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