Organic Naming Rules -...
Transcript of Organic Naming Rules -...
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Organic Naming Rules
AP Chemistry 439
For complete Rules go to:
http://www.acdlabs.com/iupac/nomenclature/
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Organic Compounds
• Consist of mainly four
elements
• Carbon
• Hydrogen
• Oxygen
• Nitrogen
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Why Do We Need a Separate Set
of Rules?
• Examine some typical organic compounds
• CH4
• C2H6
• Name these using typical covalent rules
Carbon tetrahydride
Dicarbon hexahydride
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So?
• That wasn’t so bad, right?
• How about these:
• C4H10
• C5H12
• See my point?
Tetracarbon decahydride
Pentacarbon ??? hydride
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Isomers
• If that’s not enough, how about this one:
C
H
H
C
H
H
C
H
H
C
H
H
H H
Formula?
C4H10
C
H
H
C
H
HC
H
HCH
H
H
H
Formula?
C4H10
Different
Structure
Same
Formula
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Overall Problems
• Memorizing too many prefixes for large numbers
• Different chemicals having the same formulas
• Keep in mind that thus far we’ve only dealt with TWO different elements!
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So what to do?
• Number of hydrogens is going to be the
same, regardless of isomerism
C
H
H
C
H
H
C
H
H
C
H
H
H HC
H
H
C
H
H
C
H
H
C
H H
C
H
H
H H
C
H
H C HH
C
H
H
C
H H
C
H
H
H
H
C
H
H
C5H12
C5H12
C5H12
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Solution
• Since number of
hydrogens don’t change
with isomerism, why
bother naming them?
• Name the molecule simply
based on number of
CARBONS
• We can always add
prefixes or suffixes later
for differentiation
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Name based on number of
Carbons• 1
• 2
• 3
• 4
• 5
• 6
• 7
• 8
• 9
• 10
• Methane
• Ethane
• Propane
• Butane
• Pentane
• Hexane
• Heptane
• Octane
• Nonane
• Decane
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Did that Really Help?
C
H
H
C
H
H
HH
C
H
H
HH Carbon tetrahydride becomes: Methane
Dicarbon hexahydride becomes: Ethane
C
H
H
C
H
H
C
H
H
C
H
H
H HC
H
H
C
H
H
C
H
H
C
H
H
CH4
C2H6
Octacarbon ???hydride becomes:
Octane
C8H18
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Branches• Straight-chain alkanes (Just C & H with
single bonds) are now easy
C
H
H
C
H
H
C
H
H
C
H
H
H H C4H10 Butane
• But how do we deal with branches?
C
H
H
C
H
HC
H
HCH
H
H
H
C4H10 ????
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Rules pt. 2
• Identify the longest unbranched
chain of carbons
• Name it as normal
• Identify the branch
• Name it but give it a “–yl”
suffix
• Put the names of all branches
first, then put name of longest
chain
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Example
C
H
H
C
H
HC
H
HCH
H
H
HLongest unbranched
chain of carbons is
three long
propane
Branch is one long methyl
Methyl Propane
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Practice
C
H
H
C
H
H
C
H
H C
H
H
H
C
H
H H
Methyl butane
H H H H H
C
H
C
H
CH C
H
C
H
H
C HH
C
H
HH
Ethyl pentane
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One More Practice
C C C
C
C
C C C
C
C
It doesn’t matter
which way you go!
(Provided you correctly pick
the longest unbranched chain)
Methyl Butane
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Be Careful
H
C C C C CH H H H
H H H H
HH
CH H
CH
HH
Hexane
This is your
longest
uninterrupted
chain
Methyl
Methyl Hexane
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A Small Wrinkle
H
C C C C CH H H H
H H H H
HH
CH H
H
H
C C C C CH H H H
H H H H
HH
CH H
H
Methyl Pentane
Methyl Pentane
These are different molecules, though!!!
![Page 18: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/18.jpg)
So Now What?
• Since two different
molecules can’t have
the same name, we
must differentiate
• If we look closely,
though, the only
difference between
them is the position of
the methyl group
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Positioning
H
C C C C CH H H H
H H H H
HH
CH H
H
H
C C C C CH H H H
H H H H
HH
CH H
H
Here the methyl group
is on the second carbon
from the end
Here the methyl group
is on the third carbon
from the end
Methyl Pentane Methyl Pentane
So…
2- 3-
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Rules pt. 3
• Identify the longest unbranched chain of carbons
• Name it as normal
• Identify the branch
• Name it but give it a “–yl” suffix
• Put the names of all branches first, then put name of longest
chain
• Put the number of the carbon the branch is on (start numbering
from the closest single end)
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Practice
H
C C C C CH H H H
H HH H
HH
CH H
H
CH
H
CH
H
H
C C C C CH H H H
H H H H
HH
CH H
H
C CH H
H H
CH
H
2-methyl heptane
4-methyl octane
H
C C C CH H H
H H H
H
CH H
H
CH
H
HCH
H 2-methyl hexane
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Multiple Branches
• So far we’ve only had
one branch
• What happens when
there are multple
branches?
• Just add a prefix to
indicate the number of
a particular type of
branch
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Practice
H
C C C C CH H H
H HH H
HH
CH H
H
CH
H
CH
H
CH H
H
heptane
methyl
methyl2-
2-
2-methyl, 2-methyl heptaneSounds redundant
2,2 dimethyl heptane
![Page 24: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/24.jpg)
More Practice
CH H
H
H
C C C C CH H H
H H H H
HH C CH H
HH
CH
H
CH H
H
C C C C CH H H
H H H
HH
CH H
H
H
CH H
CH H
H
CH H
H
2, 6-dimethyl
octane
3 ethyl-2,4-
dimethyl pentane
![Page 25: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/25.jpg)
Is your arm sore yet?
• Are you sick to death
of writing all those
carbons?
• Even worse, are you
sick of writing all
those Hydrogens?
• How about this…
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Shorthand notation
C
H
H
C
H
H
C
H
H
C
H
H
H HKeep in mind that we have been
ignoring the hydrogens for a long
time.
Our names have been based
entirely on the positioning of the
carbons.
So lets now ignore the hydrogens
completely!
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Is it that easy?
H
C C C C CH H H H
H HH H
HH
CH H
H
CH
H
CH
H
CH H
H
H
C C C C CH H H
H H H H
HH C CH H
HH
CH
H
CH H
H
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One More
C C C C C
H H H
H H H
HH
CH H
H
H
CH H
CH H
H
CH H
H
CH
H
Shorthand notation?
Name?
3-ethyl-2,4 dimethyl hexane
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So is that it?
• Not even close!!
• There are literally
millions of different
organic compounds.
• What else can we do
to make things more
complicated?
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Rings
• Thus far we have dealt
with chains that are
straight or branched.
• If hydrocarbons are
long enough, one end
can wrap around and
link up with itself!
• We call these cyclic
hydrocarbons.
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Cyclic Hydrocarbons
• Name the molecule as
normal
• Add the prefix cyclo-
to the front of the
name of the longest
chain
• Start numbering from
the most “important”
branch in the ring
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Examples
Cyclohexane
Cyclooctane
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More Examples
Methyl cyclopentane
1,2 dimethyl
cyclohexane
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Try These
1 ethyl, 3 methyl
cyclobutane
3 methyl, 1 propyl
cylclohexane
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Multiple Bonds
• So far, even with the cyclic structures we have dealt only with single bonds
• Carbon can make multiple bonds to another carbon
• This changes the name
• Why?
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Examine Structures
C
H
H
C
H
H
H H C2H6Ethane- notice that each
carbon has four bonds
What will happen to the structure if we double bond the two carbons?
C
H
C
H
H H
C2H4Each carbon still has four
bonds BUT now the
hydrogens have changed!!
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Naming molecules with multiple
bonds• Name the molecule as
normal
• Change the suffix of the
longest chain name
• Double bonds = ene
• Triple bonds = yne
• Use numbering and
prefixes for positioning
and multiple multiple
bonds.
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So….
C
H
H
C
H
H
H H C
H
C
H
H H C CH H
C2H6 C2H4 C2H2
ethane ethene ethyne
![Page 39: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/39.jpg)
Practice
C C C CH H
H H H
H
H
CH H
H
CH
H 3 methyl-1-pentene
H
H
C C C C CH H H H
H H H
H CH
H
CH
H
2-heptene
H
H
C CH
H
H CH
CH
H
1-butene
![Page 40: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/40.jpg)
How about in Shorthand?
Notice the two
lines means the
double bond is
there!
2 pentene
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Practice!
Methyl propene
2,4-dimethyl-2-pentene
3-ethyl-2,4,4-trimethyl-1-pentene
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Tough Ones
2 methyl 1,3 butadiene
1,2 dimethyl-1,4 cyclohexadiene
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Triples?
3, 3-dimethyl-1-butyne
1,4 cyclohexadiyne
![Page 44: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/44.jpg)
So that’s it, right?
• Not even close, bud.
• All this….all this was
just for two elements,
carbon and hydrogen!!
• We haven’t even dealt
with any of the others,
yet.
![Page 45: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/45.jpg)
Wait!! Don’t jump!!
• Get off that bridge.
• It’s not that bad
provided we arrange
things in an organized
fashion!
![Page 46: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/46.jpg)
Functional Groups
• Nature has done us a favor.
• There are many common groups that we can organized or file into different categories.
• Then we can name them based on these categories.
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Functional Groups
• A group of atoms that, when added to a
hydrocarbon chain, alter the chemical
properties of the chain.
• Just a few different functional groups to
know…
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Functional Groups
• Halogens
• Alcohols
• Ethers
• Aldehydes
• Ketones
• Carboxylic Acids
• Esters
• Amines
• R-F, R-Cl, R-Br, R-I
• R-OH
• R-O-R
• R-COH
• R-CO-R
• R-COOH
• R-COO-R
• R-NH2
![Page 49: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/49.jpg)
Halides
• Fluorides, Chlorides,
Bromides, and Iodides
• Simply name the
molecule as normal
but add the prefix
Fluoro, Chloro,
Bromo, or Iodo as
necessary
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Halides
Cl
Cl
2, 3 dichlorohexane
I
I
3, 3 diiodo-1-pentene
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Alcohols
• R-OH
• Name like normal
except add an –ol
suffix
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AlcoholsOH
OHC
H
H
C
H
H
H
OH
2 propanol
ethanol
1cyclobutenol
![Page 53: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/53.jpg)
Ethers
• R-O-R
• Name two “R” groups
with –yl endings
• End name in ether
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Ethers
ODimethyl ether
O Ethyl methyl ether
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Aldehyde
• R-COH
• This is a carbon to
oxygen double bond
with a hydrogen at the
end.
• Name as normal
except use a “-al”
suffix
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Aldehydes
C
H
H
C
H
H
C
H
H
CH H
O
butanal
C
H
H
C
Cl
Cl
C
H
H
C H
O
C
H
H
H3,3 dichloropentanal
![Page 57: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/57.jpg)
Ketones
• R-CO-R
• This is a carbon to
oxygen double bond
but in the center of a
hydrocarbon chain
rather than the end
• Name as normal but
give it a “-one” suffix
![Page 58: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/58.jpg)
Ketones
propanone
2 hexanone
C
H
H
C
H
H
CH H
O
C
H
H
C
H
H
C
H
H
C
O
C
H
H
H C
H
H
H
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Carboxylic Acids
• R-COOH or R-CO2H
• This is a carbon to
oxygn double bond
with the same carbon
single-bonded to an
OH group.
• Name as normal
except give it the
suffix “-anoic acid”.
HC
2 H3 O
2
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Carboxylic Acids
C
H
H
C
H
H
C
H
H
CH OH
O
Butanoic acid
C
H
H
C
H
H
FC
O
HO 3-Fluoropropanoic acid
![Page 61: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/61.jpg)
Esters
• R-COO-R
• This is a carbon to oxygen
double bond with a carbon
to oxygen single bonded
to another single bonded
carbon
• Name by given secondary
branch “-yl” suffix and
main branch “-anoate”
suffix.
![Page 62: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/62.jpg)
Esters
C
H
H
C
H
H
C
H
H
C
O
C
H
H
H C
H
H
HO
Secondary
BranchMain Branch
methylpentanoate
Methyl Pentanoate
![Page 63: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/63.jpg)
Esters
C
H
H
H C
H
H
C
O
C
H
H
O C
H
H
HC
H
H
C
H
H
Butyl propanoate
C
H
H
H O
H
H
C
O
C
H
H
C C
H
H
HC
H
H
C
H
H
Methyl hexanoate
![Page 64: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/64.jpg)
Amines
• R-NH2
• Name the “R” group
or groups with “-yl”
endings
• Add the word “amine”
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Amines
C
H
H
N
H
H
H Methyl amine
C
H
H
N
C
H
H
HH
H Dimethyl amine
![Page 66: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/66.jpg)
Summary
ClR
Halide
OHR
Alcohol
RR O
Ether
HR C
Aldehyde
O
RR C
Ketone
O
OHR CCarboxylic
Acid
O
OR CEster
O
R NH2R
Amine
![Page 67: Organic Naming Rules - badipillalubadipillalu.weebly.com/uploads/2/3/0/9/23097860/doc-20161109-wa0006-1.pdfWhy Do We Need a Separate Set of Rules? • Examine some typical organic](https://reader033.fdocuments.in/reader033/viewer/2022041508/5e269e0183665b20e92bc40d/html5/thumbnails/67.jpg)
• Alkanes
• Alkenes
• Alkynes
• Halides
• Alcohols
• Ethers
• Aldehydes
• Ketones
• Carboxylic Acids
• Esters
• Amines
Summary
• - “-ane”
• = “-ene”
• “-yne”
• R-X “-o”
• R-OH “-ol”
• R-O-R “-yl ether”
• R-COH “-al”
• R-CO-R “-one”
• R-COOH “-anoic acid”
• R-COO-R “-yl” “-anoate”
• R-NH2 “-yl amine”
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Can You Do This?
• YES!
• It takes:
• Memorization
• Practice
• Practice
• Practice
• Practice
• And, oh yes…
• Practice!