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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) `CI^(-)` (II) `CH_(3)O^(-)` (III) `CH_(3)S^(-)` (IV) `I^(-)`
The correct order of increasing leaving group capability of above anions

A

`III lt IV lt II lt I`

B

`II lt III lt I lt IV`

C

`II lt IV lt III lt I`

D

`I lt III lt II lt IV`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the correct order of increasing leaving group capability of the given anions (I: CI^(-), II: CH₃O^(-), III: CH₃S^(-), IV: I^(-)), we need to analyze their acidity and basicity. The leaving group ability is directly related to the acidity of the corresponding acid; the more stable the leaving group (which corresponds to a more acidic acid), the better it is as a leaving group. ### Step-by-Step Solution: 1. **Understanding Leaving Group Stability**: - A good leaving group is one that can stabilize the negative charge effectively after it leaves. This is often related to the acidity of the corresponding conjugate acid. 2. **Analyzing the Given Anions**: - **I: CI^(-)**: This is the conjugate base of hydrochloric acid (HCl). Chlorine is a halogen and has a relatively stable negative charge. - **II: CH₃O^(-)**: This is the conjugate base of methanol (CH₃OH). Oxygen is less stable with a negative charge compared to halogens. - **III: CH₃S^(-)**: This is the conjugate base of methanethiol (CH₃SH). Sulfur can stabilize the negative charge better than oxygen but not as well as halogens. - **IV: I^(-)**: This is the conjugate base of hydroiodic acid (HI). Iodine is larger and can stabilize the negative charge very effectively. 3. **Order of Acidity**: - The order of acidity for the corresponding acids is: HI > HCl > CH₃SH > CH₃OH. - This means the order of stability for the leaving groups is: I^(-) > Cl^(-) > CH₃S^(-) > CH₃O^(-). 4. **Order of Leaving Group Capability**: - Since leaving group capability increases with acidity, the order of increasing leaving group capability is the reverse of the order of acidity: - CH₃O^(-) < CH₃S^(-) < Cl^(-) < I^(-). 5. **Final Answer**: - The correct order of increasing leaving group capability is: - CH₃O^(-) < CH₃S^(-) < Cl^(-) < I^(-).
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ALLEN-ALKYL AND ARYL HALIDE-EXERCISE
  1. Nucleophilic substitution reactions generally expressed as Nu^(-) +R...

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  2. Nucleophilic substitution reactions generally expressed as Nu^(-) +R...

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  3. Nucleophilic substitution reactions generally expressed as Nu^(-) +R...

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  4. Nucleophilic aliphatic substitution reaction is mainly of two types: S...

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  5. Nucleophilic aliphatic substitution reaction is mainly of two types: S...

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  6. Nucleophilic aliphatic substitution reaction is mainly of two types: S...

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  7. An optically active compound A (assume dextrorotatory) has the molecul...

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  8. An optically active compound A (assume dextrorotatory) has the molecul...

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  9. Select the member of each pair that shows rate of S(N)2 reaction with ...

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  10. Of the following statements which are true for S(N)1 reaction. (a) T...

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  11. Of the following statements , which are true for S(N)2 reaction. (a)...

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  12. Arrange the isomers of molecular formula C(4)H(9)CI in order of decrea...

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  13. There is an overall 29-fold difference in reactivity of 1-chlorohexane...

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  14. Identify the product when A reacts with

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  15. Which is faster in the following pairs of halogen compounds undergoing...

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  16. R -Mg-Br(A) on reaction with H(2)O forms a gas (B), which occupied 1.4...

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  17. Provide structure of major product in the following reaction indicatin...

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  18. Propose mechanism of the following reactions:

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  19. Which of the following alkyl halide could be successfully used to synt...

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  20. An alkyl bromide A has molecular formula C(8)H(17)Br and four differen...

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