Reading...
Play button
Play button
Use LEFT and RIGHT arrow keys to navigate between flashcards;
Use UP and DOWN arrow keys to flip the card;
H to show hint;
A reads text to speech;
166 Cards in this Set
- Front
- Back
|
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
|
