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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

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter13: Substitution
Section: Chapter Questions
Problem 58CTQ
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The Nucleophile Recall that the rate of an Sy2 process is dependent on the concentration of the nucleophile. For the same reason, SN2 processes are also dependent on the strength of the nucleophile. A strong nucleo- phile will speed up the rate of an SN2 reaction, while a weak nuclcophile will slow down the rate of an Sy2 reaction. In contrast, an SN1 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 cffect on the competition between Sy2 and Syl: • A strong nucleophile favors Sy2. • A weak nucleophile disfavors Sy2 (and thereby allows Sy1 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. Common nucleophiles Strong Weak HS но H2S RO H20 RSH NEC ROH
Transcribed Image Text:The Nucleophile Recall that the rate of an Sy2 process is dependent on the concentration of the nucleophile. For the same reason, SN2 processes are also dependent on the strength of the nucleophile. A strong nucleo- phile will speed up the rate of an SN2 reaction, while a weak nuclcophile will slow down the rate of an Sy2 reaction. In contrast, an SN1 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 cffect on the competition between Sy2 and Syl: • A strong nucleophile favors Sy2. • A weak nucleophile disfavors Sy2 (and thereby allows Sy1 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. Common nucleophiles Strong Weak HS но H2S RO H20 RSH NEC ROH
23. Does each of the following nucleophile favor SN2 or SN1? (a) HO, (b) S. (c) (d) NaOH (e) NaCN
Transcribed Image Text:23. Does each of the following nucleophile favor SN2 or SN1? (a) HO, (b) S. (c) (d) NaOH (e) NaCN
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