(i) Give the structure of the product formed when an acidified solution of compound A is reacted with Naphthalen-2-ol (2-naphthol) and Sodium cyanide separately

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter24: Amines And Heterocycles
Section24.SE: Something Extra
Problem 38MP
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The following is an experimental account of the preparation of compound B from Phenylamine. 

2cmof 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. 

Question: Answer both (i) and (ii) below

(i) Give the structure of the product formed when an acidified solution of compound A is reacted with Naphthalen-2-ol (2-naphthol) and Sodium cyanide separately

(ii) 1g of phenylamine yielded 1.2g of compound A. Calculate the percentage yield of the reaction.

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