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61 Cards in this Set
- Front
- Back
not cyclic
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acyclic
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hydrocarbon having only single bonds; a saturated hydrocarbon; general formula CnH2n+2
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alkane
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the group of atoms remaining after a hydrogen atom is removed from an alkane; an alkane-like substituent; symbolized by R-
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alkyl group
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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)
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angle strain or Baeyer strain
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a conformation with a 180 degree dihedral angle between the largest groups; usually the lowest energy conformation
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anti conformation
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hydrocarbon having a benzene-like aromatic ring
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aromatic hydrocarbon
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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
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axial bond
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a compound containing two rings joined at nonadjacent carbon atoms
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bridged bicyclic compound
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the carbon atoms shared by two or more rings; three chains of carbon atoms connect them
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bridgehead carbons
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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.
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chair-chair interconversion
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sterioisomers that differ only with respect to their cis or trans arrangement on a ring or double bond
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cis-trans isomers (geometric isomer)
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having two similar groups directed toward the same face of a ring or double bond
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cis isomer
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having two similar groups directed toward opposite faces of a ring or double bond
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trans isomer
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a rapid oxidation at high temperatures in the presence of air or oxygen
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combustion
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names that have developed historically, generally with a specific name for each compound; also called trivial name
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common name
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study of the energetics of different confirmations
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confirmational analysis
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structures that are related by rotations about a single bond; in most cases they interconvert at room temperature and are not true isomers
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conformations or conformers
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totally eclipsed conformation; usually the highest energy conformation
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dihedral angle equal to 0 degrees
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gauche confirmation; specific staggered confirmation; lower energy than eclipsed
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dihedral angle equal to 60 degrees
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"chair", "half-chair", "boat" and "twist boat"
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conformations of cyclohexane
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the most stable conformation of cyclohexane; with one part puckered up and another part puckered down
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"chair" conformation
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two hydrogens in the "boat" conformation pointing straight up
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flagpole hydrogens
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unstable conformation half way between the chair and the boat conformations of cyclohexane; part of the ring is flat in this conformation
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half-chair conformation
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isomers whose atoms are connected differently; they differ in their bonding sequence
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constitutional isomers or
structural isomers |
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heating large alkanes to cleave them into smaller ones
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cracking
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cracking in the presence of a catalyst
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catalytic cracking
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catalytic cracking in the presence of hydrogen to give saturated mixtures of smaller alkanes
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hydrocracking
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containing a ring of atoms
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cyclic
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an alkane containing a ring of carbon atoms; general formula CnH2n
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cycloalkane
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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
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strong steric hindrance between two axial groups on cyclohexane carbons with one carbon between them
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1,3-diaxial interaction
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the angle between two specified groups in a Newman projection; differences in this angle result in the various conformations
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dihedral angle
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any conformation with bonds directly lined up with each other. one behind the other,in the Newman projection; dihedral angle equals zero
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eclipsed conformation
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one of the six bonds (three up and three down) on the cyclohexane ring that are directed out toward the "equator" of the ring
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equatorial bond
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molecule in which two or more rings share two adjacent carbon atoms
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fused-ring system
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a conformation with a 60 degree dihedral angle between the largest groups
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gauche conformation
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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 |
halogenation
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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
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heat of combustion
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two compound that differ only by one or more -CH2- groups
example: C3H8 and C4H10 |
homologs
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attracted to water; soluble in water
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hydrophilic
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repelled by water; insoluble in water
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hydrophobic
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the systematic names that follow the rules adopted by the International Union of Pure and Applied Chemistry
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IUPAC names
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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
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kerosene
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-CH- group |
methine group
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-CH2- group
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methylene group
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-CH3 group
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methyl group
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an alkane with all its carbon atoms in a single chain, with no branching or alkyl substituents
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n-alkane or
normal alkane or straight-chain alkane |
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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
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Newman projections
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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
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octane number
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another name for the larger alkanes that tend to be solid at room temperature
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paraffin "wax"
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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
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ring strain
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the strain associated with eclipsing of bonds in a ring; the resistance to twisting about a bond
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torsional strain
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having no double or triple bonds; having the maximum number of bonded hydrogen atoms in a hydrocarbon
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saturated
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a way of picturing conformations as if looking down at an angle toward the carbon-carbon bond
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sawhorse structures
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any conformation that is not precisely stagered or eclipsed (0,60,120,180 degrees)
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skew conformation
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bicyclic compounds in which the two rings share only one carbon
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spirocyclic compounds
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any conformation with the bonds equally spaced in the Newman projection
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staggered confirmation
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the interference between two bulky groups that are so close togather that their electron clouds experience a repulsion
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steric hindrance or
steric strain |
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a side chain or appendage on the main (longest) chain of a hydrocarbon
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substituent or
branch |
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the energy required to twist a bond into a specific conformation
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torsional energy or
conformational energy |
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a conformation with a dihedral angle equal to zero between the largest groups; usually the highest-energy conformation
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totally eclipsed conformation
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