1. Introduction to Organic Chemistry
Carbon: The key to organic

2. What are the purposes for studying organic chemistry
What are the purposes for studying organic chemistry? (Just information, not test material)
Organic chemistry involves a problem solving method that most of you have not seen before
Solving Organic Chemistry problems is a challenge that can be interesting
At the beginning of the Chemistry I course, if you are asked where the electrons are in an atom, you correctly say atomic orbitals. At the beginning of the Chemistry II course if I ask you how to brominate an alkane, you say use bromine and light. Did you have to memorize these two facts? No, you became familiar with these facts by using them and understanding their context. You can NOT memorize your way through this course.
2. How did it originate?
a. In the earlier period of development of chemistry, chemists tried their best to synthesize organic compounds in the laboratory. But all their efforts proved to be futile. Their failures led them to believe that organic compounds could be prepared only by and within living beings and that they could never be synthesized in the laboratory like inorganic compounds.

3. What did scientist really believe about organic chemistry and what/who changed their minds?
a. Jöns Jacob Berzelius, a physician by trade, first coined the term "organic chemistry" in 1807 for the study of compounds derived from biological sources. Up through the early 19th century, naturalists and scientists observed critical differences between compounds that were derived from living things and those that were not. Chemists of the period noted that there seemed to be an essential yet inexplicable difference between the properties of the two different types of compounds. The vital force theory (sometimes called "vitalism") was therefore proposed (and widely accepted) as a way to explain these differences. Vitalism proposed that there was something called a "vital force" which existed within organic material but did not exist in any inorganic materials.
What did Friedrich Wöhler have to do with discrediting the “vital force” theory?
He was widely regarded as a pioneer in organic chemistry as a result of his synthesizing of the biological compound urea (a component of urine in many animals) utilizing what is now called "the Wöhler synthesis."
2. in 1828 he heated an aqueous solution of two inorganic compounds, ammonium chloride and silver cyanate, and produced “urea”.

4. NH4Cl + AgNCO NH2CONH2 + AgCl
heat
NH4Cl AgNCO
NH2CONH2 + AgCl
Ammonium chloride
Silver cyanate
urea
Silver chloride
Urea was a compound that mammals produced to get rid of excess nitrogen. Urea is secreted in their urine. Friedrich Wohler created it using inorganic (non-living) salts. Everyone was surprised, but chemists then knew that it was possible to create chemicals found in the body using chemicals from the ground or air (non-living sources). So now organic compounds were not defined as only those compounds from organisms, but compounds based on carbon.
1.. Wohler was surprised b/c this didn’t fit the old definition of “organic b/c it had been isolated from human urine. This was one way the “vital force” was disproved.
*this left the theory open for the real definition of organic and inorganic
He was the first to synthesize an organic compound from an inorganic one. Also noted for transforming alcohols into carboxylic acids and the synthesis of salicylic acid, a key ingredient in aspirin.
*electrolysis of fatty (alkanoic) acids was the first known electrochemical synthesis
Many of these compounds are of immense importance, as the list below shows:
Fuels
Solvents
Explosives
Detergents
Plastics, synthetic fibres
Rubber
Wool, cotton, natural fibres
Insecticides, pesticides
Animal toxins, plant poisons
Vitamins, hormones
Synthetic pharmaceuticals
Antibiotics
Dyestuffs
Foodstuffs, flavourings and preservatives

5. 2. Hermann Kolbe, 1845, worked with Wohler, and converted carbon disulfide (CS2) to acetic acid (CH3COOH)
a pioneer in the development of structural formulas for organic compounds.
Introduced the term “synthesis” by discovering many synthesis methods of organic molecules from inorganic components.
discovered a method of electrolysis of salts of fatty acids known as the Kolbe electrolysis.
These experiments opened the floodgates for synthetically produced compounds.
This was the final proof to discredit the vitalism theory where organic compounds have some 'spark' and could only be created from other organic compounds. The Kolbe synthesis reaction is a method of making salicylic acid, the main component of aspirin.

6. How do the inorganic vs. organic compounds compare (number wise)?
Five million organic compounds to 2-3 hundred thousand inorganic compounds.
What is the modern definition of organic chemistry?
Those compounds containing carbon
The exceptions to the rule: carbonates, cyanides, carbon dioxide, and carbon monoxide. (These are exceptions because they don’t contain both carbon and hydrogen)
What is there about carbon that permits the formation of so many compounds?
1. In addition to binding to hydrogen, carbon can also bind to
other carbon atoms
Both long and short chains of carbon atoms, and even whole networks, are possible.
3. Made up in many ways, so that many combinations and arrangements of atoms are possible.
2. An organic molecule (hydrocarbon) is formed when carbon bonds to hydrogen.  The simplest hydrocarbon consists of 4 hydrogen atoms bonded to a carbon atom (called methane): Also “CHNOPS” and the halogens
ethane

7. 3. the uniqueness of carbon comes from the fact that it can bind to itself.  Carbon atoms can form long chains:
hexane
4. branched chains:
isooctane
5. rings:
cyclohexane

8. ORGANIC VS. INORGANIC 1. Few elements (CHNOPS) 1. many elements
2. Complex structures (long chains) simple structures
3. Insoluble in HOH most soluble in HOH
4. Low m.p/b.p high m.p/b.p
5. Combustible not combustible
doesn’t conduct electric conducts electric current
current
7. Consists of molecules forms ions in solution
8. Slow reaction rates fast reaction rates
9. Side reactions no side reactions
10. High product yield low product yield

9. 10 Carbon Facts—The chemical basis of life
Carbon is the basis for organic chemistry, as it occurs in all living organisms.
Carbon is a nonmetal that can bond with itself and many other chemical elements, forming nearly ten million compounds.
Elemental carbon can take the form of one of the hardest substances (diamond) or one of the softest (graphite).
Carbon is made in the interiors of stars, though it was not produced in the Big Bang.
Carbon compounds have limitless uses. In its elemental form, diamond is a gemstone and used for drilling/cutting; graphite is used in pencils, as a lubricant, and to protect against rust; while charcoal is used to remove toxins, tastes, and odors. The isotope Carbon-14 is used in radiocarbon dating.
Carbon has the highest melting/sublimation point of the elements. The melting point of diamond is ~3550°C, with the sublimation point of carbon around 3800°C.
Pure carbon exists free in nature and has been known since prehistoric time.
The origin of the name 'carbon' comes from the Latin word carbo, for charcoal. The German and French words for charcoal are similar.
Pure carbon is considered non-toxic, although inhalation of fine particles, such as soot, can damage lung tissue.
Carbon is the fourth most abundant element in the universe (hydrogen, helium, and oxygen are found in higher amounts, by mass).

10. The bonding capabilities of our organic elements
Structure of the carbon atom:
Atomic number is 6, mass is 12
Most common isotope: 6 protons, 6 neutrons,
Electron configuration
Valence electrons
Simplest molecule is methane (CH4)
Other names for methane are: swamp gas or marsh gas; very flammable
Lewis Dot structure of methane
The molecular shape of methane
*electron configuration is 1s22s22p2– the two 1s electrons are tightly held to the nucleus. The 2s and 2p are valence electrons
*the four valence electrons are available for the formation of chemical bonds.
Show the Lewis dot structure of methane; mention how it forms a tetrahedron with carbon at the center.
draw the shape of methane and do the balloon example
Sometimes two atoms are held together by two pairs of shared electrons (a double covalent bond), and even three pairs of shared electrons (a triple covalent bond). Draw ethylene, formaldehyde, acetonitrite
The bonding capabilities of our organic elements
Hydrogen and the halogens bond once. (can form single bonds only)
The family oxygen is in bonds twice. (can form single and double bonds; explain)
The family nitrogen is in bonds three times. (can form triple bonds)
The family carbon is in bonds four times. (can bond single, double, and triple bonds)

11. Structures of organic compounds:
Molecular formula —shows which atoms, and how many of each, are present in a molecule. C2H6O
Condensed formula – shows the atoms present and the bonds that connect to each other in a condensed format. ( CH3CH3 )
Expanded structure—shows all atoms and their bonds. examples
Review of the atom:
a. Atomic number
b. orbital
c. Hund’s rule
d. Octet rule, valence electrons
e. Ionic and covalent bonding
Atomic number—number of protons
Orbital—the electrons of equal energy are found in a particular space, called the electron density. Orbitals are allowed energy states for an electron. Atomic orbitals are grouped into different “shells” at different distances from the nucleus. The shells carry the principal quantum number n.
Hund’s rule—states that when there are two or more orbitals of the same energy, electrons will go into different orbitals rather than pair up in the same orbital.
Octet rule—states that a filled shell of electrons is especially stable, and atoms transfer or share electrons in such a way as to attain a filled shell of electrons. Show how carbon tetrachloride bonds to form eight electrons around the carbon.
Ionic bond—bond between metal and nonmetal. Atoms are transferred. Covalent bond—bond between two nonmetals. Atoms are shared.
Lewis structures—each valence electron is symbolized by a dot, or a bonding pair of electrons is symbolized by a dash (__). Show methane (CH4)
Nonbonding electrons—often called the lone pair—these are electrons not shared—ex. Oxygen, nitrogen, and halogens usually have nonbonding electrons.
Ammonia, water, ammonium ion, propane, ethylamine, dimethyl ether, fluoroethane, borane, boron trifluoride
f. Lewis structures
g. Nonbonding electrons
h. Draw these: C2H6, C4H10O,CH3Br, C3H8, C2H7N,C3H8O,C2H5F, C6H14, CH3PO

12. POLAR AND NONPOLAR MOLECULES
Nonpolar molecules are hydrophobic (means "water fearing"). They do not dissolve in water.
Nonpolar molecules are hydrophobic
Polar and ionic molecules are hydrophilic.
Nonpolar molecules are hydrophobic. Polar and ionic molecules are hydrophilic.
Portions of large molecules may be hydrophobic and other portions of the same molecule may be hydrophilic.

13. What is the reason for the many possible arrangements of the carbon atom?
Isomerism!! The carbon atoms can bond in more than one arrangement, giving rise to different compounds with different structures and properties.
Have identical molecular formulas but different arrangements of atoms
Structural isomers have the same molecular formula but the atoms bond in different patterns
Example: C2H6O
Functional Groups:
Combination of atoms that differentiates molecules of organic compounds of one class from those in another.
**Draw ethyl alcohol and dimethyl ether on board after giving ex. C2H6O
**Give more sample and ask which structures represents a structural isomer. Textbook page 347.
functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules.

14. The 10 Functional Groups
Term/Definition
Alkane consists of only carbon to carbon single bonds
Alkene consists of at least one carbon to carbon double bond
Alkyne consists of at least one carbon to carbon triple bond
Alcohol contains an -OH group
Aldehyde contains a terminal O=C-H group
Ketone contains an internal C=O group
Carboxylic acid contains a terminal O=C-OH group
Ether contains an internal O-O group
Ester contains an internal O=C-O- group
Amine contains a terminal NH2 group

18. Priorities of the groups: Keep rest of semester.
Subordinate groups: Nitro < halides < alkoxy
Functional groups: (from least to greatest in priorities) alkanes < alkynes <alkenes < amines < phenols < alcohol <ketones < aldehydes < nitriles < amide <acid halide < carboxylic esters <carboxylic anhydrides < carboxylic acids (TOP DOG).