Question

Write the reaction of D-Glucose with the following:
$\text{HCN}$
$\text{Br}_2 \text{water} $
$\text{(CH}_3\text{COO)}_2 \text{O}$

Hint:

In reactions involving glucose, pay attention to the types of functional groups reacting, such as hydroxyl groups, and their ability to undergo nucleophilic substitution or oxidation.

Answer 1

(a) When D-glucose reacts with HCN, it forms cyanohydrin, as the nucleophilic cyanide attacks the electrophilic carbonyl carbon in glucose. \[ \text{C}_6\text{H}_{12}\text{O}_6 + \text{HCN} \longrightarrow \text{C}_6\text{H}_{11}\text{O}_6\text{CN} \]
(b) When D-glucose reacts with $Br_2\text{water, it undergoes oxidation to form gluconic acid}$ \[ \text{C}_6\text{H}_{12}\text{O}_6 + \text{Br}_2 \longrightarrow \text{C}_6\text{H}_{12}\text{O}_7 \] 
(c) When D-glucose reacts with acetic anhydride (\( \text{(CH}_3\text{COO)}_2 \text{O} \)), it forms glucose pentaacetate.} \[ \text{C}_6\text{H}_{12}\text{O}_6 + \text{(CH}_3\text{COO)}_2 \text{O} \longrightarrow \text{C}_6\text{H}_{9}(\text{COOCH}_3)_5 \]