Question

Question: Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution.

Short answer

Answer

The order of reactivity of the given compounds is:

3>2>1

Step-by-step solution

Step-by-Step SolutionStep 1: Nucleophilic substitution reactions

Nucleophilic substitution reactions involve the reaction between an acyl group and a nucleophile.

The acyl groups connected to electron-deficient species are highly reactive towards nucleophilic substitution reactions.

Reactivity of the given compounds

Among the given compounds, the compound containing the carbonyl group connected to the chloride group is the most reactive, as chloride ion $\left({\mathrm{Cl}}^{-}\right)$is a weak base and hence does not easily donate electrons.

Therefore, the carbonyl carbon of this compound is highly electron-deficient.

Among the other two compounds, the compound in which the carbonyl carbon is connected to the OH group is less electron-deficient than the one connected to the SH group, as ${}^{-}\mathrm{OH}$is more basic than ${}^{-}\mathrm{SH}$.