Problem

The ribonucleosides that make up ribonucleic acid (RNA) are composed of D-ribose (a suga...

The 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

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.

(a) Determine which rings of these bases are aromatic.

(b) Predict which nitrogen atoms are basic.

(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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