O. Chem Question: Compounds 1 and 4d are isomers of one another. Both have the s
ID: 919115 • Letter: O
Question
O. Chem Question:
Compounds 1 and 4d are isomers of one another. Both have the same leaving
group, and should generate the same oxocarbenium ion intermediate during
hydrolysis. Investigators used 13C NMR to monitor product distributions, where
compound 8 (beta anomer) is 13C-labeled version of 1; compound 13 (alpha
anomer) is a 13C-labeled version of 4d. In these experiments, the hydrolysis was
run in the presence of added nucleophiles azide (to make 9 and 10) and acetate (to make 11 and 12). Reaction with the solvent would yield glucose. Is this data consistent with 1 and 4d generating the same intermediate? Why or why not?
What might be an explanation for differing product ratios in this case?
Explanation / Answer
1 and 4d will give different intermediates due to conformational stability.
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