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Show which of the nitrogen atoms in purine are basic, and

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 17P Chapter 16

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 17P

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.

Step-by-Step Solution:
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Solution 17P

        Basic nitrogen are those which can donate its lone pair of electrons to acid. In purine base the two nitrogen six member ring are basic and one nitrogen of five membered ring is non basic.

        They nonbonding electrons of nonbasic nitrogen are used in the ring for the delocalization. Hence they are not available for the protonation.

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Chapter 16, Problem 17P is Solved
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Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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Show which of the nitrogen atoms in purine are basic, and