c. aniline with nitrous acid followed by reaction with B-naphthol III. An unknown amine reacts with tosyi chioride in basic media to generate a clear solution. Upon addition of a strong acid, a precipitate forms. This sarme amine undergoes reaction with sodium nitrite and hydrochloric acid at cold temperature, and upon warming, a colorless gas is evolved. What information can one gather from these experiments? The precipitate inclicts that the amine is secondary, when gas is evolved the solution indicaites that amine Is primary IV. Using the chemistry learned in this experiment, how would you synthesize the following compound? N- CH30 56 EPERSES సపైపైన

c. aniline with nitrous acid followed by reaction with B-naphthol III. An unknown amine reacts with tosyi chioride in basic media to generate a clear solution. Upon addition of a strong acid, a precipitate forms. This sarme amine undergoes reaction with sodium nitrite and hydrochloric acid at cold temperature, and upon warming, a colorless gas is evolved. What information can one gather from these experiments? The precipitate inclicts that the amine is secondary, when gas is evolved the solution indicaites that amine Is primary IV. Using the chemistry learned in this experiment, how would you synthesize the following compound? N- CH30 56 EPERSES సపైపైన

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

Section23.9: Hofmann Elimination

Problem 23.14P

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Primary amines can be prepared from amides by Hoffman's reaction. Write a general equation for the reaction and give reagents with reaction conditions for this reaction. What property of amines is responsible for them being basic. Suggest one way of Increasing the basicity of an amine and give a specific example of its application.
In the preparation of p-Nitroaniline, there are three synthetic steps in this reaction, the first is acetylation of the amine, second is nitrates and the third is hydrolysis of the amide. Why must acetylation be done first if at all? Use chemical structures to illustrate your point.
Following are the steps in the industrial synthesis of glycerin. Provide structures for all intermediate compounds (AD) and describe the type of mechanism by which each is formed.
The following is an experimental account of the preparation of compound B from Phenylamine. 2cm3 of phenylamine are dissolved in 10cm3 of 0.5M hydrochloric acid in a test tube and cooled in an ice bath. 5cm3 of 0.2M sodium nitrate solution cooled to about 5o are added to the solution above and shaken. A salt A, C6H5N2Cl is formed, collected and dried. 1g of salt A is dissolved in 10cm3 of water, cooled and added drop by drop to a cold solution of 0.3g phenol in 5cm3 of 0.1M sodium hydroxide solution. B is precipitated, filtered, dried and the melting point determined. B is further crystallized twice and the melting point taken each time and found to be constant. Questions: (i) Give the name and suggest the colour of the precipitate B. Hence explain why it is necessary to recrystallize B several times. (ii) Why was it necessary to obtain a constant melting point for B?
The following is an experimental account of the preparation of compound B from Phenylamine. 2cm3 of phenylamine are dissolved in 10cm3 of 0.5M hydrochloric acid in a test tube and cooled in an ice bath. 5cm3 of 0.2M sodium nitrate solution cooled to about 5o are added to the solution above and shaken. A salt A, C6H5N2Cl is formed, collected and dried. 1g of salt A is dissolved in 10cm3 of water, cooled and added drop by drop to a cold solution of 0.3g phenol in 5cm3 of 0.1M sodium hydroxide solution. B is precipitated, filtered, dried and the melting point determined. B is further crystallized twice and the melting point taken each time and found to be constant. 1g of phenylamine yielded 1.2g of compound A. Calculate the percentage yield of the reaction.
The following is an experimental account of the preparation of compound B from Phenylamine. 2cm3 of phenylamine are dissolved in 10cm3 of 0.5M hydrochloric acid in a test tube and cooled in an ice bath. 5cm3 of 0.2M sodium nitrate solution cooled to about 5o are added to the solution above and shaken. A salt A, C6H5N2Cl is formed, collected and dried. 1g of salt A is dissolved in 10cm3 of water, cooled and added drop by drop to a cold solution of 0.3g phenol in 5cm3 of 0.1M sodium hydroxide solution. B is precipitated, filtered, dried and the melting point determined. B is further crystallized twice and the melting point taken each time and found to be constant. Why was it necessary to obtain a constant melting point for B?
The following is an experimental account of the preparation of compound B from Phenylamine. 2cm3 of phenylamine are dissolved in 10cm3 of 0.5M hydrochloric acid in a test tube and cooled in an ice bath. 5cm3 of 0.2M sodium nitrate solution cooled to about 5o are added to the solution above and shaken. A salt A, C6H5N2Cl is formed, collected and dried. 1g of salt A is dissolved in 10cm3 of water, cooled and added drop by drop to a cold solution of 0.3g phenol in 5cm3 of 0.1M sodium hydroxide solution. B is precipitated, filtered, dried and the melting point determined. B is further crystallized twice and the melting point taken each time and found to be constant. Give the structure of the product formed when an acidified solution of compound A is reacted with (i)Naphthalen-2-ol (2-naphthol) (ii) Sodium cyanide
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The following is an experimental account of the preparation of compound B from Phenylamine. 2cm3 of phenylamine are dissolved in 10cm3 of 0.5M hydrochloric acid in a test tube and cooled in an ice bath. 5cm3 of 0.2M sodium nitrate solution cooled to about 5o are added to the solution above and shaken. A salt A, C6H5N2Cl is formed, collected and dried. 1g of salt A is dissolved in 10cm3 of water, cooled and added drop by drop to a cold solution of 0.3g phenol in 5cm3 of 0.1M sodium hydroxide solution. B is precipitated, filtered, dried and the melting point determined. B is further crystallized twice and the melting point taken each time and found to be constant. Write the equation for the reaction between compound A and phenol Give the name and suggest the colour of the precipitate B. Why is it necessary to recrystallize B several times?
The following is an experimental account of the preparation of compound B from Phenylamine. 2cm3 of phenylamine are dissolved in 10cm3 of 0.5M hydrochloric acid in a test tube and cooled in an ice bath. 5cm3 of 0.2M sodium nitrate solution cooled to about 5o are added to the solution above and shaken. A salt A, C6H5N2Cl is formed, collected and dried. 1g of salt A is dissolved in 10cm3 of water, cooled and added drop by drop to a cold solution of 0.3g phenol in 5cm3 of 0.1M sodium hydroxide solution. B is precipitated, filtered, dried and the melting point determined. B is further crystallized twice and the melting point taken each time and found to be constant. (a) What is the general name given to the reaction between phenylamine and sodium nitrite and explain why it's necessary to carry out the reaction at low temperatures. (b) Write the equation for the reaction between compound A and phenol
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Rank the following amines based on basicity Rationalize the electronic effects responsible for the basicity of amines