The short answer is no. SN2 reactions are governed by several factors, the most important being how accessible and unhindered the substrate is. Easily accesible carbons such as primary carbons react readily and quickly. Secondary carbons will react too, though this occurs at a much slower rate. Tertiary carbons will not react at all due to steric hinderance. The nucleophile is unable to atttack the backside of the substrate, and since this is the essential mechanism that defines SN2, no reaction occurs. In the case of aspirin synthesis we must define the substrate and nucleophile. Acetic anhydride is the nucleophile (CH3CO2-) and salicylic acid is the substrate. If this were to act as an SN2 reaction, the nucleophile would have to attack the benzene carbon with the -OH group. First off, this carbon is tertiary, so it would not participate in this type of reaction. More importantly, this carbon is in a near-unbreakable benzene ring. Beside the massive amount of steric hinderance via the other ring carbons, this incorporation into the benzene ring does not leave the backside of the reactive carbon exposed. An SN2 reaction will not occur under any circumstance. Solution The short answer is no. SN2 reactions are governed by several factors, the most important being how accessible and unhindered the substrate is. Easily accesible carbons such as primary carbons react readily and quickly. Secondary carbons will react too, though this occurs at a much slower rate. Tertiary carbons will not react at all due to steric hinderance. The nucleophile is unable to atttack the backside of the substrate, and since this is the essential mechanism that defines SN2, no reaction occurs. In the case of aspirin synthesis we must define the substrate and nucleophile. Acetic anhydride is the nucleophile (CH3CO2-) and salicylic acid is the substrate. If this were to act as an SN2 reaction, the nucleophile would have to attack the benzene carbon with the -OH group. First off, this carbon is tertiary, so it would not participate in this type of reaction. More importantly, this carbon is in a near-unbreakable benzene ring. Beside the massive amount of steric hinderance via the other ring carbons, this incorporation into the benzene ring does not leave the backside of the reactive carbon exposed. An SN2 reaction will not occur under any circumstance..

1. The short answer is no. SN2 reactions are governed by several factors, the most important being
how accessible and unhindered the substrate is. Easily accesible carbons such as primary carbons
react readily and quickly. Secondary carbons will react too, though this occurs at a much slower
rate. Tertiary carbons will not react at all due to steric hinderance. The nucleophile is unable to
atttack the backside of the substrate, and since this is the essential mechanism that defines SN2,
no reaction occurs. In the case of aspirin synthesis we must define the substrate and nucleophile.
Acetic anhydride is the nucleophile (CH3CO2-) and salicylic acid is the substrate. If this were to
act as an SN2 reaction, the nucleophile would have to attack the benzene carbon with the -OH
group. First off, this carbon is tertiary, so it would not participate in this type of reaction. More
importantly, this carbon is in a near-unbreakable benzene ring. Beside the massive amount of
steric hinderance via the other ring carbons, this incorporation into the benzene ring does not
leave the backside of the reactive carbon exposed. An SN2 reaction will not occur under any
circumstance.
Solution
The short answer is no. SN2 reactions are governed by several factors, the most important being
how accessible and unhindered the substrate is. Easily accesible carbons such as primary carbons
react readily and quickly. Secondary carbons will react too, though this occurs at a much slower
rate. Tertiary carbons will not react at all due to steric hinderance. The nucleophile is unable to
atttack the backside of the substrate, and since this is the essential mechanism that defines SN2,
no reaction occurs. In the case of aspirin synthesis we must define the substrate and nucleophile.
Acetic anhydride is the nucleophile (CH3CO2-) and salicylic acid is the substrate. If this were to
act as an SN2 reaction, the nucleophile would have to attack the benzene carbon with the -OH
group. First off, this carbon is tertiary, so it would not participate in this type of reaction. More
importantly, this carbon is in a near-unbreakable benzene ring. Beside the massive amount of
steric hinderance via the other ring carbons, this incorporation into the benzene ring does not
leave the backside of the reactive carbon exposed. An SN2 reaction will not occur under any
circumstance.