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The order of leaving group ability is ...

The order of leaving group ability is
`.^(-)underset((I))(OAc).^(-) underset((II))(OMe).^(-)underset((III))(SO_3Me).^(-)underset((IV))(SO_3CF_3)` The order of leaving group ability is

A

`I gt II gt III gt IV`

B

`IV gt III gt II gt I`

C

`I gt III gt IV gt II`

D

`IV gt III gt I gt II`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the order of leaving group ability among the given groups, we need to analyze their basicity and the influence of their substituents. The ability of a leaving group is generally inversely related to its basicity; weaker bases are better leaving groups. ### Step-by-Step Solution: 1. **Identify the Leaving Groups**: The leaving groups provided are: - (I) OAc (Acetate) - (II) OMe (Methoxy) - (III) SO3Me (Methanesulfonate) - (IV) SO3CF3 (Trifluoromethanesulfonate) 2. **Assess Basicity**: - **OAc (Acetate)**: The acetate ion is a weak base due to the resonance stabilization of the negative charge by the carbonyl group (C=O). - **OMe (Methoxy)**: The methoxy group is a stronger base compared to acetate because the methyl group is an electron-donating group, which destabilizes the negative charge. - **SO3Me (Methanesulfonate)**: This group is a weak base due to the resonance stabilization of the sulfonate ion. It is a better leaving group than OAc. - **SO3CF3 (Trifluoromethanesulfonate)**: This is the weakest base among the groups due to the strong electron-withdrawing effects of the trifluoromethyl group, making it an excellent leaving group. 3. **Rank the Leaving Groups**: Based on the analysis of basicity: - **SO3CF3** (weakest base, best leaving group) - **SO3Me** (weak base, good leaving group) - **OAc** (moderate base, fair leaving group) - **OMe** (strongest base, poorest leaving group) 4. **Final Order of Leaving Group Ability**: The order from best to worst leaving group is: - SO3CF3 > SO3Me > OAc > OMe ### Conclusion: The correct order of leaving group ability is: **SO3CF3 > SO3Me > OAc > OMe**
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Knowledge Check

  • Order of basic strength Ph-underset((A))(NH_2),underset((B))(Ph-NH)-Me,underset((C))underset(Me)underset(|)(Ph-N-Me)

    A
    `A gt B gt C gt D`
    B
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    C
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    D
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    A
    `I gt II lt III gt IV lt V`
    B
    `V gt IV gt II gt III gt I`
    C
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    D
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