Which of the following compounds can participate in hydrogen bonding with methanol (CH₃OH)?NH₃HFCH₄

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11ecba2d_124b_928f_a3bf_d39dd03897fe_MD0008_00 Hydrogen atoms covalently bonded with N, O, or F atoms form polar bonds that yield dipoles with partial charges. Attractions between opposite partial charges of the dipoles generate a significant intermolecular force known as hydrogen bonding. This term does not refer to the covalent chemical bond between hydrogen and another atom but instead refers to the noncovalent attractions between the bond dipoles. Because of the significant difference in electronegativity between hydrogen and oxygen, O-H bonds exhibit a strong dipole. The lone pairs of electrons and partial negative charge (δ⁻) on the oxygen atom serve as a hydrogen bond acceptor, and the partially positive (δ⁺) hydrogen atom serves as the donor. As a result, water and alcohols (such as methanol) interact with other compounds that can either accept or donate hydrogen bonding interactions. Although smaller in magnitude than that of a hydroxyl group, N-H bonds have a significant dipole, and the nitrogen atom possesses a lone pair of electrons. As a result, ammonia and many organic amines readily participate in hydrogen bonding with alcohols (Number I). Likewise, the H-F bond is highly polar, and the fluorine atom has three pairs of nonbonding electrons. Accordingly, highly polar bonds involving fluorine can act as hydrogen bond acceptors with alcohols (Number II). (Number III) The carbon and hydrogen atoms in a C-H bond do not have a sufficient difference in electronegativity to generate a dipole that is capable of hydrogen bonding. Educational objective: Hydrogen atoms covalently bonded with nitrogen, oxygen, or fluorine atoms form polar bonds that yield dipoles, which exhibit significant noncovalent dipole-dipole attractions known as hydrogen bonding.

Which of the Following Compounds Can Participate in Hydrogen Bonding