Property | Glucose | Fructose | |||||||||||||||
Molecular formula | \[{{C}_{6}}{{H}_{12}}{{O}_{6}}\] | \[{{C}_{6}}{{H}_{12}}{{O}_{6}}\] | |||||||||||||||
Nature | Polyhydroxy aldehyde. | Polyhydroxy ketone | |||||||||||||||
Melting point | \[146{}^\circ C\] | more...
The compounds which are obtained by replacing the \[-OH\] of the carboxylic group by other atoms or groups such as \[{{X}^{-}},\,-N{{H}_{2}}\], – OR and \[O-\underset{O}{\mathop{\underset{||}{\mathop{C}}\,}}\,-R\] are known as acid derivatives.
Glucose is known as dextrose because it occurs in nature as the optically active dextrorotatory isomer. It is also called grape sugar as it is found in most sweet fruits especially grapes.
(1) Preparation :
(i) Laboratory method
\[\underset{\text{(Sucrose)}}{\mathop{\underset{\text{Cane sugar}}{\mathop{{{C}_{12}}{{H}_{22}}{{O}_{11}}}}\,}}\,+{{H}_{2}}O\xrightarrow{{{H}^{+}}}\underset{\text{Glucose}}{\mathop{{{C}_{6}}{{H}_{12}}{{O}_{6}}}}\,+\underset{\text{Fructose}}{\mathop{{{C}_{6}}{{H}_{12}}{{O}_{6}}}}\,\]
HCl (dil.) is used for hydrolysis. Glucose being much less soluble in alcohol than fructose separates out by crystallising on cooling. (ii) Manufacture : It is obtained on a large scale by the hydrolysis of starch (corn starch or potato starch) with dilute sulphuric acid or hydrochloric acid. \[\underset{\text{Starch}}{\mathop{{{({{C}_{6}}{{H}_{10}}{{O}_{5}})}_{n}}}}\,+n{{H}_{2}}O\underset{320{}^\circ C,\,2-3\,atm}{\mathop{\xrightarrow{{{H}^{+}}}}}\,\underset{\text{Glucose}}{\mathop{n{{C}_{6}}{{H}_{12}}{{O}_{6}}}}\,\]
A thin paste of starch is boiled with dilute acid till the hydrolysis is complete. The excess of acid is neutralised with chalk (calcium carbonate) and the filtrate containing glucose is decolourised with animal charcoal. The solution is concentrated and evaporated under reduced pressure. Glucose is obtained in crystalline form.
(2) Physical properties : It is a colourless crystalline solid, melts at \[{{146}^{o}}C\]. It is readily soluble in water. From aqueous solution, it separates as a crystalline monohydrate \[({{C}_{6}}{{H}_{12}}{{O}_{6}}.{{H}_{2}}O)\] which melts at \[{{86}^{o}}C\]. It is sparingly soluble in alcohol but insoluble in ether. It is less sweet (three-fourth) than cane sugar. It is optically active and the ordinary naturally occuring form is (+) glucose or dextro form. It shows mutarotation.
(3) Chemical properties
(i) Alcoholic reactions (Reactions due to -OH group) :
(a) Reaction with acid chlorides and acid anhydride
\[\underset{\text{Glucose}}{\mathop{\begin{matrix} CHO\ \ \ \ \\ |\ \ \ \ \ \ \ \ \ \ \\ {{(CHOH)}_{4}} \\ |\ \ \ \ \ \ \ \ \ \ \\ C{{H}_{2}}OH \\ \end{matrix}}}\,+\underset{\text{Acetyl chloride}}{\mathop{5C{{H}_{3}}COCl}}\,\xrightarrow{ZnC{{l}_{2}}}\underset{\text{Glucose penta-acetate}}{\mathop{\begin{matrix} CHO\ \ \ \ \,\,\,\,\,\,\,\,\,\,\,\,\, \\ |\ \ \ \ \ \ \ \,\,\,\,\,\,\,\,\,\,\,\,\,\ \ \ \\ {{(CHOOCC{{H}_{3}})}_{4}} \\ |\ \ \,\,\,\,\,\,\,\,\,\,\,\,\,\ \ \ \ \ \ \ \ \\ C{{H}_{2}}OOCC{{H}_{3}} \\ \end{matrix}}}\,+5HCl\]
This shows that a molecule of glucose contains 5 - OH groups.
(b) Reaction with \[PC{{l}_{5}}\]
\[\underset{\text{Glucose}}{\mathop{\begin{matrix} CHO\,\,\,\,\,\, \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {{(CHOH)}_{4}} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ C{{H}_{2}}OH \\ \end{matrix}}}\,+5PC{{l}_{5}}\underset{\text{(Glucose penta-chloride)}}{\mathop{\underset{\,\text{Penta-chloroglucose}}{\mathop{\xrightarrow{{}}\,\,\begin{matrix} CHO\,\,\,\, \\ |\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {{(CHCl)}_{4}} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\, \\ C{{H}_{2}}Cl \\ \end{matrix}}}\,}}\,+5POC{{l}_{3}}+5HCl\]
(c) Reaction with metallic hydroxides
The carbohydrates are naturally occurring organic substances. They are present in both plants and animals. "Carbohydrates are defined as a class of compounds that include polyhydric aldehydes or polyhydric ketones and large polymeric compounds that can be broken down (hydrolysed) into polyhydric aldehydes or ketones."
Carbohydrates contain \[>C=O\] and \[-OH\] groups. A carbonyl compound reacts with an alcohol to form hemiacetal.
The name of simpler carbohydrates end is ?ose. Carbohydrate with an aldehydic structure are known as aldoses and those with ketonic structure as ketoses. The number of carbon atom in the molecule is indicated by Greek prefix.
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