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The increasing order of basicity of RCN,...

The increasing order of basicity of `RCN,RCH=NR` and `RNH_(2)` is :-

A

`RCNltRCH=NRltRNH_(2)`

B

`RNH_(2)ltRCNltRCH=NR`

C

`RCH=NRltRNH_(2)ltRCN`

D

`RH_(2)NltRCH=NRltRCN`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the increasing order of basicity of the compounds RCN, RCH=NR, and RNH2, we need to analyze the hybridization and the electron-donating ability of the nitrogen atom in each compound. ### Step-by-Step Solution: 1. **Identify the Hybridization of Nitrogen in Each Compound**: - In **RCN** (nitrile), the nitrogen is **sp hybridized**. - In **RCH=NR** (imines), the nitrogen is **sp² hybridized**. - In **RNH2** (amines), the nitrogen is **sp³ hybridized**. 2. **Understand the Relationship Between Hybridization and Basicity**: - The basicity of a compound is influenced by the ability of the nitrogen atom to donate its lone pair of electrons. - **sp hybridized** nitrogen has the highest s-character (50%), making it more electronegative and less willing to donate its electrons. Thus, it is the least basic. - **sp² hybridized** nitrogen has 33% s-character, making it less electronegative than sp hybridized nitrogen, and thus more basic than RCN. - **sp³ hybridized** nitrogen has the lowest s-character (25%) and is the least electronegative, making it the most basic of the three. 3. **Rank the Compounds Based on Basicity**: - Since RCN is the least basic (due to sp hybridization), followed by RCH=NR (sp²), and RNH2 being the most basic (sp³), we can establish the order: - **RCN < RCH=NR < RNH2** ### Final Answer: The increasing order of basicity is: **RCN < RCH=NR < RNH2**
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