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प्रश्न
How will you distinguish 1° and 2° hydroxyl groups present in glucose? Explain with reactions.
उत्तर
On oxidation with nitric acid, glucose as well as gluconic acid both yield a dicarboxylic acid, saccharic acid. This indicates the presence of a primary alcoholic (–OH) group in glucose.
\[\begin{array}{cc}
\phantom{.......}\ce{CHO}\phantom{..............}\ce{COOH}\phantom{............}\ce{COOH}\phantom{....}\\
\phantom{......}|\phantom{...................}|\phantom{..................}|\phantom{........}\\
\phantom{.....}\ce{(CHOH)4 ->[Oxidation] (CHOH)4 <-[Oxidation] (CHOH)4}\\
\phantom{......}|\phantom{...................}|\phantom{..................}|\phantom{........}\\
\phantom{......}\ce{CH2OH}\phantom{............}\ce{\underset{acid}{\underset{Saccharic}{COOH}}\phantom{............}\ce{\underset{acid}{\underset{Gluconic}{CH2OH}}}\phantom{..}}\\
\end{array}\]
Acetylation of glucose with acetic anhydride gives glucose pentaacetate which confirms the presence of five –OH groups. Since it exists as a stable compound, five –OH groups should be attached to different carbon atoms.
\[\begin{array}{cc}
\phantom{...}\ce{CHO}\phantom{..................}\ce{CHO}\phantom{......}\ce{O}\phantom{..........}\\
\phantom{........}|\phantom{.......................}|\phantom{..........}||\phantom{...............}\\
\phantom{}\ce{(CHOH)4 ->[Acetic anhydride] (CH - O - C - CH3)4}\\
\phantom{.}|\phantom{.......................}|\phantom{...................}\\
\phantom{.....}\ce{CH2OH}\phantom{................}\ce{CH2 - O - C - CH3}
\phantom{.....}\\
\end{array}\]
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संबंधित प्रश्न
Enlist the properties of glucose that can not be explained on the basis of open chain structure of it
Fill in the blanks by choosing the appropriate word/words from those given in the brackets:
(iodoform, acetaldehyde, positive, greater, acidic, acetone, disaccharide, negative, increases, glucose, decreases, chloroform, polysaccharide, lactose, lesser, basic, cationic hydrolysis, anionic hydrolysis)
Sucrose is a _________ and yields upon hydrolysis, a mixture of ________ and fructose.
Write the reactions involved when D-glucose is treated with the following reagent:
H2N-OH
Which one of the following compounds is different from the rest?
Which of the following properties of glucose cannot be explained by its open chain structure?
(i) Glucose does not form hydrogen sulphite with NaHSO3.
(ii) On oxidation with HNO3 glucose gives saccharic acid.
(iii) Glucose is found to exist in two different crystalline forms which are named as α and β.
Which is the least stable form of glucose?
Which one of the following reactions is not explained by the open chain Structure of glucose?
In the following reaction, identify A and B:
\[\begin{array}{cc}
\ce{C6H12O6 ->[Acetic anhydride] A}\\
\downarrow \text{Conc. nitric acid}\phantom{...}\\
\ce{B}\phantom{.................}\end{array}\]
Consider the following reactions:
(i) \[\ce{Glucose + R-OH ->[Conc. HNO3] [A] ->[X eq of][(CH3CO)2O] Acetyl derivative}\]
(ii) \[\ce{Glucose ->[Ni/H2] [A] ->[Y eq of][(CH3CO)2O] Acetyl derivative}\]
(iii) \[\ce{Glucose ->[Z eq of][(CH3CO)2O] Acetyl derivative}\]
'X, 'Y' and 'Z' in these reactions are respectively:
Glucose with excess of phenyl hydrazine forms ______.
