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Nucleophilic substitution reactions gene...

Nucleophilic substitution reactions generally expressed as
`Nu^(-) +R-L rarr R-Nu +L^(-)`
Where `Nu^(-) rarr` Nucleophile , `R-L rarr` substrate, `L rarr` leaving group
The best leaving groups are those that become the most stable ions after they depart. since most leaving group leave as a negatibe ion, the best leaving groups are those ions that stabilize a negative charge most effectively. A good leaving group should be
(a) electron-withdrawing to polarize the carbon
(b) stable once it has left (not a strong base)
(c) polaristable to maintain partial bonding with the carbon in the transition state (both `S_(N)1` and `S_(N)2)`. This bonding helps to stabilise the transition state and reduces the activation energy.
(I) `CH_(3)Br` (II) `CH_(3)F` (III) `CH_(3)OH` (IV) `CH_(3)OSO_(2)CF_(3)`
The correct order of decreasing reactivity of the above compounds towards `CH_(3)O^(-)` in an `S_(N)2` reaction is:

A

`I gt IV gt II gt III`

B

`IV gt I gt II gt III`

C

`Iv gt I gt III gt II`

D

`IV gt II gt I gt III`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the correct order of decreasing reactivity of the given compounds towards `CH3O^(-)` in an `S_N2` reaction, we need to analyze the leaving groups in each compound based on their stability and basicity. ### Step-by-Step Solution: 1. **Identify the Compounds and Their Leaving Groups**: - (I) `CH3Br` - Leaving group: `Br^(-)` - (II) `CH3F` - Leaving group: `F^(-)` - (III) `CH3OH` - Leaving group: `OH^(-)` - (IV) `CH3OSO2CF3` - Leaving group: `OSO2CF3^(-)` 2. **Evaluate the Stability of Leaving Groups**: - A good leaving group is one that can stabilize a negative charge effectively after it departs. - The order of leaving group ability generally follows the trend of acidity: the more stable the leaving group as an ion, the better it is as a leaving group. 3. **Determine the Acidity of the Leaving Groups**: - `Br^(-)` is a weak base and thus a good leaving group. - `F^(-)` is a strong base and a poor leaving group. - `OH^(-)` is also a strong base and a poor leaving group. - `OSO2CF3^(-)` (the triflate ion) is a very stable leaving group due to resonance stabilization. 4. **Rank the Leaving Groups**: - Based on the above analysis, we can rank the leaving groups from best to worst: - `OSO2CF3^(-)` > `Br^(-)` > `OH^(-)` > `F^(-)` 5. **Determine the Reactivity Order in `S_N2` Reactions**: - Since `S_N2` reactions are directly proportional to the quality of the leaving group, we can now establish the order of reactivity: - `CH3OSO2CF3` > `CH3Br` > `CH3OH` > `CH3F` 6. **Final Order**: - Therefore, the correct order of decreasing reactivity of the compounds towards `CH3O^(-)` in an `S_N2` reaction is: - **(IV) > (I) > (III) > (II)** ### Final Answer: The correct order of decreasing reactivity is: **`CH3OSO2CF3` > `CH3Br` > `CH3OH` > `CH3F`**.
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