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
Enantiomers – mirror image stereoisomers, same connectivity (same IUPAC name) Diastereomers – non-mirror image stereoisomers, same connectivity (same IUPAC name) Structural isomers – same formula, but different connectivity (different IUPAC name) Resonance structures – same structure, different localization/view of pi electrons
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1media/section 2 key image.png2020-02-09T17:05:19-08:00Lecture 6: Stereochemistry I4image_header2020-08-28T08:08:57-07:00Objectives and skills
KEY INFORMATION SUMMARY
PROBLEMS
Problem 6.1: Isomers
Label each of the following pairs of structures as enantiomers, diastereomers, structural isomers, or resonance structures. SOLUTION
Explain the differences between the terms listed above. 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 6.2: Mirror images and enantiomers
Draw the mirror image of each structure below and determine if the images are superimposable (and represent the same compound) or non-superimposable (and represent enantiomers). 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 6.3: Stereoisomer notations
Rank the following substituents in terms of chirality priority: -OH, -SH, -Br, -C(CH3)3, -CH2OH. SOLUTION
Circle all the chiral centers in the structures below and label with R/S notation. SOLUTION
Circle all the alkenes (ignore benzene rings) in the structures below and label with E/Z notation. 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 6.4: Stereochemistry and nomenclature
Draw accurate structures (using wedges/dashes) to represent (2R,3S)-2,3-dichloropentane, (2S,3S)-2,3-dichloropentane, (2E,4S)-4-chloro-3-phenyl-2-penten-2-ol. SOLUTION
Determine the IUPAC name of each structure below. 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 ;)
