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Exam 1 Review

CHE 321

Fall 2013

Dont Forget!

You are allowed to bring a 5x8 cheat sheet to the exam. Your card must be completely handwritten. Make it ASAP. You may also bring a model kit.

Your presenters this evening are

Chapter 1: Timothy Shub Chapter 2: April Slamowitz

Chapter 1 Review
Timothy Shub

IHD (Index of hydrogen deficiency)

Index of unsaturation


(2C +2) (H + X N)

C = # of carbons H = # of hydrogens X = # of halogens (e.g. Cl, I, Br) N + # of nitrogens

C7H12 =

(2*7+2) (12 + 0 0) 2

(16) (12) 2

Counts as 2 double bonds

1 index can be either a double bond or ring 2 indices can be 2 double bonds, 2 rings, a double bond and a ring, or a triple bond Possible Isomers Slide created by Olivia Cheng

In fond memory of my orgo review..

Periodic Table Trends


Valence Electrons

S The Valence shell is the outermost shell S # Of Valence Electrons (electrons in the valence shell) at

ground state can be determined by the group number.

S Valence Electrons are responsible for creating bonds with

other atoms to form other compounds.

S Transition elements have varying valence electrons

Group # - Valence Electrons

Group #s Valence Electrons

How many carbons are in this structure?

A. B. C. D. E.

3 4 5 6 7

How many hydrogens are in this structure?

A. B. C. D. E.

10 11 12 13 14

Formal Charge
S How do we calculate formal charge? SIMPLE!

Valence e- - bonded e- - unshared eS There is 1 bonded e- per bond, so in a double bond there are 2

bonded eS

The unshared e- are simply the lone pairs or the dots

What charge does the oxygen on the right obtain? What charge does the double bonded oxygen obtain? A) -2 C) Same charge of 0 B) -1 D) +1 E) +2

Calculating Formal Charge

(Valence e- ) (bonded e- ) ( lone e- ) = Formal Charge

Oxygen (all the way on right)624=0 Oxygen (double bonded oxygen)624=0 Nitrogen 532=0 ___________________________ Oxygen (all the way on right)6 3 2 = +1 Oxygen (formerly double bonded)6 1 6 = -1 Nitrogen532 =0

________________________________ ____

S Electrons have the ability to move and so lone pairs can

become a multiple bond (double bond or triple bond) or a multiple bond can become a lone pair!
S Electrons can only move to adjacent bonds or atoms
S Many atoms cannot exceed the octet (like carbon) but

they can be deficient in their octet

What about that Nitrogen?

The nitrogen is positively charged which is OKAY!

However, that carbon has too many electrons, so many in fact it literally has no more space to put them all. It exceeded octet. That fact makes this resonance structure impossible. -

So what makes a resonance structure good?

S 1. Octet Rule/ more bonding

S 2. Formal Charge (Minimize formal charge separation)

S 3. Atom/charge compatibility

For example: A negative charge is not compatible with a carbon.

Geometrical Shapes

S Much simpler to determine than most people think. .


Geometrical Shape Examples


A) Linear
B) Bent C) Trigonal Pyramidal D) Tetrahedral E) Trigonal Planar

*Note Triple Bonds (Alkynes) are ALWAYS linear.

How many carbons are in this structure?

A. B. C. D. E.

3 4 5 6 7


S Nothing to be scared about!

S General Rule of Thumb:

Bond Pairs (not counting pi bonds) + Lone Pairs = #

S Match # with the total number of s and p orbitals.

s(1)p(1) (1+1) = 2 s(1)p2 (1+ 2) = 3 s(1)p3 (1 + 3) = 4

REMEMBER! For this system only count the sigma bonds when counting bond pairs! NOT Pi BONDS!

Lets play a game called.. DETERMINE THE HYBRIDIZATION!

A. B. C. D. E.

sp sp2 sp3 s p

A little table to help you get it down..

Hybridization state of central atom sp sp2 sp3 ~sp3 (w/1 Lone pair) ~sp3 (w/2Lone pairs)

Shape of molecule or ion Examples Linear Trigonal planar Tetrahedral Trigonal Pyramidal Angular/bent BeH2, CO2 BF3, CH3+ CH4, NH4+ NH3, CH3H2O

How do we determine how much S character and P character

S Simply count how many orbitals of s or p are present

then divide by the total amount of orbitals!

S If something is sp3. It has 1 s orbital and 3 p orbitals. To

determine how much s character it has simply take 1 and divide it by 4 (1+3) then multiply by 100 to find the %!
S Likewise, if something is sp2 and you want to know how

much p character it has, simply take 2 (since 2 p orbitals are present) and divide it by 3 (2+1).
S More s character means MORE STABLE!

(We love examplez)

s1p3 1+3 = 4 = 25% s character

s1p2 1+2 = 3 1/3 = 33% s character

What is a Constitutional Isomer?

S Different compounds with the same molecular formula!

S Note that these are not resonance structures!

Another problem for good measure..

Remember: Constitutional Isomers = Diff compounds, same molecular formula Contributing structures (resonance)= Different electronic configurations of the same molecule!

And thats about it. . .


and now I welcome my esteemed colleague APRIL SLAMOWITZ!!!!! To help you guys with chapter 2 ^_^

Chapter Two Review Exam 1

Functional groups and intermolecular forces


Functional Groups
Organic Lingo: common and specific arrangements of atoms that impart predictable reactivity and properties to a molecule Average Human Lingo: combinations of atoms that occur together on a molecule which influence the way a molecule reacts and its properties

Exam 1, 2012 Q1

Hydrocarbons: functional groups that contain only

Hydrogen and Carbon
Alkanes: contain only SINGLE bonds between carbons Natural gases (octane, pentane) Symbolized by R Alkenes: contain DOUBLE bonds between carbons Industry products such as ethene and propene Symbolized by R Alkynes: contain TRIPLE bonds between carbons Symbolized by R

Aromatic compounds: contain a special type of benzene rings Bonds are in resonance, therefore bond length is between a single and double bond (1.5 bonds) Symbolized by Ar (for aromatic)

Solved Problem 2.1

Alkyl Halides: A hydrocarbon with a halide replacing

a hydrogen
Carbon attached to a halide (Br, Cl, I, F) Represented by R-X Classified further by naming the carbon atom that the halide is attached to (primary, secondary, tertiary)

Review Problem 2.10

Alcohols: a hydrocarbon attached to an OH group

Represented by R-OH Classified further by naming the carbon atom that the hydroxyl is attached to (primary, secondary, tertiary)

Review Problem 2.12

Ethers: can be thought of as derivatives of water in

which both hydrogen groups are replaced by alkyl groups
Represented by R-O-R or R-O-R
Two of the same side chains or two different side chains

Amines: can be considered organic derivatives of

Represented by R-NH2, R2-NH Classified further by naming the carbon atom that the amino group is attached to (primary, secondary, tertiary)

Trigonal pyramidal shape

Lone pair of electrons on the nitrogen atom and three substituents sp3 hybridized

Review Problem 2.16

Review Problem 2.17

Aldehydes: a carbon chain that is attached to a

double bonded oxygen and hydrogen at the end of the molecule
Represented by RCHO Contains a carbonyl group (carbon with a double bonded oxygen)

Workshop One Part Two

Ketones: a carbon attached to a double bonded

oxygen and another chain of carbons
Represented by RCOR or RCOR Contains a carbonyl group

Workshop One Part One

Review Problem 2.18

Carboxylic Acids: a carbon that is connected to a

carbonyl and a hydroxyl
Represented by R-COOH or R-CO2H Contains a carbon attached to a double bonded oxygen (carbonyl) and an OH group (hydroxyl) Carbonyl + Hyrdroxyl = CARBOXYLic acid

Review Problem 2.20

Esters: a carbon that is attached to a carbonyl which is

attached to an oxygen which is attached to more carbons
Represented by R-CO2R or R-CO2R Contain a carbon attached to a double bonded oxygen and another oxygen which is connected to another chain of carbons

Review Problem 2.23

Amides: a carbon attached to a carbonyl group and an

amino group
Represented by RCONH2 (in which H can be replaced by R) Contains a carbon that is attached to a double bonded O (carbonyl) and an NH2 (in which H can be replaced by R) group (amino group)

Further classified by the amount of R groups attached to the nitrogen atom

Unsubtituted, N-substituted, N,N-substituted

Workshop One Part Two

Review Problem 2.24

Nitriles: a carbon tripled bonded to a nitrogen

Represented by R-CN Contains a carbon that has a triple bond to a nitrogen atom which contains one lone pair Both carbon and nitrogen are sp hybridized

Exam One 2010

In Summary

Now go home and do this. (It helps, I promise)

For Your Entertainment

Intermolecular Forces (IMF)

Forces that are found between different molecules (not within the same molecule) that determine its physical properties and molecular structure
Determines melting point (MP), boiling point (BP), solubility, color, reactivity, etc


(ion-ion )

Ion-Ion Forces: Intra-molecular force between two

or more ions of opposite charge
Organic Lingo: strong electrostatic lattice forces that act between the positive and negative ions in the orderly crystalline structure Average Human Lingo: strong forces that hold together positive and negative ions in a very structured way Forces WITHIN a molecule (not between two molecules) Usually very strong forces

Ionic Bonds: an intra-molecular bond between a

metal and a nonmetal
Because of large electronegativity differences, electrons are taken from one atom
This creates a positive ion and a negative ion These ions are held together by ion-ion forces (EN is the ability of an atom to attract electrons thats it is sharing, a numerical value of how much an atom wants an electron)

Covalent Bonds: an intra-molecular within a

molecule that are held together by the sharing of electrons
Forces WITHIN a molecule (not between two molecules) Electrons are shared between two or more molecules
Can be shared equally to form NONPOLAR covalent bonds
Due to no difference in electronegativity

Can be shared unequally to form POLAR covalent bonds

Due to electronegativity differences (EN is the ability of an atom to attract electrons thats it is sharing, a numerical value of how much an atom wants an electron)

Hydrochloric acid has a covalent bond. The electrons are shared unequally between the two atoms, creating a slightly positive and slightly negative end.

Covalent Bonds: more examples (Polar and


Solved Problem 2.4

Intermolecular Forces (IMF)

Forces that hold two or more molecules of the same or different species together Not as strong as those between ions Influence physical properties of a compound (boiling point, melting point, solubility, etc) Ion-dipole forces van der waals forces
Dipole-dipole forces Hydrogen bonds Dispersion forces

van der Waals Forces: dipole-dipole forces

Interactions between molecules that have permanent dipoles due to differences in electronegativity (non-uniform electron distribution)
Not fully ionic

van der Waals Forces: hydrogen bonds

Very strong dipole-dipole forces between hydrogen and small, highly electronegative atom (F, O, N)
Remember these three with E.T FON home Stronger than dipole-dipole, but weaker than covalent bonds BDE = 4 to 38kJ/mole

Responsible for base-pairing of DNA nucleotides (Adenine and Thymine, Cytosine and Guanine) The reason that water is a liquid at room temperature
If water did not have hydrogen bonds, water would boil at -80C and there would be no life probably
What is life?!

van der Waals Forces: dispersion forces

IMF between two nonpolar molecules
NP molecules exhibit no positive or negative ends that could attract each other So how do two molecules that are nonpolar interact with one another?

Because electrons are always moving, there is a small instant of time where one side of the molecule is more negatively or positively charged than the other
A small, temporary dipole moment will occur and this will cause an attraction between two molecules

Factors that determine the magnitude of dispersion forces

The bigger the molecule, the further the electrons are from the nucleus, the more ability they have to move and create more and larger dipole moments The smaller the molecule, the closer electrons are to the nucleus, the less ability they have to move and create less and weaker dipole moments The larger the surface area, the larger the dipole moments (more attraction) because there is more available space for IMF interactions

Ion-dipole Forces
The interaction with an ion and a permanent dipole Usually result in solvation of the ion within a solution

For Your Entertainment

Boiling Point (BP)

Organic Lingo: the temperature at which vapor pressure equals atmospheric pressure Average Human Lingo: the temperature where a liquid gets all bubbly and turns into a gas To go from the liquid to the gaseous phase, molecules must separate from one another and become more random
Therefore, IMF play a crucial role in determining the temperature at which a substance boils

Generally, the weaker the IMF, the easier it is to separate the molecules from one another, the lower the BP
Dispersion forces < dipole-dipole < hydrogen bonds < ion-dipole < covalent < ion-ion forces

Generally, the more symmetrical the molecule, the higher the BP

Review Problem 2.25

Solved Problem 2.6

2010 Exam One

The dissolution of a solid into a liquid Ions are always more soluble in water because they are able to form ion-dipole bonds with water!

The solid must have some shared properties with the liquid it is dissolving in
like dissolves like
Hyrdophobic: water fearing, will not dissolve in water, usually nonpolar Hyrdophillic: water loving, will dissolve in water, usually polar *Water is polar!*

Exam One 2010

Random, Important Information You NEED to Know

pH < pKa then the BASE is favored and pH > pKa then the ACID is favored Something is most stable when : it has the most amount of bonds, the least amount of charge separation, the most EN contains the charge (usually) Acidity and Basicity
BAAD : Bases Accept, Acids Donate (Protons, that is..) If the hydrogen on a molecule is likely to leave (to be donated), that means it is an acidic hydrogen
This also means it is least stable, most reactive! Usually if it is creating a possible resonance structure, it is the one that will get removed most easily (because resonance is a stabilizing factor) In D2O reactions, just replace D with the most acidic hydrogen(s)

Lone pairs on molecules MAKE A DIFFERENCE!

They will change the shape of the molecules! They count when determining hybridization! They are sometimes reactive, attacking positive centers!

Curved arrows are your friends

Fish are friends. Push electrons toward electronegative atoms and positive charges!

Exam One 2011

Exam One 2011

Exam One 2011

Exam One 2011

Exam One 2012

Exam One 2012

Thats it!
Go home! Good luck! Get some sleep! Dont go partying on Tuesday night! Come to office hours! Study hard!