Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 14, Problem 14.1YT
Interpretation Introduction

Interpretation:

The resonance structure corresponding to the given VB picture is to be drawn.

Concept introduction:

Chemical and structural features of molecules are unaccounted for by VB theory, most notably electron delocalization or resonance over three or more nuclei. The VB theory picture of a species that has resonance is inaccurate because it represents a single resonance structure, not the hybrid.

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Problem Set #5 III) Acid/Base Reaction - Answer the next few questions about Molecule B, shown below. a) Circle the terms that correctly describe the molecule. H-bond acceptor dextrorotatory contains ketone racemic has enantiomer H-bond donor Molecule B optically active contains aldehyde levorotatory [a] = -27.8° b) Molecule B can react with another molecule in an acid/base reaction (shown below). + H In the spaces provided, please do the following: i) Draw the structure of the missing molecule in the space provided. ii) Circle ONE: The missing molecule is a: conjugate acid conjugate base iii) Clearly draw curved arrows to show the forward mechanism. iv) Without referring to pKa values, predict whether the equilibrium will favor reactants or products, and give an explanation why. Circle ONE: reactants products Explanation:
7. Draw curved arrows indicating the movements of electrons between the following pair of resonance structures. Name the pattern of resonance shown. What is the hybridization of the carbon atoms? 8. Draw the remaining three resonance structures for the molecule in problem 7 above. 9. There are several possible forms of a trisubstituted cyclohexane with the formula C10H200. I have drawn four of them. From these, which one do you think is most commonly naturally occurring, and why? Which is least commonly occurring and why? HO HO" HO HO
What is the most polar/functionality for this compound?

Chapter 14 Solutions

Organic Chemistry: Principles and Mechanisms (Second Edition)

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