1. Chitosan is derived from the shells of crustaceans. It is only soluble in an aqueous acidic medium but not in organic solvents. When reacted with phthalic anhydride, it forms an amide. The product is no longer soluble in the aqueous medium but is now soluble in organic solvents. OH R'- HO- R" NH2 chitosan phthalic anhydride (a) Draw the product of the reaction between chitosan and phthalic anhydride. (b) Briefly explain the behavior change in solubility of the starting material and the final product.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter11: Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations
Section11.SE: Something Extra
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i found this question is really hard for me to answer, especially to explain the behaviour change in solubility.. thank you for helping me

1. Chitosan is derived from the shells of crustaceans. It is only soluble in an aqueous acidic
medium but not in organic solvents. When reacted with phthalic anhydride, it forms an amide.
The product is no longer soluble in the aqueous medium but is now soluble in organic solvents.
OH
R'-
HO
R"
NH2
chitosan
phthalic anhydride
(a) Draw the product of the reaction between chitosan and phthalic anhydride.
(b) Briefly explain the behavior change in solubility of the starting material and the final
product.
Transcribed Image Text:1. Chitosan is derived from the shells of crustaceans. It is only soluble in an aqueous acidic medium but not in organic solvents. When reacted with phthalic anhydride, it forms an amide. The product is no longer soluble in the aqueous medium but is now soluble in organic solvents. OH R'- HO R" NH2 chitosan phthalic anhydride (a) Draw the product of the reaction between chitosan and phthalic anhydride. (b) Briefly explain the behavior change in solubility of the starting material and the final product.
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