Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!)
9th Edition
ISBN: 9781305922198
Author: John E. McMurry
Publisher: CENGAGE L
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Chapter 2.SE, Problem 20VC
Interpretation Introduction
Interpretation:
A model of naphthalene is given. The position of multiple bonds in it is to be shown. The number of possible resonance structures for naphthalene is to be stated and their structures are to be drawn.
Concept introduction:
Hydrogen is monovalent. Carbon is tetravalent and it can form four bonds. The position of double bonds can be identified by looking for carbons in the model having only three bonds. Resonance forms differ only in the placement of their π and nonbonding valence electrons. Neither the position nor the hybridization of any atom changes from one resonance form to another. The shift of electrons to give another resonance structure is represented by a curved arrow.
To determine:
The position of multiple bonds in the given model of naphthalene, C10H8. The number and structures of possible resonance structures for naphthalene are to be drawn
Expert Solution & Answer
Answer to Problem 20VC
The positions of multiple bonds in naphthalene are shown in the structure given below.
Naphthalene has three resonance forms as shown.
Explanation of Solution
In the model of naphthalene shown all the carbons have formed only three bonds and all the carbons require one more bond to satisfy their fourth valence. This fourth valence of each carbon can be satisfied by placing five double bonds between adjacent carbons as shown.
By shifting the position of double bonds, in total, three resonance structures can be drawn.
Conclusion
The positions of multiple bonds in naphthalene are shown in the structure given below.
Naphthalene has three resonance forms as shown.
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Chapter 2 Solutions
Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!)
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