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23. Does each of the following nucleophile favor SN2 or SN1? (a) (b) HO, SH (c) (d) NaOH (e) NaCN

23. Does each of the following nucleophile favor SN2 or SN1? (a) (b) HO, SH (c) (d) NaOH (e) NaCN

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**The Nucleophile** Recall that the rate of an S<sub>N</sub>2 process is dependent on the concentration of the nucleophile. For the same reason, S<sub>N</sub>2 processes are also dependent on the *strength* of the nucleophile. A strong nucleophile will speed up the rate of an S<sub>N</sub>2 reaction, while a weak nucleophile will slow down the rate of an S<sub>N</sub>2 reaction. In contrast, an S<sub>N</sub>1 process is not affected by the concentration or strength of the nucleophile because the nucleophile does not participate in the rate-determining step. In summary, the nucleophile has the following effect on the competition between S<sub>N</sub>2 and S<sub>N</sub>1: - A strong nucleophile favors S<sub>N</sub>2. - A weak nucleophile disfavors S<sub>N</sub>2 (and thereby allows S<sub>N</sub>1 to compete successfully). We must therefore learn to identify nucleophiles as strong or weak. The strength of a nucleophile is determined by many factors that were first discussed in Section 6.7. Figure 7.26 shows some strong and weak nucleophiles that we will encounter. **Figure Explanation: Common Nucleophiles** The diagram presents a table of common nucleophiles, divided into two columns labeled "Strong" and "Weak": - **Strong Nucleophiles:** - I⁻ - HS⁻ - HO⁻ - Br⁻ - H₂S - RSH - **Weak Nucleophiles:** - F⁻ - H₂O - ROH
Transcribed Image Text:**The Nucleophile** Recall that the rate of an S<sub>N</sub>2 process is dependent on the concentration of the nucleophile. For the same reason, S<sub>N</sub>2 processes are also dependent on the *strength* of the nucleophile. A strong nucleophile will speed up the rate of an S<sub>N</sub>2 reaction, while a weak nucleophile will slow down the rate of an S<sub>N</sub>2 reaction. In contrast, an S<sub>N</sub>1 process is not affected by the concentration or strength of the nucleophile because the nucleophile does not participate in the rate-determining step. In summary, the nucleophile has the following effect on the competition between S<sub>N</sub>2 and S<sub>N</sub>1: - A strong nucleophile favors S<sub>N</sub>2. - A weak nucleophile disfavors S<sub>N</sub>2 (and thereby allows S<sub>N</sub>1 to compete successfully). We must therefore learn to identify nucleophiles as strong or weak. The strength of a nucleophile is determined by many factors that were first discussed in Section 6.7. Figure 7.26 shows some strong and weak nucleophiles that we will encounter. **Figure Explanation: Common Nucleophiles** The diagram presents a table of common nucleophiles, divided into two columns labeled "Strong" and "Weak": - **Strong Nucleophiles:** - I⁻ - HS⁻ - HO⁻ - Br⁻ - H₂S - RSH - **Weak Nucleophiles:** - F⁻ - H₂O - ROH
**Question 23:** Does each of the following nucleophiles favor SN2 or SN1? **Nucleophiles:** (a) CH₃CH₂OH (b) CH₃CH₂SH (c) CH₃CH₂O⁻ (d) NaOH (e) NaCN **Explanation:** This question examines whether each given nucleophile favors an SN2 or SN1 reaction mechanism. Here’s a general guideline: - **Strong nucleophiles** tend to favor SN2 reactions, especially when paired with primary substrates. - **Weaker nucleophiles** or those that are also good leaving groups often participate in SN1 reactions, particularly with tertiary substrates. Below is a description of each nucleophile: - **(a) CH₃CH₂OH (Ethanol):** Typically regarded as a weaker nucleophile, often favoring SN1 in the presence of a tertiary carbon due to its neutral oxygen atom. - **(b) CH₃CH₂SH (Ethanethiol):** A stronger and soft nucleophile, particularly suitable for SN2 reactions. - **(c) CH₃CH₂O⁻ (Ethoxide Ion):** A strong, negatively charged nucleophile that favors SN2 reactions because of its high reactivity. - **(d) NaOH (Sodium Hydroxide):** A strong base and nucleophile, typically promoting SN2 reactions with primary substrates. - **(e) NaCN (Sodium Cyanide):** A strong nucleophile that typically drives SN2 reactions due to the strong nucleophilic character of the CN⁻ ion. This classification can help students predict the likely pathway for reactions involving these nucleophiles.
Transcribed Image Text:**Question 23:** Does each of the following nucleophiles favor SN2 or SN1? **Nucleophiles:** (a) CH₃CH₂OH (b) CH₃CH₂SH (c) CH₃CH₂O⁻ (d) NaOH (e) NaCN **Explanation:** This question examines whether each given nucleophile favors an SN2 or SN1 reaction mechanism. Here’s a general guideline: - **Strong nucleophiles** tend to favor SN2 reactions, especially when paired with primary substrates. - **Weaker nucleophiles** or those that are also good leaving groups often participate in SN1 reactions, particularly with tertiary substrates. Below is a description of each nucleophile: - **(a) CH₃CH₂OH (Ethanol):** Typically regarded as a weaker nucleophile, often favoring SN1 in the presence of a tertiary carbon due to its neutral oxygen atom. - **(b) CH₃CH₂SH (Ethanethiol):** A stronger and soft nucleophile, particularly suitable for SN2 reactions. - **(c) CH₃CH₂O⁻ (Ethoxide Ion):** A strong, negatively charged nucleophile that favors SN2 reactions because of its high reactivity. - **(d) NaOH (Sodium Hydroxide):** A strong base and nucleophile, typically promoting SN2 reactions with primary substrates. - **(e) NaCN (Sodium Cyanide):** A strong nucleophile that typically drives SN2 reactions due to the strong nucleophilic character of the CN⁻ ion. This classification can help students predict the likely pathway for reactions involving these nucleophiles.
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