Alkanes and Cycloalkanes

Vocabulary

alkane

hydrocarbon containing only CC{\rm C{-}C} single bonds and hydrogen with CnH2n+2 stoichiometry

alkene

hydrocarbon containing at least one carbon-carbon double bond (C=C{\rm {C{=}C}}) with CnH2n stoichiometry

alkyne

hydrocarbon that contains at least one carbon-carbon triple bond (CC{\rm {C{\equiv}C}} ) with CnH2n-2 stoichiometry

angle strain

molecular instability resulting from carbon atoms bonded in alkanes at angles less than 109.5°

anti-conformation

staggered conformation that exhibits no steric strain due to two groups on adjacent atoms having a dihedral angle of 180°

axial

position in which a substituent is parallel to the axis of the ring

bicyclic compound

molecule containing two rings

boat conformation

less stable, nonplanar conformation seen in cyclohexane rings

chair conformation

stable, nonplanar conformation seen in cyclohexane rings

cis-trans isomerism

one of two or more molecules that have the same molecular formula and bond structure but differ in the positions of their substituents around a rigid part of the molecule

conformational analysis

three-dimensional analysis of molecules to find the least-strained conformation or arrangement in three-dimensional space

cyclic

describes a molecule containing a ring with at least three carbons

dihedral angle

angle between two atoms on adjacent carbons in a Newman conformation

eclipsed conformation

conformation of an alkane where the dihedral angle is 0°

equatorial

position in which a substituent is perpendicular to the axis of the ring

flip-chair conformation

conversion of one cyclohexane chair conformation to another by rotation around the carbon-carbon single bonds

gauche conformation

staggered conformation that exhibits steric strain due to two groups on adjacent atoms having a dihedral angle of 60°

locant

position or location of a substituent in an organic molecule

Newman projection

projection that depicts the molecular conformation and is particularly useful for determining the best conformation of the molecule around a bond

ring strain

combination of angle and torsional strain that determines a molecule's stability

sawhorse projection

representation of a molecule from an angle that resembles a carpenter's sawhorse

staggered conformation

conformation of an alkane where the dihedral angle is 60°

steric strain

strain resulting from nonbonded atoms being forced close to each other

substituent

atom or group of atoms (functional group) that replaces a CH{\rm {C{-}H}} bond in an organic compound

torsional strain

resistance to bond rotation due to electronic repulsion that results from nonbonded atoms being forced close to each other

wedge-and-dash projection

way to represent molecular conformation with solid and dashed wedges to indicate the position of substituents