Which of the following pairs undergoes the strongest hydrogen bonding?

Question

BlackTom AI · Accepted Answer

To compare which pair exhibits the strongest hydrogen bonding, we need to look at both hydrogen-bond donors (sites that bear H attached to highly electronegative atoms like N, O, or F) and hydrogen-bond acceptors (lone pairs on electronegative atoms such as N, O, or F).

Option a: NaCl and (CH3)2CO. Sodium chloride is an ionic compound and does not participate in hydrogen bonding as a donor or a typical acceptor in this context, and acetone (CH3)2CO has a carbonyl oxygen that can act as a hydrogen-bond acceptor but not a donor. Since there is no compatible H-bond donor-acceptor pairing between these two, any hydrogen bonding would be weak or nonexistent overall.

Option b: CH3NH2 and CH3OCH3. Methylamine (CH3NH2) has N–H bonds capable of donating hydrogen bonds, and dimethyl ether (CH3OCH3) has an electronegative oxygen with lone pairs that can accept hydrogen bonds. This combination provides a clear, mutually stabilizing donor (N–H) to acceptor (O) interaction, enabling relatively strong hydrogen bonding between the molecules.

Option c: NH3 and CCl4. Ammonia (NH3) can donate hydrogen bonds via its N–H bonds, but carbon tetrachloride (CCl4) has no lone pairs on electronegative atoms capable of accepting hydrogen bonds and no hydrogens to donate either. The lack of an effective hydrogen-bond acceptor makes any H-bonding interaction very weak or effectively absent.

Option d: NF3 and CF4. Both species have low basicity and NF3’s nitrogen lone pair is tied up in bonding, making it a poor hydrogen-bond acceptor, and there are no hydrogen atoms bound to electronegative atoms to donate H-bonds. Thus, meaningful hydrogen bonding between NF3 and CF4 is not expected.

Option e: CH3OCH3 and CF3Cl. The ether (CH3OCH3) can accept hydrogen bonds via its oxygen, but CF3Cl has no suitable hydrogen-bond donating capability and is not a strong acceptor in typical hydrogen-bonding terms. The pair does not establish a strong H-bonding interaction.

Overall, option b presents the strongest and most feasible hydrogen-bonding interaction due to the donor ability of the N–H in methylamine and the acceptor capability of the ether oxygen in dimethyl ether, while the other options lack compatible donor-acceptor pairs or involve species with negligible H-bonding contributions.

Which of the following pairs undergoes the strongest hydrogen bonding?

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