Hydrogen bonds can form between: 1. The positively charged H atom of water and an an electronegative atom (N, O or F) with lone pairs on another molecule. 2. The positively charged H atom of another molecule that is bonded to N, O or F and the O atom of water. CH3CH2OCH2OH: will H-bond with water through O or O-H CH3CH2CH2F: probably not, but may form weak H-bond with water through F. However, the interaction if any is weak as F is a poor H-bond donor due to its high electronegativity which tightly binds its lone pairs to the nucleus, making them less accessible for H-bonding. CH3CH2CH2NHCH3: will H-bond to water through N or N-H CH3CH2CH2COOH: will H-bond to water through O or OH CH3CH2N(CH3)2: will H-bond to water through N Solution Hydrogen bonds can form between: 1. The positively charged H atom of water and an an electronegative atom (N, O or F) with lone pairs on another molecule. 2. The positively charged H atom of another molecule that is bonded to N, O or F and the O atom of water. CH3CH2OCH2OH: will H-bond with water through O or O-H CH3CH2CH2F: probably not, but may form weak H-bond with water through F. However, the interaction if any is weak as F is a poor H-bond donor due to its high electronegativity which tightly binds its lone pairs to the nucleus, making them less accessible for H-bonding. CH3CH2CH2NHCH3: will H-bond to water through N or N-H CH3CH2CH2COOH: will H-bond to water through O or OH CH3CH2N(CH3)2: will H-bond to water through N.