Specific Rotation of 4-Methoxy-d-Mannose in Tetrasaccharide Hydrolysis

In summary, the specific rotation of a tetrasaccharide was measured to be -20.5°, and after complete hydrolysis in acid, the optical rotation of the solution was found to be -36.9°. Using the specific rotations of n-acetylgalacosamine, 3-deoxy-l-fucose, and 2-deoxy-D-ribose, the specific rotation of 4-methoxy-d-mannose can be calculated to be approximately 14.2°. However, the question is not entirely clear and may require further assumptions.
  • #1
amit25
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Homework Statement

The specific rotation of a tetrasaccharide was measured to be -20.5°. Upon complete hydrolysis in acid the optical rotation of the solution was found to be -36.9°. Knowing that the specific rotations of n-acetylgalacosamine,3-deoxy-l-fucose and 2-deoxy-D-ribose are -105°,-75.7° and 18.7°. What is the specific rotation of 4-methoxy-d-mannose?
b]2. Homework Equations [/b]

The Attempt at a Solution



1/4(-105)+1/4(-75.5)+1/4(18.7)+1/4x=-36.9

and solve for x=14.2 for 4-methoxy-d-mannose

Can anyone tell me If I am doing this correctly? It seems too simple...
 
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  • #2
Close, but not necessarily correct. You can't assume hydrolyzing tetrasaccharide solution that is 1 g/mL of the original compound you will get 0.25 g/mL of each produced monosaccharide, their concentrations will be in general higher (hydrolysis consumes water, so the mass of products is higher than the mass of the main reactant). To find exact concentrations you need to follow the reaction stoichiometry and molar masses.

I don't like the question. It says "optical rotation of the solution was found", not defining the solution. Either we are expected to do some unlikely assumptions, or whoever worded the question didn't think about it for long enough. We can assume it is a hydrolyzed solution that was used for the specific rotation measurement (so it was initially 1 g/mL of tetrasaccharide) but I find it hard to believe in practice nothing has changed - hydrolysis requires adding of an acid, heating and so on - final solution is definitely different, unless we did some unmentioned extra tricks.
 
  • #3
Thanks, hmmm..im not sure if we're expected to make some assumptions but that's how the Question was worded exactly.
 

Related to Specific Rotation of 4-Methoxy-d-Mannose in Tetrasaccharide Hydrolysis

1. What is specific rotation and why is it important in chemistry?

Specific rotation is a measure of the rotation of polarized light caused by a substance in a solution. It is important in chemistry because it can provide information about the structure, purity, and concentration of a compound.

2. How is specific rotation calculated?

Specific rotation is calculated using the formula [α] = α/(cl), where α is the observed angle of rotation, c is the concentration of the solution in grams per milliliter, and l is the path length of the sample cell in decimeters.

3. What are the units of specific rotation?

The units of specific rotation are degrees per decimeter per gram (°/(dm⋅g)).

4. What factors can affect specific rotation?

The temperature, wavelength of light, concentration, and purity of the substance can all affect specific rotation. Additionally, the specific rotation of a compound can vary depending on the solvent used in the solution.

5. How is specific rotation used in chiral analysis?

Specific rotation is used in chiral analysis to determine the enantiomeric purity of a compound. By comparing the measured specific rotation to the literature value for a pure enantiomer, the percentage of each enantiomer present in a sample can be determined.

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