Question

Which of the following compounds show hydrogen bonding? (a) \(\mathrm{CH}_{3} \mathrm{~F}\) (b) \(\mathrm{HO}-\mathrm{OH}\) (c) \(\mathrm{NH}_{3} \mathrm{~F}\) (d) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{O}-\mathrm{CH}_{3}\)

Short answer

(a) \(\mathrm{CH}_{3} \mathrm{~F}\) (b) \(\mathrm{HO}-\mathrm{OH}\) (c) \(\mathrm{NH}_{3} \mathrm{~F}\) (d) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{O}-\mathrm{CH}_{3}\) Based on the step by step analysis, the compounds that exhibit hydrogen bonding are: (b) \(\mathrm{HO}-\mathrm{OH}\) (c) \(\mathrm{NH}_{3} \mathrm{~F}\)

Step-by-step solution

Identify electronegative atoms in all compounds.

We can first look at the chemical structure of each compound and identify, if they contain any of the electronegative atoms involved in hydrogen bonding (namely nitrogen, oxygen, or fluorine). (a) \(\mathrm{CH}_{3} \mathrm{~F}\) - Contains fluorine (F) (b) \(\mathrm{HO}-\mathrm{OH}\) - Contains oxygen (O) (c) \(\mathrm{NH}_{3} \mathrm{~F}\) - Contains nitrogen (N) and fluorine (F) (d) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{O}-\mathrm{CH}_{3}\) - Contains oxygen (O)

Check for the presence of hydrogen bonding.

After identifying the presence of nitrogen, oxygen, or fluorine, we now check whether these compounds exhibit hydrogen bonding. (a) \(\mathrm{CH}_{3} \mathrm{~F}\) - There is hydrogen on the carbon, but not hydrogen directly connected to fluorine. (b) \(\mathrm{HO}-\mathrm{OH}\) - There is hydrogen directly connected to oxygen, forming strong hydrogen bonding. (c) \(\mathrm{NH}_{3} \mathrm{~F}\) - There is hydrogen directly connected to nitrogen, and through nitrogen, it interacts with fluorine, resulting in hydrogen bonding. (d) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{O}-\mathrm{CH}_{3}\) - There is no hydrogen atom directly connected to the oxygen atom.

Conclusion on which compound show hydrogen bonding.

Based on the analysis above, we can conclude that: (a) \(\mathrm{CH}_{3} \mathrm{~F}\) - Does not show hydrogen bonding. (b) \(\mathrm{HO}-\mathrm{OH}\) - Shows hydrogen bonding. (c) \(\mathrm{NH}_{3} \mathrm{~F}\) - Shows hydrogen bonding. (d) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{O}-\mathrm{CH}_{3}\) - Does not show hydrogen bonding.