Q.The compound incapable of hydrogen bonding with water is ......
A. $CH_3-CH_2-O-CH_3$
B. $CH_3-CH_2-CH_2-CH_3$
C. phenol (drawn: benzene ring with -OH)
D. $CH_3-CH_2-CH_2-OH$

Step 1. Check each option for hydrogen-bonding capacity with water. A. CH3-CH2-O-CH3 (an ether) has no O-H of its own but its oxygen lone pairs CAN accept a hydrogen bond from water's O-H (section 11.5.2) -- capable of H-bonding with water. B. CH3-CH2-CH2-CH3 (n-butane) is a pure hydrocarbon with no oxygen (or nitrogen) atom anywhere in the molecule -- it has neither an O-H to donate nor a lone pair to accept a hydrogen bond, so it CANNOT hydrogen-bond with water at all. C. Phenol (C6H5-OH) has an -OH group that both donates (its H) and accepts (its O lone pairs) hydrogen bonds with water (section 11.4.3) -- capable. D. CH3-CH2-CH2-OH …

Checking each compound for the presence of an O-H group (hydrogen-bond donor) or at least a lone-pair-bearing oxygen (hyd …

• Picking the ether (A), forgetting that section 11.5.2 explicitly states an ether's oxygen lone pairs CAN still accept a hydrogen bond from water even without an O-H of its own. …