (\((CH_3)_3CO^-K^+\)) strongly favour elimination (E2) over substitution. The steric bulk of the base prevents it from attacking the carbon centre (backside attack needed for SN2); instead, it abstracts a proton from the \(\beta\)-carbon to give elimination. SN1 requires no base. Therefore, with bulky bases and secondary/tertiary substrates, E2 is the predominant pathway.