Question

Rank the amines in each set in order of increasing basicity.(e)

Accepted Answer

Step 1: Identify the functional groups attached to the benzene ring in each compound. The first compound has an amino group (-NH2), the second compound has a methylamino group (-CH2NH2), and the third compound has an amide group (-CONH2). Step 2: Understand the basicity of each functional group. Amines (-NH2 and -CH2NH2) are generally basic because the nitrogen atom has a lone pair of electrons that can accept a proton. Amides (-CONH2), on the other hand, are less basic because the lone pair on the nitrogen is delocalized into the carbonyl group, reducing its availability to accept a proton. Step 3: Consider the effect of the benzene ring on basicity. In the first compound, the amino group (-NH2) is directly attached to the benzene ring, which can reduce its basicity due to resonance effects. The lone pair on the nitrogen can delocalize into the aromatic ring, making it less available for protonation. In the second compound, the methylamino group (-CH2NH2) is not directly attached to the benzene ring, so resonance effects are absent, and the nitrogen remains more basic. Step 4: Compare the basicity of the amide group (-CONH2) in the third compound. The amide group is the least basic because the nitrogen's lone pair is delocalized into the carbonyl group, making it significantly less available for protonation compared to the amino groups in the first and second compounds. Step 5: Rank the compounds in order of increasing basicity based on the above analysis. The amide group (-CONH2) is the least basic, followed by the amino group (-NH2) directly attached to the benzene ring, and the methylamino group (-CH2NH2) is the most basic.

Rank the amines in each set in order of increasing basicity.
(e)

비슷한 문제에 대한 검증된 영상 답변:

주요 개념

Basicity of Amines

Inductive Effect

Steric Hindrance