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Chapter 23: Q43P (page 1245)

Cytosine, uracil and guanine have tautomeric forms with aromatic hydroxyl groups. Draw these tautomeric forms.

Short Answer

Expert verified

Tautomers of cytosine:

Tautomers of guanine:

Tautomers of Uracil:

Step by step solution

01

Explanation:

Tautomerism is a phenomenon where a single chemical compound tends to exist in two or more interconvertible structures which are different in terms of the relative position of one atomic nucleus, generally the hydrogen. Guanine and cytosine have both amino and carbonyl groups, thus they can exhibit both amino-imino and keto-enol, whereas uracil has lactam and lactim tautomers.

02

Tautomers of cytosine:

Tautomers of cytosine:

03

Tautomers of guanine:                                                          

Tautomers of guanine:

04

Tautomers of Uracil:                                                                                                                          

Tautomers of Uracil:

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Most popular questions from this chapter

Draw the structures (using chair conformations of pyranoses) of the following disaccharides.

(a) 4-O-(α -D-glucopyranosyl)-D-galactopyranose

(b) α -D-fructofuranosyl-β -D-mannopyranoside

(c) 6-O-(β -D-galactopyranosyl)-D-glucopyranose

Predict the products formed when the following sugars react with excess acetic anhydride and pyridine.

  1. α-D-glucopyranose
  2. β-D-ribofuranose

Ruff degradation of D-arabinose gives D-erythrose. The Kiliani-Fischer synthesis converts D-erythrose to a mixture of D-arabinose and D-ribose. Draw out these reactions and give the structure of D-ribose.

Question. (a) Figure 23-2 shows that the degradation of D-glucose gives D-arabinose, an aldopentose. Arabinose is most stable in its furanose form. Draw D-arabinofuranose.

(b) Ribose, the C2 epimer of arabinose, is most stable in its furanose form. Draw D-ribofuranose.

(a) Which of the D-aldopentoses will give optically active aldaric acids on oxidation with HNO3 ?

(b) Which of the D-aldotetroses will give optically active aldaric acids on oxidation withHNO3 ?

(c) Sugar X is known to be a D-aldohexose. On oxidation with HNO3 , X gives an optically inactive aldaric acid. When X is degraded to an aldopentose, oxidation of the aldopentose gives an optically active aldaric acid. Determine the structure of X.

(d) Even though sugar X gives an optically inactive aldaric acid, the pentose formed by degradation gives an optically active aldaric acid. Does this finding contradict the principle that optically inactive reagents cannot form optically active products?

(e) Show what products results if the aldopentose formed from degradation of X is further degraded to an aldotetrose. DoesHNO3 oxidize this aldotetrose to an optically active aldaric acid?
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