Question

The formation of an azo compound is a slow reaction, however the rate can be increased by raising the pH of the solution. Explain what is the reason for that? Make sure to include relevant chemical reactions using CHEM DRAW. please DO NOT RESPOND if you are not going to use CHEMDRAW :) this is the 4th time I am posting this question and have paid an extra $3 per question this month. CHEM draw only :)

Answer 1

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Dr. Rakhee

CD New - Document - Selection Structure Reaction - Utilities - Help Custor , M erQ10 Q2QQI ODO ODOO A x? E CHA X, . Or hele mo [] ** G 0 , 0,0 Diazonium salt formed by diazotization of primary aromatic amine with NaNO2/dil HCI at zero to 5 degree centigrade. NEN This diazo compound formation will involve aromatic electrophile substitution mechanism where rate is slow because the nucleophilicity of -OH and -NH2 is not very high Hence, pH should be increased to convert it as O and NHO with the addition of NaOH addition which increase its nucleophilicity Hence, rate of azo compound formation in this slow step will increase due to increase the electron donating effect of O and NHO SLOW FAST AZO COMPOUND AZO COMPOUND

CD New - Document Selection Structure Reaction - Utilities Help era ora @all O ODOA x. . Or le OOO CH2 X2 [1X , O Diazonium salt formed by diazotization of primary aromatic amine with NaNO2/dil HCI at zero to 5 degree centigrade. This diazo compound formation will involve aromatic electrophile substitution mechanism where rate is slow because the nucleophilicity of -OH and -NH2 is not very high Hence, pH should be increased to convert it as O and NHO with the addition of NaOH addition which increase its nucleophilicity Hence, rate of azo compound formation in this slow step will increase due to increase the electron donating effect of and NHO H STEP 2 SLOW Or STEP 3 FAST gain of aromaticity and newtralizaiton Rate of RDS step will increase due to increase of electron donating power. NH" pH increase with addition of NaOH reagent STEP 1 AZO COMPOUND AZO COMPOUND