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What is the decreasing order of strength...

What is the decreasing order of strength of the bases `OH^(-),NH_(2)^(-),HC-=C^(-) and CH_(3)CH_(2)^(-)`?

A

`CH_(3)CH_(2)^(-) gt NH_(2)^(-) gt HC -=C^(-) gt OH^(-)`

B

`HC -= C^(-) gt CH_(3)CH_(2)^(-) gt NH_(2)^(-) gt OH^(-)`

C

`OH^(-) gt NH_(2)^(-) gt HC -= C^(-) gt CH_(3)CH_(2)^(-)`

D

`NH_(2)^(-) gt HC-=C^(-) gt OH^(-) gt CH_(3)CH_(2)^(-)`

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AI Generated Solution

The correct Answer is:
To determine the decreasing order of strength of the bases \( \text{OH}^-, \text{NH}_2^-, \text{HC} \equiv \text{C}^-, \text{and } \text{CH}_3\text{CH}_2^- \), we need to analyze the basicity of each species based on their structure and the electronegativity of the atoms involved. ### Step-by-Step Solution: 1. **Identify the Species**: We have four species to compare: - \( \text{OH}^- \) (hydroxide ion) - \( \text{NH}_2^- \) (amide ion) - \( \text{HC} \equiv \text{C}^- \) (acetylide ion) - \( \text{CH}_3\text{CH}_2^- \) (ethyl ion) 2. **Analyze Electronegativity**: - **Oxygen (in \( \text{OH}^- \))**: Oxygen is highly electronegative, which means it holds onto its lone pairs tightly and is less willing to donate them. - **Nitrogen (in \( \text{NH}_2^- \))**: Nitrogen is less electronegative than oxygen, making it more willing to donate its lone pair compared to oxygen. - **Carbon (in \( \text{HC} \equiv \text{C}^- \))**: The carbon in the acetylide ion is sp-hybridized, which gives it a higher electronegativity than sp3 hybridized carbon but lower than nitrogen. - **Carbon (in \( \text{CH}_3\text{CH}_2^- \))**: The carbon here is sp3 hybridized, which is the least electronegative of the four species. 3. **Determine Basicity**: - More electronegative atoms hold onto their lone pairs more tightly, making them less basic. - The order of basicity can be inferred from the electronegativity: - \( \text{CH}_3\text{CH}_2^- \) (most basic, least electronegative) - \( \text{NH}_2^- \) (more basic than \( \text{HC} \equiv \text{C}^- \)) - \( \text{HC} \equiv \text{C}^- \) (less basic than \( \text{NH}_2^- \)) - \( \text{OH}^- \) (least basic, most electronegative) 4. **Final Order**: Based on the analysis, the decreasing order of basic strength is: \[ \text{CH}_3\text{CH}_2^- > \text{NH}_2^- > \text{HC} \equiv \text{C}^- > \text{OH}^- \] ### Conclusion: The decreasing order of strength of the bases is: \[ \text{CH}_3\text{CH}_2^- > \text{NH}_2^- > \text{HC} \equiv \text{C}^- > \text{OH}^- \]
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