o rganic c hemistry the study of carbon compounds
TRANSCRIPT
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ORGANIC CHEMISTRYThe study of carbon compounds
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ORGANIC CHEMISTRY INTRODUCTIONVideo 10.1
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ORGANIC VERSUS HYDROCARBON Organic molecules must have the
element C. Hydrocarbons can only have the
elements H and C. Therefore hydrocarbons are organic but
not all organic compounds are hydrocarbons:CH4 is a hydrocarbon and is organicCCl4 is organic but not a hydrocarbonO2 is neither organic nor a hydrocarbon
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ORGANIC MOLECULES
Found in fossil fuels, plants and animals.
Examples include gasoline, oil, kerosene, butane, propane…
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HYDROCARBON PROPERTIES Mostly insoluble (nonpolar) Non-electrolytes (do not conduct
electricity) React very slowly because they are
covalent (nonmetals only). As size increases, the melting point and
boiling point of the hydrocarbons increase.
Small hydrocarbons may be gases and large hydrocarbons may be solids at room temperature.
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CARBON
Remember carbon has four valence electrons. Therefore carbon will bond four times to achieve an octet.
Each bond shown shares two electrons. One from C and one from H.
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ORGANIC MOLECULES
Sometimes double and triple bond will be needed to fulfill all octets.
A double bond shares four electrons. A triple bond shares six electrons.
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ORGANIC MOLECULES
All single bonded hydrocarbons are in the same family known as alkanes.
All double bonded hydrocarbons are in the same family known as alkenes.
All triple bonded hydrocarbons are in the same family known as alkynes.
Refer to table Q
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ORGANIC MOLECULES
Notice the picture shows you the number of bonds.
Table Q also shows that if you know how many carbon atoms are present in a molecule and what type of bonds it has, you can CALCULATE the number of hydrogen atoms using the general formula. But drawing it out might be easier.
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ORGANIC MOLECULES
Table P shows your prefixes to determine how many Carbon atoms a compound has.
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GIVE THE PREFIX FOR THE FOLLOWING:
1. C2H6
2. C3H6
3. C4H6
4. C5H12
5. C6H12
6. C7H14
7. C8H18
8. C9H16
9. C10H20
1.Eth2.Prop3.But
4.Pent5.Hex6.Hept7.Oct8.Non9.Dec
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ORGANIC COMPOUNDS Putting P and Q together we can name
simple hydrocarbons:
MethaneEthene
ButaneEthyne
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SATURATION Compounds like fats that are saturated
have many hydrogen atoms. This requires single bonds. Alkanes are saturated with single bonds.
Compounds that are unsaturated have double and triple bonds, therefore, they have less hydrogen atoms. Alkenes and alkynes are unsaturated.
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CYCLIC AND BRANCHED HYDROCARBONSVideo 10.2
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CYCLIC HYDROCARBONS To name them, use the prefix “cyclo”:
A four member ring is cyclobutane
A five member ring is cyclopentane
A six member ring in cyclohexane
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NAME
cyclopentyne1,3-cyclohexadiene
1, 3, 5-cyclooctatriene
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BENZENE An important aromatic hydrocarbon is
benzene. It has alternating double and single bonds. It is very stable and gives off pleasant
odors like cinnamon and vanilla. (“aroma”)
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BRANCHED HYDROCARBONS When naming branched hydrocarbons,
name the longest chain and use that as the ‘last name.’ Then name the shorter chains, specifying the position of each branch. Also make sure that your branches are numbered as low as possible. 3-ethyl 1-heptene
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BRANCHED HYDROCARBONS
These are all just butane!!!
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BRANCHED HYDROCARBONS
2 methyl propane2 methyl hexane
The little branches are known as alkyl groups which is why they have a “yl” ending.
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BRANCHED HYDROCARBONS
2,5 dimethyl hexane
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CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3
CH3
CH3
Find the longest continuous chain of carbons. This is the parent chain. Look at all bonds between carbons to determine type of hydrocarbon . Count from the side with the alkyl groups
1234567
There are 7 continuous carbons, so the parent chain is heptane
All single bonds so ending is…ane.
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Number the carbons in the main sequence starting with the end that will give the alkyl groups the smallest #.
The chain is numbered from right to left because it gives the attached groups the lowest possible number
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3
CH3
CH3
1234567
1 2 3 4 5 6 7
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Add numbers to the names of the groups to identify their positions on the chain. These are prefixes with a “yl” ending.
In this ex. the positions are:- methyl, - methyl, - ethyl
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3
CH3
CH3
1234567
2 3 4
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Use prefixes to indicate the appearance of a group more than once in the structure. And list them in alpha order
CH3 - CH2 - CH2 – CH – CH – CH - CH3 CH2 CH3
CH3
CH3
1234567
Di =
Tri =
= four times
= five times
twice
three timesTetra
Penta
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The name of this compound is:
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3
CH3
CH3
1234567
2,3-dimethyl – 4-ethyl heptane
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BRANCHED HYDROCARBONS
3 hexyne3,4 diethyl octane
3, 5, 6 trimethyl 7 ethyl decane
Each angle is a carbon
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BRANCHED HYDROCARBONS
2, 3 dimethyl 4 propyl 2 heptene
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OTHER GROUPS More groups can be on the ring/branch
such as:F fluoroCl chloroBr bromoI iodo
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BRANCHED HYDROCARBONS
2 bromo 3 methyl butane
2 bromo 2 methyl propane
1 bromo 4 methyl benzene
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ISOMERSVideo 10.3
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FORMULAS
1. Molecular Formula: shows the number of atoms of each element in a compound.
2. Structural Formula: diagram of the molecular shape of a compound.
3. Condensed Structural Formula: each carbon is written separately followed by atoms bonded to it.
C2H6
CH3CH3
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ISOMERS
Isomers have the same molecular formula but rearranged in a different structure with different properties.
Draw three isomers of butene:
Why not 3-butene?
cyclobutane
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CIRCLE THE ISOMERS:
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BENZENE SUBSTITUTION The benzene ring consists of 6 carbons
in a ring of alternating double and single bonds.
When substituted once, just use prefixes such as methylbenzene:
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BENZENE SUBSTITUTION When the benzene is substituted twice
you can number the groups:
1,2 dimethyl benzene 1,3 dimethyl benzene
Name: 1, 3 di methyl benzene!
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FUNCTIONAL GROUPSVideo 10.4
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TAKE OUT TABLE R!!!!!
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HALIDES
Have one of the halogens as a branched group. Names as we did in the previous lessons.
1, 2 dibromo ethane
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ALCOHOL
Suffix: -ol
Flammable, soluble
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ETHER
Name small chain, large chain, suffix: -ether
Anesthetic, soluble
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ALDEHYDE
Suffix: -al
Soluble, reactive
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KEYTONE
Suffix: -one
Somewhat soluble, needs at least 3 carbons
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ACIDS
Suffix: -anoic acid
Also known as carboxylic acids: weak acids/ weak electrolytes
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ESTERS
Name chain adjacent to double bonded O last, Suffix: -anoate
Smells great (perfumes, foods)
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AMINE
Nitogen is present
Prefix: amino- Basic, used in dyes, found in proteins:
DNA
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AMINE
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AMIDE
Suffix: -amideUsed in dyes
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POLYMERS
Long Carbon chains (C2H4)n
Used in all plastics, runner, nylons…
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ORGANIC REACTIONSVideo 10.5
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ADDITION Similar to synthesis reactions: one product
forms
C2H4 + Br2 C2H4Br2
Notice the first compound is unsaturated. The bond breaks to allow new Bromine atoms into the chemical.Before:
After:
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SUBSTITUTION
Similar to single replacement: two atoms switch
CH4 + Br2 CH3Br + HBr
Notice the first compound is saturated. One H is switched with one Br. Otherwise, it would have been addition, breaking the bonds.Before: After:
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COMBUSTION
An organic compound is burned in the presence of oxygen to form CO2 and H2O only.
CH4 + 2O2 CO2 + 2H20
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ESTERIFICATION
An ester is formed after the reaction of an organic acid and an alcohol
C3H6COOH + C2H5OH C3H6COOC2H5 + H2O
The H of the acid and the OH of the alcohol come off and the two chains combine. Water is left over.
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FERMENTATION
Alcohol is formed from the decomposition of sugar. This takes a long time so yeast is often used as a catalyst. The sugar can be from grapes, rice, etc.
C6H12O6 2C2H5OH + 2CO2
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SAPONIFICATIONSaponification: Bases added to fats yield
glycerol and soap. Look for large molecules and bases!
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POLYMERIZATION: USED IN PLASTICS
Addition Polymerization: Adding two small alkenes (such as ethene) together by breaking the double bond, to create a large chain.
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POLYMERIZATION
Condensation Polymerization: Adding acids and alcohols by extracting water.
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CRACKING Breaking large hydrocarbons into smaller
chains by heating them. Fossil fuels are cracked into many
components such as octane (gasoline) propane, etc.
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AP EXTENSION
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MEMORIZE MEMORIZE MEMORIZE
And functional groups, definitions, and reactions!
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BENZENE SUBSTITUTION
But, most scientists use designated terms to represent substituted benzene rings:
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FOR EXAMPLE:
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NAME:
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STEREOISOMERS Groups around a
single bond can rotate around the central atoms.
Double and triple bonds have groups that cannot rotate and are, therefore, rigid.
2-butene can actually represent two different structures, cis-2-butene and trans-2 butene.
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STEREOISOMERS
“Cis” means the 2 similar groups are on the same side.
“Trans” means the two groups are on opposite sides. You’ve probably heard of cis and trans-fats.
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NAME:
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OTHER NAMES
Notice there are other informal ways to name these compounds. The prefix “form” in formaldehyde is used to show the first member in the series of aldehydes which is methanol. Formic acid would be the same as metanoic acid. The prefix “ace” is the second member of the series. Acetic acid is also known as ethanoic acid (HC2H3O2).
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SPECIAL ALCOHOLS
Alcohols can have more than one hydroxide group. If there are two hydroxide groups it is known as a dihydroxy alcohols. Alcohols with three hydroxide groups are called trihydroxy alcohols. The hydroxide groups have to be numbered to show which carbon they are attached to.
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SPECIAL ALCOHOLS
Alcohols can also be classified by which carbon the hydroxide it attached to. If the hydroxide is on the end of a chain and only connected to a carbon atom that is attached to only one other carbon atom it is known as a primary alcohol. If the hydroxide group is attached to a carbon atom which is also attached to two other carbons it is known as a secondary alcohol. Finally, if a hydroxide group is attached to a carbon atom which is then attached to three other carbon atoms, it is known as a tertiary alcohol.
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SPECIAL ALCOHOLS