Order each of the following sets of compounds with respect to SN 2 reactivity: (a) (b) (c)

step 1 So it wants us to order these with respect to the S -N -2 reactivity. And it wants us to do C of

Order each of the following sets of compounds with respect...

Order each of the following sets of compounds with respect to $\mathrm{S}_{\mathrm{N}} 2$ reactivity: (a) (b) $\begin{array}{lll}\text { (c) } \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OCH}_{3} & \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OTos} & \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}\end{array}$

Order each of the following sets of compounds with respect to $\mathrm{S}_{\mathrm{N}} 2$ reactivity:
(a)
(b)
$\begin{array}{lll}\text { (c) } \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OCH}_{3} & \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OTos} & \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}\end{array}$

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Key Concepts

Leaving Group Ability

Leaving group ability is the ease with which the leaving group can depart from the substrate, carrying the electron pair. A good leaving group can stabilize the negative charge upon leaving, which accelerates the SN2 reaction. Typical good leaving groups, such as tosylate and bromide, enhance the reaction rate compared to poorer leaving groups like ethers.

Steric Hindrance

Steric hindrance refers to the repulsion and crowding around the reaction center due to bulky groups attached to the substrate. In SN2 reactions, less sterically hindered substrates allow the nucleophile easier access for a backside attack, thus significantly increasing the reactivity compared to substrates with bulky substituents.

SN2 Reaction Mechanism

The SN2 reaction is a bimolecular nucleophilic substitution process occurring in a single, concerted step where the nucleophile attacks the electrophilic carbon from the opposite direction of the leaving group. This backside attack leads to the inversion of the configuration at the reactive center and its rate depends simultaneously on the concentration of both the substrate and the nucleophile.

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