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Chemistry, 22.01.2020 22:31 tiffanibell71
Choose the statements that describe why the isomerization reaction is critical for the subsequent cleavage reaction that results in formation of two threeĆ¢carbon sugars in the glycolytic pathway.
the carbon of a carbonyl group has a partial positive charge and can delocalize electrons to facilitate cleavage of the c-c bond. without the isomerization reaction, c-1 will be the carbonyl carbon and the c-c cleavage will occur between c-2 and c-3
breaking a c-c bond is energetically unfavorable and can only proceed if a functional group with electronegative atoms is adjacent to the cleavage site to stabilize the reaction intermediates
to cleave a c-c bond, a nucleophilic carbon attacks the adjacent electrophilic carbon. the isomerization reaction moves the carbonyl group to c-2 thus making it a nucleophile that can attack c-3 to generate two three-carbon sugars
the partial positive charge on the carbonyl carbon can stabilize the carbon radicals formed by the homolytic cleavage of the c-c bond in the six-carbon sugar. since the c-c cleavage occurs between c-3 and c-4 of the six-carbon sugar, the carbonyl group needs to be on c-2
cleavage of a c-c bond in the six-carbon sugar occurs via a decarboxylation reaction that requires a carbonyl group adjacent to cleavage site to stabilize the carbanion intermediate
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