(a) CI (b) F NO2 O,N. CH;NH2 1. NaOH ? 2. Н,О, НС Br NO2 In nucleophilic aromatic substitution reactions that proceed by the nucleophilic addition-elimination mechanism, the reaction rate increases as the electronegativity of the halogen leaving group increases: Ar-I < Ar-Br < Ar-CI < Ar-F. Which step does this suggest is the rate-determining step of the mechanism-the addition step or the elimination step? Explain.

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Chapter1: Chemical Foundations
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Draw the detailed mechanism and predict the major product for each of the following reactions. Hint: See Problem 23.75

(a) CI
(b)
F
NO2
O,N.
CH;NH2
1. NaOH
?
2. Н,О, НС
Br
NO2
Transcribed Image Text:(a) CI (b) F NO2 O,N. CH;NH2 1. NaOH ? 2. Н,О, НС Br NO2
In nucleophilic aromatic substitution reactions that proceed by the nucleophilic addition-elimination mechanism, the
reaction rate increases as the electronegativity of the halogen leaving group increases: Ar-I < Ar-Br < Ar-CI <
Ar-F. Which step does this suggest is the rate-determining step of the mechanism-the addition step or the
elimination step? Explain.
Transcribed Image Text:In nucleophilic aromatic substitution reactions that proceed by the nucleophilic addition-elimination mechanism, the reaction rate increases as the electronegativity of the halogen leaving group increases: Ar-I < Ar-Br < Ar-CI < Ar-F. Which step does this suggest is the rate-determining step of the mechanism-the addition step or the elimination step? Explain.
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