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مع مسن NO₂ NaCN CN NO₂ Although aromatic substitution reactions usually occur by an electrophilic mechanism, aryl halides that have electron-withdrawing substituents can also undergo a nucleophilic substitution reaction, termed SAr. The electron-withdrawing substituent(s) must be oriented ortho and/or para to the halogen. The reaction proceeds by nucleophilic attack of the nucleophile on the ring carbon bound to the halogen leaving group, an intermediate carbanion is formed which is termed a Meisenheimer complex. The Meisenheimer complex is stabilized via resonance by the electron-withdrawing groups. Expulsion of the halogen restores aromaticity to the ring and completes the reaction. Draw curved arrows to show the movement of electrons this step of the mechanism. Arrow-pushing Instructions 20 →XT NC CI NC gr - gr

مع مسن NO₂ NaCN CN NO₂ Although aromatic substitution reactions usually occur by an electrophilic mechanism, aryl halides that have electron-withdrawing substituents can also undergo a nucleophilic substitution reaction, termed SAr. The electron-withdrawing substituent(s) must be oriented ortho and/or para to the halogen. The reaction proceeds by nucleophilic attack of the nucleophile on the ring carbon bound to the halogen leaving group, an intermediate carbanion is formed which is termed a Meisenheimer complex. The Meisenheimer complex is stabilized via resonance by the electron-withdrawing groups. Expulsion of the halogen restores aromaticity to the ring and completes the reaction. Draw curved arrows to show the movement of electrons this step of the mechanism. Arrow-pushing Instructions 20 →XT NC CI NC gr - gr

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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(Draw curved arrows to show the movement of electrons in this step of the mechanism.)

من مع NO₂ NA NaCN Although aromatic substitution reactions usually occur by an electrophilic mechanism, aryl halides that have electron-withdrawing substituents can also undergo a nucleophilic substitution reaction, termed SNAr. The electron-withdrawing substituent(s) must be oriented ortho and/or para to the halogen. The reaction proceeds by nucleophilic attack of the nucleophile on the ring carbon bound to the halogen leaving group, an intermediate carbanion is formed which is termed a Meisenheimer complex. The Meisenheimer complex is stabilized via resonance by the electron-withdrawing groups. Expulsion of the halogen restores aromaticity to the ring and completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions х ш CN NC CI NC CI gr - gr
Transcribed Image Text:من مع NO₂ NA NaCN Although aromatic substitution reactions usually occur by an electrophilic mechanism, aryl halides that have electron-withdrawing substituents can also undergo a nucleophilic substitution reaction, termed SNAr. The electron-withdrawing substituent(s) must be oriented ortho and/or para to the halogen. The reaction proceeds by nucleophilic attack of the nucleophile on the ring carbon bound to the halogen leaving group, an intermediate carbanion is formed which is termed a Meisenheimer complex. The Meisenheimer complex is stabilized via resonance by the electron-withdrawing groups. Expulsion of the halogen restores aromaticity to the ring and completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions х ш CN NC CI NC CI gr - gr
Specifying Hotspot End Position Instructions Make the ends of your curved arrows specify the destination of the reorganizing electron(s) as exactly as possible. Keep in mind that not all hotspots are interchangeable; for example, an arrow starting/ending at the interior of an atom (represented by an atomic symbol) is not the same as an arrow starting/ending at a lone pair. correct Hoti: incorrect correct HCI: H H₂C C+ incorrect H CH3 H₂C-C+ CH3 CH3 CH3 -H* -H* H+ H* H₂C=C H₂C= :CI: CH3 CH3 CH3 CH3
Transcribed Image Text:Specifying Hotspot End Position Instructions Make the ends of your curved arrows specify the destination of the reorganizing electron(s) as exactly as possible. Keep in mind that not all hotspots are interchangeable; for example, an arrow starting/ending at the interior of an atom (represented by an atomic symbol) is not the same as an arrow starting/ending at a lone pair. correct Hoti: incorrect correct HCI: H H₂C C+ incorrect H CH3 H₂C-C+ CH3 CH3 CH3 -H* -H* H+ H* H₂C=C H₂C= :CI: CH3 CH3 CH3 CH3
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