Chapter 03 Structure and Stereochemistry of Alkanes.ppt

Cyclopropane Large ring strain due to angle compression Very reactive, weak bonds Cyclopropane (2) Torsional strain because of eclipsed hydrogens Cyclobutane Angle strain due to compression Torsional strain partially relieved by ring-puckering Cyclopentane If planar, angles would be 108?, but all hydrogens would be eclipsed. Puckered conformer reduces torsional strain. Cyclohexane Combustion data shows it’s unstrained. Angles would be 120?, if planar. The chair conformer has 109.5? bond angles and all hydrogens are staggered. No angle strain and no torsional strain.   Chair Conformer Boat Conformer Conformational Energy Axial and Equatorial Positions Monosubstituted Cyclohexanes 1,3-Diaxial Interactions Disubstituted Cyclohexanes Cis-Trans Isomers Bonds that are cis, alternate axial-equatorial around the ring. Bulky Groups Groups like t-butyl cause a large energy difference between the axial and equatorial conformer. Most stable conformer puts t-butyl equatorial regardless of other substituents. Bicyclic Alkanes Fused rings share two adjacent carbons. Bridged rings share two nonadjacent C’s. bicyclo[3.1.0]hexane bicyclo[2.2.1]heptane Cis- and Trans-Decalin Fused cyclohexane chair conformers Bridgehead H’s cis, structure more flexible Bridgehead H’s trans, no ring flip possible. cis-decalin trans-decalin End of Chapter 3 IUPAC Names Find the longest continuous carbon chain. Number the carbons, starting closest to the first branch. Name the groups attached to the chain, using the carbon number as the locator. Alphabetize(依字母顺序) substituents. Use di-, tri-, tetra, etc. for multiples of same substituent. di-, tri-, tetra, etc. are ignored in alphabetizing. Name Alkyl Groups CH3-, methyl CH3CH2-, ethyl CH3CH2CH2-, n-propyl CH3CH2CH2CH2-, n-butyl Propyl Groups H n-propyl isopropyl H A primary carbon A secondary carbon Bu