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The basic principle of valence bond theory is that a covalent bond forms when orbitals
of two atoms overlap and a pair of electrons occupy the overlap region
o Remember, covalent bonds form between atoms to the right of the staircase on
the periodic table.
The process of orbital mixing is known as hybridization and the new atomic orbitals are
known as hybrid orbitals
The book uses a lot of complicated terminology when attempting to describe what
hybridization is and how to find it. I promise, there is a much simpler way to break it
down.
o You see, you can merely memorize the hybridizations from the molecular
orbitals. Just, consult the VSEPR chart. Hybridizations can simply be categorized
based off of what electron group arrangement (electronic geometry, remember
that these are the five broad categories) the molecule has.
o Linear: sp
o Trigonal planar: sp2
o Tetrahedral: sp3
o Trigonal bipyramidal: sp3d
o Octahedral: sp3d2
If you know the geometry, you know the hybridization. Don’t be lazy and do yourself a
favor by putting in an hour or two memorizing the VSEPR chart.
There is another short cut way to calculate hybridization when given a molecule.
Imagine each bonding domain (either a lone pair of atoms sitting on an atom or bonds
connecting that atom to another atom) as representing a letter. To find the
hybridization of this molecule, count the number of domains.
o Take methane (CH4) for example. The carbon is the central atom and there are
four bonds, one to each hydrogen. Take one of the C-H bonds to represent s, the
second to represent p, the third to represent the second p, and the fourth to
represent the third p. This leaves you with the final answer of sp3.
o In our next example, take something such as carbon dioxide (CO2). The carbon is
the central atom and both oxygens are double bonded to the carbon. The first
double bond (which only counts as a singular bonding domain) can be assigned
the s. The second double bond can be assigned the p. This gives the hybridization
of the carbon as sp.
There are a couple limitations to the concept of hybridization. I wouldn’t worry about
the details of them, but know the two main ones in case they are asked on the exam.
o Hybridization typically does not apply to large nonmetal hydrides (an example
would be H2S)
o d orbital hybridization is less important because d orbitals have such high energy
that they do not hybridize effectively with the much more stable s and p orbitals
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What is the hybridization of CH4?
sp3
What is the hybridization of SF6?
sp3d2
What is the hybridization of water?
sp3
What is the hybridization of PCl5?
sp3d
What is the hybridization of NH3?
sp3
What is the hybridization of SO3?
sp2
The ketene molecule has the formula H2C2O. The Lewis structure for ketene has both
hydrogens bound to one of the carbon atoms. What is the hybridization of the oxygen
atom of ketene?
(a)sp
(b)sp2
(c)sp3
(d)s2
(e)no hybridization occurs for O, it is linked via a p orbital
According to valence bond theory, which orbitals on N and H overlap in the NH3
molecule?
(a)2p on N overlaps with 2s on H
(b)2p on N overlaps with 1s on H
(c)2s on N overlaps with 1s on H
(d)sp3 on N overlaps with 1s on H
(e)sp3 on N overlaps with sp on H
For a given molecule, the hybridization of orbitals on the central atom is sp2. The
electron-group arrangement around this central atom is _____.
(a)octahedral
(b)linear
(c)trigonal bipyramidal
(d)tetrahedral
(e)trigonal planar
2
What is the hybridization on the leftmost carbon below?
Which of the following drawings or statements does NOT correctly describe the central atom in
SiCl4? (either in the hybridized or unhybridized state)
3
Complete the Lewis structure shown below.
In the same molecule above, how many pi bonds are there in the entire molecule?
(a) 2
(b) 3
(c) 4
(d) 7
(e) 8
4
Organic Chemistry
Organic chemistry is all about carbon and its derivatives. Almost always, an organic
molecule will contain a carbon, bonder to another carbon, bonded to another carbon,
etc.
Why is carbon special? It lies right smack dab in the middle between two different
electron levels. The scientific term for this is tetravalent, meaning carbon has the ability
to form four different covalent bonds with many different atoms. It has four valence
electrons and it is much easier for carbon to share all four of them covalently rather
than gain four or lose four.
o Carbon also has the ability to bond to other carbons in many different ways. This
leads to an array of many different molecules.
o Carbon chains are very stable and do not break apart easily.
Chemical diversity of carbon
o Carbon can be bonded to what are called heteroatoms (atoms other than C or
H). Typically they are N or O but can also be S, P, and the halogens.
o Differences in electron densities are why most organic molecules react.
C-O bonds have a large difference in electronegativity and is polar. These
bonds are reactive.
C-heteroatom are also reactive because these atoms are often large. This
means the bonds to carbon are long and weak and will thus break easily.
C-C bonds and C-H bonds are not reactive
o Functional groups are attached to carbon which all make it reactive. A functional
group is a defined set of atoms bonded to a carbon that will typically react in the
same manner regardless of what else might be also attached to the carbon. We
will discuss these shortly.
Hydrocarbons are the simplest type of organic compound. They contain only carbon and
hydrogen.
When drawing hydrocarbons, you have several options.
o Option 1: Straight chain
o Option 2: branched
o Option 3: ring
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There are four types of hydrocarbons
o Alkanes are composed of ONLY carbons single bonded to other carbons and
hydrogens.
They have the general structure CnH2n+2
Boiling point increases with chain length
o Alkenes have at least one double bond
General structure of CnH2n
There is restricted rotation in alkenes due to the double bond
o Alkynes have at least one triple bond
General structure of CnH2n-2
o Aromatic hydrocarbons are a ring of six hydrocarbons with a ring of double
bonds
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Naming hydrocarbons follows a set of hierarchal rules.
1. Figure out how many carbons are in the parent chain.
2. Look to see if there are double bonds or triple bonds (alkenes or alkynes).
a. Alkanes receive the suffix –ane
b. Alkenes receive the suffix –ene
c. Alkynes receive the suffix –yne
d. If it is an alkene or alkyne, the main chain must contain the double or triple
bond. Place a number before the name. This number denotes what carbon the
double or triple bond starts on.
3. Look to see if there is branching
a. Name the branched chain similarly to how you named the parent chain. But
instead of ending in ane, ene, or yne, the ending is –yl
i. A one carbon chain would be known as a methyl cahin
ii.A two carbon chain would be known as an ethyl chain
iii. A three carbon chain would be known as a propyl chain
4. Figure out where the branched chain is in relation to the parent chain
a. The branched chain will receive a number. Look at the isopentane molecule on
the previous page. Another name for this molecule would be 2-methylbutane.
The parent chain is four carbons (but-), it has only single bonds so it is an alkane.
The second carbon has a one carbon branch stemming from it (2-methyl).
i. Warning: You might ask: “Why can’t the previous molecule be named 3-
methyl butane?” It is because whenever you have two different options
on numbering a branch, you always choose the lower number.
Skeletal structures are another way to visualize an organic molecule
o The carbon-carbon bonds are depicted as zig zag lines. Think of every carbon
existing every time there is a point.
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What is the name of this molecule?
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A cyclic hydrocarbon (compound containing only carbon and hydrogen) contains 6
carbon atoms and two double bonds. How many hydrogen atoms are there in this
molecule?
(a) 6
(b) 8
(c)10
(d)12
(e)14
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Functional groups are select groups of atoms that are prearranged and are added to a
parent chain of a hydrocarbon. There are many examples that you may need to know
(pg 655 in your book).
o I unfortunately don’t have any trick to memorizing any of them. But I do have a
couple of practice problems to try.
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Monomers and Polymers
Polymers are extremely large molecules composed of many monomeric units that
repeat.
There are two types of polymers
o Addition polymers
Look for a carbon double bonded to another carbon
In these types of polymers, a peroxide will generate what is called a free
radical in two different monomers which will typically come together to
form the polymer
o Condensation polymers
In these polymers, two different monomers are linked together because
their functional groups reacted with each other and undergo what is
called a dehydration-condensation reaction (loss of H2O).
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13
IR Spectroscopy
Which of the following bonds will have the lowest IR stretching frequency?
(a)C–C
(b)C–P
(c)C–Se
(d)C–I
(e)Si–I
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CH3CH2CH2OH CH3CH2CH=O
(a)The CO bond in the molecule on the left because it is the stronger bond.
(b)The CO bond in the molecule on the left because it is the weaker bond.
(c)The C=O bond in the molecule on the right because it is the weaker bond.
(d)The C=O bond in the molecule on the right because it is the stronger bond.
(e)It is impossible to tell without more information.
Which of the following bonds would you expect to have the lowest vibrational
frequency?
(a)13C–18O
(b)12C=16O
(c)12C–16O
(d)13C=18O
(e)12C≡16O
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Biochemistry
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To form proteins, amino acids lose _________ in order to form a ________ bond.
A) water; peptide
B) water; ionic
C) carboxylic acid; peptide
D) an amino group; covalent
E) an -OH group; peptide
Which of the levels of protein structure is associated with the overall shape and structure of a
protein complex, such as the potassium ion channel?
(a) Primary
(b) Secondary
(c) Tertiary
(d) Quaternary
(e) Quintinary
Which of the levels of protein structure results from interactions between the backbone atoms
of the polypeptide chain?
(a)Primary
(b)Secondary
(c)Tertiary
(d)Quaternary
(e)Quintinary
Each amino acid has two functional groups in common and one of 20 other groups (the R-
group) attached to the -carbon. The two functional groups in common are
(a)carboxylic acid and peptide.
(b)ester and amine.
(c)carboxylic acid and amide.
(d)alcohol and amine.
(e)carboxylic acid and amine
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Helical and sheet-like segments in proteins are stabilized by
(a)disulfide bridges.
(b)salt bridges.
(c)crosslinking via covalent bonds.
(d)dispersion forces within the protein's interior.
(e)hydrogen bonding.
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In the cell nucleus, DNA exists as two chains wrapped around each other in a double
helix. The chain is held together by hydrogen bonds between the nitrogenous bases.
o A will always pair with T
o C will always pair with G
o “Apple trees and collard greens”
o In DNA, the polar exterior contain the phosphate groups (which are negatively
charged) and interact with aqueous surroundings via ion-dipole and H bonding
forces.
The interior of DNA contains the nitrogenous bases. On one strand of the helix, a base will
interact with the base stacked above it via _________ and will interact with the complementary
base in the other strand via _________.
A) Hydrogen bonding; Dispersion forced
B) Dispersion forces; dipole-dipole interactions
C) Dispersion forces; hydrogen bonding
D) hydrogen bonds; hydrogen bonds
E) Dispersion forces; dispersion forces
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Lipids are a biological molecule that are soluble in nonpolar solvents.
o Found in soaps, membranes (phospholipid bilayer) and in certain antibiotics.
Lipids can sometimes can together to form fatty acids.
o A saturated fatty acid maximizes the number of bonds it has (no double bonds)
o An unsaturated fatty acid contains at least one double bond.
Melting point of lipids:
o Unsaturated fatty acids have lower melting points than saturated fatty acids of
the same length
o As the chain length increases, so does the melting point
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Colligative Properties/Phase Changes
What is a phase change? There are three phases that matter can exist in on Earth. These
are solid, liquid, or gas. A phase change is a fancy way of saying matter going from one
of these forms to another.
Heat is released or absorbed in a phase change
There are several terms to be familiar with
o Condensation: gas to liquid
o Fusion (melting): solid to liquid
o Vaporization: liquid to gas
o Freezing: liquid to solid
o Solid to liquid: melting, fusion
o Deposition: gas to solid
o Sublimination: solid to gas
When a substance changes from one phase to another, there is a standard change in
enthalpy that accompanies it. The units are given in kj/mol
o For vaporization: (ΔH˚vap)
o For fusion: (ΔH˚fus)
o In the case of water, the standard value for (ΔH˚vap)=40.7 kj/mol and
(ΔH˚fus)=6.02kj/mol
o For the reverse processes of above (condensation and freezing) the values are
the same but are of opposite signs
Whenever you encounter a phase change problem, it is important to remember that
there are several steps to each of them. You must consider the temperature change that
gets you to the border of the next phase and also the standard enthalpy that is
encountered during the changing of phases
o For example, let us say we want to heat a -5˚C block of ice to 2˚C. We would first
need to find the enthalpy change from -5˚C to 0˚C. This would bring us to the
“border” between solid and liquid. We would then find the standard enthalpy
change of fusion for water (ΔH˚fus). We would find a third and final enthalpy
change for heating the now liquid water 2˚C. Add up the three values to get the
final answer.
o Equations to use for solving these problems
q=nCΔT where q=heat, n=mol, C= molar heat capacity, T=temperature
change
q=n(ΔH˚insert applicable phase change here )
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Here is a practice problem for you to try. Notice that instead of molar heat capacity (C), I have
given you specific heat capacity (c). The two are stoichiometrically related and you should be
able to solve this problem using the same outline I provided above. Instead of using moles and
the molar heat capacity, mass is grams and the specific heat capacity is what is listed.
A) 17kJ
B) 110kJ
C) 200kJ
D) 222kJ
E) None of the above
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Estimate the enthalpy of fusion per gram. (Use same graph and same assumption)
(a)50 J
(b)100 J
(c)200 J
(d)300 J
(e)400 J
Vapor pressure is the point where a substance’s rate of vaporization and rate of condensation
are equal. Liquid ↔gas
Takes place in a closed system
Changing the conditions will change the equilibrium
A closed container of water is sitting on a table. Its vapor pressure has been reached but the
pressure in the container is suddenly increased. What happens?
A) The rate of vaporization increases to compensate
B) The rate of condensation increases to compensate
C) No change in either rate of condensation or vaporization
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Concentration terms
o Molarity (M) = mol of solute/L solution
Drawbacks of Molarity
Changes with temperature because liquid expands when heated
Mixing solutions may not give a homogeneous mixture
o Molality (m) = mol of solute/kg of solvent
o Parts by mass (mass %)= (mass of solute/mass of solution) x100
This can also be seen similarly as parts per million (ppm) by mass and
parts per billion (ppb) by mass
o Parts by volume (volume percent) = volume of solute/volume of solution x (100)
o Mole fraction = mol of solute/mol of solute + mol of solvent
Most solvents, including water, will expand and become less dense at higher temperatures. For
example, the density of water is 0.9998 g/mL at 0°C and 0.9718 g/mL at 80°C. Based on this
information:
(a)the molarity of an NaCl solution in water will increase as the temperature is increased.
(b)the molality of an NaCl solution in water does not change with temperature.
(c)the molarity of an NaCl solution in water does not change with temperature.
(d)the mass percent of NaCl in water solution will increase as the temperature is increased.
(e)the molality of an NaCl solution in water will decrease as the temperature is increased.
Calculate the molarity of FeCl3 in a 34.5% by mass aqueous solution (density = 1.280 g/mL).
(a)2.72 x 10–3M
(b)0.213 M
(c)1.66 M
(d)2.13 M
(e)2.72 M
Calculate the molarity of a 3.55 Molal H2SO4 solution that has a density of 1.01 g/mL.
(a)0.0103 M
(b)2.61 M
(c)2.66 M
(d)3.51 M
(e)3.55 M
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Chlorine, Cl2, is added to the West Lafayette water supply to control the growth of microbes. In
2013, analysis of a water sample showed that the water contained 0.80 parts per million Cl2.
Calculate the molar concentration of Cl2 in the water sample. Assume that the density of the
water is 1.0 g/mL–1.
(a)1.1×10–8 M
(b)2.3 ×10–8M
(c)8.0 ×10–7M
(d)4.5 ×10–6 M
(e)1.1 ×10–5M
Calculate the molarity of NH3in an 8.00 mass % aqueous solution (d = 0.9651 g/mL)
Electrolytes are substances that can conduct a current when dissolved in a solute
Strong electrolytes dissociate completely. These are your soluble salts, strong acids, and
strong bases
Weak electrolytes dissociate but only very little. There are weak acids and weak bases.
Nonelectrolytes do not disassociate at all. These will not conduct a current. Examples
include sugars and alcohols.
When a compound is dissolved in water and the resulting solution conducts electricity,
we can conclude that
A. the compound is a strong electrolyte
B. the compound is a weak electrolyte
C the compound is a non-electrolyte
D. Both A and B
E. None of the above
The vapor pressure of a nonvolatile electrolyte solution is always lower than the vapor
pressure of the pure solvent. The difference in vapor pressures is vapor pressure
lowering (ΔP).
Raoult’s Law states that the vapor pressure of solvent above a solution (Psolvent) equals
the mole fraction of solvent (Xsolvent) times the vapor pressure of the pure solvent (P˚solvent).
Simplified for what you actually need to know: ΔP = Xsolute x P˚solvent.
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o The change in vapor pressure is equal to the mole fraction of whatever is
dissolved multiplied by the solvent’s pure vapor pressure
o I provided the definition of mole fraction on this packet. If you know how to find
mole fraction, then you can do vapor depression problems since the solvent’s
vapor pressure is almost always given to you.
Boiling Point elevation
o A similar concept to changing of vapor pressure. A solution will boil at a higher
temperature than the pure solvent.
If something is dissolved in water, the water’s boiling point increases.
o Boiling point elevation is proportional to the concentration of solute added.
o ΔTb=Kbm where Kb is a known constant and m is molality
Freezing point depression
o A solution will free at a lower temperature than the pure solvent
Think of why we add salt to ice. The ice will make it so that it will take a
colder temperature for the ice to stay frozen
o ΔTf= Kfm where Kf is a constant and m is also molality.
Osmotic pressure = MRT
o Make sure you use the proper units for osmotic pressure problems. Osmotic
pressure should be in atm, temperature in Kelvin, and .0821=R.
When adding a solute like NaCl or ethylene glycol to a solvent like water, the boiling
point ______________ and the freezing point _________
(a)increases, decreases
(b)decreases, decreases
(c)decreases, increases
(d)increases, increases
(e)stays the same, decreases
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Aqueous solutions of two non-dissociating compounds A and B have identical osmotic
pressure at a given temperature. What can be correctly inferred from this information?
(a)The molarities of the two solutions are identical.
(b)The number of moles of A is the same as the number of moles of B in the solutions.
(c)The molecular mass of A equals molecular mass of B.
(d)Both A and B.
(e)Both A and C.
Pepsin is an enzyme in the intestines of mammals that breaks down proteins into amino acids.
A 12 mL aqueous solution contains .200g of pepsin and has an osmotic pressure of 8.98 torr at
27 degrees Celsius. What is the molar mass of pepsin?
For strong electrolyte solutions, the solute formula tells us the number of particles for
determining colligative properties. For instance, the boiling point elevation of .050m
NaCl should be 2xΔTb. Why?
We must remember that NaCl is a strong electrolyte which means it will dissociate
completely into sodium and chloride ions. We need to account for this in our
calculations.
The van’t Hoff factor (i) is used to account for strong electrolyte dissociation
o In the case of NaCl, i would equal 2.
o In the case of MgCl2, i would equal 3.
How many total moles of solute particles are present in 1L of each of the following solutions?
0.3 M KBr
0.004 M Ba(OH)2
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A solution is made with 100 g of water. Which solute will produce the lowest freezing
point?
(a)10.0 g NaCl
(b)10.0 g C6H12O6
(c)10.0 g CH3CH2OH
(d)10.0 g NaOH
(e)10.0 g KNO3
Which of the solutions below would you expect to have the lowest freezing point?
(a)1 m CaCl2
(b)2 m methanol (CH3OH)
(c)2 m NaOH
(d)1 m NaOH
(e) 2.5 m methanol (CH3OH)
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Answer Key
Theories of Covalent Bonding:
IR Spectroscopy
Sp3
D
Sp3d2
E
Sp3 B
Sp3d A
Sp3 C
Sp2
B Biochemistry:
A
D
D
E D
Sp B
C E
D E
B D
E
C
C
E
Colligative Properties:
Organic Chemistry: B
3-methyloctane B
2-pentene C
B
Ethyne
B
Propene
E
D C
E E
E 4.3
B D
D Strong, strong, non, weak
A
A
C
B A
3.48x104 g/mol
Monomers/Polymers: .6, .012, .06
C D
B C
Written and compiled by John Petroskey. Review session on Saturday, December 9 starting a 1 p.m.
Location is Owen Hall East Activity Room (the big room in the lobby where there are ping pong tables) First
part of the review session will cover stuff from after exam three. I will then open it up and take questions
from the other packets/concepts.
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