Stereochemistry of Alkanes and Cycloalkanes

Stereochemistry of Alkanes and Cycloalkanes: 3-D Structures of Molecules -- Section 3 of Organic Chemistry Notes is 13 pages in length (page 3-1 through page 3-13) and covers ALL you'll need to know about the following lecture/book topics:

SECTION 3 – Stereochemistry of Alkanes and Cycloalkanes: 3-D Structures of Molecules

3-1 -- Stereochemistry
3-1 -- Conformation of Alkanes

_· Rotations Around Sigma (σ) Bonds
_· Conformational Isomers
_· Conformers of Ethane (Staggered vs. Eclipsed)
3-2 -- Newman Projections
_· Dihedral Angles (θ)
_· Staggered vs. Eclipsed
_· Energy Diagrams for Corresponding Newman Projections
_· Newman Projections for Butane - Gauche Conformers and Anti Conformers
_· Steric Interactions Between Substituents
_· Preferred Combinations of n-Alkanes (all-Anti)
3-4 -- Stability of Alkanes
_· Enthalpies (ΔH), Heats of Combustion (ΔHcomb) and Heats of Formation (ΔHf)
_· Branched Alkanes (Relative b.p.’s, m.p.’s, and ΔHf values
3-5 – Cycloalkane Stability
_· Cyclopropane, Cyclobutane, and Cyclopentane
_· Angle Strain (Planarity vs. Non-planarity)
3-7 -- Three Different Sources of Strain in Cycloalkanes
_· Angle Strain, Steric Strain, and Torsional Strain
3-8 -- Detailed Look at the Stereochemistry of Cyclohexane
_· Chair Conformations
_· Axial H’s and Equatorial H’s
_· The Newman Projection of Cyclohexane
_· Ring-Flip Between Chair Conformations
_· Monosubstituted Cyclohexanes
_· 1,3-Diaxial Interactions
_· Disubstituted Cyclohexanes (cis vs. trans)
3-11 -- A Closer Look at the Cyclohexane Ring-Flip
_· The “Twist-Boat” Intermediate
3-12 -- Bicyclic Compounds
_· Bicyclo[l.m.n]alkanes
_· Bridge Carbons and General Structure of Bicyclic Compounds
3-13 -- Steroid Skeletal Structures
_· Always Trans
_· Chair Conformations for Steroid Molecules

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Stereochemistry of Alkanes and Cycloalkanes

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