Compared with an alkylamine of similar size, why is the compound shown only very weakly basic?

AThe nitrogen is sp3 hybridised and strongly shielded
BThe carbonyl carbon donates electrons to nitrogen by +I effect
CThe molecule has no lone pair on nitrogen
DThe nitrogen lone pair is delocalised onto the carbonyl oxygen by resonance

Answer: D

The compound shown is acetamide. Resonance

N - C = O N X^{+} = C - O X^{-}

delocalises the nitrogen lone pair over the O=C-N unit, making it largely unavailable for protonation. Amides are therefore almost neutral in water, unlike alkylamines.

Practice Amines and Aromatic Nitrogen Compounds More on Basicity order among drawn amines and anilines

Previous questionNext question

More questions on Basicity order among drawn amines and anilines

The compound shown is an aromatic amine. Which one of the structures shown is a stronger base than it in water? NEET level
The nitrogen lone pair in the compound shown is used in the aromatic sextet. What does this imply for its basicity compared with pyridine? NEET level
The compound shown is substituted in the para position with different groups. Which structure is the weakest base in water? JEE Main level
The compound shown has two types of ring atoms that could be protonated, one of which is an N-H. Which statement correctly identifies the si... JEE Advanced level
The compound shown has a very high basicity (the pKa of its conjugate acid is about 13). What is the best reason? JEE Main level
Consider the compound shown. Select all the correct statements, comparing it with aniline and ammonia in water. JEE Main level