Transcript Organic

ORGANIC
By Mr. M
What is it?
• Organic chemistry is a field of chemistry that deals with
carbon and the elements that can covalently bond to carbon
• Carbon often bonds with hydrogen so organic is nicknamed
hydrocarbon chemistry
• Organic does not mean fresh and natural
• They can be made in a lab
• Many poisons/pesticides/herbicides are organic
Nomenclature
• Organic chemistry has its own system of naming
• The name tells you the elements in the molecule and the
function of that molecule
• Part of a name is called a functional group
• All chemicals that end in –ol are alcohols
Six Step Process
1)
2)
3)
4)
5)
Find the longest carbon chain
Name it
Determine any ending
Number the carbon atoms
Separate and name side/substituent
groups
6) List side/substituent groups
alphabetically
4
Step 1: Find the longest carbon chain


Find the longest, uninterrupted, continuous
carbon chain
It is not required that in the picture or
drawing of the carbon chain that atoms all
are in line only that it is the longest
continuous carbon chain
5
Step 2: Name it
• Name it.
• Count the number of carbons in the chain
and select the appropriate root name
based on the number of carbon atoms on
the chain
Ethane
Butane
Octane
6
Root Names
Number of
Root Name
Carbon Atoms
Number of
Root Name
Carbon Atoms
1
2
3
meth
eth
prop
11
12
13
undec
dodec
tridec
4
5
6
7
8
9
10
but
pent
hex
hept
oct
non
dec
14
15
20
21
22
30
40
tetradec
pentadec
icos
henicos
docos
triacont
7
tetracont
Step 3: Determine any ending
• Determine if any ending needs to be added to
the base name
• This is determined by the presence of a
functional group on any of the carbon atoms
– A list of functional groups and their structure can be found on the reference link
of the class website.
Ethanol
Butane
Octane
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Compound Class
Ending
Functional Group
Alkanes
-ane
None
Haloalkanes
-ane
―X
Alcohols
-ol
―OH
Ethers
ether
―O―
Alkenes
-ene
Alkynes
-yne
Aldehydes
-al
Ketones
-one
Carboxylic Acids
-oic acid
Esters
-oate
Anhydrides
anhydride
Amides
-ide
Nitriles
-ile
Amines
-amine
―C≡C―
―C≡N
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Step 4: Number the carbon atoms
• Start at both ends of the carbon chain, naming
the first carbon #1, the next #2, and so on
– Find which end leads to or arrives at a side group first
– That end then becomes the carbon #1 end
• Number each carbon continuously through to
the other end of the main chain starting with #1
2
1
2
3
1
4
Octane
Ethanol
Butane
1
2
3
4
5
6
7
8
10
Step 4: Number the carbon atoms

If both ends of the chain come to a side group with
the same number of carbons, then the side with the
more complex group (contains more atoms)
becomes the end that receives the #1 label on its
end carbon


If that also is a tie then the next tie breaker is alphabetizing
the side groups
The higher order or first occurring alphabetical character
side group becomes carbon #1
6
5
4
3
2
1
11
Step 5: Separate and name
substituent groups
 Separate out and individually name all the
substituent side groups or chains, sometimes
referred to as pendent groups
 The common names for side groups are
–
–
–
–
–
–
–
Cl = chloro
F = fluoro
Br = bromo
OH = hydroxy
NH2 = amino
CN = cyano
NO2 = nitro
There is a list of additional
substituent groups on the reference
page of the class webpage.
1, 3 - dibromo - 2 - butanone
Substituent group = Side group
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Some Substituent Groups
13
Step 5: Separate and name substituent
groups
 The presence of a double bond between two
carbons gives the –ene ending to the root
and the number of carbon of the pair is put
proceeding the root
 A triple bond gives a –yne ending, and the
same proceeding number system
butadiene
1-butyne
14
Step 5: Separate and name
substituent groups
• If two of the same atoms appear in a molecule,
the word “di” is used to describe it
• If three similar atoms appear in a molecule, the
word “tri” is used to describe it
– 4-tetra
– 5-penta
• These prefixes are inserted directly before the
name of the group
butadiene
tetraflouroethylene
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Step 6: List substituent chains in
alphabetical order

Write in alphabetical order all
substituent chains or groups preceded
by the carbon atom number where they
are attached
1, 6 – Dichloro – 2, 5 – dimethyl – 3 – hexyne
16
Cycloalkanes and Aromatic
Hydrocarbons
• Cycloalkanes are alkanes (only carbon to carbon single bonds) which
form a ring structure.
• An aromatic compound is one that is based on the benzene ring.
• A benzene ring that is attached to another compound is given the name
phenyl.
Key Words
Fermentation – making alcohol
Cracking – breaking down petroleum
Aromatics - rings
Isomers – different shapes of same thing
Cis - same
Trans - opposite
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Isomers
• Isomers have the same number/type of atoms, but they are
rearranged differently
• Mirror images are sometimes isomers
• Going backwards does not count
Alkenes Cis-Trans
Polymers
Review
• A polymer is a large molecule composed of structural units
called monomers
• Poly = many
• Mer = units
Polymer Intro
• Homopolymer = a polymer composed of one type of
monomer
• Ex. Polyethylene
• Copolymer = a polymer composed of different monomers
• Ex.
Picture Reference:
"Miscible Polymer Blends." 2005. University of Southern
Mississippi. 25 Sept. 2007
<http://pslc.ws/macrogcss/blend.html>.
Size of Polymers
• Polymers are so large their size is measured in a ratio called
degree of polymerization(DP)
• DP of homopolymer = MW polymer / MW of monomer
• DP of copolymer is the average DP of the different units
Entanglement
• A polymer can become so massive that it collapses in on itself
and becomes tangled
"Protein-Protein Complexes."
Dockground. 2007. Vasker Lab.
<http://dockground.bioinformatics.k
u.edu/BOUND/help.php>.
…..
• Polymer molecules even entangle which promotes
intermolecular forces like Vann der Waals forces
"Protein-Protein Complexes." Dockground. 2007.
Vasker Lab.
<http://dockground.bioinformatics.ku.edu/BOUN
D/help.php>.
“Polymer Sliding”
Silly Putty Chemistry
“Polymer Sliding”
• Silly putty stretches if pulled slowly
• Silly putty cleaves smoothly if pulled fast
• Similar to needing enough activation energy to start a reaction
• When the silly putty breaks the polymer molecules do NOT
break
Continued…
When pulled slowly the molecules “slide together” as follows:
….
• When pulled fast the molecules separate as follows:
Silly Putty Togetherness
• Silly putty illustrates “polymer sliding”
• This sliding is also what allows for silly putty to be put back
together once ripped apart
So why can’t a broken rubber band
go back together
• Rigid polymers cannot undergo sliding if there is an
intermolecular connecting agent
• Tires are made by adding sulfur into a gooey rubber. The sulfur
connects the entangled molecules making them affectively
one giant molecule