Answered: Compound A has two functional groups…

Biochemistry

9th Edition

ISBN:9781319114671

Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.

Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.

Chapter1: Biochemistry: An Evolving Science

Section: Chapter Questions

Problem 1P

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Compound A has two functional groups and it will formed an oily yellow liquid when it reacts with nitrous acid. They discovered that compound B is produced during the halogenation process of compound A. When compound B is reacted with nitric acid, compound C is formed. While Friedel Crafts alkylation of compoundAproduces compoundD. CompoundE was produced by Friedel Crafts acylation of compound A. This compound E reacts positively with alkaline iodine and 2,4-dinitrophenylhydrazine. However, it returns negative results for Tollens' and Benedict's tests. (a) Illutsrate the potential carbon-13 NMR spectrum for compound A. (b) Identify the possible structural formula of compound A (according to the carbon type) based on your proposed 13C NMR spectrum. (c) Predict the possible structural formula compounds B to E. The carbon atoms for compound A should more than SIX (6). (d) Distinguish between compound A with benzenedizonium chloride. (e) Predict the possible chemical reaction for formation of compounds B and E from compound A and explain your answer. (f) PredictthepossiblechemicalreactionforformationofcompoundCfrom compound B and explain your answer. (g) Explain why compound E gives negative results for Tollens' and Benedict's tests. (h) Discuss why compound A formed an oily yellow liquid when it reacts with nitrous acid. (i) With the aid of diagram, discuss the solubility of compound B and compound C and identify which compound is the most soluble.

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