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Organic Nomenclature
Organic Compounds
• Organic Compounds - any covalently bonded
compound containing carbon (except
carbonates and oxides)
Organic Compounds
 Contain carbon
 Have covalent bonds
 Have low melting points
 Have low boiling points
 Burn in air (oxygen)
 Are soluble in nonpolar solvents
 Form large molecules
General Characteristics of Organic
Molecules
• Organic molecules exhibit three different types of
hybridization at the carbon center:
– sp3 hybridized carbons for tetrahedral geometries;
– sp2 hybridized carbons for trigonal planar geometries; and
– sp hybridized carbons for linear geometries.
Stabilities of Organic Molecules
• Carbon forms very strong bonds between H, O, N,
and halogens.
• Carbon also forms strong bonds with itself.
• Therefore, C can form stable long chain or ring
structures.
• Bond strength increases from single to double to
triple bond.
• Bond length decreases in the same direction.
Hydrocarbons
• Hydrocarbons - Organic compounds that
contain only carbon & hydrogen
• Alkanes - contain only single covalent bonds
• Alkenes - contain one or more carbon - carbon
double bond
• Alkynes - contain one or more carbon-carbon
triple bond
Saturated & Unsaturated Hydrocarbons
• Saturated hydrocarbons – contain only single
carbon-carbon bonds (alkanes)
• Unsaturated hydrocarbons – contain double
carbon-carbon bonds (alkenes) or triple
carbon-carbon (alkynes) bonds
Formulas
• Alkanes = CnH2n+2
• Alkenes = CnH2n
• Alkynes = CnH2n-2
Nomenclature
• Must memorize prefixes
• To name, look at the
formula for the
hydrocarbon
• Determine if it is an alkane,
alkene, or alkyne
• Use the prefix for the
number of carbons
• Add ending (ane, ene, yne)
Prefix
# of carbon
atoms
Meth-
1
Eth-
2
Prop-
3
But-
4
Pent-
5
Hex-
6
Hept-
7
Oct-
8
Non-
9
Dec-
10
Example
•
•
•
•
•
•
Name C3H8
This falls under the equation CnH2n+2
Therefore it is an alkane
Since n=3 we will use the prefix prop
Since it is an alkane we will use the ending ane
propane
Alkanes
 Contain C and H only
 Contain single bonds
C-C
 Have 4 bonds to every carbon (C) atom
 Are nonpolar
Complete Structural Formulas
Show the bonds between each of the atoms
H
H

HCH
H C H

H
H
CH4 , methane
Drawing structures: it’s all good
H
2-butene
C
CH
H
H
3
H
C
C
C
C
H
H
H
H
H3C
H
C
H
CH
H3C
CH3
CH
CH3
H3C CH CH CH3
H3C
This is called the
“condensed structure” On a test, choose a
method that shows all Hs
CH3CH=CHCH3
Using brackets can also shorten some formulas:
CH3(CH2)4CH3 vs. CH3CH2CH2CH2CH2CH3
More Alkanes
H
H C
H
H
C H
H
Condensed Structural Formulas
CH3 CH3
Ethane
H H H
H
C C C H
H
H H
CH3 CH2 CH3
Propane
IUPAC Names
Name
# carbons
Structural Formula
Methane 1
CH4
Ethane
2
CH3CH3
Propane
3
CH3CH2CH3
Butane
4
CH3CH2CH2CH3
Pentane
5
CH3CH2CH2CH2CH3
Naming: common vs. IUPAC
• Common names used in the 1800’s are still
used for some compounds today:
O
O
H
C
H
OH
Formic acid
C
C
Acetylene
H
C
H3C
CH3
Acetone
• The International Union of Pure and Applied
Chemistry (IUPAC) was established in 1900s
• Frequent revisions to nomenclature
• Systematic method allows an infinite number
of compounds to be named given a few rules
IUPAC NAMES
Name # carbons
Structural Formula
Hexane 6
CH3CH2CH2CH2CH2CH3
Heptane 7
CH3CH2CH2CH2CH2CH2CH3
Octane 8
CH3CH2CH2CH2CH2CH2CH2CH3
Nonane 9
CH3 CH2 CH2CH2CH2CH2CH2CH2CH3
Decane 10 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3
Learning Check Alk1
A. What is the condensed formula for
H H H H
H
C C C C
H
H H H H
B. What is its molecular formula?
C. What is its name?
Solution Alk1
A.
CH3CH2CH2CH3
B.
C4H10
C.
butane
Example
•
•
•
•
Name C5H12
5 carbons = pent
CnH2n+2 = alkane (ane)
pentane
• Alkenes and Alkynes
– Alkenes are hydrocarbons with at least one double
carbon to carbon bond.
• To show the presence of the double bond, the –ane
suffix from the alkane name is changed to –ene.
– The alkenes are unsaturated with respect to hydrogen
• This means it does not have the maximum number of
hydrogen atoms as it would if it were an alkane (a
saturated hydrocarbon).
– Naming is similar to naming alkanes except:
• The longest continuous chain must contain the
double bond.
• The base name now ends in –ene.
• The carbons are numbered so as to keep the number
for the double bond as low as possible.
• The base name is given a number which identifies the
location of the double bond.
– An alkyne is a hydrocarbon with at least one carbon to
carbon triple bond.
– Naming an alkyne is similar to the alkenes, except the
base name ends in –yne.
Alkenes
Carbon-carbon double bonds
Names end in -ene
H2C=CH2
H2C=CH-CH3
ethene (ethylene)
propene (propylene)
cyclohexene
Alkynes
Carbon-carbon triple bonds
Names end in -yne
HCCH
HCC-CH3
ethyne(acetylene)
propyne
Naming Alkenes and Alkynes
When the carbon chain has 4 or more C atoms, number
the chain to give the lowest number to the double or
triple bond.
1
2 3 4
CH2=CHCH2CH3
CH3CH=CHCH3

CH3CH CHCH3
1-butene
2-butene
2-butyne
Numbering carbons
Q- draw pentene
A- Where’s the bond? H C
3
5
1
We number C atoms
H
H
1-pentene
C
C
C
C
H
H
H
H
4
2
3
2
4
1
5
H
• Thus, naming compounds with multiple bonds
is more complex than previously indicated
• Only if 2+ possibilities exist, are #s needed
• Always give double bond the lowest number
• Q - Name these
H
C 2H 4
H3 C
C
2-butene
C
CH3
Ethene
H
H3C
CH3 3-nonyne
Multiple multiple bonds
H 3C
CH3 2,3-heptadiene
H3C
C
C
C
C
C
C
2,4,6-nonatriyne
•
•
•
•
CH2
CH3
Give 1st bond (1st point of difference) lowest #
include di, tri, tetra, penta, etc. before ene/yne
Comma between #s, hyphen between #-letter
You do not need to know ene + yne
H
H
C
H
C
C
C
HC
2-butyne
H
H2C
C
CH2
CH
1,2,4-pentatriene
CH3CH2CH2CH=C=CH2 1,2-hexadiene
H
H
Cyclic structures
H
H
H
H
C
C
C
H
• Cyclic structures are circular
C C
• Have “cyclo” in name
H
H
H
H
• Benzene is not a cyclic structure
• cyclopentane
Q- Draw these (note: carbons in a double bond
should be consecutive- 1 and 2, 5 and 6, etc.):
cyclobutene 1,3-cyclopentadiene cyclopropane
H
Naming side chains
CH
CH
3
H
H3C
C
• Names are made up
of: side chains, root
• 2,3-dimethylpentane
C
H3
CH
• Root is the longest possible HC chain
• Must contain multiple bonds if present
• Add -yl to get name of side chain H C
3
• Common side chains include:
CH
CH3- methyl
CH3CH2ethyl
*
CH3CH2CH2- propyl (CH3)2CHisopropyl
• “iso” (branched) is not an IUPAC convention
• Br- (bromo), Cl- (chloro), F- (fluoro), I- (iodo)
C H3
CH
CH3
Naming side chains
Example: use the rules on the bottom of
handout to name the following structure
CH2
CH3 CH2 C
CH2 CH3
CH2 C
CH3
CH3
Rule 1: choose the correct ending
ene
Naming side chains
CH2
CH3 CH2 C
CH2 CH3
CH2 C
CH3
CH3
Rule 2: longest carbon chain
ene
Naming side chains
CH2
CH3 CH2 C
CH2 CH3
CH2 C
CH3
CH3
Rule 3: attach prefix (according to # of C)
1-hexene
ene
Naming side chains
CH2
CH3 CH2 C
CH2 CH3
CH2 C
CH3
CH3
Rule 4: Assign numbers to each carbon
1-hexene
Naming side chains
CH2
CH2 CH3
1
CH3 CH2 C
2
5
CH2 C
3
4
6
CH3
CH3
Rule 4: Assign numbers to each carbon
1-hexene
Naming side chains
ethyl
CH2
CH2 CH3
1
CH3 CH2 C
2
5
6
CH2 C
3
CH3
methyl
4
CH3
methyl
Rule 5: Determine name for side chains
1-hexene
Naming side chains
ethyl
CH2
CH2 CH3
1
CH3 CH2 C
2
5
CH2 C
3
4
CH3
6
CH3
methyl
methyl
Rule 6: attach name of branches
2-ethyl-4,4-dimethyl-1-hexene
Learning Check HA3
Write the IUPAC name for each of the following
unsaturated compounds:
A.CH3CH2CCCH3
CH3
CH3
B.
CH3C=CHCH3
C.
Solutions HA3
Write the IUPAC name for each of the following
unsaturated compounds:
A.CH3CH2CH=CHCH3
2-pentyne
CH3
CH3
B.
CH3C=CHCH3
2-methyl-2-butene
C.
3-methylcyclopentene
Alkyl Groups
Branches on carbon chains
H
H C
CH3
methyl
H
H H
H C
C
H H
CH3CH2
ethyl
Branched Alkanes
CH3
CH3CHCH3
methyl groups
CH3
CH3
CH3CHCH2CHCH3
Naming Branched Alkanes
CH3 methyl branch
CH3CH2CH2CHCH2CH3
6
5
4
3
2
1
Count
Naming Branched Alkanes
CH3 methyl branch
CH3CH2CH2CHCH2CH3
6
5
4 3 2 1
Count
3-Methylhexane
on third C
CH3
six carbon chain
group
IUPAC
• Carbon chains need to be numbered in order
to designate the carbon atom that the
substituted group is added.
• Follow these guidelines:
– Find the longest continuous carbon chain
– Number the chain so the substituent's have the
lowest possible number.
– Give priority to the multiple bonds.
Numbering priority
• 1. functional groups
• 2. double and triple bonds
• 3. substituents
• Once all groups have been numbered, place
them in alphabetical order in the final
compounds name.
• Numbers are separated by commas
• Names and numbers are separated by dashes.
• Use mathematical prefixes for multiple
substituent's.
• Ex:
• CH3CH2CHClCH2CH=CHCHBrCH3
• 2-bromo-6-chloro-3-octene
Learning Check Alk4
A.
CH3
CH3
CH3CHCH2CHCH3
B.
CH3
CH3
CH3CH2CHCH2CCH2CH3
CH3
Solution Alk4
A.
CH3
CH3
CH3CHCH2CHCH3
B.
CH3
2,4-dimethylpentane
CH3
CH3CH2CHCH2CCH2CH3
CH3
3,3,5-trimethylheptane
Learning Check Alk5
Write a condensed structure for
A.
3,4-dimethylheptane
B.
2,2-dimethyloctane
Solution Alk5
A. 3,4-dimethylheptane
CH3
CH3CH2CHCHCH2CH2CH3
CH3
B. 2,2-dimethyloctane CH3
CH3CCH2CH2CH2CH2CH2CH3
CH3
Cycloalkanes
Cyclopropane
CH2
CH2
CH2
Cyclobutane
CH2
CH2
CH2
More Cycloalkanes
Cyclopentane
CH2
CH2
CH2
CH2
CH2
Cyclohexane
CH2
CH2 CH2
CH2
CH2
CH2
Naming Cycloalkanes with
Side Groups
Number of Naming side groups
1. Side group name goes in front of the cycloalkane
name.
2. Number the ring in the direction that gives the lowest
numbers to the side groups.
Cycloalkanes with Side Groups
CH3
methylcyclopentane
CH3
CH3
1,2-dimethylcyclopentane
CH3
CH3
1,2,4-trimethylcyclohexane
CH3
Learning Check Alk8
CH 3
CH 3
CH 3
CH 3
CH3
Solution Alk8
CH3
1,2-dimethylcyclobutane
CH3
CH3
methylcyclopentane
CH3
1,3-dimethylcyclohexane
CH3
Aromatic Compounds and Benzene
Aromatic compounds contain benzene.
Benzene, C6H6 , is represented as a six carbon ring
with 3 double bonds.
Two possible can be drawn to show benzene in this
form.
H
H
H
H
H
H
H
H
H
H
H
H
Benzene Structure
The structures for benzene can also be written as a
single structure where the alternating double bonds
are written as a circle within the ring.
Benzene
structure
Aromatic Compounds in Nature and
Health
Many aromatic compounds are common in nature and
in medicine.
CHO
COOH
COOCH3
CH3
CH3
CH3CHCH2
CHCOOH
OCH3
OH
Aspirin
Vanillin
Ibuprofen
Naming Aromatic Compounds
Aromatic compounds are named with benzene as the
parent chain. One side group is named in front of the
name benzene.
CH3
methylbenzene
(toluene)
Cl
chlorobenzene
Naming Aromatic Compounds
When two groups are attached to benzene, the ring is
numbered to give the lower numbers to the side
groups. The prefixes ortho (1,2), meta (1,3-) and para
(1,4-) are also used.
Cl
CH3
Cl
CH3
Cl
1,2-dimethylbenzene
1,3-dichlorobenzene
(ortho-dimethylbenzene)
(meta-dichlorobenzene)
CH3
1-chloro-4-methylbenzene
(para-chloromethylbenzene)
Some Common Names
Some substituted benzene rings also use a common
name. Then naming with additional more side groups
uses the ortho-, meta-, para- system.
CH3
OH
CH3
Cl
Toluene
(Methylbenzene)
meta-chlorotoluene
(meta-chloromethylbenzene)
phenol
(hydroxybenzene)
Learning Check Alk9
Select the names for each structure:
Cl
1. Chlorocyclohexane
2. Chlorobenzene
3. 1-chlorobenzene
CH 3
CH 3
1. Meta-methyltoluene
2. Meta-dimethylbenzene
3. 1,3-dimethylbenzene
Solution Alk9
Select the names for each structure:
Cl
2. Chlorobenzene
CH 3
1. Meta-methyltoluene
2. Meta-dimethylbenzene
3. 1,3-dimethylbenzene
CH 3
Learning Check Alk10
Write the structural formulas for each of the following:
A. 1,3-dichlorobenzene
B. Ortho-chlorotoluene
Solution Alk10
Write the structural formulas for each of the following:
Cl
A. 1,3-dichlorobenzene
B. Ortho-chlorotoluene
Cl
CH3
Cl
Functional Groups
 Part of an organic molecule where chemical



reactions take place
Composed of an atom or group of atoms
Replace a H in the corresponding alkane
Provide a way to classify organic compounds
Functional Groups
Class
Alcohol
Functional group
R – OH
Ether
R — O — R’
Aldehyde
O
||
R—C—H
Ketone
O
||
R — C — R’
Carboxylic acid
O
||
— C — OH
Ester
O
||
R — C — O — R’
Amine
R’
|
R — N — R’’
Some Types of Functional Groups
Haloalkane -F, -Cl, -Br CH3Cl
Alcohol
-OH
CH3OH
Ether
CH3-O-CH3
-O-
O
O
Aldehyde
C H
Ketone
O
O
C
CH3CCH3
CH3CH
More Functional Groups
Carboxylic acid
-COOH
CH3COOH
Ester
-COO-
CH3COOCH3
Amine
-NH2
CH3NH2
Amide
-CONH2
CH3CONH2
Haloalkanes
An alkane in which one or more H atoms is
replaced with a halogen (F, Cl, Br, or I)
CH3Br
1-bromomethane
(methyl bromide)
Br
CH3CH2CHCH3
2-bromobutane
Cl
chlorocyclobutane
Hydrocarbons: Basic Concepts
Topic
27
Organic Compounds Containing
Halogens
• Any organic compound that contains a
halogen substituent is called a halocarbon.
• If you replace any of the hydrogen atoms in
an alkane with a halogen atom, you form an
alkyl halide.
Hydrocarbons: Basic Concepts
Topic
27
Organic Compounds Containing
Halogens
• An alkyl halide is an
organic compound
containing a halogen atom
covalently bonded to an
aliphatic carbon atom.
• The first four halogens—
fluorine, chlorine, bromine,
and iodine—are found in
many organic compounds.
Hydrocarbons: Basic Concepts
Topic
27
Organic Compounds Containing
Halogens
• For example, chloromethane is the alkyl
halide formed when a chlorine atom replaces
one of methane’s four hydrogen atoms.
Hydrocarbons: Basic Concepts
Topic
27
Organic Compounds Containing
Halogens
• An aryl halide is an organic compound
containing a halogen atom bonded to a
benzene ring or other aromatic group.
• The structural formula for an
aryl halide is created by first
drawing the aromatic
structure and then replacing
its hydrogen atoms with the
halogen atoms specified.
Learning Check HA1
Name the following:
Br
Cl
Cl
Solution HA1
Name the following:
Br
bromocyclopentane
Cl
1,3-dichlorocyclohexane
Cl
Substituents
List other attached atoms or group in alphabetical
order
Br = bromo, Cl = chloro
Cl
Br
CH3CHCH2CHCH2CH2CH3
4-bromo-2-chloroheptane
Learning Check HA2
The name of this compound is:
Cl
CH3
CH3CH2CHCH2CHCH3
1)
2,4-dimethylhexane
2)
3-chloro-5-methylhexane
3)
4-chloro-2-methylhexane
Solution HA2
The name of this compound is:
Cl
CH3
CH3CH2CHCH2CHCH3
3) 4-chloro-2-methylhexane
Haloalkanes as Anesthetics
Halothane (Fluothane)
F Cl
F
C
C
Br
F H
Fluothane is a haloalkane that is widely used as an
anesthetic, which is a compound that decreases the
ability of the nerve cells to conduct pain.
Ozone Layer
Ozone layer
Stratosphere
(10-30 miles
Above Earth)
Chlorofuorocarbons (CFCs and the
Ozone Layer
ozone O3 layer absorbs most of the sun’s
harmful radiation.
CFCs - chlorofluorocarbons - are depleting that
ozone layer.
CFCs are used as Freons in refrigeration,
air conditioning, and foam insulation.
Their use in spray cans is no longer allowed.
Alcohols
• Alcohols have a OH group attached to a C
somewhere along the chain.
• The ending changes to “ol”
• If there are 2 OH groups the are referred to as
a “diol”
• The OH group has to be identified using the
IUPAC numbering system
• Ex: CH2ClCHOHCHClCH3
• 1,3-dichloro-2-butanol
Hydrocarbons: Basic Concepts
Topic
27
Alcohols
• An oxygen-hydrogen group covalently bonded
to a carbon atom is called a hydroxyl group
(—OH).
• An organic compound in which a hydroxyl
group replaces a hydrogen
atom of a hydrocarbon is
called an alcohol.
• The general formula for
an alcohol is ROH.
Naming Alcohols
 A carbon compound that contain -OH (hydroxyl)
group
 In IUPAC name, the -e in alkane name is replaced
with -ol.
CH4 methane
CH3OH
CH3CH3
methanol
(methyl alcohol)
ethane
CH3CH2OH ethanol
(ethyl alcohol)
Ethanol CH3CH2OH
 Acts as a depressant
 Kills or disables more people than any other drug
 12-15 mg/dL ethanol metabolized by a social
drinkers in one hour
 30 mg/dL ethanol metabolized by an alcoholic in
one hour.
Alcohol in Some Products
% Ethanol
Product
50%
40%
15-25%
12%
3-9%
Whiskey, rum, brandy
Flavoring extracts
Listerine, Nyquil, Scope
Wine, Dristan, Cepacol
Beer, Lavoris
More Names of Alcohols
 IUPAC names for longer chains number the chain from
the end nearest the -OH group.
CH3CH2CH2OH
1-propanol
OH
CH3CHCH3
CH3
2-propanol
OH
CH3CHCH2CH2CHCH3
5-methyl-2-hexanol
Some Typical Alcohols
OH
“rubbing alcohol”
CH3CHCH3
2-propanol (isopropyl alcohol)
antifreeze HO-CH2-CH2-OH
1,2-ethanediol (ethylene glycol)
OH
glycerol
HO-CH2-CH-CH2OH
Learning Check Al 2
Name the following alcohols:
A.
OH
CH3CHCHCH2CH3
CH3
OH
B.
Solution Al 2
Name the following alcohols:
A.
OH
3-methyl-2-pentanol
CH3CHCHCH2CH3
CH3
OH
B.
cyclobutanol
Reactions of Alcohols
Combustion
CH3OH + 2O2
Dehydration
H OH
CO2 + 2H2O + Heat
H+, heat
H-C-C-H
H-C=C-H + H2O
H H
alcohol
H H
alkene
Aldehydes and Ketones
 In an aldehyde, an H atom is attached to a carbonyl
group
O
carbonyl group

CH3-C-H
 In a ketone, two carbon groups are attached to a
carbonyl group
O

CH3-C-CH3
carbonyl group
aldehydes
• Aldehydes contain a CHO attached to the end
of a carbon chain The C has a double bonded
O and a single bonded H attached to it. Since
it is at the end of a chain there is no need to
number.
• The ending changes to “al”
• Ex: CH3CHICH2CH2CHICHO
• 2,5-diiodohexanal
Naming Aldehydes
 IUPAC Replace the -e in the alkane name -al
 Common Add aldehyde to the prefixes form (1C), acet
(2C), propion(3), and butry(4C)
O
O
O


II
H-C-H
CH3-C-H
CH3CH2C-H
methanal
ethanal
propanal
(formaldehyde) (acetaldehyde) (propionaldehyde)
Aldehydes as Flavorings
O
O
CH
CH
O
CH=CH CH
HO
OCH3
Benzaldehyde
(almonds)
Vanillin
(vanilla beans)
Cinnamaldehyde
(cinnamon)
Glucose is an aldehyde
O
H
C
H
C
OH
HO
C
H
H
C
OH
H
C
OH
CH 2 OH
glucose
Ketones
• Ketones have a C=O bond embedded within a
chain .
• The IUPAC system of numbering applies here
and the “e” of the chain gets replaced with a
“one” ending
•
O
•
║
• Ex: CH3CH2CCH2CH2CH2CH2CH3
• 3-octanone
Naming Ketones
 In the IUPAC name, the -e in the alkane name is
replaced with -one
 In the common name, add the word ketone
after naming the alkyl groups attached to the
O
carbonyl group
O

CH3 -C-CH3
2- Propanone
O
II
CH3-C-CH2-CH3
2-Butanone
(Dimethyl ketone) (Ethyl methyl ketone)
Cyclohexanone
Ketones
OO

Butter flavor
CH3-C-C-CH3 butanedione
O

Clove flavor CH3-C-CH2CH2CH2CH2CH3
2-heptanone
Fructose is a Ketone
CH 2OH
C
HO
O
C H
H
C
OH
H
C
OH
CH 2OH
D-Fructose
Ketones as Hormones
CH2OH
O
CH3
O
OH
CH3
O
Cortisone
Learning Check AK 1
Classify each as an aldehyde (1), ketone (2) or
neither(3).
O
II
A. CH3CH2CCH3
B. CH3-O-CH3
O
CH3 O

C. CH3-C-CH2CH
CH3
D.
Solution AK 1
Classify each as an aldehyde (1), ketone (2) or
neither(3).
O
II
A. CH3CH2CCH3 2
B. CH3-O-CH3 3
CH3 O
O

C. CH3-C-CH2CH 1
CH3
D.
2
Learning Check AK 2
Name the following
O

A. CH3CH2CCH3
CH3 O
II
C. CH3-C-CH2CH
CH3
O
B.
Solution AK 2
O
O

A. CH3CH2CCH3
B.
2-butanone (ethyl methyl ketone)
CH3 O

C. CH3-C-CH2CH
CH3
2,2-dimethylbutanal
cyclohexanone
Learning Check AK 3
Draw the structural formulas for each:
A. 3-Methylpentanal
B. 2,3-Dichloropropanal
C. 3-Methyl-2-butanone
Solution AK 3
Draw the structural formulas for each:
CH3
A. 4-Methylpentanal
O

CH3CHCHCH2CH
Br O

B. 2,3-Dibromopropanal Br-CH2CHCH
O

C. 3-Methyl-2-butanone CH3CHCCH3
CH3
ethers
• Have an O atom within the carbon chain itself.
In other words C-O-C.
• Components of the chain on both sides of the
O have to be named.
• Ethers have the general formula ROR′.
• No numbering system is needed since the
chain is broken.
• The name remains the same just add the
ending ether
Ethers
• The simplest ether is one in which oxygen
is bonded to two methyl groups.
• Note the relationship between methanol and
methyl ether in the following diagram.
Ethers
• Contain an -O- between two carbon groups
• Simple ethers named from -yl names of the
attached groups and adding ether.
CH3-O-CH3
dimethyl ether
CH3-O-CH2CH3
ethyl methyl ether
• Ex: CH3OCH2CH2CH2CH2CH3
• Methyl-n-pentyl ether The “n” signifies that
the carbons are in a straight chain with no
branches.
Ethers as Anesthetics
 Anesthetics inhibit pain signals to the brain
 CH3CH2-O-CH2CH3 used for over a century (Morton, 1846)
 Causes nausea and is highly flammable
 1960s developed nonflammable anesthetics
Cl F F
Cl F H
H-C-C-O-C-H
F F
H-C-C-O-C-H
F
HF
H
Ethane(enflurane)
Penthrane
MTBE
 Methyl tert-butyl ether
CH3
CH3-O-C-CH3
CH3
 Second in production or organic chemicals
 Additive to improve gasoline performance
Carboxylic acids
• These compounds end with a COOH group
where the C has a double bonded O and a
single bonded OH
• The ending of the parent chain changes from
“ane” etc. to “oic” and add the word acid
• Ex: CH3CH2CH2COOH
• Butanoic acid
Carboxyl Group
Carboxylic acids contain the carboxyl group on
carbon 1.
O

CH3 — C—OH =
CH3—COOH
carboxyl group
Naming Carboxylic Acids
Formula
IUPAC
alkan -oic acid
Common
prefix – ic acid
HCOOH
methanoic acid
formic acid
CH3COOH
ethanoic acid
acetic acid
CH3CH2COOH
CH3CH2CH2COOH
propanoic acid
butanoic acid
propionic acid
butyric acid
Naming Rules
• Identify longest chain
• (IUPAC) Number carboxyl carbon as 1
•
•
CH3
|
CH3 — CH—CH2 —COOH
IUPAC
3-methylbutanoic acid
Learning Check CA1
Give IUPAC and common names:
A. CH3COOH
CH3
|
B. CH3CHCOOH
Solution CA 1
A. CH3COOH
ethanoic acid; acetic acid
CH3
|
B. CH3CHCOOH
2-methylpropanoic acid;
Properties
• Carboxylic acids are weak acids
CH3COOH + H2O
• Neutralized by a base
CH3COOH + NaOH
CH3COO– + H3O+
CH3COO– Na+ + H2O
Phenols
 IUPAC name for benzene with a hydroxyl group
 Many are used as antiseptics and disinfectants
OH
Phenol
Phenols in Medicine
OH
OH
OH
OH
OH
CH2CH2CH2CH2CH2CH3
Phenol
Resorcinol
(antiseptic)
4-Hexylresorcinal
(antiseptic)
Compounds with Oxygen
Atoms
Alcohols
-OH hydroxyl
CH3-OH
CH3CH2-OH
OH
OH
Phenols
Ethers
-O-
CH3-O-CH3
Learning Check Al1
Classify each as an alcohol (1), phenol (2), or an ether
(3):
A. _____ CH3CH2-O-CH3 C. _____ CH3CH2OH
OH
B. _____
CH3
Solution Al 1
Classify each as an alcohol (1), phenol (2), or an ether
(3):
A. __3__ CH3CH2-O-CH3 C. __1__ CH3CH2OH
OH
B. _ 2__
CH3
Thiols
 Contain the functional group -SH
 Named by adding thiol to the name of the longest
carbon chain
 Number the -SH group in longer chains
CH3-SH
methanethiol
CH3-CH2SH ethanethiol
SH
CH3-CH-CH3 2-propanethiol
Thiols
 Many thiols have disagreeable odors
 Used to detect gas leak
 Found in onions, oysters, garlic and oysters
Onions CH3CH2CH2-SH 1-propanethiol
Garlic CH2= CHCH2-SH 2-propene-1-thiol
Skunk spray
CH3
trans-2-butene-1-thiol
CH = CH
CH2SH
Amines
• Organic compounds of nitrogen N
• Classified as primary, secondary, tertiary
CH3
CH3


CH3—NH2
CH3—NH
CH3—N — CH3
1°
2°
3°
Naming Amines
IUPAC aminoalkane
CH3CH2NH2
aminoethane
(ethylamine)
Common alkylamine
CH3—NH —CH3
N-methylaminomethane
(dimethylamine)
NH 2
NH CH3
NH2
|
CH3CHCH3
2-aminopropane
(isopropylamine)
Aniline
N-methylaniline
Learning Check AM1
Give the common name and classify:
A. CH3NHCH2CH3
CH3
|
B. CH3CH2NCH3
Solution AM1
A. CH3NHCH2CH3
ethylmethylamine, 2°
CH3
|
B. CH3CH2NCH3
ethyldimethylamine, 3°
Alkaloids
• Physiologically active nitrogen-containing
compounds
• Obtained from plants
• Used as anesthetics, antidepressants, and
stimulants
• Many are addictive
Nicotine
CH3
N
Nicotine, leaves of tobacco plant
Caffeine
O
CH3
O
CH3
N
N
N
N
CH3
Caf f e in e , cof f e e b e an s an d t e a
Procaine
CH3CH2
O
N
CH2CH2 O C
NH2
CH3CH2
Procaine (novocaine), painkiller
Leaning Check AM2
Write a structural formula for
A.
2-aminopentane
B. 1,3-diaminocyclohexane
Solution AM2
A. 1-aminopentane
CH3CH2CH2CH2CH2-NH2
B. 1,3-diaminocyclohexane
NH2
NH2
Amides
Derivatives of carboxylic acids where an
amino (-NH2) group replaces the –OH group.
O
O

CH3 — C—OH
carboxylic acid
acetic acid

CH3 — C—NH2
amide
acetamide
Naming Amides
Alkanamide
O

HC–NH2
O

CH3CH2C–NH2
from acid name
methanamide (IUPAC)
formamide (common)
propanamide (IUPAC)
propionamide(common)
Naming Amides with N-Groups
O

CH3C–NHCH3
N-methylethanamide (IUPAC)
N-methylacetamide (common)
O

CH3CH2C–N(CH3)2
N,N-dimethylpropanamide
N,N-dimethylpropionamide
Aromatic Amides
O
O
C NH2
C NHCH3
Benzamide
N -methylbenzamide
Learning Check AM3
Name the following amides:
O

A.
CH3CH2CH2C–NH2
B.
O

CH3C–N(CH2CH3)2
Solution AM3
O

A. CH3CH2CH2C–NH2
butanamide; butryamide (common)
O

B.
CH3C–N(CH2CH3)2
N,N-diethylethanamide;
N,N-diethylacetamide
Learning Check AM4
Draw the structures of
A. Pentanamide
B. N-methylbutyramide
Solution AM4
A.
Pentanamide
O

CH3CH2CH2CH2C–NH2
B.
N-methylbutyramide
O

CH3CH2CH2C–NHCH3
Esters
In and ester, the H in the carboxyl group is replaced
with an alkyl group
O

CH3 — C—O —CH3
= CH3—COO —CH3
ester group
Esters in Plants
Esters give flowers and fruits their pleasant
fragances and flavors.
Naming Esters
• Name the alkyl from the alcohol –O• Name the acid with the C=O with –ate
acid
alcohol
O

methyl
CH3 — C—O —CH3
Ethanoate
methyl ethanoate (IUPAC)
(acetate)
methyl acetate (common)
Some Esters and Their Names
Flavor/Odor
Raspberries
HCOOCH2CH3
ethyl methanoate (IUPAC)
ethyl formate (common)
Pineapples
CH3CH2CH2 COOCH2CH3
ethyl butanoate (IUPAC)
ethyl butyrate (common)
Learning Check CA 2
Give the IUPAC and common names of the
following compound, which is responsible for
the flavor and odor of pears.
O

CH3 — C—O —CH2CH2CH3
Solution CA2
O

propyl
CH3 — C—O —CH2CH2CH3
ethyl propanoate (IUPAC)
propyl acetate (common)
Learning Check CA 3
Draw the structure of the following compounds:
A. 3-bromobutanoic acid
B. Ethyl propionoate
Isomers
Same molecular formula
Same number and types of atoms
Different arrangement of atoms
isomers
• Isomers- al the possible spatial arrangements
for a given hydrocarbon.
• Follow these steps=
• 1. start with the longest straight chain.
• 2. shorten the chain by one carbon, and add
that extra carbon as a methyl group in all the
possible positions starting from the left and
moving right.
• 3. check each time to make sure the names
don’t repeat.
• 4. shorten the chain by 2 carbons. Add each
carbon separately as a methyl to all the
possible places. Keep your numbering system
correct. Then add the 2 carbons as an ethyl
group following the same pattern.
• Ex: Try heptane and octane
Examples of Isomers
The formula C4H10 has two different structures
CH3
CH3CH2CH2CH3
Butane
CH3CHCH3
2-methylpropane
When a CH3 is is used to form a branch, it makes a
new isomer of C4H10.
H
H
H
H
H
H
H
H
H
H
H
C
C
C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
Decane
Draw 4 isomers of decane
c
c c c c c c c cc
c
c c c c c ccc
c
c
cc c c c c ccc
c
c
c c c c c cc
c
H
Learning Check Alk6
Write 3 isomers of C5H12 and name each.
Solution Alk6
CH3CH2CH2CH2CH3 pentane
CH3
CH3CHCH2CH3
2-methylbutane
CH3
CH3CCH3
CH3
2,2-dimethylpropane
Learning Check Alk7
Write the structural formulas of 3 isomers that have
the formula C5H12. Name each.
Solution Alk7
Write the structural formulas of 3 isomers that have
the formula C5H12. Name each.
CH3CH2CH2CH2CH3
CH3
CH3CHCH2CH3
2-methylbutane
pentane
CH3
CH3CCH3
CH3
2,2-dimethylpropane
Cis trans isomers
• This also occurs around the double or triple
bonds in straight chains.
• Ex: C4H8 has 4 isomers
Cis and Trans Isomers
Double bond is fixed
Cis/trans Isomers are possible
CH3
CH3
CH = CH
cis
CH3
CH = CH
trans
CH3
•
•
•
•
•
1-butene
Cis-2-butene
Trans-2-butene
2-methylpropene ( isobutene)
Cis is also called the Z isomer for the German
word zusammen = together
• Trans are also called the E isomer for the word
entegen = opposite.
Draw all the isomers
• For – C5H10 and C6H12 and name them include
all cis /trans isomers
conformations
• 3 dimensional molecular structures
interrelated by rotations about the bonds.
• Ex. Ethane C2H6
• Can be described as eclipsed and staggered.
• See handout
Hydrogenation
Adds a hydrogen atom to each carbon atom
of a double bond
H H
H–C=C–H + H2
Ni
H H
H–C–C–H
H H
ethene
ethane
Products of Hydrogenation
Adding H2 to vegetable oils produces compounds
with higher melting points
 Margarines
 Soft margarines
 Shortenings (solid)
Learning Check HA4
What is the product of adding H2 (Ni
catalyst) to 1-butene?
Solution HA4
What is the product of adding H2 (Ni
catalyst) to 1-butene?
Ni
CH2=CHCH2CH3 + H2
CH3CH2CH2CH3
Adding Halogens
Halogens also add to the double bond of an alkene.
H2CCH2
+
Cl2
Cl Cl
H2C CH2
CH3C CCH2CH3
+ Br2
Br Br
CH3C CCH2CH3
Br Br
Learning Check HA5
Write the product of the following addition
reactions:
CH3CH=CHCH3 + H2
+ Br2
Solution HA5
Write the product of the following addition reactions:
CH3CH=CHCH3 + H2
+ Br2
CH3CH2CH2CH3
Br
Br
Unsaturated Fatty Acids
 Fatty acids in vegetable oils are omega-6 acids (the first
double bond occurs at carbon 6 counting from the methyl
group)
 A common omega-6 acid is linoleic acid
CH3CH2CH2CH2CH2CH=CHCH2CH=CH(CH2)7COOH
6
linoleic acid, a fatty acid
Trans Fats
In vegetable oils, the unsaturated fats usually contain
cis double bonds.
During hydrogenation, some cis double bonds are
converted to trans double bonds (more stable)
causing a change in the fatty acid structure
If a label states “partially” or “fully hydrogenated”,
the fats contain trans fatty acids.
Trans Fats
In the US, it is estimated that 2-4% of our total Calories
is in the form of trans fatty acid.
trans fatty acids behave like saturated fatty acids in the
body.
Several studies reported that trans fatty acids raise
LDL-cholesterol. Some studies also report that trans
fatty acid lower HDL-cholesterol
The trans fatty acids controversy will continue to be
debated.
Fats and Atheroschlerosis
 Inuit people of Alaska have a high fat diet and high
blood cholesterol levels, but a very low occurrence
of atherosclerosis and heart attacks.
 Fat in the Intuit diet was primarily from fish such as
salmon, tuna and herring rather than from land
animals (as in the American diet).
Omega-3 Fatty Acids
 Fatty acids in the fish oils are mostly the omega-3 type
(first double bond occurs at the third carbon counting
from the methyl group).
 linolenic acid 18 carbon atoms
CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH

 eicosapentaenoic acid (EPA) 20 carbon atoms
CH3CH2(CH=CHCH2)5(CH2)2COOH
Learning Check HA6
(1) Ture or (2) False
A. ____ There are more unsaturated fats in vegetable
oils.
B. ____ Vegetable oils have more omega-3 oils than
found in fish.
C. ____ Hydrogenation of oils converts some cis-double
bonds to trans- double bonds.
D. ____ Animal fats have more saturated fats.