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Organic Chemistry: A Guided Inquiry

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter5: Resonance

Section: Chapter Questions

Problem 28CTQ

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Curved arrows are used to illustrate the flow of electrons.
Using the provided resonance structures, draw the
curved electron-pushing arrows to show the
interconversion between resonance hybrid contributors.
Be sure to account for all bond-breaking and bond-
making steps.
Incorrect, 3 attempts remaining
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HO
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Criteria for success All molecular drawings must be valid Lewis structures (octet rule, formal charge, valence, geometry). Curved arrows will be interpreted very strictly. Thus, they must clearly indicate the origin and destination of electron delocalization. Tasks 1. Generate at least three reasonable resonance contributors of the molecule in Fig. 3. 2. Rank reasonance contributors from least significant to most significant (#1 = most significant) and explain your choice. 3. Are the lone pairs of electrons on alcohol groups localized or delocalized? Briefly explain. HO OH F Figure 3: Molecule with delocalized electrons

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