organic chemistry(ex: methane, propane, etc.) 2. number the chain consecutively, starting at the end...
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Organic Chemistry
Nomenclature:
Alkanes
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Alkanes
• Hydrocarbon chains where all the bonds
between carbons are SINGLE bonds
• Name uses the ending –ane
• Examples: Methane, Propane, Butane,
Octane, 2-methylpentane
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• For straight chain hydrocarbons. The prefix indicates
the number of carbon atoms.
• The suffix -ane is added to designate that the
compound is an alkane
• General Formula: CnH2n+2
Naming Alkanes
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Prefixes for # of Carbons
1 Meth 6 Hex
2 Eth 7 Hept
3 Prop 8 Oct
4 But 9 Non
5 Pent 10 Dec
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• Alkenes have one (or more) carbon to carbon double bonds
• When there are 4 or more carbon atoms in a chain, the location of the double bond is indicated by a number.
• Numbering the location of the double bond(s) takes precedence over the location of side chains
• General Formula: CnH2n
Alkenes
1 butene 2-butene methylpropene
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• Alkenes have one (or more) carbon to carbon triple bonds
• When there are 4 or more carbon atoms in a chain, the location of the double bond is indicated by a number.
• Numbering the location of the triple bond(s) takes precedence over the location of side chains
• General Formula: CnH2n-2
Alkynes
1 butene 2-butene methylpropene
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• For branched chain hydrocarbons, identify the longest
consecutive (straight) chain first. Then name the side
chains or branches.
• The name of the branches end in “yl” and go before
the name of the straight chain
Naming Alkanes with
branched chains
-methylpropane
methyl butane
dimethyl propane
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Summary: IUPAC Rules for Branched
Alkane Nomenclature
1. Find and name the longest continuous carbon chain. This is called the parent chain. (Ex: methane, propane, etc.)
2. Number the chain consecutively, starting at the end nearest an attached group (alkyl or substituent).
3. Identify and name groups attached to this chain. (Examples: methyl-, bromo-, etc.)
4. Designate the location of each substituent group with the number of the carbon parent chain on which the group is attached. Place a dash between numbers and letters. (Example: 3-chloropentane)
5. Assemble the name, listing groups in alphabetical order. The prefixes di, tri, tetra etc., used to designate several groups of the same kind, are not considered when alphabetizing. Place a comma between multiple numbers. (Example: 2,3-dichloropropane)
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Step 1. Find the parent chain.
• Where is the longest continuous chain of
carbons?
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Step 2. Number the parent chain.
• Number the parent chain so that the
attached groups are on the lowest
numbers
1 2 3 4 5
Methyl is on carbon #2 of the parent chain
5 4 3 2 1
Methyl is on carbon #4 of the parent chain
GREEN is the right
way for this one!
1 2
3 7 8
4 5 6
8 7
6 2 1
5 4 3
Groups on 2, 3, and 5
Groups on 4, 6, and 7
1 2 3 4 5 6
7
Groups on 2 and 5
7 6 5 4 3 2
1
Groups on 3 and 6
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Step 3. Name the attached groups.
• Carbon (alkyl) groups: – Methyl CH3 -
– Ethyl CH3CH2-
– Propyl CH3CH2CH2 – (if connected by center carbon, it is ISOPROPYL)
• Substituents: (we’ll discuss later) – Halogens
• Fluoro (F-)
• Chloro (Cl-)
• Bromo (Br-)
• Iodo (I-)
– Functional Groups
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Step 4. Designate where the group
is attached to the parent chain.
• Use the numbers of the parent chain from
step 2 to designate the location of the
attached groups to the parent chain.
1 2 3 4 5
2-methyl
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Step 5. Alphabetize the groups, combine like
groups, and assemble.
• The prefixes di, tri, tetra etc., used to designate several
groups of the same kind. ***Prefixes are not considered
when alphabetizing (Example: dimethyl = m for
alphabetizing)
• Parent chain goes LAST
2-methyl pentane
5-ethyl, 2,3-dimethyl octane
5-isopropyl-2-methyl heptane
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Structural Formulas
• “Lazy” way to write the Hydrogens
• Instead of drawing the bonds, just state
how many hydrogens are attached
• NOTE: The bonds are between
CARBONS in a parent chain, and not
hydrogens!
Condensed
Structural Formula Lewis Structure
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Draw Some Simple Alkanes
• 2-methylpentane
• 3-ethylhexane
• 2,2-dimethylbutane
• 2,3-dimethylbutane
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Types of Carbon Atoms
• Primary carbon (1o)
– a carbon bonded to
one other carbon
• Secondary carbon (2o)
– a carbon bonded to
two other carbons
• Tertiary carbon (3o)
– a carbon bonded to
three other carbons
C
C
C
C
H
H
H
C C
H
H
C
C
C
H
C
C
C
C
H
H
H
C C
H
H
C
C
C
H
C
C
C
C
H
H
H
C C
H
H
C
C
C
H
C
C
C
C
H
H
H
C C
H
H
C
C
C
H
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Isomers
• Straight chain alkanes: An alkane that has all its carbons connected in a row.
• Branched chain alkanes: An alkane that has a branching connection of carbons.
• Isomers: Compounds with same molecular formula but different structures.
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• There is only one possible way that the
carbons in methane (CH4), ethane (C2H6),
and propane (C3H8) can be arranged.
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• However, carbons in butane (C4H10) can be arranged in two ways; four carbons in a row (linear alkane) or a branching (branched alkane). These two structures are two isomers for butane.
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•Different isomers are completely different
compounds. They have different structures,
different physical properties such as melting point
and boiling point, and may have different
physiological properties.
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Learning Check
• Draw all possible structural isomers of C5H12
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Alkanes
Example: Name the following compounds:
CH3
CH3CH(CH
3)2CH
2CH
2Br
CH3
CH CH CH2
CH CH3
CH2CH
3C
CH
CH3
CH3
CH3
CH3
CH3
C CH2
CH2Br
CHCH3
CH2CH
3
CH3
CH3
CH CH CH2
CH CH3
CH2CH
3C
CH
CH3
CH3
CH3
CH3
CH3
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Alkanes
Example: Write the condensed
structure for the following compounds:
3,3-dimethylpentane
4-sec-butyl-2-methyloctane
1,2-dichloro-3-methylheptane
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Naming Compounds With
Functional Groups • Various functional groups have unique suffixes that
designate the functional group.
• The functional group takes precedence in
numbering the carbon chain.
• Branches to the carbon chain are named in the
usual manner.
alcohols “ol” Amides “amide”
Aldehydes “al” Amines “amine” or amino as a prefix
Ketones “one” Ethers Ethoxy as prefix
Acids “oic” halohydrocarbons Fluoro, bromo, chloro or
iodo
Esters “oate” 27
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Alcohols
Suffix = “ol” 1- Propanol
2- Propanol
2-methyl-2-propanol
28
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Suffix = “al”
Propanal
Note that the
aldeyhde group is
always on an end
carbon or carbon 1
Aldehydes
29
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Suffix = “one”
Propanone
(also known as acetone)
Butanone
(also known as methyl ethyl ketone)
2-Pentanone
(note the number is necessary
Because the C=O could be on carbon
2 or carbon 3)
Ketones
30
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Suffix = “oic”
Butanoic acid
Note that the acid group
(called a “carboxyl”) is
always on an end carbon
or carbon 1
Carboxylic Acids
31
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Suffix = “oate”
Ethyl butanoate
Butyl ethanoate
There are two branches. The
branch with the carbonyl gets
the suffix
Esters
32
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Suffix = “amide”
butanamide
Note that the amide group is
always on an end carbon or
carbon 1
Amides
33
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Suffix = “amine”
Or prefix = “amino”
Propylamine or 1-aminopropane
2-propylamine or 2-aminopropane
2-methyl-2-propylamine or
2-methyl -2- aminopropane
Amines
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prefixes = “fluoro,
chloro, bromo,
iodo”
1-bromopropane
2 chlorobutane
1,2 diiodoethane
Cis 1,2difluroethene
Trans 1,2 difluoroethene
1,1,2 trifluorothene
Halohydrocarbons
35
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Suffix = “oxy”on first branch
Ethoxyethane
(diethylether)
Ethoxybutane
(ethylbutyl ether)
Ethers
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Aromatic Compounds With
Functional Groups
Benzoic acid
2 hydroxybenzoic acid
3 bromobenzoic acid
37
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Nitriles
38
Nitriles have a cyanide group. The
name is based on the longest carbon
chain that includes the carbon atom in
the nitrile group.
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Order of Priority
• IN A TIE, halogens get the lower number
before alkyl groups
4-chloro-2-methylpentane or
2-chloro-4-methylpentane?
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Order of Priority
• IN A TIE between SIMILAR GROUPS, the
group lower ALPHABETICALLY gets the
lower number
4-bromo-2-chloropentane or
2-bromo-4-chloropentane ?