How do you determine if a reaction will be #"S"_N1# or #"S"_N2#?

Answer 1

There are many things that determine if a reaction is #S_N 1# or #S_N2#. The things are briefly shown here.

1 .Effect of the Nucleophile :- The nucleophile takes part in the slow step (the only step)
of the #S_N 2# reaction but not in the slow step of the Therefore, a strong nucleophile
promotes the #S_N 2# but not the #S_N 1# . Weak nucleophiles fail to promote the #S_N 2# reaction;
therefore, reactions with weak nucleophiles often go by the mechanism if the substrate
is secondary or tertiary.
#S_N 1# :- Nucleophile strength is unimportant (usually weak).
SN2:- Strong nucleophiles are required.
2. Effect of the Substrate :- The structure of the substrate (the alkyl halide) is an important
factor in determining which of these substitution mechanisms might operate.
Most methyl halides and primary halides are poor substrates for #S_N 1# substitutions because
they cannot easily ionize to high-energy methyl and primary carbocations. They
are relatively unhindered, however, so they make good #S_N 2# substrates.
Tertiary halides are too hindered to undergo #S_N 2# displacement, but they can ionize
to form tertiary carbocations. Tertiary halides undergo substitution exclusively through
the mechanism. Secondary halides can undergo substitution by either mechanism,
depending on the conditions.
.
3. Effect of the Solvent :-

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Answer 2

Here are some "rules" that will usually work.

1. Primary substrates undergo #"S"_"N"2# reactions because

  • they form unstable primary carbocations and
  • are unhindered to attack by the nucleophile

    2. Tertiary substrates undergo #"S"_"N"1# reactions because they

    • are too hindered to undergo backside attack by the nucleophile and
    • can form stable tertiary carbocations.

      3. Secondary substrates can undergo substitution by either #"S"_text(N)1# or #"S"_text(N)2# mechanisms.

      The mechanism will be

      #"S"_"N"2# if

      • the nucleophile has a negative charge (#"e.g. RO"^"-", "HO"^"-", "NH"_2^"-", "SH"^"-", "CN"^"-", "N"_3^"-", "RCOO"^"-", "X"^"-"#) or
      • the solvent is a polar aprotic solvent (DMF , DMSO, acetone) or
      • the leaving group is the conjugate base of a weak acid (#"p"K"a" < 0#). Examples are #"F"^"-"# and #"RCOO"^"-"#.
        • #"S"_"N"1# if

        • the nucleophile is uncharged or

        • the solvent is a polar protic solvent (#"H"_2"O", "ROH, RCOOH")# or
        • the leaving group is the conjugate base of a strong acid (#"p"K_"a" > 14#). Examples are #"X"^"-", "TsO"^"-", "MsO"^"-", and "TfO"^"-"#.

          Here's a summary of the above factors

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Answer 3

The determination between SN1 and SN2 reactions depends on several factors, including the substrate, nucleophile, and solvent. SN1 reactions occur with tertiary or secondary substrates, in polar protic solvents, and proceed through a carbocation intermediate. SN2 reactions occur with primary or methyl substrates, in polar aprotic solvents, and involve a one-step concerted mechanism. Substrate structure, nucleophile strength, and solvent polarity influence the reaction mechanism.

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Answer from HIX Tutor

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

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