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Organic Chemistry

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Batool Zeini

on 21 March 2013

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Transcript of Organic Chemistry

Reaction mechanism Hydrocarbons Simplest type of organic molecule containing only the elements carbon and hydrogen Other topics I needed to learn What is organic chemistry? It is the chemistry that involves the study of carbon containing compounds Carbon bonds to organic elements such as hydrogen, nitrogen, oxygen, phosphorus, and sulfur to form organic compounds The level of atom's attraction to an electron in a bond is called electronegativity Example: NaCl ionic bond The electron completely transferred
Chlorine pulls in the electron because it has a higher electronegativity
Ionic bonds have the greatest difference in electronegativity Molecular structure and polarity CCl has polar bonds but it
still is a nonpolar molecule Non polar methane Polarity of a molecule determined by the polarity of bonds
molecular structure determined by VSEPR Alkane: single bonds between carbons Alkene: double bonds between carbons Alkynes: triple bonds between carbons Group formula Class name Example IUPAC name Common name C C Alkane H 4 C Methane C C C C Alkene Alkyne H 2 C = C H 2 Ethene Ethylene Acetylene HC _ _ _ CH Ethyne What IUPAC stands for and what it is I U P A C nternational nion of ure pplied hemistry International board in charge of all rules for naming chemical substances, including organic molecules Nomenclature Number of carbon atoms Stem name Side chain (alkyl group) name Multiplier 1 2 3 4 5 6 7 8 9 10 meth eth prop but pent hex hep oct non dec methyl ethyl propyl butyl pentyl hexyl heptyl octyl nonyl decyl Steps for naming branched alkanes Step 1: identify longest carbon chain

Step 2: number carbon atoms starting with the end that is closest to the branch (or side branch)

Step 3: Name each branch and identify location

Step 4: Write IUPAC name (number of location)-(branch name) (parent chain)

Step 5: When there are multiple branches and list in ABC order. Steps for naming branched alkenes and alkynes Step 1: longest chain

Step 2: number carbon atoms

Step 3: number prior to the main hydrocarbon chain name shows the location of the double or the triple bond

Step 4: the presence of a multiple double or triple bond goes in the prefixes (di, tri, etc.) Functional groups Hydrocarbons are only made of C and H but when, for example, OH is added to it, it changes the makeup of the hydrocarbon and becomes an alcohol molecule Methane
hydrocarbon gas CH 4 CH 3 OH Methanol
alcohol liquid Functional groups determine the chemical and physical properties of the compound. Alcohols Structure: with the functional group -OH, molecule names have the suffix -ol Naming: look for the longest carbon chain Add a # to wherever the OH is 2 2-pent 5 carbon chain anol Example of alcohol: isopropanol (rubbing alcohol disinfection) Esters the structure of esters are similar to those of carboxylic acids except the H on the end is replaced with an alkyl group or carbon chain Carboxylic acids How do I approach what labs to do and how are they different from last year? Time Steps Equipment Precision What did I use to determine how my lab went? Stoichiometry calculations: by using the balanced equation for my reaction, I can determine the mass I should make and compare it to the mass I made to calculate the percent yield Percent yield: measures how efficient your lab procedure was--you want it to be close to 100% for it to be a good percent yield BIODIESEL LAB hydrocarbons, alcohols, and esters Synthesizing biodiesel vegetable oil reaction known as
transesterification The oil is a lipid—oils are triglycerides which are glycerol esters of fatty acids. convert the triglycerides from glycerol esters (aka oil) to methyl esters of fatty acids (biodiesel) which is the process known as transesterification. I had to use NaOH which is a base to convert the methanol into methoxide ions which yields glycerol and three fatty acids (3 methyl esters). Because I got 2 products, I separated them glycerol biodiesel ASPIRIN LAB Carboxylic acids Procedure: In order to get the mass of the crystals, I had to filter out the two products mass of the crystals
(aspirin) acetic acid I found the theoretical mass (how much I was supposed to make) of the aspirin and I divided that by the actual mass of aspirin I made in the lab. 1. Percent yield=124% 2. Percent yield=97% TITRATION Esters Alcohol This is the process that determines how much acid is in a solution by adding JUST enough base of a known concentration to neutralize the acid I did a titration with my lab aspirin product and store brought crushed aspirin Base: NaOH Aiming for a faint, light pink color Moles acid
=
moles of the base Finding the melting point Found the melting point of: first lab aspirin product
the second one
the crushed store product aspirin 1. Addition What is a reaction mechanism? Types of reactions C=CH 2 + HCl CH Cl CH CH 3 3 3 C CH 3 CH 3 Ether 2. Elimination 3. Substitution 4. Rearrangement •Describes how organic reactions occur
•Describes which bonds are broken and in what order
•Which bonds are formed and the rate of each step Polar organic reactions Electrophile Nucleophile "electron rich" it creates a bond by donating a pair of electrons to electron poor atoms
donate it to electrophiles "electron poor" forms a bond by accepting a pair of electrons from a nucleophile •Arrows show where electrons move when reactant bonds are broken and products bonds are formed A + + :B A : B electrophile
(electron poor) Nucleophile
(electron rich) Predicting products Orientation of electrophilic addition comes from Markovnikov’s Rule His rule stated in the addition of an HX (hydrogen and another element) to an alkene... the hydrogen attaches to the carbon with fewer alkyl groups (methyl, ethyl, propyl, etc.), and the X attaches to the carbon with the most alkyl groups 2 alkyl groups on this carbon No alkyl groups on this carbon Electrophilic addition of Br 2 This lab was the process of adding bromine to trans-stilbene, but Bromination of trans-stilbene Finding the melting point (-) (+) organic chemistry is focused on elements in the area of Polar and non polar bonds There are two types of covalent bonding:

1. Non-polar bonding with an equal sharing of electrons.
2. Polar bonding with an unequal sharing of electrons. POLAR BONDING-when two different non-metals unequally share electrons between them H Cl NON-POLAR BONDING- when two identical non-metals equally share electrons between them 4 4 C S Each atom has the same electronegativity so that's why the covalent bond is considered non polar A bond is formed where the electron pair is displaced toward the more electronegative atom (the Cl). This atom then obtains a partial-negative charge (Cl) while the less electronegative atom has a partial-positive charge (H). CH The expected temperature was either going to be 140 degrees celcius or 240 degrees celcius.

The melting station went up to 220 degrees celcius but the product still hadn't reached a melting point by 220 degrees celcius.

Conclusion: the product must have been 240 degrees celcius. : : : : : . : : : . Stands for: Valence Shell Electron Pair Repulsion Valence electrons are involved in bondings and they are going to repel because they are like charges.
Since they are going to repel, the electrons should be placed as far as possible Example 4 bonding pairs of electrons
geometry is tetrahedral di tri tetra penta hexa hepta octa nona deca this is the carbon with "leaves of hydrogen" number the longest carbon chain starting with the -COOH group
name the chain using the alkane name and replacing the -e ending with an -oic acid ending Naming Example: acetic acid (vinegar) Naming The two reactants were salicylic acid and acetic anhydride. limiting reactant: salicylic acid
excess reactant: acetic anhydride Acid: aspirin Why? has non polar bonds and it's a non polar molecule. It has no dipole. aspirin Formaldehyde has a dipole
polar molecule complex geometry Methane The functional group is an -OH 6 carbons which is hexan + oate 2 carbon ethyls IUPAC name is ethyl hexanoate Example Pineapple scent I added salicylic acid and acetic anahydride together in a flask, but I neutralized the acetic anahydride by adding distilled water. Then, I put the flask in a cool water bath and scratched the side of the flask until crystals appeared. Procedure
I added trans-stilbene and pyridinium tribromide in a heated test tube in addition to acetic acid to get the product, trans dibromide. So, what did this all do for me?
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