When the gum of the shrub Sterculia setigera is subjected to acidic hydrolysis, one of the water-soluble components of thehydrolysate is found to be tagatose. The following information is known about tagatose:(1) Molecular formula C6H12O6(2) Undergoes mutarotation.(3) Does not react with bromine water.(4) Reduces Tollens reagent to give d-galactonic acid and d-talonic acid.(5) Methylation of tagatose (using excess CH3 I and Ag2O) followed by acidic hydrolysis gives1,3,4,5-tetra-O-methyltagatose.(a) Draw a Fischer projection structure for the open-chain form of tagatose.(b) Draw the most stable conformation of the most stable cyclic hemiacetal form of tagatose
Carbohydrates
Carbohydrates are the organic compounds that are obtained in foods and living matters in the shape of sugars, cellulose, and starch. The general formula of carbohydrates is Cn(H2O)2. The ratio of H and O present in carbohydrates is identical to water.
Starch
Starch is a polysaccharide carbohydrate that belongs to the category of polysaccharide carbohydrates.
Mutarotation
The rotation of a particular structure of the chiral compound because of the epimerization is called mutarotation. It is the repercussion of the ring chain tautomerism. In terms of glucose, this can be defined as the modification in the equilibrium of the α- and β- glucose anomers upon its dissolution in the solvent water. This process is usually seen in the chemistry of carbohydrates.
L Sugar
A chemical compound that is represented with a molecular formula C6H12O6 is called L-(-) sugar. At the carbon’s 5th position, the hydroxyl group is placed to the compound’s left and therefore the sugar is represented as L(-)-sugar. It is capable of rotating the polarized light’s plane in the direction anticlockwise. L isomers are one of the 2 isomers formed by the configurational stereochemistry of the carbohydrates.
When the gum of the shrub Sterculia setigera is subjected to acidic hydrolysis, one of the water-soluble components of the
hydrolysate is found to be tagatose. The following information is known about tagatose:
(1) Molecular formula C6H12O6
(2) Undergoes mutarotation.
(3) Does not react with bromine water.
(4) Reduces Tollens reagent to give d-galactonic acid and d-talonic acid.
(5) Methylation of tagatose (using excess CH3 I and Ag2O) followed by acidic hydrolysis gives
1,3,4,5-tetra-O-methyltagatose.
(a) Draw a Fischer projection structure for the open-chain form of tagatose.
(b) Draw the most stable conformation of the most stable cyclic hemiacetal form of tagatose
Trending now
This is a popular solution!
Step by step
Solved in 2 steps with 2 images
