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Arrange given compounds in order of decr...

Arrange given compounds in order of decreasing acidity
1. `CH_3-NO_2`
2. `NO_2-CH_2-NO_2`
3. `CH_3-CH_2-NO_2`
4. `NO_2-underset(NO_2)underset(|)(CH)-NO_2`

A

`4 gt 2 gt 1 gt 3`

B

`4 gt 2 gt 3 gt 1`

C

`3gt 1 gt 2 gt 4`

D

`3 gt 1 gt 4 gt 2`

Text Solution

AI Generated Solution

The correct Answer is:
To arrange the given compounds in order of decreasing acidity, we need to analyze the effects of the nitro groups (-NO2) on the acidity of the compounds. The presence of electron-withdrawing groups like -NO2 increases acidity by stabilizing the negative charge on the conjugate base formed after deprotonation. ### Step-by-Step Solution: 1. **Identify the Compounds:** - 1. `CH3-NO2` (Nitromethane) - 2. `NO2-CH2-NO2` (1,2-Dinitroethane) - 3. `CH3-CH2-NO2` (Ethyl nitrite) - 4. `NO2-CH(NO2)-NO2` (1,3-Dinitro-2-propanol) 2. **Assess the Acidity:** - **Compound 1: `CH3-NO2`**: This compound has one nitro group which can stabilize the negative charge after deprotonation. - **Compound 2: `NO2-CH2-NO2`**: This compound has two nitro groups, which significantly increases its acidity due to greater stabilization of the conjugate base. - **Compound 3: `CH3-CH2-NO2`**: This compound has one nitro group but is less acidic than `CH3-NO2` because the ethyl group is less electron-withdrawing than the methyl group. - **Compound 4: `NO2-CH(NO2)-NO2`**: This compound has three nitro groups, making it the most acidic due to maximum stabilization of the conjugate base. 3. **Rank the Compounds:** - The compound with the most nitro groups will be the most acidic. - Therefore, the order of decreasing acidity is: - 4. `NO2-CH(NO2)-NO2` (most acidic) - 2. `NO2-CH2-NO2` - 1. `CH3-NO2` - 3. `CH3-CH2-NO2` (least acidic) ### Final Order of Acidity: 4 > 2 > 1 > 3
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