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Organic Chemistry Main Menu Lecture 1: Introduction to Molecular Orbitals Lecture 10: Intermolecular Forces and Intro to Reactivity Lecture 11: Alkenes as Nucleophiles I Lectures 12 and 13: Alkenes II & III Lecture 14: Benzenes as Nucleophiles I Lecture 15 objectives and skills Lecture 2: Molecular Orbitals in Organic Structures Lecture 3: Molecular Orbitals and Resonance Lecture 4: Molecular Orbitals and Aromaticity Lecture 5: Nomenclature and IR Spectroscopy Lecture 6: Stereochemistry I Lecture 7: Stereochemistry II Lecture 8: Newman and Fisher Projections Lecture 9: Conformations and Cyclohexane Rings

SOLUTION 15.1b

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The major product (meta substitution) comes from the most stable carbocation intermediate (lowest activation energy barrier, fastest reaction, most preferred pathway). The meta carbocation does not ever have a resonance structure where the positive charge is adjacent to the C=O withdrawing group, whereas the orth and para intermediates do. This is especially bad as it puts a withdrawing group adjacent to a deficient carbon center.

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Lecture 15: Benzenes as Nucleophiles II 10 image_header 2020-04-03T12:45:44-07:00
Objectives and Skills

KEY INFORMATION SUMMARY

PROBLEMS

Problem 15.1: Reaction Coordinate Diagrams
1. Draw a mechanism and reaction coordinate diagram to describe the reaction below. SOLUTION
2. Explain why the major product is favoured. SOLUTION
If you made some mistakes or want to practice more, review the concepts that gave you trouble and work on this extra problem. If you're good, move to the problem below ;)

Problem 15.2: Reactivity
1. Fill in the missing pieces to complete the transformations below. SOLUTION
1. Propose a reasonable synthesis of each of the following molecules from benzene. SOLUTION
1. Find the error(s) in the two-step synthesis below. Propose a corrected synthesis. SOLUTION
If you made some mistakes or want to practice more, review the concepts that gave you trouble and work on this extra problem. If you're good, move to the next lecture!! ;)