Organic ChemistryMain MenuLecture 1: Introduction to Molecular OrbitalsLecture 10: Intermolecular Forces and Intro to ReactivityLecture 11: Alkenes as Nucleophiles ILectures 12 and 13: Alkenes II & IIILecture 14: Benzenes as Nucleophiles ILecture 15 objectives and skillsLecture 2: Molecular Orbitals in Organic StructuresLecture 3: Molecular Orbitals and ResonanceLecture 4: Molecular Orbitals and AromaticityLecture 5: Nomenclature and IR SpectroscopyLecture 6: Stereochemistry ILecture 7: Stereochemistry IILecture 8: Newman and Fisher ProjectionsLecture 9: Conformations and Cyclohexane RingsJulio Terra2fb22914f73f9e5a767bf7fb83987dca0e153e4a
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.
Draw a mechanism and reaction coordinate diagram to describe the reaction below. SOLUTION
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
Fill in the missing pieces to complete the transformations below. SOLUTION
Propose a reasonable synthesis of each of the following molecules from benzene. SOLUTION
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!! ;)
