18. Aromaticity
Aromatic Heterocycles
9:58 minutes
Problem 16-43c
Textbook Question
Textbook QuestionThe ribonucleosides that make up ribonucleic acid (RNA)
are composed of d-ribose (a sugar) and
four heterocyclic “bases.” The general structure of a
ribonucleoside is shown here.
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The four heterocyclic bases are cytosine, uracil, guanine,
and adenine. Cytosine and uracil are called pyrimidine bases
because their structures resemble pyrimidine.
Guanine and adenine are called purine bases because
their structures resemble purine.
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(c) Do any of these bases have easily formed tautomers
that are aromatic? (Consider moving a proton from nitrogen
to a carbonyl group to form a phenolic derivative.)
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