Organic Chemistry 1

Front 1

acid-dissociation constant

Back 1

Ka= [H30+][A-]/[HA]
pKa=-log10Ka

Front 2

Arrhenius acid/base

Back 2

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

Back 4

acid:electron-pair acceptor (electrophile)
base:electron-pair donor (nucleophile)

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covalent bonding

Back 5

bonding that occurs by the sharing of electrons in the region between two nuclei

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degenerate orbitals

Back 6

orbitals with identical energies

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electronegativity

Back 7

a measure of an element's ability to attract electrons. Higher electronegativity attracts electrons more strongly

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electrostatic potential map (EMP)

Back 8

red shows electron rich areas, blue shows electron poor areas

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empirical formula

Back 9

the ratios of atoms in a compound

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ionic bonding

Back 10

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

Back 18

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

Back 25

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.

Front 26

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

Back 29

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

Back 32

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

Back 37

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

Back 48

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

Back 62

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

Back 79

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.