Question

Why is sn2 concerted?

Answer 1

Because the intermediate is short-lived.

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A concerted reaction, like an ideal `"S"_N2`, is simply one that happens in essentially one step.

SN2 MECHANISM

The typical `"S"_N2` mechanism is a backside-attack of the electrophilic carbon, inverting the stereochemistry at that carbon.

• For this mechanism example, the `"N"-="C":^(-)` simply approaches carbon-2 from behind, and the three groups on carbon-2 "flip" backwards.

• Then, `"N"-="C":^(-)` attaches by donating a pair of electrons to carbon-2's antibonding orbital, and `"Br"^(-)` leaves after retracting its bonding pair of electrons.

(The planar transition state illustrates a halfway-point between the initial and final stereochemistry.)

STRENGTH OF NUCLEOPHILE VS STRENGTH OF C-LG BOND

For an ideal `"S"_N2` reaction, the `"C"-"LG"` bond is strong enough that it doesn't break on its own before the nucleophile attacks, and it's up to the nucleophile to "brute-force" the reaction.

If the nucleophile isn't that strong:

A nucleophile that isn't strong enough leaves an opportunity for the `"C"-"LG"` bond to break before the nucleophile has a chance to backside-attack.

This forms a carbocation intermediate through the active participation of only the substrate initially, as in an `"S"_N1` reaction mechanism. (The nucleophile attacks later.)

If the nucleophile is fairly strong:

A strong-enough nucleophile allows for the mechanism to involve the participation of both molecules (hence `"S"_Ncolor(blue)(2)`).

In this situation, essentially no carbocation intermediate forms (if it does, it is short-lived).

Hence, the ideal `"S"_N2` mechanism is concerted.