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Chapter 16: Q17P (page 822)

Show which of the nitrogen atoms in purine are basic, and which one is not basic. For the nonbasic nitrogen, explain why its nonbonding electrons are not easily available to become protonated

Short Answer

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Purine with basic and non-basic nitrogen

Step by step solution

01

Purine

Purines are heterocyclic aromatic organic compounds is comprised of two rings that are fused together. These rings contain nitrogen atoms which can be acidic or basic.

02

Acidic or basic nitrogen in purine

In general basic nitrogen is those which can donate its lone pair of electrons to acid. In purine base the two nitrogen of six-member ring are basic and one nitrogen of five-membered ring non-basic. The nonbonding electrons of nonbasic nitrogen are used in the ring for delocalization. Hence they are not available for protonation, thus, they are non-basic.

Purine with basic and non-basic nitrogen

The delocalization of nitrogen electrons in purine is represented as follows:

Delocalization of electrons

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Most popular questions from this chapter


(a) Draw all the Kekulé structures of anthracene and phenanthrene.

(b) Propose mechanisms for the two additions shown.

(c) In Chapter 8, most of the additions of bromine to double bonds gave entirely anti stereochemistry. Explain why the addition to phenanthrene gives a mixture of syn andanti stereochemistry.

(d) When the product from (c) is heated, HBr is evolved, and 9-bromophenanthrene results. Propose a mechanism for this dehydrohalogenation.

Show the product of the Diels–Alder dimerization of cyclobutadiene.

Explain why each compound is aromatic, antiaromatic, or nonaromatic

(a) Isoxazole

(b) 1,3-thiazole

(c) Pyran

(d) Pyrylium ion

(e) γ - pyrone

(f) 1,2-Dihydropyridine

(g)Cytosine

(h)

The following hydrocarbon has an unusually large dipole moment. Explain how a large dipole moment might arise

(a)Cyclopnonatetraene cation

(b) Cyclononatetraene anion

(c) [16] annulene dianion

(d) [18] annulene dianion

(e)

(f) [20] annulene dication

Question: The benzene ring alters the reactivity of a neighboring group in the benzylic position much as a double bond alters the reactivity of groups in the allylic position.

Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates.

  1. Use resonance forms to show the delocalization (over four carbon atoms) of the positive charge, unpaired electron, and negative charge of the benzyl cation, radical, and anion.
  2. Toulene reacts with bromine in the presence of light to give benzyl bromide. Propose a mechanism for this reaction.

    c. Which of the following reactions will have the faster rate and give the better yield? Use a drawing of the transition state to explain your answer.
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