Chapter 7 - Chapter 7. Cyclic Compounds....

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Unformatted text preview: Chapter 7. Cyclic Compounds. Stereochemistry of Reac8ons Monocyclic alkanes CnH2n 10 12 20 Drawing a cyclohexane Axial vs. equatorial Interconversion of chair conforma8ons Boat and Twist ­boat conforma8on Rela8ve enthalpies Conforma8onal analysis of monosubs8tuted diastereomers Chair interconversion 1,3 ­diaxial interac8ons Comparison with gauche ­butane Trans ­ and cis ­ Disubs8tuted Cyclohexanes Use planar structure for cyclic compounds Cis ­1,2 ­dimethylcyclohexane Cis ­1,3 ­dimethylcyclohexane Cyclic compound with asymmetric carbons Cyclopentane, cyclobutane, and cyclopropane cyclopentane Cyclobutane Bicyclic and polycyclic compounds Bredt’s Rule Steroids Rela8ve reac8vi8es of enan8omers Enan8omers react at the same rates with an achiral reagent Enan8omers react at different rates with a chiral reagent Enzymes ­catalyzed reac8ons are stereoselec8ve Rxns that give enan8omeric products Rxns that give diastereomeric products Stereochemistry of addi8on reac8ons Stereochemistry of bromine addi8on Stereochemistry of hydrobora8on ­ oxida8on Cataly8c hydrogena8on Oxymercura8on ­reduc8on Subs8tu8on reac8on Key Points Cyclohexane has the same stability as a typical unbranched alkane; Chair, boat, twist ­boat conforma8ons, and their interconversion; Drawing chairs/boats; Conforma8onal analysis of mono ­ and di ­ subs8tuted cyclohexanes; Planar structures of cyclo ­alkane; Stereochemical consequences of the chair interconversion; Ring fusion; Enan8omers react at the same rates with an achiral reagent; at different rates with a chiral reagents; •  Stereochemistry of alkene addi8on; •  Reten8on and inversion of configura8on in subs8tu8on reac8ons. •  •  •  •  •  •  •  •  ...
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This note was uploaded on 08/24/2010 for the course CHEM 3351 at Colorado.

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