Question
Write the reactions involved when D-glucose is treated with the following reagents:
i. $\mathrm{Br}_2$ water
ii. $\mathrm{H}_2 \mathrm{N}-\mathrm{OH}$
iii. $\left(\mathrm{CH}_3 \mathrm{CO}\right)_2 \mathrm{O}$

Answer

  1. $\ \text{CHO}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{COOH}\\\ \ | \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ | \$\text{CHOH})_4\xrightarrow{\ \ {\text{Br}_2 \text{water}}\ \ }(\text{CHOH})_4\\ \ \ \ |\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\ \ \ \text{CH}_2\text{OH}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_2\text{OH}$
  2. $\ \text{CHO}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}=\text{N}-\text{OH}\\\ \ | \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ | \$\text{CHOH})_4\xrightarrow{\ \ {\text{NH}_2 \text{OH}}\ \ }(\text{CHOH})_4\\ \ \ \ |\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\ \ \ \text{CH}_2\text{OH}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_2\text{OH}$
  3.  

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