organic chemistry long-chained carbon molecules and basic functional groups
TRANSCRIPT
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Organic Chemistry
Long-Chained Carbon Molecules and
Basic Functional Groups
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Standards10. The bonding characteristics of carbon allow the formation of many different organic
molecules of varied sizes, shapes, and chemical properties and provide the biochemical basis of life. As a basis for understanding this concept:
10. b. Students know the bonding characteristics of carbon that result in the formation of a large variety of structures ranging from simple hydrocarbons to complex polymers and biological molecules.
10. d.* Students know the system for naming the ten simplest linear hydrocarbons and isomers that contain single bonds, simple hydrocarbons with double and triple bonds, and simple molecules that contain a benzene ring.
10. e.* Students know how to identify the functional groups that form the basis of alcohols, ketones, ethers, amines, esters, aldehydes, and organic acids.
10. f.* Students know the R-group structure of amino acids and know how they combine to form the polypeptide backbone structure of proteins.
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Lewis Dot Shorthand• Each corner (or endpoint) is a carbon atom. Carbon
normally has 4 bonds. • Single bonds with hydrogen atoms are not shown they
are implied.
C
H
H
C
H
H
H
C
H
H
H
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Lewis Dot Shorthand• Each corner (or endpoint) is a carbon atom. Carbon
normally has 4 bonds. • Single bonds with hydrogen atoms are not shown they
are implied.
C
H
H
C
H
H
H
C
H
O
H
H OH
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Lewis Dot Shorthand• Each corner (or endpoint) is a carbon atom. Carbon
normally has 4 bonds. • Single bonds with hydrogen atoms are not shown they
are implied.
C
H
C
H
H
H
C Cl
H
Cl
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Lewis Dot Shorthand• Each corner (or endpoint) is a carbon atom. Carbon
normally has 4 bonds. • Single bonds with hydrogen atoms are not shown they
are implied.
C
HH
C
H
H C
H
H
C
HH
C
H
H C
H
H
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Lewis Dot Shorthand• Each corner (or endpoint) is a carbon atom. Carbon
normally has 4 bonds. • Single bonds with hydrogen atoms are not shown they
are implied.
C
H
CH
CH
C
H
CH
CH
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Organic Chemistry PrefixesHow many Carbons does it have in a row?
(the longest continual chain)
# of Carbons Prefix6 hex-7 hept-8 oct-9 non-
10 dec-
# of Carbons Prefix1 meth-2 eth-3 prop-4 but-5 pent-
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AlkanesAll hydrogen and carbons with only single bonds
End with “-ane” suffix.
methane
1C
H
H
HH
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AlkanesAll hydrogen and carbons with only single bonds
End with “-ane” suffix.
C
H
H
C
H
H
H
C
H
H
Hpropane
propane
1 32
1 32
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Alkyl- GroupsSometimes there is an extra branch coming off
of the main carbon chain.
3-methyl pentane
1 32 4
5
The number comes from the carbon (with the lowest number) that has the feature (aka functional group).
# of Carbons Name1 methyl2 ethyl3 propyl4 butyl5 pentyl
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Alkyl- GroupsSometimes there is an extra branch coming off
of the main carbon chain.
3-ethyl pentane
1 32 4
5
The number comes from the carbon (with the lowest number) that has the feature (aka functional group).
# of Carbons Name1 methyl2 ethyl3 propyl4 butyl5 pentyl
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Alkyl- GroupsSometimes there is an extra branch coming off
of the main carbon chain.
2-methyl 3-ethyl pentane
1 32 4
5
The number comes from the carbon (with the lowest number) that has the feature (aka functional group).
# of Carbons Name1 methyl2 ethyl3 propyl4 butyl5 pentyl
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Alkyl- GroupsSometimes there is an extra branch coming off
of the main carbon chain.
2, 3-dimethyl pentane
1 32 4
5
The number comes from the carbon (with the lowest number) that has the feature (aka functional group).
# of Carbons Name1 methyl2 ethyl3 propyl4 butyl5 pentyl
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Alkyl- GroupsSometimes there is an extra branch coming off
of the main carbon chain.
2, 3, 4-trimethyl pentane
1 32 4
5
The number comes from the carbon (with the lowest number) that has the feature (aka functional group).
# of Carbons Name1 methyl2 ethyl3 propyl4 butyl5 pentyl
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PracticeColor the longest continuous carbon chain (turning is okay, not splitting). Do not color the hydrogens.
H
H
HHC
H
HH
HH
C
H
H
CC CH
H
H
C
C
C
HH
H
H
C
H
H
H CH
H C
H
HH
H
C C H
5-propyl decane
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PracticeColor the longest continuous carbon chain (turning is okay, not splitting). Do not color the hydrogens.
H
H
HHC
H
HH
HH
C
H
H
CC CH
H
H
C
C
C
HH
H
H
C
H
H
H CH
H C
H
HH
H
C C H
5-propyl decane
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PracticeColor the longest continuous carbon chain (turning is okay, not splitting). Do not color the hydrogens.
H
H
HHC
H
HH
HH
C
H
H
CC CH
H
H
C
C
C
HH
H
H
C
H
H
H CH
H C
H
HH
H
C C H
5-propyl decane
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PracticeColor the longest continuous carbon chain (turning is okay, not splitting). Do not color the hydrogens.
H
H
HHC
H
HH
HH
C
H
H
CC CH
H
H
C
C
C
HH
H
H
C
H
H
H CH
H C
H
HH
H
C C H
5-propyl decane
10 carbonson main chain
= decane
3 carbonson branch= propyl
Off #5 Carbon
7
1
5
3
6
4
2
109 8
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AlkenesAll hydrogen and carbons with single bonds and some
carbon-carbon double bonds. End with “-ene” suffix.
ethene
1
ethene
21
2C
H
HC
H
H
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AlkenesAll hydrogen and carbons with single bonds and some
carbon-carbon double bonds. End with “-ene” suffix.
2-butene2-butene
1 421 3
2C
H
C
H
H
H
C
H
H
HC
H
34
The number comes from the carbon (with the lowest number) that has the feature (aka functional group).
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AlkenesAll hydrogen and carbons with single bonds and some
carbon-carbon double bonds. End with “-ene” suffix.
1-butene1-butene
1 421 3
2C
H
CH
H
H
C
H
H
HC
H
34
The number comes from the carbon (with the lowest number) that has the feature (aka functional group).
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AlkenesAll hydrogen and carbons with single bonds and some
carbon-carbon double bonds. End with “-ene” suffix.
2, 4-hexadiene
1 32 4
The number comes from the carbon (with the lowest number) that has the feature (aka functional group).
65
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AlkenesAll hydrogen and carbons with single bonds and some
carbon-carbon double bonds. End with “-ene” suffix.
1, 3-hexadiene
1 32 4
The number comes from the carbon (with the lowest number) that has the feature (aka functional group).
65
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Alkenes with Alkyl GroupsAll hydrogen and carbons with single bonds and some
carbon-carbon double bonds. End with “-ene” suffix.
2-methyl 1, 3-hexadiene
1 32 4
The number comes from the carbon (with the lowest number) that has the feature (aka functional group).
65
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AlkynesAll hydrogen and carbons with single bonds and some
carbon-carbon triple bonds. End with “-yne” suffix.
ethyneethyne
1 2 1 2CCH H
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AlkynesAll hydrogen and carbons with single bonds and some
carbon-carbon triple bonds. End with “-yne” suffix.
propynepropyne
1 2 1 323CCH C
H
H
H
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AlkynesAll hydrogen and carbons with single bonds and some
carbon-carbon triple bonds. End with “-yne” suffix.
1 - pentyne
1
32 4
5
The number comes from the carbon (with the lowest number) that has the feature (aka functional group).
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Alkynes with Alkyl GroupsSometimes there is an extra branch coming off
of the main carbon chain.
3-methyl 1-pentyne
1
32 4
5
The number comes from the carbon (with the lowest number) that has the feature (aka functional group).
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AlcoholsJust like an alkane, except they have an –OH
functional group hanging somewhere. End with “-anol” suffix.
1-propanol
1-propanol1 3
2 1 32
C
H
H
C
H
H
H
C
H
O
H
H HO
The number comes from the carbon (with the lowest number) that has the feature (aka functional group).
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AlcoholsJust like an alkane, except they have an –OH
functional group hanging somewhere. End with “-anol” suffix.
2-propanol2-propanol
1 32
1 32C
H
H
C
H
H
H
C
HO
H
H
HO
The number comes from the carbon (with the lowest number) that has the feature (aka functional group).
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KetonesThey have an =O functional group hanging
somewhere in the middle of the carbon chain. End with “-anone” suffix.
acetone
acetone1 3
2 1 32
CH C
H
H
H
C
HO
H
O
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KetonesThey have an =O functional group hanging
somewhere in the middle of the carbon chain. End with “-anone” suffix.
3-pentanone
1 32
The number comes from the carbon (with the lowest number) that has the feature (aka functional group).
O
45
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KetonesThey have an =O functional group hanging
somewhere in the middle of the carbon chain. End with “-anone” suffix.
2-pentanone
1 32
The number comes from the carbon (with the lowest number) that has the feature (aka functional group).
O
45
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AldehydesThey have an =O functional group hanging at the end
of the carbon chain. End with “-anal” suffix.
propanal
propanal
1 32
1 32
C
HH C
HC
H
OH
H
O
H
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R- GroupsR- Groups are a generic way of saying that there is some kind of larger carbon chain attached (even
though we won’t specify what it is).
aldehydeR
CH
O
RC
R’
O
ketoneR
COH
O
carboxalic acid
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NeFONCBBe
He
Li
H
Kr
ArCl
Br
XeI
SPSiMg Al
Ca
Na
K
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NeFONCBBe
He
Li
H
Kr
ArCl
Br
XeI
SPSiMg Al
Ca
Na
K
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4 e– in valence shell
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Organic Chemistry PrefixesHow many Carbons does it have in a row? (the longest continual chain)
# of Carbons Prefix # of Carbons Prefix1 meth- 6 hex-2 eth- 7 hept-3 prop- 8 oct-4 but- 9 non-5 pent- 10 dec-
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Finish• How many Cs and Hs in benzene, show abbreviated hexagon. (only for alkanes?)• Number of carbon prefixes: 1-10 (done)• Meth-, eth-, prop-, but-, pent-, hex-, hept-, oct-, non-, dec- (done)• Alkanes, alkene, alkynes, alcohols, ethers?, ketones, aldehydes, amino acids (nope?)• What do R groups stand for
C
HH
C
H
H C
H
H
C
HH
C
H
H C
H
H