Organic Chemistry
Long-Chained Carbon Molecules and
Basic Functional Groups
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.
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
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
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
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
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
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-
AlkanesAll hydrogen and carbons with only single bonds
End with “-ane” suffix.
methane
1C
H
H
HH
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
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
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
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
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
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
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
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
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
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
10 9 8
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
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).
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).
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
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
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
AlkynesAll hydrogen and carbons with single bonds and some
carbon-carbon triple bonds. End with “-yne” suffix.
ethyneethyne
1 2 1 2CCH H
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
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).
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).
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).
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).
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
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
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
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
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
NeFONCBBe
He
Li
H
Kr
ArCl
Br
XeI
SPSiMg Al
Ca
Na
K
NeFONCBBe
He
Li
H
Kr
ArCl
Br
XeI
SPSiMg Al
Ca
Na
K
4 e– in valence shell
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-
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