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83 Cards in this Set
- Front
- Back
acid-dissociation constant
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Ka= [H30+][A-]/[HA]
pKa=-log10Ka |
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Arrhenius acid/base
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acid:dissociates in water to give H30+
base:dissociates in water to give OH- |
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Bronsted-Lowry acid/base
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acid:proton donor
base:proton acceptor |
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Lewis acid/base
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acid:electron-pair acceptor (electrophile)
base:electron-pair donor (nucleophile) |
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covalent bonding
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bonding that occurs by the sharing of electrons in the region between two nuclei
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degenerate orbitals
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orbitals with identical energies
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electronegativity
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a measure of an element's ability to attract electrons. Higher electronegativity attracts electrons more strongly
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electrostatic potential map (EMP)
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red shows electron rich areas, blue shows electron poor areas
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empirical formula
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the ratios of atoms in a compound
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ionic bonding
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bonding that occus by the attraction of oppositely charged ions. ionic bonding usually results in the formation of a large, three-dimensional crystal lattice
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formal charge
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FC= [group #]-[nonbonding electrons]-1/2[shared electrons]
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resonance structure rules
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1.must be valid lewis structures. 2.only e- can be shifted. 3.# of lone pairs must remain the same. 4.major contributor has the lowest energy. 5.stabilization is most important when it serves to delocalize a charge over 2 or more atoms.
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calculation of empirical formula
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percentage given. assume the sample contains 100g. divide the percent value by atomic weight. divide these numbers (moles) by the smallest one to give the ratios.
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structural effects on acidity
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as electronegativity increases, acidity increases. as size increases, acidity increases. as resonance delocalization helps stabilize and ion and acidity increases.
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acid chloride
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an acid derivative with a chlorine atom in place of the hydroxyl group.
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alcohol
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a compound that contains a hydroxyl group
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aldehyde
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a carbonyl group with one alkyl group and one hydrogen. Carbon bonded to H, R and double bond with O
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alkanes
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hydrocarbons containing only single bonds
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alkenes
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hydrocarbons containing C=C double bonds
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alkynes
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hydrocarbons containing C-C triple bonds
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alkyl group
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a hydrocarbon group with only single bonds; an alkane with one hydrogen removed, to allow bonding to another group; symbolized by R.
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amide
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an acid derivative that contains an amine instead of the hydroxyl group of the acid
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amine
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an alkylated analogue of ammonia; R-NH2, R2NH, or R3N
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aromatic hydrocarbons (arenes)
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hydrocarbons containing a benzene ring, a six-membered ring with three double bonds.
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bond dipole moment
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a measure of the polarity of an individual bond in a molecule, defined as u=(4.8xdx&), where u is the dipole moment in debyes(10e-10esu-A), d is the bond length in angstroms, and & is the effective amount of charge separated, in units of the electronic charge.
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carbonyl group
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the functional group, as in a ketone or aldehyde. Carbon double bonded with Oxygen and two other bonds
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carboxyl group
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The --COOH functional group, as in a carboxylic acid
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carboxylic acid
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a compound that contains the carboxyl group. Carbon bonded to R and OH and double bonded to O
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cis-trans isomers
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stereoisomers that differ in their cis-trans arrangement on a ring or a double bond. The cis isomer has similar groups on the same side, and the trans isomer has similar groups on opposite sides
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constitutional isomers
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isomers whose atoms are connected differently; they differ in their bonding sequence
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cyano group
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The -C-N (triple bond)functional group, as in nitrile
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ester
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an acid derivative with an alkyl group replacing the acid proton
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ether
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a compound with an oxygen bonded between two alkyl groups
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functional group
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the reactive, nonalkane part of an organic molecule
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hybrid atomic orbital
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sp: 180 deg.
sp2:120 deg. sp3:109.5 deg. |
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ketone
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a carbonyl group with two alkyl groups attached.
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linear combination of atomic orbitals
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wave functions can add to each other to produce the wave functions of new orbitals. The number of new orbitals generated equals the original number of orbitals
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molecular orbital
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an orbital formed by the overlap of atomic orbitals on different atoms. MOs can be either bonding or antibonding, but only the bondng MOs are filled in most stable molecules
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bonding molecular orbital
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places a large amount of electron density in the bonding region between the nuclei. The energy of an electron in a bonding MO is lower than it is in an atomic orbital
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antibonding molecular orbital
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places most of the electron density outside the bonding region. The energy of an electron in an antibonding MO is higher than it is in an atomic orbital
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nitrile
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a compound containing a cyano group
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pi bond
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a bond formed by sideways overlap of two p orbitals. a pi bond has its electron density in two lobes, one above and one below the line joining the nuclei
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sigma bond
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a bond with most of its electron density centered along the line joining the nuclei; a cylindrically symmetrical bond. single bonds are normally sigma bonds
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wave function
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the mathematical description of an orbital. The square of the wave function is proportional to the electron density
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alkane
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a hydrocarbon having only single bonds, a saturated carbon
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alkyl group
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the group of atoms remaining after a hydrogen atom is removed from an alkane; an alkanelike substituent. R
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angle strain
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the strain associated with compressing bond angles to smaller angles
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anti conformation
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a conformation with a 180deg. dihedral angle between the largest groups. usually the lowest energy conformation
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aromatic hydrocarbon
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a hydrocarbon having a benzene like aromatic ring
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axial bond
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one of six bonds on the chair conformation of the cyclohexane ring that are parallel to the axis of the ring
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bridged bicyclic compound
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a compound containing two rings joined at nonadjacent carbon atoms
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bridgehead carbons
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the carbon atoms share by two or more rings. three chains of carbon atoms (bridges) connect the bridgeheads
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chair-chair interconversion
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the process of one chair conformation of a cyclohexane flipping into another one, wth all the axial and equatorial positions reversed. The boat conformation is an intermediate for the chair-chair interconversion
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cis-trans isomers
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geometric isomers, steroisomers that differ only with respect to their cis or trans arrangement on a ring or double bond. cis: same. trans: opposit
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combustion
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a rapid oxidation at high temperatures in the presence of air or oxygen
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conformations
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structures that are related by rotations about single bonds. in most cases conformations interconvert at room temperature, and they are not true isomers.
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constitutional isomers
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structural isomers, isomers whose atoms are connected differently, they differ in bonding sequence.
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cracking
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heating large alkanes to cleave them into smaller molecules
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cycloalkane
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an alkane containing a ring of carbon atoms
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degree of alkyl substitution
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the number of alkyl groups bonded to a carbon atom in a compound or in an alkyl group. primary for one, secondary for two, etc.
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1,3-diaxial interaction
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the strong steric strain between two axial groups on cyclohexane carbons with one carbon between them
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dihedral angle
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the angle between two specified groups in a Newman projection
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eclipsed conformation
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any conformation with bonds directly lined up with each other, one behind the other, in the Newman projection. The conformation with theta=0deg. is an eclipsed conformation
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equatorial bond
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one of the six bonds on the cyclohexane ring that are directed out toward the equator of the ring.
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fused-ring system
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a molecule in which two or more rings share two adjacent carbon atoms
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gauche conformation
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a conformation with a 60deg. dihedral angle between the largest groups
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halogenation
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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
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heat of combustion
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the heat given off when a mole of a compound is burned with excess oxygen to give CO2 and H20 in a bomb calorimeter. a measure of energy content of a molecule
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homologs
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two compounds that differ by one or more -CH2 groups
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kerosene
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a thin, volatile oil distilled from petroleum, with a boiling range higher than that of gasoline and lower than diesel fuel.
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methane hydrate
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an icelike substance consisting of individual methane molecules trapped inside cages of water molecules
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methine group
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a CH group with three other bonds
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methylene group
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a CH2 group with two other bonds
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methyl group
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a CH3 group with one other bond
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n-alkane/straight-chain alkane
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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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octane number
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a rating of the antiknock properties of a gasoline blend. Its octane number is the percentage of isooctane in an isooctane/heptane blend that begins to knock at the same compression ratio as the gasoline being tested
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paraffins
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another term for alkanes
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spirocyclic compounds
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bicyclic compounds in which the two rings share only one carbon atom
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steric strain
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the interference between two bulky groups that are so close together that their electron clouds experience a repulsion
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torsional energy
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the energy required to twist a bon into a specific conformation
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torsional strain
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the resistance to twisting about a bond
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row two and halogens in periodic table
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Li, Be, B, C, N, O, F
down: F, Cl, Br, I |
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highest electronegativity
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found at the top right corner, higher electronegativity indicates a stronger acid.
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