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Chapter 7: Problem 4

Give the sequence of reactions when D-glucose reacts with excess of \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NHNH}_{2}\) in the presence of acetic acid?

Short Answer

Expert verified
Answer: The sequence of reactions involves the formation of a phenylhydrazone followed by an osazone.

Step by step solution

01

Formation of phenylhydrazone

Initially, D-glucose reacts with phenylhydrazine to form a phenylhydrazone. During this reaction, the carbonyl group (C=O) on the glucose molecule reacts with phenylhydrazine, and water is released as a by-product. The reaction can be represented as: D-Glucose + Phenylhydrazine \(\rightarrow\) D-Glucose phenylhydrazone + H\(_2\)O
02

Formation of osazone by continuous reaction with phenylhydrazine

Since there is an excess of phenylhydrazine, the D-Glucose phenylhydrazone will continue to react with more phenylhydrazine, resulting in the second carbonyl group also being converted to a phenylhydrazone. Finally, these phenylhydrazones condense to form an osazone, with the release of two molecules of ammonia. This reaction can be represented as: D-Glucose phenylhydrazone + 2 Phenylhydrazine \(\rightarrow\) D-Glucose osazone (Phenyl-2,3,4,5-tetra-acetyl-n-hexosazone) + 2 NH\(_3\) The overall sequence of reactions when D-glucose reacts with excess phenylhydrazine in the presence of acetic acid includes the formation of a phenylhydrazone and then an osazone.

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