Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 5, Problem 30CTQ
Interpretation Introduction

Interpretation: The reason that explains benzene and other aromatic molecule has low potential energy should be determined.

Concept introduction: When one single structure is unable to describe all the properties of single molecule, a phenomenon called resonance comes into play. This arises when two or more than two Lewis structures are possible for one molecule. All such structures are called resonating structures and have same placement of atoms in them but these have different locations of bond pairs and lone pairs. The resonating structures are inter-convertible with each other. The resultant of all the resonating or contributing structures is called the resonance hybrid.

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What is Resonance Theory? Sate five conclusions that can be drawn from the theory. State the two main experiments that were used to establish the extra stability of the benzene molecule. What are the factors that confer Aromaticity to an organic molecule? i. State the effects of substituents on a benzene derivative towards further aromatic substitution.  Based on the above suggest the various types of substituents that can be attached to Benzene. What are the various ways by which alkenes may be synthesized? i. Give two examples each of Unsymmetrical alkenes and reagents. Give two examples of reactions of alkenes that result in Anti-Markonikov’s addition products
When drawing the resonance structures for a toluene carbocation (like the one attached below), should I include the structure created after a bond shift from the fourth structure, even though it mimicks the first structure? What about in the second picture- should the crossed out structure be included despite its similarity to the first one? Overall, I'm having trouble determining whether two compounds are the same and don't need to be drawn twice or just similar and need to drawn twice.
3. Justify aromaticity (or lack thereof) in the biological molecules below. H2N NH2 H H `NH2 `NH2 N- NH N. `NH ADP ADP N. `NH2 H ОН ОН ОН ОН adenine guanine cytosine thymine NAD+ NADH H OH H3C. H3C. CH30. CH30 10 10 H3C 'N' N. H3C N. CH30 CH30 N' CH2 OH CH2 H H-C-OH H -OH- ubiquinone ubiquinol H-C-OH H- -он Н-С—он H Ċ-OH CH2 CH2 ADP ADP FAD FADH2

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Organic Chemistry: A Guided Inquiry

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