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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

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.

Like glucose, galactose mutarotates when it dissolves in water. The specific rotation of 伪-D-galactopyranoseis +150.70 , and that of the 尾 anomer is +52.80 . When either of the pure anomers dissolves in water, the specific rotation gradually changes to +80.20. Determine the percentages of the two anomers present at equilibrium.

Which of the following sugars are reducing sugars? Comment on the common name sucrose for table sugar.

(a) methyl伪鈥�D鈥�galactopyranoside (b) 尾鈥�L鈥�idopyranose (an aldohexose)

(c) 伪鈥�D鈥�allopyranose (d) 尾鈥�L鈥�ribofuranoside

(e) (f)

After a series of Kiliani鈥揊ischer syntheses on (+)-glyceraldehyde, an unknown sugar is isolated from the reaction mixture. The following experimental information is obtained:

(1) Molecular formula C6H12O6

(2) Undergoes mutarotation.

(3) Reacts with bromine water to give an aldonic acid.

(4) Reacts with HNO3 to give an optically active aldaric acid.

(5) Ruff degradation followed by HNO3 oxidation gives an optically inactive aldaric acid. (6) Two Ruff degradations followed by HNO3 oxidation give meso-tartaric acid.

(7) When the original sugar is treated with CH3I and Ag2O, a pentamethyl derivative is formed. Hydrolysis gives a tetramethyl derivative with a free hydroxy group on C5.

(a) Draw a Fischer projection for the open-chain form of this unknown sugar. Use Figure 23-3 to name the sugar.

(b) Draw the most stable conform

All of the rings of the four heterocyclic bases are aromatic. This is more apparent when the polar resonance forms of the amide groups are drawn, as is done for thymine at left. Redraw the hydrogen-bonded guanine-cytosine and adenine-thymine pairs shown in figure 23-24, using the polar resonance forms of the amides. Show how these forms help to explain why the hydrogen bonds involved in these pairings are particularly strong. Remember that a hydrogen bond arises between an electron-deficient hydrogen atom and electron-rich pair of nonbonding electrons.

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