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Chapter 2
Structure and Reactivity
119
Organic Chemistry
Undergraduate 2
09/02/2014

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Term
chemical thermodynamics
Definition
deals with the changes in energy that take place when processes such as chemical reactions occur; extent at which a reaction goes to completion
Term
chemical kinetics
Definition
concerns the velocity or rate at which the concentrations of reactants & products change; speed at which a reaction goes to completion
Term
thermodynamic control
Definition
a transformation that yields the most stable products
Term
kinetic control
Definition
a reaction in which the product obtained is the one formed fastest
Term
state of equilibrium
Definition
when the concentrations of reactants & products no longer change
Term
driving force
Definition
when a reaction goes to completion; indicated by a large value for K
Term
equation for K (equilibrium constant)
Definition
[products][products]
_____________________

[reactants][reactants]
Term
equation for Gibbs standard free energy change (delta G degrees) related to K
Definition
-RTln(K)
Term
equation for Gibbs standard free energy change related to enthalpy & enropy
Definition
enthalpy - T(entropy)
Term
enthalpy change
Definition
the heat absorbed or released at constant pressure during the course of the reaction
Term
equation for enthalpy change in a reaction
Definition
(sum of bonds broken) - (sum of bonds formed)
Term
exothermic
Definition
when the bonds formed are stronger than those broken; negative H; releasing heat
Term
endothermic
Definition
positive H; heat-absorbing
Term
potential-energy diagram
Definition
plots energy as a function of reaction progress
Term
reaction coordinate
Definition
the combined processes of bond breaking & bond formation that constitutes the overall change from the structures of the starting compounds into those of the products; how reaction progress is measured
Term
transition state
Definition
when the energy of a reaction first rises to the maximum
Term
activation energy (Ea)
Definition
the energy input required to raise the energy of the starting compounds to that of the transition state
Term
Boltzmann distribution curve
Definition
depicts the distribution of kinetic energy
Term
rate constant
Definition
proportionality constant "k" in rate equation
Term
second-order
Definition
a reaction for which the rate depends on the concentrations of two molecules
Term
first order
Definition
the rate of the reaction only depends on the concentration of one reactant
Term
elecrophilic
Definition
electron friendly
Term
nucleophile
Definition
a basic atom when it attacks an atom other than hydrogen
Term
acid
Definition
a proton donor
Term
base
Definition
a proton acceptor
Term
acid dissociation constant (Ka)
Definition
Ka=K[H2O] = ([H3O+][A-])/[HA] * molL^-1
Term
equation for pKa
Definition
pKa = -log(Ka)
Term
conjugate base
Definition
the species A- derived from the acid HA
Term
conjugate acid
Definition
the species HA derived from the base A-
Term
Lewis acid
Definition
a species that contains an atom that is at least two electrons short of a closed outer shell
Term
Lewis base
Definition
contains at least one lone pair of electrons
Term
haloalkanes
Definition
organic compounds possessing carbon-halogen bonds
Term
functional group
Definition
center of chemical reactivity
Term
functional groups/functionalities
Definition
the atoms or groups of atoms that tend to be the site of high chemical reactivity on molecules
Term
alkanes
Definition
hydrocarbons which contain only single bonds
Term
cycloalkanes
Definition
molecules whose carbons form a ring
Term
alkanes lack _____
Definition
functional groups
Term
alkenes
Definition
hydrocarbons with double bonds
Term
alkynes
Definition
hydrocarbons with triple bonds
Term
haloalkanes
Definition
contain polar carbon-halogen bonds as their functional groups
Term
hydroxy functional group
Definition
-O-H
Term
alcohols
Definition
contain a hydroxyl group
Term
ethers
Definition
contain an oxygen bonded to two carbon atoms; -C-O-C-
Term
carbonyl functional group
Definition
C=O
Term
aldehydes
Definition
O=CH
Term
ketones
Definition
O=CC
Term
carboxylic acids
Definition
contains the carbonyl group and an -OH
Term
amines
Definition
contain a nitrogen
Term
thiols
Definition
replacement of oxygen in alcohols by sulfur
Term
symmetrical ether
Definition
R-O-R
Term
unsymmetrical ether
Definition
R-O-R'
Term
straight-chain alkanes
Definition
linear in structure
Term
branched alkanes
Definition
the carbon chain contains one or several branching points
Term
primary carbon
Definition
one attached directly to only one other carbon atom
Term
secondary carbon
Definition
a carbon attached directly to two other carbon atoms
Term
tertiary carbon
Definition
a carbon attached directly to three other carbon atoms
Term
quaternary carbon
Definition
a carbon attached directly to four other carbon atoms
Term
stem chain
Definition
the longest carbon chain in a molecule
Term
substituents
Definition
groups other than hydrogen that are attached to a carbon chain
Term
methane
Definition
n = 1
Term
ethane
Definition
n = 2
Term
propane
Definition
n = 3
Term
butane
Definition
n = 4
Term
pentane
Definition
n = 5
Term
hexane
Definition
n = 6
Term
heptane
Definition
n = 7
Term
octane
Definition
n = 8
Term
nonane
Definition
n = 9
Term
decane
Definition
n = 10
Term
undecane
Definition
n = 11
Term
dodecane
Definition
n = 12
Term
tridecane
Definition
n = 13
Term
tetradecane
Definition
n = 14
Term
pentadecane
Definition
n = 15
Term
hexadecane
Definition
n = 16
Term
heptadecane
Definition
n = 17
Term
octadecane
Definition
n = 18
Term
nonadecane
Definition
n = 19
Term
icosane
Definition
n = 20
Term
barrier to rotation
Definition
the energy required to move the hydrogen atoms past each other
Term
there is _____ about all single bonds at room temperature
Definition
free rotation
Term
conformations/conformers
Definition
the many forms of a molecule that are created by rotations of the functional groups
Term
conformational analysis
Definition
the study of conformations' thermodynamic & kinetic behavior
Term
rotational energy/torsional energy/torsional strain
Definition
the change in energy resulting from bond rotation from the staggered to the eclipsed conformation
Term
ground state
Definition
the lowest energy state of a molecule
Term
activation energy
Definition
the difference in energy between ground and transition states
Term
anti
Definition
the most stable arrangement of a molecule; steric hindrance is minimized (functional groups are as far from each other as possible)
Term
general structure: haloalkanes
Definition
R-X (X = F, Cl, Br, I)
Term
general structure: alcohols
Definition
R-OH
Term
general structure: ethers
Definition
R-O-R
Term
general structure: thiols
Definition
R-SH
Term
general structure: alkenes
Definition
R - - R
C = C
R - - R
Term
general structure: alkynes
Definition
R-C(triple)C-R
Term
general structure: aromatic compounds
Definition
ring of carbons (alternating double bonds)
Term
general structure: aldehydes
Definition
R-C-H
ll
O
Term
general structure: ketones
Definition
R-C-R'
ll
O
Term
general structure: carboxylic acids
Definition
R-C-O-H
ll
O
Term
general structure: anhydrides
Definition
R-C-O-C-R'
ll ll
O O
Term
general structure: esters
Definition
R-C-O-R
ll
O
Term
general structure: amides
Definition
R - C - N - R
ll l
O R
Term
general structure: nitriles
Definition
R-C(triple)N
Term
general structure: amines
Definition
R-N-R
l
R
Term
pKa: HI
Definition
-10
Term
pKa: HBr
Definition
-9
Term
pKa: HCl
Definition
-8
Term
pKa: H3O+
Definition
-2
Term
pKa: NH4+
Definition
+9
Term
pKa: NH3
Definition
+35
Term
pKa: H2O
Definition
+16
Term
pKa: ROH2+
Definition
-2
Term
pKa: ROH
Definition
+16
Term
pKa: carboxylic acid
Definition
+5
Term
pKa: aromatic acid
Definition
+10
Term
pKa: CH3-aromatic-S(double bonded to two oxygens)-OH
Definition
-3
Term
pKa: H3C-H
Definition
+50
Term
pKa: H2C=C-H
l
H
Definition
+44
Term
pKa: HC(triple bond)CH
Definition
+25
Term
pKa: N(triple bond)C-H
Definition
+9.2
Term
pKa: R - C - C - H
ll l
O H2
Definition
+20
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