• SDN Site Updates

    Hey everyone! The site will be down for approximately 2 hours on Thursday, August 5th for site updates.

  • How To ACE Your Medical School Interview

    In this webinar hosted by SDN with experts from BeMo Academic Consulting, you will learn a simple five-step process to help you translate your interview invitation into an acceptance.


S.D.N. Vet
7+ Year Member
15+ Year Member
Mar 23, 2003
Status (Visible)
When given an alkyl halide, depending on the reagent (strong nucleophile, weak nucleophile, strong base, or weak base), the reaction can undergo SN1, SN2, E1, or E2 mechanisms, right? I know SN1 and SN2 reactions require nucleophiles, while E1 and E2 reactions requires bases. My question:

If given an alkyl halide and a reagent, how do you determine whether the reagent is a nucleophile or a base?

This is confusing to me because the reagent can be both a nucleophile and a base at the same time. If a reagent has the properties of both a nucleophile and a base, how do you tell whether to use SN1, SN2, E1, or E2?

The University of Colorado has a flow chart regarding this topic:

The University of Eastern Illinois also has one:

Still, I am stumped on how to differentiate between a nucleophile reagent or a basic reagent. Can you help me out here? If not, can you point me in the right direction? Thank you for your time.
This thread is more than 14 years old.

Your message may be considered spam for the following reasons:

  1. Your new thread title is very short, and likely is unhelpful.
  2. Your reply is very short and likely does not add anything to the thread.
  3. Your reply is very long and likely does not add anything to the thread.
  4. It is very likely that it does not need any further discussion and thus bumping it serves no purpose.
  5. Your message is mostly quotes or spoilers.
  6. Your reply has occurred very quickly after a previous reply and likely does not add anything to the thread.
  7. This thread is locked.