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166 Cards in this Set

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Addition Reaction
two reactants add to form one product with no atoms left over
Elimination Reaction
single reactant splits into two products
Substitution Reaction
two reactants exchange parts to yield two new products
Rearrangement
single product undergoes a rearrangement of bonds to yield a single isomeric product
Reaction Mechanism
describes the bonds broken and formed in a chemical reaction and accounts for all reactants and products
Bond breaking is symmetrical...
if one electron remains with each fragment
Bond breaking is unsymmetrical...
if both electrons remain with one fragment and the other fragment has a vacant orbital
Bond formation is symmetrical...
if one electron in a covalent bond comes from each reactant
Bond formation is unsymmetrical...
if both electrons in a covalent bond come from one reactant
Radical Reactions
involve symmetrical bond breaking and symmetrical bond formation
Polar Reactions
involve unsymmetrical bond breaking and unsymmetrical bond formation
Why are radicals highly reactive?
Because they contain an atom with an unpaired electron
A substitution reaction occurs...
when a radical abstracts an electron from another molecule
An addition reaction occurs...
when a radical adds to a double bond
In radical reactions...
all bonds are broken and formed by reactions with species with odd numbers of electrons
Steps in a Radical Reaction
initiation - produces radical by symmetrical cleavage
propagation - radical abstracts an atom to produce a new radical and a stable molecule
termination - occurs when two radicals combine
Nucleophile
compound with an electron rich atom
Electrophile
compound with an electron poor atom
The bond dissociation energy describes...
the heat needed to break a bond
In exothermic reactions, the bonds formed...
are stronger than the bonds broken
Functional Group
group of atoms within a molecule that has a characteristic chemical behavior
Alcohol
carbon singly bonded to the oxygen of a hydroxyl group
Ether
two carbons singly bonded to one oxygen
Alkyl Halide
aka haloalkane, carbon singly bonded to a halogen
Amine
carbon atom bonded to a nitrogen
Thiol
carbon atom bonded to an -SH (sulfhydryl) group
Disulfide
carbon atom bonded to two sulfurs that are joined together
Sulfide
two carbons joined to the same sulfur
Amide
nitrogen bonded to the C=O
Ester
oxygen bonded to the C=O
Carboxylic Acid
-OH group bonded to the C=O
Ketone
two carbons bonded to the C=O
Aldehyde
@ least one hydrogen bonded to the C=O
Orbital Filling
1s>2s>2p>3s>3p>4s>3d>4p>5s>4d>5p>4f
∆EN > 2.0
ionic bond
∆EN < 0.5
nonpolar covalent
∆EN between 0.5 and 2.0
polar covalent
Prefixes 1-10
meth
eth
prop
but
pent
hex
hept
oct
non
dec
Inductive Effect
an atom's ability to polarize a bond
Three Categories of Functional Groups
those with carbon-carbon multiple bonds
those with carbon singly bonded to an electronegative atom
groups with a carbon-oxygen double bond
Alkanes are saturated...
because they contain only single bonds
Constitutional Isomers
are always different compounds with different chemical properties but with the same molecular formula
Alkyl Group
the partial structure that remains following the removal of a hydrogen from an alkane
4 Degrees of Alkyl Substitution for Carbon
A primary carbon is bonded to one other carbon
A secondary carbon is bonded to two other carbons
A tertiary carbon is bonded to three other carbons
A quaternary carbon is bonded to four other carbons
Prim, Sec, and Tert Hydrogens
primary hydrogens are bonded to primary carbons
secondary hydrogens are bonded to secondary carbons
tertiary hydrogens are bonded to tertiary carbons
Atoms consist of...
a dense positively charged nucleus surrounded by negatively charged electrons
The nucleus is made up of...
positively charged protons and uncharged neutrons. Most of the mass of the atom is found in the nucleus
Z number
number of protons in the nucleus
A number
total number of protons and neutrons
Atoms of the same element with different values of (A)...
are called isotopes
Wave Equation
describes the distribution of electrons in an atom
Psi
represents an orbital and is the solution to a wave equation
The two lowest energy electrons...
are in the 1s orbital
The ground state electron configuration of an atom...
is a listing of the orbitals occupied by the electrons of the atom
Rules for Predicting GSEC
lowest energy orbitals are filled first
only two electrons in a single orbital with spins paired
if two or more orbitals of equal energy exist, all are half filled first and then electrons are paired
all the electrons in a half filled shell have the same spin
Wedged Line (solid)
represents a bond point toward you
Wedged Line (dashed)
represents a bond pointing away from you
Solid Line
represents a bond which lies in the plane of the page
Atoms bond together because...
the resulting compound is more stable than the individual atoms
Atoms tend to achieve the electron configuration...
of the nearest noble gas
The number of covalent bonds formed by an atom...
is dependent upon the number of electrons it has and the number it needs to achieve an octet
Valence electrons not used for bonding are called?
lone pair electrons
Covalent bonds are formed by?
The overlap of two atomic orbitals each of which contains one electron. The two electrons have opposite spins
The greater the orbital overlap...
the greater the strength of the chemical bond
Bonds formed by the head on overlap of two atomic orbitals are called?
Sigma bonds and they have cylindrical symmetry
Bond Strength
is the measure of the amount of energy needed to break a bond
Bond Length
is the optimum distance between two nuclei
SP3 Bond Angle
109.5˚
SP2 Bond Angle
120˚
SP Bond Angle
180˚
Formal Charge
FC = VE - (1/2BE - NBE)
VE -> valence electrons
BE -> bonding electrons
NBE -> nonbonding electrons
Resonance structures differ only in...
placement of pi and nonbonding electrons
Individual resonance forms...
are imaginary, not real. The real structure of the atom is a resonance hybrid
Any three atom grouping with a multiple bond adjacent to a nonbonding p orbital has ___ resonance forms.
Two
A Bronsted-Lowry acid...
donates an proton (H+ ion)
A Bronsted-Lowry base...
accepts a proton (H+)
The product that results when a base accepts a proton is?
the conjugate acid of the base
The product that results when the acid loses a proton is?
the conjugate base of the acid
Stronger acids have ____ acidity constants
Larger
Weaker acids have ____ acidity constants
Smaller
A strong acid has a ____ pKa
small
A weak acid has a ____ pKa
large
The conjugate base of a strong acid...
is a weak base
The conjugate base of a weak acid...
is a strong base
Two kinds of organic acids
those with H bonded to O and those that have a hydrogen bonded to a carbon next to a C=O group
The main type of organic base contains?
a nitrogen atom with a lone electron pair
A Lewis acid...
accepts an electron pair
A Lewis base...
has a pair of non-bonding electrons
n-Alkyl groups are formed by?
the removal of an end carbon of a straight chain alkane
Branched chain alkyl groups are formed by?
the removal of a hydrogen atom from an internal carbon
In the IUPAC system of nomenclature, a chemical system name has?
a prefix, a parent and a suffix
The parent shows?
the number of carbons in the principle chain
The suffix identifies?
the functional group family
The prefix shows?
the location of functional groups
Staggered Conformation
is the lowest energy conformer and results when all the C-H bonds are as far from one another as possible
Eclipsed Conformation
is the highest energy conformer and results when all the C-H bonds are as close to each other as possible
Lab reactions are carried out it in?
organic solvents and take place over a wide temperature range
Biological reactions take place in?
aqueous medium and take place at the organism's body temperature
An Intermediate is?
the species that lies at an energy minimum between two transition states in a reaction of at least two steps
The difference in energy between the reactants and the transition state is?
the energy of activation. its value ranges from 40 to 150kJ/mol
After reaching the transition state a molecule can?
either go on to form products or revert to the starting material
what is the formula to calculate ∆G˚?
∆G˚ = ∆H - T∆S
A reaction that produces one product molecule from two reactant molecules has _____ entropy.
negative
A reaction that produces two product molecules from one reactant molecule has _____ entropy?
positive
If ∆H is negative?
the reaction is exothermic
If ∆H is positive?
the reaction is endothermic
What is ∆H a measure of?
the change in total bonding energy during a reaction
∆S equals?
entropy. the measure of freedom of motion of a reaction
If ∆G is negative then the reaction is ______ and will be ______.
favorable, exergonic
If ∆G is positive then the reaction is _____ and will be _____.
unfavorable, endergonic
For a reaction to proceed as written...
the energy of the products must be lower than the energy of the reactants
If Keq is greater than one.
[products]>[reactants]
If Keq is less than one.
[reactants]>[products]
∆G˚ describes?
the energy change that occurs during a reaction, the Gibbs free energy change.
Electrons must move from _____ to ______.
a nucleophilic source, an electrophilic sink
A nucleophile can be either ______ charged or ______.
negatively charged, neutral
An electrophile can be either _____ charged or ______.
positively charged, neutral
If two substituents are on the same side of the ring?
it is cis disubstituted
If two substituents are on opposing sides of the ring?
it is trans disubstituted
Factors accounting for Ring Strain
torsional strain - due to eclipsing of bonds
steric strain - results when atom approach too closely
angle strain - occurs when bond angles are distorted from their normal values
Polar reactions occur as a result of?
positive and negative charges within molecules due to differences in electronegativity between atoms
Biological reactions take place in _________ each of which has a _________.
several small steps, small activation energy
The equilibrium constant (Keq) shows what?
the ratio of product concentration to reactant concentration
-RT(lnKeq) = ?
∆G˚
In radical reactions all bonds are broken and formed by reactions of species with ____________.
odd numbers of electrons
Steroids have ______ fused rings.
four
Bicyclic ring systems have rings that are _____________.
connected by bridges
In cis 1,2-dimethylcyclohexane, one methyl group is ______ and one is _______ in both chair conformations which are of ______ energy
axial, equatorial, equal
In trans 1,2-dimethylcyclohexane, both methyl groups are either _____________.
both axial or both equatorial
After a ring flip...
an axial bond becomes an equatorial bond and vice versa
Two kinds of bonding positions on a cyclohexane ring?
axial - perpendicular to the plane of the ring
equatorial - hydrogens roughly in the plane of the ring
Each carbon in a cyclohexane has?
one axial hydrogen and one equatorial hydrogen
Each side of a cyclohexane ring has?
alternating axial and equatorial hydrogens
The chair conformation of cyclohexane is __________.
strain free
The twist boat conformation of cyclohexane little ______ strain but experiences both ________ strain and ________ strain.
angle, steric, torsional
In a standard drawing of cyclohexane the ________ bond is in the front.
lower
Cyclopentane has little ______ strain but considerable ________ strain.
angle, torsional
In an effort to relieve strain, cyclopentane adopts a puckered conformation. In this conformation one carbon is ________ and the hydrogens are _________.
bent out of plane, nearly staggered
Cyclopropane has _____ bonds
bent
Because of bent bonds, cyclopropane is ____________ than other cycloalkanes.
more reactive
Cyclobutane has less _______ strain than cyclopropane but more _______ strain.
angle, torsional
Cyclobutane has almost the same total strain as _________.
cyclopropane
The more strained the compound the _______ the heat of combustion.
higher
The most favored conformation for any straight chain alkane has carbon-carbon in _________ arrangements and large substituents ______ to each other.
staggered, anti
Steric Strain
the repulsive interaction that results from forcing atoms to be closer together than their atomic radii allow
Anti Conformation
one of the staggered conformers of butane. positions the methyl groups as far apart as possible (lowest energy)
Gauche Conformation
one of the staggered conformations of cyclobutane. positions the methyl groups 60˚ apart (second lowest energy)
The boiling and melting points of an alkane increase with _________________.
increasing molecular weight
Increased branching _________ an alkane's boiling point.
lowers
If the carbons are in a row the alkane is?
a straight chain alkane
If the carbon chain has a branch then the alkane is?
a branched chain alkane
Isomers whose atoms are connected differently are?
constitutional isomers
The chemistry of every organic molecule is determined by?
its functional group
Hydrophilic substances dissolve in water because?
they are able to form hydrogen bonds
The products of an acid-base reaction are _____________ than the reactants
more stable
What is dipole moment?
a measure of a molecule's overall polarity
A crossed arrow is used to indicate?
bond polarity. the tail of the arrow is electron poor, the tip electron rich.
Carbon has an EN of?
2.5
Elements on the right side of the periodic table are ________ electronegative than elements on the left side.
more
2 ways two 1s orbitals can combine.
additive combination - bonding MO, lower in energy than the two hydrogen 1s orbitals
subtractive combination - antibonding MO, higher in energy than the two hydrogen 1s orbitals
Torsional Strain
is due to eclipsing of bonds
Angular Strain
is due to distortion of bonding angles from their normal values
Additive Combination
bonding MO, lower in energy than the two 1s orbitals
Subtractive Combination
antibonding MO, higher in energy than the two 1s orbitals
Axial bonds lie...
perpendicular to the plane of the ring
Equatorial bonds lie...
roughly in the plane of the ring