Which of the following compounds is not capable of hydrogen bonding between its molecules?

• A. CH3F
• B. H2O
• C. CH3Cl
• D. NH3

Answer: (C)

Verified step by step guidance

1. Recall that hydrogen bonding occurs when a hydrogen atom is directly bonded to a highly electronegative atom such as nitrogen (N), oxygen (O), or fluorine (F), and this hydrogen can interact with lone pairs on N, O, or F atoms of neighboring molecules.
2. Examine each compound to identify if it has hydrogen atoms bonded to N, O, or F: H2O has hydrogen bonded to oxygen, NH3 has hydrogen bonded to nitrogen, and CH3F has hydrogen bonded to carbon but also contains fluorine which can participate in hydrogen bonding due to its high electronegativity.
3. Consider CH3Cl: it has hydrogen atoms bonded to carbon and chlorine attached to the carbon. Chlorine is electronegative but not as much as N, O, or F, and importantly, hydrogen is not bonded directly to chlorine, so it cannot form hydrogen bonds.
4. Conclude that CH3Cl cannot form hydrogen bonds between its molecules because it lacks hydrogen atoms bonded to N, O, or F, which are necessary for hydrogen bonding.
5. Therefore, the compound not capable of hydrogen bonding between its molecules is CH3Cl.