How do you explain the absence of aldehyde group in the pentaacetate of $D$-glucose?

Vedclass pdf generator app on play store
Vedclass iOS app on app store
(N/A) -glucose exists in equilibrium between its open-chain form and cyclic hemiacetal forms. The open-chain form contains a free aldehydic $(-CHO)$ group,which reacts with hydroxylamine $(NH_2OH)$ to form an oxime.
However,when $D$-glucose is treated with acetic anhydride,all five hydroxyl $(-OH)$ groups are acetylated to form $D$-glucose pentaacetate. In this derivative,the hemiacetal hydroxyl group at $C-1$ is also converted into an ester group. Consequently,the pentaacetate cannot undergo ring-opening to form the open-chain aldehyde structure. Due to the absence of a free aldehydic group,$D$-glucose pentaacetate does not react with $NH_2OH$ to form an oxime.

Explore More

Similar Questions

Which of the following pairs is a $C_2$-epimer?

Which of the following derivatives is useful for the identification of reducing sugars?

$CHO-(CHOH)_4-CH_2OH \xrightarrow{Br_2/H_2O} P$; $P$ is:

Glucose $\xrightarrow{Br_2 - H_2O}$ Product; the product is:

Which of the following pairs of carbohydrates produce an equal quantity of glucose on hydrolysis per mole?

Vedclass Products

For Students

Vedclass Test Series

Mock tests in real JEE/NEET style with performance analysis. 5-day free trial.

Start Free Trial
For Teachers

Exam Paper Generator

Generate Set A/B/C/D exam papers from 7.5L+ questions in 2 minutes. 3 chapters free.

Try Free
For Institutes

Online Exam Module

Live online exams with unlimited students, 360° analytics & white-label branding.

See Demo