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OCHEM Test 1
OCHEM Test 1
675
Organic Chemistry
Undergraduate 2
06/05/2017

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Term
the one distinguishing characteristic of all organic compounds
Definition
they all contain the element carbon
Term
organic chemistry
Definition
the study of carbon compounds
Term
Why is C special? Why do most presently known chemical compounds contain C?
Definition
because of its structure and its consequent position on the periodic table
Term
why C is able to form so many compounds
Definition
because of its ability to bond

-can share 4 ve's and form 4 strong covalent bonds
-C atoms can bond to each other, forming long chains and rings
Term
some elements commonly found in organic compounds
Definition
-C
-H
-O
-N
-F
-P
-S
-I
-Cl
-Br
Term
the color used to represent H
Definition
some kind of dull yellow
Term
the color used to represent C
Definition
gray
Term
the color used to represent N
Definition
blue
Term
the color used to represent O
Definition
red
Term
the color used to represent F
Definition
some kind of pale turquoise color
Term
the color used to represent P
Definition
purple
Term
the color used to represent S
Definition
yellow
Term
the color used to represent Cl
Definition
green
Term
the color used to represent Br
Definition
brown
Term
the color used to represent I
Definition
looks magenta to me
Term
the general composition of an atom
Definition
-small, dense nucleus with protons and neutrons
-electrons circling it at a relatively large distance
Term
the electron density in an atom
Definition
denser closer to the nucleus than towards the outer edge
Term
isotopes
Definition
atoms with the same atomic number but different mass numbers
Term
the behavior of a specific electron in an atom can be described by...
Definition
the wave equation
Term
the solution to a wave equation
Definition
an orbital
Term
orbital
Definition
the solution to a wave equation
Term
Ψ
Definition
this is the Greek letter psi

this denotes the orbital, which is the solution to a wave function
Term
how an orbital describes the volume of space around a nucleus that an electron is most likely to occupy
Definition
by plotting the square of the wave function, Ψ2, in 3D space
Term
the 4 types of orbitals
Definition
-s
-p
-d
-f
Term
the orbitals we're primarily concerned with in OCHEM and biochem
Definition
s and p because they're the most common
Term
the shape of an s orbital
Definition
spherical
Term
the shape of a p orbital
Definition
dumbbell
Term
the shape of a d orbital
Definition
4 of the 5 are shaped like a 4-leaf clover

the other one is shaped like a dumbbell inside a donut
Term
the atoms in an orbital are organized into...
Definition
different electron shells
Term
electron shells
Definition
a group of an atom's electrons with the same principal quantumn number
Term
each orbital in a shell can be occupied by how many electrons?
Definition
2
Term
composition of the first energy level in an atom
Definition
a 1s orbital, thus just 2 electrons
Term
composition of the second energy level in an atom
Definition
a 2s orbital and 3 2p orbitals, thus 8 electrons
Term
composition of the third energy level in an atom
Definition
a 3s orbital, 3 3p orbitals, and 5 3d orbitals, thus 18 electrons
Term
the types of p orbitals
Definition
-px -py -pz
Term
how the p orbitals are arranged
Definition
along mutually perpendiculat directions, denoted px, py, and pz [image]
Term
the lobes of an orbital are separated by...
Definition
an area of zero electron density called a node
Term
node
Definition
an area of zero electron density between the nodes of an orbital
Term
how the lobes of the orbital are denoted in the wave function
Definition
with the algebraic signs + and -
Term
ground-state electron configuration
Definition
the orbitals occupied by an atom's electrons at its lowest energy arrangement (its ground state)
Term
the 3 rules for listing the orbitals occupied by an atom's electrons (WRITE THIS DOWN!)
Definition
1: Aufbau principle; the lowest energy orbitals fill up first, according to the order 1s --> 2s --> 2p --> 3s --> 3p --> 4s --> 4d. Note that the 4s orbital lies between the 3p and 3d orbitals.
2: Pauli exclusion principle; electrons act in some ways as if they were spinning around an axis, somewhat like how the Earth spins. This spin can have different orientations, denoted as up (/|\) and down (\|/). Only 2 electrons can occupy an orbital, and they must be of opposite spin.
3: Hund's rule; if 2 or more orbitals of equal energy are available, one electron occupies each with spins parallel until all orbitals are half full.
Term
Aufbau principle
Definition
The lowest energy orbitals fill up first, according to the order 1s --> 2s --> 2p --> 3s --> 3p --> 4s --> 4d
Term
Pauli exclusion principle
Definition
Only 2 electrons can occupy an orbital, and they must be of opposite spin
Term
Hund's rule
Definition
If 2 or more orbitals of equal energy are available, one electron occupies each with spins parallel until all orbitals are half full
Term
the orbitals that fill up first
Definition
the lowest energy orbitals
Term
how many electrons can occupy an orbital?
Definition
2
Term
how must the electrons in an orbital spin?
Definition
they must be of opposite spin
Term
what electrons do when 2 or more orbitals of equal energy are available
Definition
one electron occupies each with spins parallel until all orbitals are half full
Term
how to predict ground state electron configuration:
Definition
[image]
Term
the valency of carbon in organic compounds
Definition
tetravalent; always forms 4 bonds when it joins other elements to form stable compounds
Term
tetravalent
Definition
always forms 4 bonds when it joins other elements to form stable compounds
Term
the spatial orientation of a carbon atom's bonds
Definition
a regular tetrahedron (basically a trigonal pyramid)
Term
how bonds coming out of the page toward the viewer
Definition
[image]

heavy, wedge-shaped line
Term
how bonds on the same plane as the page are represented
Definition
[image]

solid line
Term
how bonds receding back behind the page away from the viewer are represented
Definition
[image]

dotted line
Term
why do atoms bond together?
Definition
because the the compound that results is more stable and lower in energy than the separate atoms
Term
flow of energy when a bond is formed
Definition
energy, usually as heat, always flows out of a chemical system when a bond is formed
Term
flow of energy when a bond is broken
Definition
energy must be put into a chemical system to break a bond
Term
why do atoms want an octet?
Definition
to obtain noble gas configuration
Term
ionic bond
Definition
electrostatic attraction between an anion and a cation
Term
covalent bond
Definition
sharing of electrons between atoms
Term
molecule
Definition
neutral collection of atoms held together by covalent bonds
Term
Lewis structures aka...
Definition
electron-dot structures
Term
a stable molecule results when...
Definition
a noble gas configuration is achieved for all the atoms
Term
Kekulé structures aka line-dot structures
Definition
kinda like Lewis structures, but the bonds are represented with lines instead of electron pairs
Term
lone-pair electrons
Definition
valence electrons that are not used for bonding

aka nonbonding erlectrons
Term
2 models that have been developed to describe covalent bonding
Definition
-valence bond theory
-molecular orbital theory
Term
valence bond theory
Definition
According to this theory, a covalent bond forms when 2 atoms approach each other closely and a singly occupied orbital on one atom overlaps a singly occupied orbital on the other atom. The electrons are now paired in the overlapping orbitals and are attracted to the nuclei of both atoms, thus bonding the atoms together.
Term
sigma (σ) bond
Definition
covalent bond formed by head on overlap of atomic orbitals

this is basically what happens in a single bond
Term
why molecules are more stable than the free atoms
Definition
because the product molecule has less energy than the starting free atoms
Term
1 kJ = ______ kcal
Definition
0.2390 kcal
Term
1 kcal = ______ kJ
Definition
4.184 kJ
Term
bond length
Definition
the distance between 2 nuclei that leads to maximum stability; this is at the minimum energy point between the 2 nuclei
Term
rxn coordinate diagram
Definition
see if you can find it in the video
Term
sp3 hybrid orbital
Definition
hybrid of an s orbital and three p orbitals
Term
depiction of unhybridized s and p orbitals
Definition
[image]
Term
depiction of sp3 hybrid orbitals
Definition
[image]
Term
why there's directionality in a tetrahedral molecule
Definition
because the sp3 hybrid orbitals have 2 lobes and are unsymmetrical about the nucleus, giving them directionality and allowing them to form strong covalent bonds when they overlap with orbitals from other atoms
Term
why sp3 hybrid orbitals form stronger bonds than unhybridized s and p orbitals
Definition
because one of the 2 lobes is larger and can therefore overlap more effectively with an orbital from another atom to form a bond
Term
why sp3 hybrid orbitals are asymmetrical
Definition
because the 2 lobes of the p orbital have different algebraic signs (+ and -). Thus, when a p orbital hybridizes with an s orbital, the positive p lobe adds to the s orbital but the negative p lobe subtracts from the s orbital, making the orbital strongly oriented in one direction
Term
the bond length between C and H
Definition
109 pm
Term
the bond angle in a tetrahedral molecule
Definition
109.5°
Term
chemical formula for methane
Definition
CH4
Term
chemical formula for ethane
Definition
C2H6
Term
the simplest molecule with a C-C bond
Definition
ethane
Term
the overlap between the C atoms in an ethane molecule
Definition
sigma
Term
the hybrid orbital that comes from each C atom in an ethane molecule
Definition
sp3
Term
length of the C-C single bond
Definition
154 pm
Term
the bond angles when an atom has 4 electron domains
Definition
about 109.5°
Term
sp2 hybrid orbitals
Definition
this occurs when an s orbital hybridizes with the px and py orbitals, but not the pz orbital; it remains unchanged
Term
the orientation of sp2 hybrid orbitals
Definition
trigonal planar with the 3 lobes 120° apart from each other and the unchanged p orbital perpendicular to the sp2 plane
Term
pi (π) bond
Definition
covalent bond between 2 p orbitals
Term
the regions occupied by the sigma (σ) bond
Definition
the region centered between nuclei
Term
the regions occupied by the sigma (π) bond
Definition
the regions above and below a line drawn between the nuclei
Term
length of the C-H single bond
Definition
108.7 pm
Term
length of the C=C double bond
Definition
134 pm
Term
why a double bond is less than twice as strong as a single bond
Definition
because the sideways overlap in the pi (π) part is not as much as the head on overlap in thew (σ) sigma part
Term
sp hybrid orbital
Definition
this happens when an s orbital hybridizes with the px orbital, but not the py and pz orbitals; they remain unchanged
Term
how a triple bond occurs
Definition
sp-sp bond between the sp orbitals and py-py pi bond between the py orbitals and pz-pz pi bond between the pz orbitals
Term
length of then C-C triple bond
Definition
120 pm
Term
length of the C-H bond
Definition
often 109 pm, but sometimes 106 pm
Term
electron domain alignment associated with sp hybrid orbitals
Definition
linear
Term
electron domain alignment associated with sp2 hybrid orbitals
Definition
trigonal planar
Term
electron domain alignment associated with sp3 hybrid orbitals
Definition
tetrahedral
Term
bond angle associated with sp hybrid orbitals
Definition
180°
Term
bond angle associated with sp2 hybrid orbitals
Definition
120°
Term
bond angle associated with sp3 hybrid orbitals
Definition
109.5°
Term
why P can form 5 covalent bonds
Definition
due to its position on the Periodic Table, it can expand its outer shell octet and form more than the typical number of covalent bonds
Term
why S can form 4 covalent bonds
Definition
due to its position on the Periodic Table, it can expand its outer shell octet and form more than the typical number of covalent bonds
Term
organophosphate
Definition
com[pounds that contain a P atom bonded to 4 O, with one of the O bonded to a C
Term
thiol
Definition
compound with a S atom bonded to one H and one C
Term
sulfide
Definition
compound that has a S atom bonded to 2 C
Term
molecular orbital (MO) theory
Definition
describes covalent bond formation as arising from a mathematical combination of atomic orbitals (wave functions) on different atoms to form molecular orbitals, so called because they belong to the entire molecule rather than to an individual atom
Term
the 2 ways for a molecular orbital to occur
Definition
-the additive way
-the subtractive way
Term
the additive way for molecular orbitals to occur
Definition
this combination leads to a molecular orbital that is lower in energy and is roughly egg-shaped
Term
the subtractive way for molecular orbitals to occur
Definition
this combo leads to a molecular orbital that's higher in energy and has a node between nuclei
Term
bonding molecular orbital (MO)
Definition
molecular orbital that's lower in energy than the atomic orbitals from which it is formed
Term
antibonding molecular orbital (MO)
Definition
molecular orbital that's higher in energy than the atomic orbitals from which it is formed

can't contribute to bonding because the electrons it contains can't occupy the central region
Term
condensed structures
Definition
shorthand method for writing structures in which C-H and C-C single bonds aren't shown, but instead understood example: propane being written as CH3CH2CH3
Term
skeletal structures
Definition
shorthand way of writing structures in which C atoms are assumed to be at each intersection of 2 lines (bonds) and at the end of each line
Term
rules for drawing skeletal structures (WRITE THIS DOWN!)
Definition
1: C atoms aren't usually shown. Instead, a C atom is assumed to be at each intersection of 2 lines (bonds) and at the end of each line. Occasionally, a C atom might be indicated for emphasis or clarity.
2: H atoms bonded to C aren't shown. Because C always has a valence of 4, we mentally supply the correct number of H atoms for each C.
3: Atoms other than C and H are shown.
Term
what the end of the line in a skeletal structure represents
Definition
CH3
Term
what a 2-way intersection in a skeletal structure represents
Definition
CH2
Term
what a 3-way intersection in a skeletal structure represents
Definition
CH
Term
what a 4-way intersection in a skeletal structure represents
Definition
C
Term
bonds that have a circular cross-section and are formed by head-on interaction
Definition
sigma (σ) bonds
Term
bonds formed by sideways interaction of p orbitals
Definition
pi (π) bonds
Term
shape of a hexagonal benzene molecule
Definition
planar
Term
hybridization of C+ ion when it forms 3 single bonds
Definition
sp2
Term
geometry of C+ ion when it forms 3 single bonds
Definition
trigonal planar
Term
electronic relationship refers to...
Definition
# of valence electrons
Term
singlet (spin-paired) orbital
Definition
has pair of electrons, opposite spin
Term
triplet (spin-unpaired) orbital
Definition
has one electron
Term
how the chemical symbols in an organic compound's molecular formula are ordered
Definition
first C, then H, then alphabetical from there
Term
why the 4 bonds of C can be arranged in a variety of ways
Definition
because of differences in hybridization
Term
bond angle of tetrahedral bonds
Definition
109.5°
Term
hybridization of tetrahedral
Definition
sp3
Term
hybridization of trigonal planar
Definition
sp2
Term
bond angle of trigonal planar
Definition
120°
Term
where the p orbital is in trigonal planar
Definition
perpendicular to the sp2 orbitals on the trigonal planar
Term
hybridization of linear
Definition
sp
Term
bond angle of linear
Definition
180°
Term
some other elements that are often found in organic compounds
Definition
-H
-O
-N
-S
-P
-halogens
Term
functional group
Definition
small collection of atoms that gives a molecule specific properties
Term
volume of an atom has to do with...
Definition
the electron cloud
Term
the most common C isotope
Definition
C-12

99% of the C in mature
Term
distance between energy layers vs. distance from nucleus
Definition
the further you get from the nucleus, the closer and closer those energy layers get
Term
s orbitals always cone ______ at a time
Definition
1
Term
p orbitals always cone ______ at a time
Definition
3
Term
shape of an s orbital
Definition
spherical
Term
shape of a p orbital
Definition
dumbbell (2 lobes)
Term
node
Definition
point of zero electron density between the nodes of an orbital
Term
the difference between the p orbitals
Definition
the orientation; they're the same except for the axis
Term
degenerate
Definition
exactly the same in energy
Term
d orbitals always cone ______ at a time
Definition
5
Term
f orbitals always cone ______ at a time
Definition
7
Term
why the 1st energy level can have only 2 electrons
Definition
because it has only 1 s orbital
Term
stability of orbital vs. distance from nucleus
Definition
the further from the nucleus, the less stable the orbital
Term
where the node is in a p orbital
Definition
nucleus
Term
the most common elements we will deal with in OCHEM
Definition
CHON
Term
electronegativity
Definition
an atom's affinity for electrons
Term
general trend for electronegativity
Definition
northeast
Term
what causes polarity in bonds?
Definition
diff in enegativity
Term
some elements that have the same electronegativities as C
Definition
H
S
I
Term
why the C-O bond is more polar than the C-Cl bond
Definition
because O is 2 elements to the right of C and Cl is just 1 element to the right of S
Term
# of nodes vs. energy of orbital
Definition
the more nodes, the higher the energy
Term
the difference between a 1st energy orbital (such as 1s) and a 2nd energy orbital (such as 2s)
Definition
an extra node
Term
the type of node in an s orbital
Definition
spherical node
Term
why the valence electrons are so special
Definition
because the define the chemistry and size of the element
Term
trend in size of atoms as you go down the columns of the PTable
Definition
size increases, but by increasingly smaller increments
Term
trend in size of atom as you go right along the rows of the PTable
Definition
size of the atom decreases
Term
electronegativity vs. size of atom in the same row
Definition
inverse relationship
Term
the 2 main types of bonds
Definition
-ionic
-covalent
Term
ionic bond
Definition
bond created by attraction of electric charge
Term
the elements that typically yield anions
Definition
nonmetals
Term
the elements that tend to form anions are the ones that are more...
Definition
electronegative
Term
covalent bond
Definition
sharing of electron density between 2 separate nuclei
Term
polar covalent bonds
Definition
covalent bonds with unequal sharing of electrons
Term
is bond formation endothermic or exothermic?
Definition
exothermic
Term
which is more stable? molecule or individual atoms?
Definition
molecule
Term
is bond breaking endothermic or exothermic?
Definition
endothermic
Term
bond dissociation energy
Definition
the energy input needed to break bonds apart
Term
rxn coordinate diagram
Definition
[image]

the bond length is nominal bond length
Term
nominal bond length
Definition
average length of bond
Term
what happens to the energy of the bond as the nuclei get further apart?
Definition
increases
Term
how wavelength is related to energy
Definition
ΔE = hv

ΔE = change in energy
h = Planck's constant
v = wavelength (nm)
Term
Planck's constant
Definition
6.626 × 10-34 m2 kg / s
Term
bond length vs. bond strength
Definition
inversely related
Term
1 nm = ______ m
Definition
1 / 1 billionth 1 x 10-9 meter
Term
1 pm = ______ m
Definition
1 / trillionth 1 x 10-12 meter
Term
frequency of vibration of bonds vs. length of bond
Definition
inversely proportional
Term
why the length and strength of bonds between atoms is important for chemistry
Definition
because it helps predict reactivity
Term
length of bond between atoms vs. reactivity
Definition
directly proportional
Term
how size of atom affects reactivity
Definition
affects internuclear distance, thus affecting bond length and frequency
Term
is the covalent bond between 2 atoms static?
Definition
no
Term
how a covalent bond between 2 atoms vibrates
Definition
at a specific frequency characteristic to that bond
Term
depiction of where this equation, ΔE = hv, fits into internuclear bonds
Definition
[image]
Term
Heisenberg's uncertainty principle
Definition
you can know either the location or energy of the electron, but not both
Term
the amount of time an electron spends in its specific orbital
Definition
about 95%
Term
the spin of an electron
Definition
+ or - 1/2
Term
depiction of how to draw a p ordital
Definition
[image]
one lobe is shaded to indicate that one of the numbers is positive
the horizontal line is a plane where the node is
Term
the 2 key types of orbitals you gotta pick up on in molecular orbital theory
Definition
sigma and pi
Term
energy vs. # of nodes
Definition
as you increase the energy, you increase the # of nodes
Term
depiction of how s orbitals interact in covalent bonding
Definition
[image]

the one on top shows antibonding orbitals as a result of destructive interference at high energy and the one on bottom shows bonding molecular orbitals as a result of constructive interference at low energy
the arrows at the bottom represent the opposite spins of paired electrons
Term
what a theory is used for
Definition
it's used to make predictions
Term
example of how to characterize a bond (ON TEST!)
Definition
[image]

this shows the orbitals involved in forming the bond
Term
depiction of how electron configuration contributes to covalent bonds when bonding atoms are tetrahedral
Definition
[image]
Term
how to characterize double bonds when the bonding atoms are trigonal planar
Definition
[image]
Term
why the bond angles that are assumed are often approximations
Definition
because of the molecule not being entirely symmetrical
Term
the orbitals that are relevant in VSEPR theory
Definition
only s orbitals
Term
the type of orbitals used by sigma bonds
Definition
hybrid orbitals
Term
how to characterize triple bonds when the bonding molecule is linear
Definition
[image]

remember, a triple bond contains 1 sigma bond and 2 pi bonds
Term
what a triple bond contains
Definition
1 sigma bond and 2 pi bonds
Term
depiction of unhybridized s and p orbital overlapping
Definition
[image]

the shaded area of the p orbital is positive
everything unshaded is negative
Term
depiction of sp hybrid orbital
Definition
[image]

the shaded area is positive
Term
the effect of hybridization on the sp orbital
Definition
destructive interference causes the positive lobe to decrease in amplitude and the negative lobe to increase in amplitude

[image]
Term
the orbitals that define shape of an atom
Definition
hybrid
Term
σ (sigma) system
Definition
the electrons that are in the hybridized orbitals
Term
what causes π (pi) bonds?
Definition
overlap of p orbitals
Term
the symmetry a sigma bonding orbital has
Definition
cylindrically symmetrical (cross section along any point in the bond is circular)
Term
if a bond is cylindrically symmetrical, it's a ______ bond
Definition
sigma
Term
if a bond is not cylindrically symmetrical, it's a ______ bond
Definition
pi
Term
π (pi) system
Definition
the electrons in the unhybridized π (pi) bonds
Term
which electrons are more energetic? those in the sigma system or those in the pi system?
Definition
those in the pi system
Term
why are the electrons in the pi system more energetic than those in the sigma system?
Definition
further from nucleus
Term
which electrons are most likely to be reactive in a chemical reaction?
Definition
the more energetic ones; those in the pi system
Term
can electrons that influence shape of an atom be part of the pi system?
Definition
no, they're part of the sigma system
Term
principal quantum number (n)
Definition
this defines the energy level of an electron
Term
angular momentum quantum number (l)
Definition
this defines the shape of the orbital
Term
subshell
Definition
set of electrons that have the same n and l values
Term
how a subshell is designated
Definition
by a letter and a number, such as s1, s2, and p2
Term
magnetic quantum number (ml)
Definition
describes the orientation of the orbital in space

can have values of l to -l, including 0
Term
value of l for the s orbital
Definition
0
Term
value of l for the p orbital
Definition
1
Term
subshell designation for the s orbital
Definition
ns

n = principal quantum number
Term
subshell designation for the p orbital
Definition
np

n = principal quantum number
Term
possible values of ml for the s orbital
Definition
0
Term
possible values of ml for the p orbital
Definition
1, 0, -1
Term
the elements with their valence electrons in the s orbital
Definition
He and the Group 1A and 2 A elements
Term
the elements with their valence electrons in the p orbital
Definition
Group 3A to 8A elements
Term
the elements with their valence electrons in the d orbital
Definition
transition metals
Term
the elements with their valence electrons in the f orbital
Definition
inner transition metals
Term
polar covalent bonds
Definition
bonds between atoms such that the electrons are more strongly attracted by one atom than the other such that the electron distribution between atoms is not symmetrical
Term
δ

indicate what this is used for
Definition
lower case Greek letter delta

used to indicate partial charge
Term
δ+
Definition
partial positive charge, used for electron poor atom
Term
δ-
Definition
partial negative, used for electron rich atom
Term
bond polarity is due to...
Definition
differences in enegativity (EN)
Term
electronegativity (EN)
Definition
an atom's ability to attract electrons
Term
periodic trend in electronegativity
Definition
increases as you go northeast
Term
electronegativity difference in covalent bonds
Definition
less than 0.5
Term
electronegativity difference in polar covalent bonds
Definition
0.5-2
Term
electronegativity difference in ionic bonds
Definition
greater than 2
Term
depiction of how arrows are used to indicate electron distribution
Definition
[image]

This is a crossed arrow, with the arrow pointing to the negative end and the other end being crossed to indicate positive end. Electrons are displaced in the direction of the arrow.
Term
inductive effect
Definition
the shifting of electrons in a δ bond in response to the electronegativity of nearby atoms
Term
partial charge on atom or bong?
Definition
atom
Term
molecular polarity results from...
Definition
the vector summation of all individual bond polarities and lone-pair contributions in the molecule
Term
net molecular polarity is measured by...
Definition
dipole moment
Term
dipole moment (μ mu)
Definition
the magnitude of the charge Q at either end of the molecular dipole times the distance r between the charges
Term
how to calculate dipole moment
Definition
μ = Q X r

μ = dipole moment (C • m)
Q = magnitude of charge (C)
r = distance between charges (m)
Term
how dipole moments are expressed in SI
Definition
in debyes (D)
Term
1 D = ______ coulomb meters (C • m)

D = debye
Definition
3.336 X 10-30 coulomb meters (C • m)
Term
some elements with substantially different enegativities from C
Definition
-O
-N
-F
-Cl
-Br
Term
effect of lone pairs on dipole moment
Definition
lone pairs can alter the direction of the dipole moment
Term
formal charge
Definition
the charge on a particular atom in a molecule if that atom was by itself
Term
what formal charges are used for
Definition
electron "bookkeeping"
Term
why it's helpful to identify and calculate formal charges correctly
Definition
because they can give clues about chemical reactivity
Term
resonance forms
Definition
individual structural forms of a resonance hybrid
Term
the only difference between resonance forms
Definition
the placement of the π and nonbonding valence electrons
Term
resonance hybrid
Definition
molecule that can't be represented adequately using a single line structure and must instead be considered as an average of 2 or more resonance forms
Term
rules for resonance forms
Definition
1: Individual resonance forms are imaginary, not real.
2: resonance forms differ only in the placement of their π or nonbonding electrons
3: different resonance forms of a substance don't have to be equivalent
4: resonance forms obey normal rules of valency
5: the resonance hybrid is more stable than any individual resonance form
Term
the real structure of resonance forms
Definition
a composite, or resonance hybrid
Term
how the movement of electrons is represented on drawings
Definition
using a curved arrow
Term
# of resonance forms vs. stability of substance and why
Definition
the more resonance forms, the more stable the substance because its electrons are spread out over a larger part of the molecule and are closer to more nuclei
Term
a useful technique for drawing resonance forms
Definition
in general, any 3 atom grouping with a p orbital on each atom has 2 resonance forms
Term
radical
Definition
atom that contains a single unpaired electron
Term
Brønstead-Lowry acid
Definition
donates a proton (H+)
Term
Brønstead-Lowry base
Definition
accepts a proton (H+)
Term
conjugate base (Brønstead-Lowry)
Definition
the ion that results when an acid loses a proton
Term
conjugate acid (Brønstead-Lowry)
Definition
the ion that results when a base gains a proton
Term
how acids and bases interact in the general sense
Definition
acid + base <--> conjugate base + conjugate acid
Term
how water can act as an acid or a base
Definition
by accepting (base) or donating (acid) a proton
Term
acidity constant (Ka)
Definition
measures the exact strength of a given acid in water
Term
how to calculate acidity constant (Ka)
Definition
Ka = ([H3O+][CB])/([acid]) Ka = acidity constant CB = conjugate base
Term
pKa
Definition
negative common logarithm of the Ka
Term
how to calculate pKa
Definition
pKa = -log Ka
Term
size of pKa vs. size of Ka
Definition
inverse relationship
Term
size of pKa for stronger acid
Definition
smaller
Term
size of Ka for stronger acid
Definition
larger
Term
size of pKa for weaker acid
Definition
larger
Term
size of Ka for weaker acid
Definition
smaller
Term
some acids in order of size of pKa (highest to lowest) refer to video to complete the list
Definition
-R (group of C's and H's) -ammonia (NH3) and R2NH2NH3 -water and ROH -Hydronium (H3O+) -[image] -HCl, HBr, H2SO4
Term
acid strength vs. strength of conjugate base
Definition
inverse relationship
Term
the direction the proton goes in an acid-base reaction goes
Definition
from the stronger acid to the stronger base
Term
where the strong acids and bases and weak acids and bases must be in an acid-base reaction
Definition
starting acids and bases should be stronger and ending acids and bases should be weaker
Term
how to convert pKa into Ka
Definition
Ka = 10-pKa write it in scientific notation
Term
organic acids are characterized by...
Definition
the presence of a positively polarized H atom
Term
the 2 main kinds of organic acids
Definition
-those that contain a H atom bonded to an electronegative O atom (O-H)
-those that contain a H atom bonded to a C atom next to C=O bond (O=C-C-H)
Term
some ways anions can be stabilized
Definition
-having a negative charge on a highly electronegative atom
-resonance
Term
why organic acids with O-H bonds are acidic
Definition
because the conjugate base is stabilized by having its negative charge on a strongly electronegative atom
Term
why organic acids with C=O bonds are acidic
Definition
because the conjugate base is stabilized by resonance
Term
carboxylic acids
Definition
organic acids that contain the -CO2H grouping
Term
organic bases are characterized by...
Definition
the presence of an atom with a lone pair of electrons that can bond to H+
Term
Lewis acid
Definition
accepts an electron pair
Term
Lewis base
Definition
donates an electron pair

has pair of nonbonding electrons that it can use to bond to a Lewis acid
Term
what happens to the electron pair in the interaction of Lewis acids and bases?
Definition
it is shared in a covalent bond
Term
why metal cations can be Lewis acids
Definition
because they accept a pair of electrons when they bond to a base
Term
why some metal compounds can be Lewis acids
Definition
because they have unfilled valence orbitals and can accept electron pairs from Lewis bases
Term
why most O and N containing organic compounds act like Lewis bases
Definition
because they have lone pairs of electrons
Term
if an acid-base rxn forms a complex, can it go back and forth?
Definition
no
Term
other than bonds within molecules, this is also important in chemical reactions
Definition
noncovalent interactions
Term
noncovalent interactions
Definition
interactions between molecules

aka intermolecular forces and van der Waals forces
Term
types of noncovalent interactions between molecules
Definition
-dipole-dipole forces
-(London) dispersion forces
-H bonds
Term
dipole-dipole forces
Definition
they occur between polar molecules as a result of electrostatic interactions among dipoles
-can be attractive or repulsive depending on orientation of the molecules
-attractive predominates because it's lower in energy
Term
dipole-dipole forces can be attractive or repulsive depending on...
Definition
orientation of the molecules
Term
attractive dipole-dipole forces predominate because...
Definition
they're lower in energy
Term
depiction of attractive and repulsive dipole-dipole forces
Definition
[image]
Term
(London) dispersion forces
Definition
occur between all neighboring molecules and arise because the electron distribution within molecules is consistently changing
Term
what causes dispersion forces in nonpolar molecules?
Definition
dipole moments that are caused by consistently changing electron distribution
Term
H bond
Definition
attractive interaction between a H bonded to an O or N atom and an unshared electron pair on another N or O atom
Term
depiction of (London) dispersion forces
Definition
[image]
Term
depiction of H bond
Definition
[image]
Term
what causes water to be liquid at standard temperatures?
Definition
H bonds
Term
what makes a sugar molecule hydrophilic?
Definition
the -OH groups in its structure that enable it to form H bonds
Term
what makes vegatable oil hydrophobic?
Definition
has no groups that have H bonds, so it's limited to (London) dispersion forces
Term
1 pm = ______ m
Definition
10-12 m
Term
magnitude of charge in ionic bonds
Definition
1.6 X 10-19 C
Term
what the pKa of an acid must be to react almost completely with water
Definition
at least 3 units lower than that of water the pKa of water is 15.74; therefore, the pKa must be 12.74 or less
Term
pKa of water
Definition
15.74
Term
how to calculate pH using molarity (M) and pKa
Definition
1: find Ka 2: plug M and Ka into the Ka formula 3: solve for neumerator 4: plug what you get into the pH equation
Term
what does an acid need to have if it wants to significantly react with the salt of another acid?
Definition
a lower pKa
Term
why reactions of the same chemical can yield different results
Definition
change in distribution of electrons caused by resonance
Term
one reason two acids that contain an OH group can have differing acidity
Definition
because one is better able to be stabilized by resonance, i.e., more resonance structures
Term
can resonance contribute to whether or not a molecule or ion has a dipole moment?
Definition
if uniform, then no

if not uniform, then it could
Term
why an O atom with 2 single bonds can have a dipole moment
Definition
because of the lone pair electrons, which contribute its tetrahedral shape
Term
in which direction are acid-base reactions favored?
Definition
the direction in which the pKa pf the acid increases
Term
why CH3CH2CH2OH has a higher boiling point than CH4
Definition
H bonding
Term
when a molecule has H bonding and dipole moments, which contributes greater to interactions with other molecules?
Definition
H bonding
Term
how more electronegative elements can increase the acidity of organic acids that contain an O-H bond
Definition
pulling electrons, the effect going down the chain, ultimately weakening the O-H bond
Term
example of how to draw a 3D representation of a tetrahedral molecule
Definition
[image]

especially note that the wedge and dotted line have to track together; one is essentially hiding behind the other
Term
example depiction of bond polarity and dipole moment
Definition
[image]
Term
how the length of the nonpolar zig-zag line on these 2 molecules affects the dipole moment

[image]
Definition
the longer the nonpolar zig-zag line, the lower the net dipole moment
Term
does the sigma system change when drawing resonance structures?
Definition
no
Term
the difference between resonance forms
Definition
where you put the pi electrons
Term
when drawing resonance forms, never mess with...
Definition
geometry
Term
one thing that can make one resonance form more prominent than the other
Definition
electronegativity of a certain atom
Term
the absence of this system makes a molecule or ion unable to have resonance
Definition
pi system
Term
the most important thing to look for when determining which resonance form is better than the other
Definition
whether or not atoms obey the octet rule; this supersedes electronegativity
Term
what it means when one resonance form is better than the other
Definition
the actual thing looks more like one than the other
Term
rules for assessing which resonance structures are the best representations
Definition
1: the most important resonance contributors have the greatest numbers of filled octets
2: the structure with fewer formal charges is the better representation
3: electronegativity of specific elements
Term
when all resonance structures for a particular molecule or ion are equally good representations of it, they are...
Definition
degenerate
Term
s-character
Definition
measures involvement of s orbital as part of the hybrid
Term
s-character of an sp3 hybridized atom
Definition
25%
Term
s-character of an sp2 hybridized atom
Definition
33.333%
Term
s-character of an sp hybridized atom
Definition
50%
Term
importance of s-character
Definition
the higher an atom's s-character, the higher its electronegativity
Term
length of C-C bond vs. strength of bond
Definition
inversely proportional
Term
hydride
Definition
H anion
Term
strong acid
Definition
completely dissociates in water
Term
why ionic compounds (salts) will dissolve in water
Definition
because water supports the presence of ions
Term
why salts won't dissolve in nonpolar solvents
Definition
because the nonpolar solvent has no "handle" to grab onto ions
Term
pKa of water
Definition
about 16
Term
this is constant once e'librium is established
Definition
c'trations of products and reactants
Term
can Keq be negative?
Definition
no, because you can't have negative c'trations
Term
relationship between ΔG and Keq
Definition
ΔG = -RT lnKeq
Term
Keq
Definition
e'librium constant
Term
pKa of ammonia (NH3)
Definition
about 36
Term
why is a proton more likely to dissociate from O than from C?
Definition
because O is more e'negative
Term
pKa of R
Definition
> 50 to 70 something
Term
what R is used to represent
Definition
collection of H's and C's
Term
pKa of ROH
Definition
approx 16
Term
pKa of H3O+
Definition
-2
Term
pKa of HCl
Definition
<-2
Term
pKa of HBr
Definition
<-2
Term
pKa of H2SO4
Definition
<-2
Term
pKa of R2NH2NH3
Definition
36
Term
how to calculate Keq
Definition
Keq = ([CA][CB]) / ([A][B])
Term
once e'librium is established, the side containing which base will be favored?
Definition
the side containing the more stable base

a base that undergoes resonance could be the more stable base
Term
pKa of this molecule [image]
Definition
4-5
Term
when you go down a column on the PTable, e'negativity gives way to...
Definition
polarizeability
Term
polarizeability
Definition
the ability to obtain an induced polarity
Term
PTable trend in polarizeability
Definition
the further down you go down the column, the more polarizeable
Term
how polarizeability affects strength of acid
Definition
the more polarizeable the element from which an anion is derived, the stronger the acid
Term
why acids containing more polarizeable elements tend to be more acidic
Definition
because the anion derived from a more polarizeable element tends to be more stable than that derived from a less polarizeable anion
Term
polarizeability of an element vs. the stabylity of its anion
Definition
directly proportional
Term
depiction of an endothermic reaction for an endothermic reaction
Definition
[image]
Term
the 2 commandments of resonance
Definition
1: don't break any single bonds
2: don't exceed an octet for 2nd row elements
Term
questions to ask once resonance is established
Definition
1: can we convert any lone pairs into pi bonds without violating the two commandments?
2: can we convert any pi bonds into lone pairs without violating the 2 commandments?
3: can we convert any pi bonds into pi bonds without violating the 2 commandments?
Term
rules for assessing the relative importance of a resonance structure
Definition
1: the most important resonance forms have the greatest number of filled octets
2: the structure with fewer fortmal charges is more important
3: other things being equal, a structure with negative charge on the more electronegative element will be more important
4: resonance structures with equally good Lewis structures are described as equivalent and contribute equally to the resonance hybrid
Term
some factors that affect stability of conjugate bases
Definition
1: atom - what atom is the charge on?
2: resonance - does resonance make one conjugate base more stable than the other?
3: induction - are any conjugate bases stabilized by inductive effects?
4: orbital - in what orbital do we find the negative charge for each conjugate base?
Term
an ac id's willingness to give up a proton is affected by...
Definition
stability of that bond between the H and the other atom
Term
trend in the ability of an element to stabilize charge
Definition
increases as you go down the column
Term
why HI would be more willing to give up its proton, i.e., more acidic, than HF
Definition
because I has a larger volume over which to spread the charge, tius being more stable when it gives up its proton
Term
why resonance is such a stabilizing force
Definition
because a delocalized negative charge is more stable than a localized negative charge
Term
if the conjugate base of one acid has resonance and the other one doesn't, which acid will be more acidic?
Definition
the one with resonance
Term
induction (acid-base context)
Definition
the pulling of electron density caused by differences in electronegativity
Term
how orbital affects acidity of an atom
Definition
sp orbitals tend to be more stable than sp2 and sp3 or bitals because sp orbitals tend to have their electrons closer to the nucleus
Term
which H is more acidic: H bonded to sp3 hybridized N or H bonded to sp hybridized C?
Definition
H bonded to sp hybridized C
Term
solvating effect
Definition
the effect of CH groups hindering interaction with the solvent
Term
mechanism
Definition
shows how the electrons move during a reaction to form the products
Term
how to show the mechanism of an acid-base rxn
Definition
draw an arrow to indicate floe of electrons from Lewis acid to
Lewis base
Term
functional groups
Definition
groups of atoms within a molecule that have a characteristic chemical behavior
Term
the chemistry of every organic molecule is determined by...
Definition
its functional groups
Term
3 categories functional groups can be categorized into
Definition
-those w/ C-C multiple bonds
-those in which C forms a single bond with an enegative atom
-those w/ C=O 2bl bond
Term
alkanes are formed by...
Definition
ovrlap of C sp3 orbitals
Term
alkanes are described as...
Definition
saturated hydrocarbons
Term
why alkanes are hydrocarbons
Definition
because they contain only C and H
Term
why alkanes are saturated
Definition
because all bonds are single
Term
the general formula for alkanes
Definition
CnH2n+2
Term
straight-chain alkane
Definition
alkane w/ all the C's in a row
Term
branched-chain alkane
Definition
alkane that has a branched C chain
Term
constitutional isomers
Definition
isomers whose atoms are connected differently
Term
do constitutional isomers have different properties?
Definition
alwauys
Term
straight-chain alkanes are named according to...
Definition
# of C's in their C chain
Term
alkyl group
Definition
the partial structure that results from the removal of 1 H from an alkane
Term
how alkyl groups are named
Definition
by replacing -ane with -yl
Term
n-alkyl group
Definition
formed by removal of an H atom from the end of a straight-chain alkane
Term
branched-chain alkyl groups
Definition
formed by removing an H from an internal C
Term
the prefixes sec- and tert- refer to...
Definition
the number of other C atom attached to the branching C atom
Term
sec-
Definition
secondary (2 C's attached to the branching C)
Term
tert-
Definition
tertiary (3 C's attached to the branching C)
Term
the possible degrees of alkyl substitution for C
Definition
-primary
-2ndary
-tertiary
-quarternary
Term
primary C
Definition
bonded to 1 other C
Term
secondary C
Definition
bonded to 2 other C's
Term
tertiary C
Definition
bonded to 3 other C's
Term
quarternary C
Definition
bonded to 4 other C's
Term
R
Definition
this symbol refers to the rest of the molecule
Term
primary H's
Definition
bonded to primary C's
Term
secondary H's
Definition
bonded to secondary C's
Term
tertiary H's
Definition
bonded to tertiary C's
Term
the system of nomenclature used in this book for naming alkanes
Definition
IUPAC system
Term
the components of a chemical name in the IUPAC system
Definition
-locant
-prefix
-parent
-suffix
Term
locant
Definition
shows the location of substituents and functional groups
Term
prefix
Definition
indicates the type of constituent or functional group
Term
parent
Definition
# of C's in the principal chain
Term
suffix
Definition
identifies functional group family
Term
how to name an alkane
Definition
1: find the parent hydrocarbon
2: number the atoms in the parent chain
3: identify and number the substituents
4: write the name as a single word
5: name a complex substituent as if it was a compound, and set it off in parentheses
Term
how to find the parent hydrocarbon in an alkane
Definition
1: find the longest continuous chain of C's, and use its name as the parent name
2: if 2 chains have the same number of C's, choose the one with more branch points
Term
how to number the atoms in the parent chain
Definition
1: start numbering at the end nearer the 1st branch point
2: if branching occurs an equal distance from both ends, begin numbering at the end nearer the second branch point
Term
how to identify and number the substituents
Definition
1: give each substituent a number that corresponds to its number on the parent chain
2: 2 substituents on the same C receive the same #
Term
how to write the name as a single word
Definition
1: use hyphens to separate prefixes and commas to separate numbers
2: use the prefixes di-, tri-, and tetra- if necessary, but don't use them for alphabetizing
Term
how to name a complex substituent as if it was a compound and set it off within parentheses
Definition
1: some simple branched-chain alkyl groups have common names
2: the prefix iso- is used for alphabetixing, but sec- and tert- are not
Term
some properties of alkanes
Definition
-alkanes are chemically inert to most laboratory reagents -alkanes react with O2 (combustion) and Cl2 (substitution) -the boiling and melting points of alkanes increase with increasing molecular weight -increased branching lowers an alkane's boiling point
Term
reactivity of alkanes to most laboratory reagents
Definition
chemically inert
Term
rxn of alkanes with O2
Definition
combustion
Term
rxn of alkanes with Cl2
Definition
substitution
Term
boiling and melting points of alkanes vs. molecular weight
Definition
directly proportional
Term
why the boiling and melting poiunts of alkanes increase with increasing molecular weight
Definition
weak dispersion forces
Term
strength of dispersion forces vs. molecular weight
Definition
directly proportional
Term
branching vs. an alkane's boiling point
Definition
the more branching, the higher the boiling point
Term
some straight-chain alkanes
Definition
-ethane
-propane
-butane
Term
stereochemistry
Definition
the branch of chemistry concerned with the 3D aspects of molecules
Term
conformations of ethane
Definition
photograph figure 3-5
Term
what produces isomers of ethane at different conformation?
Definition
rotation about a single bond
Term
2 ways isomers can be represented
Definition
-sawhorse representations
-Newman projections
Term
sawhorse representation
Definition
views the C-C bond at an oblique angle
Term
Newman projection
Definition
views the C-C bond end-on-end and represents the 2 C's as a circle
Term
staggered conformation
Definition
the lowest energy conformation

occurs when all C-H bonds are as far from each other as possible (H's not lining up with each other)
Term
eclipsed conformation
Definition
the highest energy conformation

occurs when all the C-H bonds are as close to each other as possible (H's lining up with each other)
Term
the energy difference in staggered conformation is due to...
Definition
torsional strain from interactions between C-H bonding orbitals on one C and C-H bonding antibonding orbitals on an adjacent C, stabilizing the staggered conformation
Term
torsional strain
Definition
the extra energy in eclipsed conformation
Term
graph showing potential energy vs. angle of rotation
Definition
photograph figure 3-7
Term
conformations of propane
Definition
photograph figure 3-8
Term
conformations of butane
Definition
photograph the conformations in section 3.7
Term
the lowest energy conformation of butane occurs when...
Definition
the 2 large methyl groups are as far from each other as possible
Term
gauche conformation of butane
Definition
when 2 methyl groups are 60 degrees apart
Term
the energy difference in different conformations of molecules is due to...
Definition
steric strain
Term
steric strain
Definition
the repulsive interaction that results from forcing atoms to be closer together than their atomic radii allow
Term
the highest energy conformations of butane occur when...
Definition
the 2 methyl groups are eclipsed
Term
the most favored conformation for any straight-chain alkane
Definition
has C-C bonds in staggered arrangements and large substituents anti to each other
Term
the conformation adopted by most molecules
Definition
the most stable conformation
Term
the 5 parts to every name when naming organic molecules
Definition
1: stereoisomerism
2: substituents
3: parent
4: unsaturation
5: functional group
Term
stereoisomerism
Definition
indicates whether 2bl bonds are cis/trans and indicates stereocenters (R,S)
Term
substituents
Definition
groups connected to the main chain
Term
parent
Definition
the main chain
Term
unsaturation
Definition
identifies whether there are any 2bl or triple bonds
Term
functional group
Definition
the group after which the compound is named
Term
why you must name an organic molecule starting with the functional group
Definition
because the position of the functional group affects which parent chain you chose
Term
alkene (double bond) functional group
Definition
R2C=CR2
Term
R2C=CR2
Definition
alkene (double bond) functional group
Term
alkyne (triple bond) functional group
Definition
RCCR
Term
RCCR
Definition
alkyne (triple bond) functional group
Term
arene (aromatic ring) functional group
Definition
6 trigonal planar C's in a ring
Term
6 trigonal planar C's in a ring
Definition
arene (aromatic ring) functional group
Term
halide functional group
Definition
R-X

X = halogen
Term
R-X

X = halogen
Definition
halide functional group
Term
alcohol functional group
Definition
R-OH
Term
R-OH
Definition
alcohol functional group
Term
ether functional group
Definition
R-O-R
Term
R-O-R
Definition
ether functional group
Term
monophosphate functional group
Definition
R-PO42-
Term
R-PO42-
Definition
monophosphate functional group
Term
diphosphate functional group
Definition
R-P2O73-
Term
R-P2O73-
Definition
diphosphate functional group
Term
amine functional group
Definition
R-NH2
Term
R-NH2
Definition
amine functional group
Term
imine (Schiff base) functional group
Definition
R=NH
Term
R=NH
Definition
imine (Schiff base) functional group
Term
nitrile functional group
Definition
RN

the bond is a triple bond
Term
RN

the bond is a triple bond
Definition
nitrile functional group
Term
thiol functional group
Definition
R-SH
Term
R-SH
Definition
thiol functional group
Term
sulfide functional group
Definition
R-S-R
Term
R-S-R
Definition
sulfide functional group
Term
disulfide functional group
Definition
R-S-S-R
Term
R-S-S-R
Definition
disulfide functional group
Term
sulfoxide functional group
Definition
R2-S+-O-
Term
R2-S+-O-
Definition
sulfoxide functional group
Term
aldehyde functional group
Definition
[image]
Term
[image]
Definition
aldehyde functional group
Term
ketone functional group
Definition
[image]
Term
[image]
Definition
ketone functional group
Term
carboxylic acid functional group
Definition
[image]
Term
[image]
Definition
carboxylic acid functional group
Term
ester functional group
Definition
[image]
Term
[image]
Definition
ester functional group
Term
thioester functional group
Definition
[image]
Term
[image]
Definition
thioester functional group
Term
amide functional group
Definition
[image]
Term
[image]
Definition
amide functional group
Term
acid chloride functional group
Definition
[image]
Term
[image]
Definition
acid chloride functional group
Term
carboxylic acid anhydride functional group
Definition
[image]
Term
[image]
Definition
carboxylic acid anhydride functional group
Term
suffix associated with alkene
(double bond) functional group
Definition
-ene
Term
suffix associated with alkyne (triple bond) functional group
Definition
-yne
Term
suffix associated with arene (aromatic ring) functional group
Definition
none
Term
suffix associated with halide functional group
Definition
none
Term
suffix associated with alcohol functional group
Definition
-ol
Term
suffix associated with ether functional group
Definition
ether
Term
suffix associated with monophosphate functional group
Definition
phosphate
Term
suffix associated with diphosphate functional group
Definition
diphosphate
Term
suffix associated with amine functional group
Definition
-amine
Term
suffix associated with imine (Schiff base) functional group
Definition
none
Term
suffix associated with nitrile functional group
Definition
-nitrile
Term
suffix associated with thiol functional group
Definition
-thiol
Term
suffix associated with sulfide functional group
Definition
sulfide
Term
suffix associated with disulfide functional group
Definition
disulfide
Term
suffix associated with sulfoxide functional group
Definition
sulfoxide
Term
suffix associated with aldehyde functional group
Definition
-al
Term
suffix associated with ketone functional group
Definition
-one
Term
suffix associated with carboxylic acid functional group
Definition
-oic acid
Term
suffix associated with ester functional group
Definition
-oate
Term
suffix associated with thioester functional group
Definition
-thioate
Term
suffix associated with amide functional group
Definition
-amide
Term
suffix associated with acid chloride functional group
Definition
-oyl chloride
Term
suffix associated with carboxylic acid anhydride functional group
Definition
-oic anhydride
Term
suffix to use when there's no functional group involved
Definition
put an e at the end of it
Term
when naming the parent chain, meth means...
Definition
1 C atom in the alkane or parent chain
Term
when naming an alkane or the parent chain, eth means...
Definition
2 C atoms in the alkane or parent chain
Term
when naming an alkane or the parent chain, prop means...
Definition
3 C atoms in the alkane or parent chain
Term
when naming an alkane or the parent chain, but means...
Definition
4 C atoms in the alkane or parent chain
Term
when naming an alkane or the parent chain, pent means...
Definition
5 C atoms in the alkane or parent chain
Term
when naming an alkane or the parent chain, hex means...
Definition
6 C atoms in the alkane or parent chain
Term
when naming an alkane or the parent chain, hept means...
Definition
7 C atoms in the alkane or parent chain
Term
when naming an alkane or the parent chain, oct means...
Definition
8 C atoms in the alkane or parent chain
Term
when naming an alkane or the parent chain, non means...
Definition
9 C atoms in the alkane or parent chain
Term
when naming an alkane or the parent chain, dec means...
Definition
10 C atoms in the alkane or parent chain
Term
methane
Definition
alkane or parent chain with 1 C atom
Term
ethane
Definition
alkane or parent chain with 2 C atoms
Term
propane
Definition
alkane or parent chain with 3 C atoms
Term
butane
Definition
alkane or parent chain with 4 C atoms
Term
pentane
Definition
alkane or parent chain with 5 C atoms
Term
hexane
Definition
alkane or parent chain with 6 C atoms
Term
heptane
Definition
alkane or parent chain with 7 C atoms
Term
octane
Definition
alkane or parent chain with 8 C atoms
Term
nonane
Definition
alkane or parent chain with 9 C atoms
Term
decane
Definition
alkane or parent chain with 10 C atoms
Term
methyl
Definition
methane with one H replaced by R
Term
ethyl
Definition
ethane with 1 H replaced by R
Term
propyl
Definition
propane with 1 H replaced by R
Term
butyl
Definition
butane with 1 H replaced by R
Term
pentyl
Definition
pentane with 1 H replaced by R
Term
hexyl
Definition
hexane with 1 H replaced by R
Term
heptyl
Definition
heptane with 1 H replaced by R
Term
octyl
Definition
octane with 1 H replaced by R
Term
nonyl
Definition
nonane with 1 H replaced by R
Term
decyl
Definition
decane with 1 H replaced by R
Term
when there is a double bond, should the parent chain include the double bond?
Definition
yes
Term
when there is no double bond, but there is a functional group attached, should the parent chain include the C next to the functional group?
Definition
yes
Term
depiction of propyl
Definition
[image]

attached to the end C
Term
[image]
Definition
propyl
Term
depiction of isopropyl
Definition
[image]

attached to the middle C
Term
[image]
Definition
isopropyl
Term
isobutane
Definition
[image]
Term
[image]
Definition
isobutane
Term
depiction of butyl
Definition
[image]

here, it's connected to a Cl
Term
[image]
Definition
butyl
Term
sec-butyl
Definition
[image]

notice the Cl is attached to the secondary C
Term
[image]
Definition
sec-butyl
Term
tert-butyl
Definition
[image]

notice the R is attached to the tertiary C
Term
[image]
Definition
tert-butyl
Term
primary C
Definition
bonded to 1 R
Term
secondary C
Definition
bonded to 2 R
Term
tertiary C
Definition
bonded to 3 R
Term
quarternary C
Definition
bonded to 4 R
Term
what R is used for
Definition
to represent a generalized organic group
Term
what characters to use to indicate whether a C is primary, 2ndary, tertiary, or quarternary
Definition
p
s
t
q
Term
is an H bonded to a primary C primary, secondary, or tertiary?
Definition
primary
Term
is an H bonded to a secondary C primary, secondary, or tertiary?
Definition
secondary
Term
is an H bonded to a tertiary C primary, secondary, or tertiary?
Definition
tertiary
Term
the template for the name of an alkane
Definition
locant-prefix-parent-suffix
Term
what the locant in the name of an alkane is supposed to indicate
Definition
where the substituents and functional groups are
Term
what the prefix in the name of an alkane is supposed to indicate
Definition
what the substituents are
Term
what the parent in the name of an alkane is supposed to indicate
Definition
how many carbons in alkane
Term
what the suffix in the name of an alkane is supposed to indicate
Definition
primary functional group
Term
if 2 hydrocarbon chains of equal length have different numbers of branch points, which hydrocarbon chain is the parent?
Definition
the one with more branch points
Term
when numbering the C's in the hydrocarbon chain, where should you begin?
Definition
at end nearer to the first branch point
Term
when numbering the hydrocarbons in a molecule with branching an equal distance away from the parent chain, where should you begin?
Definition
at the end nearer to the 2nd branch point
Term
order to list substituents when naming an alkane
Definition
alphabetical order
Term
how a substituent that is itself branched is included in the name of an alkane
Definition
1: numbered beginning at its point of attachment to the main chain
2: it is then set off in parentheses
Term
why a positive charge can be an indicator of acidity
Definition
because having the positive charge, it's more like hydronium
Term
what arrows in acid-base reactions indicate
Definition
mechanisms
Term
what do you compare when comparing bases?
Definition
stability of the electrons on each base
Term
number of resonance forms vs. stability of an anion
Definition
the more resonance forms, the more stable
Term
the only intermolecular force that deals with nonpolar molecules
Definition
London forces
Term
London forces
Definition
intermolecular forces that occur as the result of induced dipoles between molecules

induced dipoles occur as the result of an instantaneous uneven distribution of electrons
Term
how the size of the molecule's electron cloud affects London forces
Definition
the bigger the electron cloud, the easier it is to distort the London forces into greases
Term
polarizeability vs. strength of London forces
Definition
directly proportional
Term
what branching of molecule does to boiling point
Definition
general rule of thumb: branching tends to lower the boiling point
Term
how the shape of different isomers of the same compound can affect boiling point
Definition
the more spherical the molecule, the lower the boiling point due to less area of overlap between adjacent molecules and weaker London forces
Term
dipole-dipole forces
Definition
positive end of a bond on one molecule being attracted to the negative end of a bond on another molecule
Term
H-bond
Definition
a dipole-dipole force between a proton attached to an N or O and an O or N

this isn't a bond; it's an association or attraction
Term
in an organic molecule, a functional group is...
Definition
a group of atoms that isn't a sp3 hybridized CH group
Term
constitutional isomer
Definition
isomers that have their atoms connected in a different order
Term
amount of substitution arount a bond vs. amount of strain
Definition
the more substitution around a bond, the more strain
Term
the general formula for cycloalkanes that have 1 ring
Definition
CnH2n
Term
how to name cycloalkanes
Definition
1: find the parent
2: number the substituents
Term
how to find the parent in a cycloalkane
Definition
-if the number of C atoms in a ring is larger than the number in the largest substituent, the compound is named as an alkyl-substituted cycloalkane
-if the number of C atoms in the ring is smaller than the number in the largest substituent, the compound is named as a cycloalkyl-substituted alkane
Term
alkyl-substituted cycloalkane
Definition
cycloalkane where the # of C atoms in the ring is larger than the number in the largest substituent
Term
cycloalkyl-substituted alkane
Definition
cycloalkane where the # of C atoms in the ring is smaller than the number in the largest substituent
Term
how to number the substituents in a cycloalkane
Definition
1: start at a point of attachment and number the substituents so that the second substituent has the lowest possible number
2: if necessary, proceed until a point of difference is found
3: if 2 or more substituents might potentially receive the same number, number them by alphabetical priority
4: halogens are treated in the same way as alkyl groups
Term
size of a cycloalkane's ring vs. amount of rotational freedom
Definition
directly proportional
Term
cis-disubstituted cycloalkane ring
Definition
has 2 substituents on the same side of the ring
Term
trans-disubstituted cycloalkane ring
Definition
has 2 substituents on opposite sides of the ring
Term
general principles of conformation of cycloalkanes
Definition
1: ring strain
2: heats of combustion of cycloalkanes
3: the nature of ring strain
Term
how to measure the strain in cycloalkanes
Definition
measure the total energy of a compound and compare it to a strain-free reference compound
Term
heat of combustion
Definition
the amount of heat released when a compound is completely burned in oxygen
Term
amount of strain vs. heat of combustion
Definition
directly proportional
Term
how strain a per CJH2 unit can be calculated and plotted
Definition
as a function of ring size
Term
the rings that have serious strain
Definition
small rings
Term
rings tend to adopt these conformations
Definition
puckered
Term
factors that account for ring strain
Definition
-angle strain occurs when bond angles are distorted from their normal values
-torsional strain is due to eclipsing of bonds
-steric strain results when atoms approach too closely
Term
angle strain
Definition
occurs when bond angles are distorted from their normal values
Term
torsional strain
Definition
caused by eclipsing of bonds
Term
steric strain
Definition
results when atoms approach too closely
Term
some small cycloalkane rings
Definition
-cyclopropane
-cyclobutane
-cyclopentane
Term
why cyclopropane is more reactive than other cycloalkanes
Definition
because of bent bonds
Term
what cyclopentane does to relieve torsional strain
Definition
adopts a puckered conformation
Term
puckered conformation
Definition
in this conformation, one C is bent out of plane and the H's are nearly staggered
Term
a conformation of cyclohexane
Definition
chair cyclohexane
Term
where the bonds are in chair conformation cyclohexane
Definition
lower bonds in front and upper bonds in back
Term
the strain in chair conformation cyclohexane
Definition
no strain
Term
the strain that results when chair conformation cyclohexane converts to boat conformation cyclohexane
Definition
has little ange strain, but experiences both steric and torsional strain
Term
the 2 kinds of positions on a cyclohexane ring
Definition
-6 axial H's
-6 equatorial H's
Term
axial H's
Definition
perpendicular to the plane of the ring
Term
equatorial H's
Definition
roughly in the same plane of the ring
Term
the orientation of the H's of each C in cyclohexane
Definition
each C has 1 axial H and 1 equatorial H
Term
orientation of the H's on the side of the ring in cyclohexane
Definition
each side of the ring has alternating axial and equatorial H's
Term
if all the H's in a cyclohexane ring are on the same face, they are...
Definition
cis
Term
how different chair conformations of cyclohexanes interconvert
Definition
by a ring flip
Term
what a ring flip does to the axial and equatorial bonds in cyclohexane
Definition
an axial bond becomes equatorial and an equatorial bond becomes axial
Term
the energy barrier to conversion in cyclohexane
Definition
45 kJ/mol
Term
diaxial interactions
Definition
interactions between an axial group and a ring H 2 C's away
Term
what causes diaxial interactions?
Definition
steric strain
Term
the interactions that occur in gauche butane
Definition
diaxial interactions caused by steric energy
Term
the position in which substituents on a cycloalkane are more stable
Definition
equatorial position
Term
the size of the strain between substituents in a cyclohexane depends on...
Definition
the size and nature of the group
Term
the orientation of the substituents in the chair conformations of a cis isomer
Definition
one is axial and the other is equatorial
Term
the orientation of the substituents in the chair conformations of a trans isomer
Definition
both are either axial or equatorial
Term
why axial orientation is less stable than equatorial orientation
Definition
because there's diaxial interactions in the axial orientation
Term
2 ways cycloalkane rings can be fused
Definition
-cis-fused
-trans-fused
Term
bicyclic ring systems
Definition
have rings that are connected by bridges
Term
why a compound with an OH group has a higher boiling point than an otherwise identical compound with a lone O
Definition
because of H bonding
Term
stability vs. ΔHcombustion
Definition
inversely proportional
Term
energy of bond vs. size of atoms involved
Definition
inversely proportional
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