Question 2: An unknown disaccharide, obtained from a partial hydrolysis of starch found in rice, was subjected to exhaustive methylation with methyl iodide (CH31, 8 equivalents) yielding an octa-methylated product, followed by acid hydrolysis of the acetal which yielded the following products, shown in the Fischer projection:

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Question 2:
An unknown disaccharide, obtained from a partial hydrolysis of starch found in rice, was
subjected to exhaustive methylation with methyl iodide (CH31, 8 equivalents) yielding an
octa-methylated product, followed by acid hydrolysis of the acetal which yielded the
following products, shown in the Fischer projection:
unknown CH3I, AICI 3
disaccharide
H+, H₂O
H.
-OCH3
H-C
H3CO-C-H
H-C OCH 3
H-C-OH
CH₂OCH 3
Product A
+
H.
H-C
-OCH3
H3CO- C-H
H-C -OCH3
H-C-OH
CH₂OH
Product B
a) Copy product A and B into your answering booklet and indicate all stereocenters.
Determine if the products are D or L. For two stereocenters of your choice in product A,
indicate the absolute configuration according to the R/S system.
b) What is the structure of the unknown disaccharide? Explain.
c) Is the unknown disaccharide a reducing sugar? How could this be confirmed
experimentally? Describe two different approaches to such experiments.
d) Spectroscopy is useful for the identification and quantification of many drug molecules.
How useful are the spectroscopy techniques that have been covered so far for the
identification and quantification of products A and B?
Transcribed Image Text:Question 2: An unknown disaccharide, obtained from a partial hydrolysis of starch found in rice, was subjected to exhaustive methylation with methyl iodide (CH31, 8 equivalents) yielding an octa-methylated product, followed by acid hydrolysis of the acetal which yielded the following products, shown in the Fischer projection: unknown CH3I, AICI 3 disaccharide H+, H₂O H. -OCH3 H-C H3CO-C-H H-C OCH 3 H-C-OH CH₂OCH 3 Product A + H. H-C -OCH3 H3CO- C-H H-C -OCH3 H-C-OH CH₂OH Product B a) Copy product A and B into your answering booklet and indicate all stereocenters. Determine if the products are D or L. For two stereocenters of your choice in product A, indicate the absolute configuration according to the R/S system. b) What is the structure of the unknown disaccharide? Explain. c) Is the unknown disaccharide a reducing sugar? How could this be confirmed experimentally? Describe two different approaches to such experiments. d) Spectroscopy is useful for the identification and quantification of many drug molecules. How useful are the spectroscopy techniques that have been covered so far for the identification and quantification of products A and B?
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