Question

In the following pair of compounds, which compound is more nucleophilic in a polar-protic solvent?

${CH}_{3}Cl$ or ${CH}_{3}OH$

• A. ${CH}_{3}Cl$
• B. ${CH}_{3}OH$
• C. ${CH}_{3}Cl={CH}_{3}OH$
• D. None of these

Answer 1

The correct option is A ${CH}_{3}Cl$

Hydrogen bonding takes place in the polar-protic solvent when solute compound includes one of FON (Flourine, Oxygen and Nitrogen) atom.

So, in case of $C{H}_{3}OH$ hydrogen bonding will take place between O and H atom, which decreases its nucleophilicity. Polar protic-solvent consists of $H^{+}$ ions which can form H-bond with methanol and shield the solute molecule from donating electron thus decreases its nucleophilicity. However, there is no H-bonding present as such in case of methyl chloride $\left(C{H}_{3}OH\right)$.

Therefore, $C{H}_{3}Cl$ is more nucleophilic than $C{H}_{3}OH$.
Hence, the correct option is A.