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What is the correct order of decreasing ...

What is the correct order of decreasing stability of the following cations
I. `CH_(3) - overset(oplus)(C) H - CH_(3)` II. `CH_(3) - overset(oplus)(C)H - OCH_(3)`
III. `CH_(3) - overset(oplus)(C)H - CH_(2) - OCH_(3)`

A

`II gt I gt III`

B

`II gt III gt I`

C

`III gt I gt II`

D

`I gt II gt III`

Text Solution

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The correct Answer is:
To determine the correct order of decreasing stability of the given cations, we will analyze the structure and the effects of the substituents attached to the cationic carbon. ### Step-by-Step Solution: 1. **Identify the Structures of the Cations**: - **Cation I**: `CH3 - C^+ - CH3` - **Cation II**: `CH3 - C^+ - OCH3` - **Cation III**: `CH3 - C^+ - CH2 - OCH3` 2. **Determine the Degree of Each Cation**: - All three cations are secondary (2°) carbocations, as each has two carbon atoms attached to the positively charged carbon. 3. **Analyze the Effects of the Substituents**: - **Cation I**: The methyl groups (`CH3`) exhibit a +I (inductive) effect, which is electron-donating but relatively weak. - **Cation II**: The methoxy group (`OCH3`) has both +R (resonance) and +I (inductive) effects. The +R effect is stronger than +I, and since the positive charge is adjacent to the methoxy group, it stabilizes the cation significantly through resonance. - **Cation III**: The methoxy group is further away from the positively charged carbon, and while it can still exhibit +R, the presence of the `CH2` group between them reduces the resonance stabilization. Additionally, the methoxy group can also exhibit a -I effect due to the electronegativity of oxygen, which can pull electron density away from the cation, further destabilizing it. 4. **Compare the Stability**: - **Cation II** is the most stable due to the strong resonance effect from the methoxy group. - **Cation I** is next, as it has two methyl groups providing +I effect but lacks the resonance stabilization present in Cation II. - **Cation III** is the least stable because the methoxy group is less effective at stabilizing the positive charge due to the distance and potential -I effect. 5. **Order of Stability**: - The order of decreasing stability is: **Cation II > Cation I > Cation III**. - In numerical terms, this can be represented as: **II > I > III** or **213**. ### Final Answer: The correct order of decreasing stability of the cations is **Cation II > Cation I > Cation III** (213).

To determine the correct order of decreasing stability of the given cations, we will analyze the structure and the effects of the substituents attached to the cationic carbon. ### Step-by-Step Solution: 1. **Identify the Structures of the Cations**: - **Cation I**: `CH3 - C^+ - CH3` - **Cation II**: `CH3 - C^+ - OCH3` - **Cation III**: `CH3 - C^+ - CH2 - OCH3` ...
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