Please show the electron-flow mechanism of the general synthesis of Benzyl Chloride from Phenol. This involves predicting major and by-products using electronic and structural effects. The arrow push mechanism must be shown. OHNH,N2CIAnhydrousZncCl2NANO2 + HCI+ NH3300°C0°-5°CPhenolaniline1-chloro-2-phenyldiazeneCH2-CICH-OHCH,NH,PCI, / SOCI,HNO2(1) CUCN/KCN(II) LialH,Benzyl chloride Benzyl alcoholBenzyl amine

OH NH, N2CI Anhydrous ZnCl2 NANO2 + HCI + NH, 300°C 0°-5°C Phenol aniline 1-chloro-2-phenyldiazene CH2 CI ÇH,-OH CH,NH, PCI, / SOCI, HNO2 (1) CUCN/KCN (1I) LialH, Benzyl chloride Benzyl alcohol Benzyí amine

OH NH, N2CI Anhydrous ZnCl2 NANO2 + HCI + NH, 300°C 0°-5°C Phenol aniline 1-chloro-2-phenyldiazene CH2 CI ÇH,-OH CH,NH, PCI, / SOCI, HNO2 (1) CUCN/KCN (1I) LialH, Benzyl chloride Benzyl alcohol Benzyí amine

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter23: Amines

Section: Chapter Questions

Problem 23.52P

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Question

Please show the electron-flow mechanism of the general synthesis of Benzyl Chloride from Phenol. This involves predicting major and by-products using electronic and structural effects. The arrow push mechanism must be shown.

OH
NH,
N2CI
Anhydrous
ZncCl2
NANO2 + HCI
+ NH3
300°C
0°-5°C
Phenol
aniline
1-chloro-2-phenyldiazene
CH2-CI
CH-OH
CH,NH,
PCI, / SOCI,
HNO2
(1) CUCN/KCN
(II) LialH,
Benzyl chloride Benzyl alcohol
Benzyl amine

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