Using the information below explain why CN- is a stronger Bronsted base even though in the reaction given it is only 300 fold more nucleopihlic.

Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Using the information below explain why CN- is a stronger Bronsted base even though in the reaction given it is only 300 fold more nucleopihlic. 

 

### Nucleophiles and Reaction Rates

#### Nucleophile Comparison

The table below contrasts two nucleophiles, Br⁻ and CN⁻, by examining the pKa of their conjugate acids and their second-order rate constants in a specific chemical reaction:

| Nucleophile Name | pKₐ of Conjugate Acid | k (Second Order Rate Constant, M⁻¹·s⁻¹) |
|------------------|-----------------------|----------------------------------------|
| Br⁻              | -8                    | 1.3                                    |
| CN⁻              | 9.4                   | 3.2 x 10²                               |

#### Chemical Reaction

The reaction under study is depicted as follows:

\[ \text{Nuc:}^- + \text{CH}_3\text{I} \xrightarrow{\text{DMF, 25 °C}} \text{Nuc-CH}_3 + \text{I}^- \]

- **Nuc:⁻** represents a generic nucleophile.
- The reaction is carried out in dimethylformamide (DMF) at 25 °C. 

This comparison illustrates how different nucleophiles can vary significantly in terms of their basicity and reaction rates.
Transcribed Image Text:### Nucleophiles and Reaction Rates #### Nucleophile Comparison The table below contrasts two nucleophiles, Br⁻ and CN⁻, by examining the pKa of their conjugate acids and their second-order rate constants in a specific chemical reaction: | Nucleophile Name | pKₐ of Conjugate Acid | k (Second Order Rate Constant, M⁻¹·s⁻¹) | |------------------|-----------------------|----------------------------------------| | Br⁻ | -8 | 1.3 | | CN⁻ | 9.4 | 3.2 x 10² | #### Chemical Reaction The reaction under study is depicted as follows: \[ \text{Nuc:}^- + \text{CH}_3\text{I} \xrightarrow{\text{DMF, 25 °C}} \text{Nuc-CH}_3 + \text{I}^- \] - **Nuc:⁻** represents a generic nucleophile. - The reaction is carried out in dimethylformamide (DMF) at 25 °C. This comparison illustrates how different nucleophiles can vary significantly in terms of their basicity and reaction rates.
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