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61 Cards in this Set

  • Front
  • Back
not cyclic
hydrocarbon having only single bonds; a saturated hydrocarbon; general formula CnH2n+2
the group of atoms remaining after a hydrogen atom is removed from an alkane; an alkane-like substituent; symbolized by R-
alkyl group
the strain associated with compressing bond angles to smaller angles (less than 109.5); the strain associated with stretching bond angles to larger angles (greater than 109.5)
angle strain or Baeyer strain
a conformation with a 180 degree dihedral angle between the largest groups; usually the lowest energy conformation
anti conformation
hydrocarbon having a benzene-like aromatic ring
aromatic hydrocarbon
one of the six bonds (three up and three down) on the "chair" conformation of the cyclohexane ring that are parallel to the "axis" of the ring
axial bond
a compound containing two rings joined at nonadjacent carbon atoms
bridged bicyclic compound
the carbon atoms shared by two or more rings; three chains of carbon atoms connect them
bridgehead carbons
ring-flip; the process of one "chair" conformation of a cyclohexane flipping into another one (with all axial and equatorial positions reversed); the "boat" conformation is an intermediate for the chair-chair interconversion.
chair-chair interconversion
sterioisomers that differ only with respect to their cis or trans arrangement on a ring or double bond
cis-trans isomers (geometric isomer)
having two similar groups directed toward the same face of a ring or double bond
cis isomer
having two similar groups directed toward opposite faces of a ring or double bond
trans isomer
a rapid oxidation at high temperatures in the presence of air or oxygen
names that have developed historically, generally with a specific name for each compound; also called trivial name
common name
study of the energetics of different confirmations
confirmational analysis
structures that are related by rotations about a single bond; in most cases they interconvert at room temperature and are not true isomers
conformations or conformers
totally eclipsed conformation; usually the highest energy conformation
dihedral angle equal to 0 degrees
gauche confirmation; specific staggered confirmation; lower energy than eclipsed
dihedral angle equal to 60 degrees
"chair", "half-chair", "boat" and "twist boat"
conformations of cyclohexane
the most stable conformation of cyclohexane; with one part puckered up and another part puckered down
"chair" conformation
two hydrogens in the "boat" conformation pointing straight up
flagpole hydrogens
unstable conformation half way between the chair and the boat conformations of cyclohexane; part of the ring is flat in this conformation
half-chair conformation
isomers whose atoms are connected differently; they differ in their bonding sequence
constitutional isomers or
structural isomers
heating large alkanes to cleave them into smaller ones
cracking in the presence of a catalyst
catalytic cracking
catalytic cracking in the presence of hydrogen to give saturated mixtures of smaller alkanes
containing a ring of atoms
an alkane containing a ring of carbon atoms; general formula CnH2n
number of alkyl groups bonded to a carbon atom in a compound or an alkyl group:
primary(1st degree): C-R1
secondary (2nd degree): C-R2
tertiary (3rd degree): C-R3
quaternary (4th degree): C-R4
degree of alkyl substitution
strong steric hindrance between two axial groups on cyclohexane carbons with one carbon between them
1,3-diaxial interaction
the angle between two specified groups in a Newman projection; differences in this angle result in the various conformations
dihedral angle
any conformation with bonds directly lined up with each other. one behind the other,in the Newman projection; dihedral angle equals zero
eclipsed conformation
one of the six bonds (three up and three down) on the cyclohexane ring that are directed out toward the "equator" of the ring
equatorial bond
molecule in which two or more rings share two adjacent carbon atoms
fused-ring system
a conformation with a 60 degree dihedral angle between the largest groups
gauche conformation
the reaction of alkanes with halogens, in the presence of heat or light, to give products with halogen atoms substituted for hydrogen atoms
R-H + X2 -> R-X + HX X=F,CL,Br
heat given off when a mole of a compound is burned with excess oxygen to give CO2 and H2O in a bomb calorimeter; a measure of the energy content of a molecule
heat of combustion
two compound that differ only by one or more -CH2- groups
example: C3H8 and C4H10
attracted to water; soluble in water
repelled by water; insoluble in water
the systematic names that follow the rules adopted by the International Union of Pure and Applied Chemistry
IUPAC names
a thin, volatile oil distilled from petroleum, with a boiling range higher than that of gasoline and lower than that of diesel fuel; once used for lanterns and heaters, but now most of this petroleum fraction is further refined for use as jet fuel
-CH- group
methine group
-CH2- group
methylene group
-CH3 group
methyl group
an alkane with all its carbon atoms in a single chain, with no branching or alkyl substituents
n-alkane or
normal alkane or
straight-chain alkane
method of drawing conformations of a molecule as if looking straight down the bond connecting two carbon atoms; reveals the eclipsed, staggered (skewed), gauche, and anti conformations
Newman projections
rating of the antiknock properties of a gasoline blend; the percentage of isooctane (2,2,4-trimethylpentane) in an isooctane/heptane blend that begins to knock at the same compression ratio as the gasoline being tested
octane number
another name for the larger alkanes that tend to be solid at room temperature
paraffin "wax"
the extra strain associated with the cyclic structure of a compound, as compared with a similar acyclic compound; composed of angle strain and torsional strain
ring strain
the strain associated with eclipsing of bonds in a ring; the resistance to twisting about a bond
torsional strain
having no double or triple bonds; having the maximum number of bonded hydrogen atoms in a hydrocarbon
a way of picturing conformations as if looking down at an angle toward the carbon-carbon bond
sawhorse structures
any conformation that is not precisely stagered or eclipsed (0,60,120,180 degrees)
skew conformation
bicyclic compounds in which the two rings share only one carbon
spirocyclic compounds
any conformation with the bonds equally spaced in the Newman projection
staggered confirmation
the interference between two bulky groups that are so close togather that their electron clouds experience a repulsion
steric hindrance or
steric strain
a side chain or appendage on the main (longest) chain of a hydrocarbon
substituent or
the energy required to twist a bond into a specific conformation
torsional energy or
conformational energy
a conformation with a dihedral angle equal to zero between the largest groups; usually the highest-energy conformation
totally eclipsed conformation