Chem 334 - Fall 1999
Organic Chemistry I

Dr. Carl C. Wamser

Chapter 2 Skills

Knowledge - Level 1

know the names of the alkanes up to decane

know the common names isopropyl, isobutane, isopentane, neopentane

know the common names of the four butyl groups

know the IUPAC rules for systematic nomenclature of alkanes, cycloalkanes, and bicycloalkanes

Concepts - Level 2

understand the physical properties of the alkane family as typical nonpolar molecules

distinguish straight-chain, branched-chain, and cyclic alkanes

distinguish different types of isomers: constitutional, stereoisomers, conformers

distinguish different types of conformers: eclipsed, staggered, gauche, anti

understand the classification system for carbon atoms and functional groups
( 1° , 2° , 3° , 4° )

recognize the causes of ring strain in small rings and the special stability of the six-membered ring

distinguish cis and trans isomers in cyclic compounds

recognize the conformational possibilities for cyclohexane
(the ring can flex and interconvert axial and equatorial positions)

recognize the reasons for greater stability of equatorial over axial substituents

Applications - Level 3

apply the IUPAC rules to naming alkanes, cycloalkanes, and bicycloalkanes

from a given name, be able to write the structure

classify carbon atoms, hydrogen atoms, and functional groups in a molecule
( 1° , 2° , 3° , 4° )

write different conformations for a given molecule from various viewpoints

use Newman diagrams to view molecules from a particular angle
(down a C-C bond)

be able to write an accurate chair conformation for cyclohexane

be able to locate substituents on a chair cyclohexane

Analytical Skills - Level 4 & higher

assign the relative energy of different conformers

use potential energy diagrams to correlate energy changes with structural changes

be able to write both possible chair conformations for a given substituted cyclohexane