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Molecules
study of carbon-containing
compounds and their properties.
The vast majority of organic
compounds contain chains or rings
of carbon atoms.
The study of the chemistry of living
matter
2
Hydrocarbons
H H
3
C
H
4
Propane
Butane
Formula
M.P.
B.P.
# Structural
Methane CH4
-183 -162
C1
- C4 are
Ethane C2H
-172Gases
-89
6
Propane Cat
-187 -42
Temperature
3HRoom
8
Butane C4H10
Pentane C5H12
Hexane C6H14
Heptane
Octane
-138
-130
0
36
-95
-91
68
98
C7H16
C5
C16
are
Liquids
C8H18
-57 126
Room Temperature
Nonane Cat
-54 151
9H20
Decane C10H22
-30 174
1
1
1
2
3
5
9
18
35
75
10
Find and name the parent chain in the hydrocarbon this forms the root of the hydrocarbon name
Number the carbon atoms in the parent chain
starting at the end closest to the branching
Name alkane branches by dropping the ane from
the names and adding yl. A one-carbon branch is
called methyl, a two-carbon branch is ethyl,
etc
When there are more than one type of branch (ethyl
and methyl, for example), they are named
alphabetically
Finally, use prefixes to indicate multiple branches
11
13
C-C-C-C-C-C
3-methylhexane
Start numbering at the end closest to the
branching
4. Location and name are followed
by root alkane name. Substituents
are given in alphabetical order and
use di-, tri-, etc.
14
CH3
CH2
CH3
CH2
CH2
CH2
CH
CH3
CH3
CH3
Structural Isomerism
CH3
CH2
CH2
CH2
CH3
n-pentane, C5H12
CH3
CH2
CH
CH3
CH3
2-methlbutane, C5H
16 12
Optical Isomerism
Arises when at least one carbon atom in a molecule is
bonded to four different atoms or groups, HCIBrCl is
Exercise
18
2
The parent chain is
4
CH2 5
CH2 3
indicated by the ROOT of
1
the name - pentane. This CH
CH3
CH2
3
means there are 5 carbons
in the parent chain.
dimethyl
dimethyl tells us that there are
TWO methyl branches on the
parent chain. A methyl branch is
made of a single carbon atom.
CH3
4
C
1
CH3
CH2
CH3
CH2
CH3
5
2,2-
2,2 tell us that BOTH methyl
branches are on the second
carbon atom in the parent chain.19
CH3
CH3
CH
CH
CH3
CH3
CH
CH2
CH2
CH2
2
1
CH3
CH2
CH2
CH2
CH2
H2C 6
CH3
2,4-dimethyl
2,4-dimethyl tells us there are
TWO methyl branches on the
parent chain, at carbons #2 and
#4.
CH3
3-ethyl-
3-ethyl tell us there is an ethyl
branch (2-carbon branch) on 20
Example: 2,3,3-trimethyl-4-propyloctane
5
4
6
7
5
4
6
7
8
CH3
CH3
CH2
CH2
4-propyl-
is a propyl
4-propyl tell us there
CH3
CH2
branch (3-carbon branch) on
3
carbon #4 of the CH
parent
chain. 21
2,3-dimethylpentane
CH3
CH3
CH2
CH
CH
CH3
CH3
5-ethyl-3,4-dimethyl octane
22
Reactions of alkanes
Combustion reactions
2C4H10 + 13 O2
H2O(g)
8CO2 + 10
Substitution Reactions
CH4 + Cl2
CH3Cl + HCl
CH3Cl + Cl2
CH2Cl2 + HCl
CH2Cl2 + Cl2
CH Cl3 + HCl
CHCl3 + Cl2
C Cl4
23
Dehydrogenation Reactions
CH3CH3
CH2
CH2
Ethylene
24
Cyclic alkanes
CnH2n
CH3
CH2
CH3
n-propane
C3H8
H2C
60 bond angle
unstable!!
CH2
cyclopropane
C3H6
Note that two hydrogen atoms were lost in forming the ring
25
Ring Structures
26
Boat
chair
27
Ethene
CC=C
propene
Ethyne
CCC CC
2-pentyne
28
Alkenes are
hydrocarbons that
contain at least
one carbon-carbon
double bond
Alkynes are
hydrocarbons that
contain at least
one carbon-carbon
triple bond
Alkenes, CnH2n
30
is ethene
Nomenclature of alkenes
and alkynes
32
CH3
CH3
CH = CH
cis
CH3
CH = CH
trans
CH3
33
34
Hydrogenation reaction
Adds
HC=CH + H2
H C C H
CH3-CH3
H H
Ethene
Ethane
35
Halogenation reaction
Adds
HC=CH + Cl2
HCCH
Cl Cl
Ethene
ethane
Dichloro
36
Halogenation Reactions
CH2
CHCH2CH2CH2 + Br2
CH2Br
CHBrCH2CH2CH2
1,2-dibromopentane
37
Alkynes, CnH2n2
sp triple bonding makes a rigid 180
segment in a hydrocarbon.
ethyne(acetylene)
propyne
38
The Bonding in
Acetylene
39
1-butene
CH3CH=CHCH3
2-butene
2-butyne
CH3CH CHCH3
40
Question
Write the IUPAC name for each of the
following unsaturated compounds:
A.
CH3CH2CCCH3
CH3
2-pentyne
CH3
B.
CH3C=CHCH3
methyl-2-butene-2
C.
3-methylcyclopentene
41
Question
4 5
CH3CH2C CCHCH2CH3
CH2
CH3
5-ethyl-3-heptyne
42
+ Br2
CH3C CCH2CH3
Br Br
43
Delocalized bonds
possess a great stability
thus benzene does not
react like unsaturated
hydrocarbons
44
Benzene C6H6
structure is
often preserved in
benzene chemical
reactions
Aromatic rings
do not add, they
substitute instead
The
sp2
sp2
sp2
45
Aromatic Hydrocarbons
Substitution reaction
Nitroobenzene
Chlorobenzene
Cl
+ Cl2
benzene
FeCl 3
HNO3
CH3Cl
-NO2
-CH3
Toluene
+ HCl
+H2O
+HCl
47
48
49
50
C H
52
Class
Formula
Ketones
Carboxylic Acids
Esters
General
R
O
C R'
O
C OH
O
C OR'
NH2
Amines
53
Aldehyde
Ketone
CH3-OO
CH 3CH
CH3CCH3
54
-COO-NH2
-CONH2
-COOH
CH3COOH
CH3COOCH3
CH3NH2
CH3CONH2
55
56
Haloahydrocarbons
An alkane in which one or more H
atoms is replaced with a halogen (F,
Cl, Br, or I)
CH3Br bromomethane
Br
(methyl bromide)
CH3CH2CHCH3 2-bromobutane
Cl
chlorocyclobutane
57
rC
B
lC
l
bromocyclopentane
1 2
3
1,3dichlorocyclohexane
58
Substituents
List other attached atoms or groups
in alphabetical order
Br = bromo, Cl = chloro
Cl
Br
1
CH3CHCH2CHCH2CH2CH3
4-bromo-2-chloroheptane
59
Nomenclature
The name of this compound is:
Cl
CH3
CH3CH2CHCH2CHCH3
4-chloro-2-methylhexane
60
Alcohols: ROH
The OH makes alcohol polar enough
to hydrogen bonding
Thus, they are water soluble
Ethanol is produced by the
fermentation of glucose
C6H12O6
Glucose
yeast
2CH3CH2OH
Ethanol
+ 2 CO2
CO + 2H2O
CH3OH
Methanol
61
Uses of alcohols
Methanol is used to synthesize
adhesives, fibers, plastics and recently as
motor fuel
It is toxic to human and can lead to
blindness and death
Ethanol can be added to gasoline to form
gasohol and used in industry as solvent
Commercial production of ethanol:
CH2=CH2 + H2O
CH3CH2OH
62
Classes of alcohols
Alcohols can be classified according to the
number of hydrocarbon fragments bonded to
the carbon where the OH group is attached
R
CHOH Secondary alcohol
R'
R
R' C OH Tertiary alcohol
R"
63
Naming Alcohols
methanol
(methyl
alcohol)
CH3CH3
ethane
CH3CH2OH ethanol
(ethyl alcohol)
64
OH
Phenol
(Aromatic alcohol)
65
CH3CHCH3
HO-CH2-CH2-OH
66
Naming Alcohols
CH3CH2CH2OH
1-propanol
OH
CH3CHCH3
CH3
2-propanol
2
OH
CH3CHCH2CH2CHCH3 5-methyl-2-hexanol
67
Example
Name the following alcohols:
OH
CH3CHCHCH2CH3
CH3
3-methyl-2-pentanol
68
CH3-C-H
In a ketone, two carbon groups are
attached to a carbonyl group
CH3-C-CH3
carbonyl group
69
Naming Aldehydes
IUPAC name: Replace the -e in the alkane
name by -al
Common Add aldehyde to the prefixes form
(1C), acet (2C), propion(3), and butyr(4C)
O
O
O
methane
propane
ethane
H-C-H CH3-C-H
CH3CH2C-H
methanal
ethanal propanal
(formaldehyde) (acetaldehyde)
(propionaldehyde)
70
Aldehydes as Flavorings
O
CH
CH
O
CH=CH CH
HO
OCH3
Benzaldehyde
(almonds)
Vanillin
(vanilla beans)
Cinnamaldehyde
(cinnamon)
71
Naming Ketones
propane
CH3 -C-CH3
2-Propanone
cyclohexane
CH3-C-CH2-CH3
2-Butanone
Cyclohexanone
Acetone
72
A. CH3CH2CCH3
O
B.
C. CH3-C-CH2CH
cyclohexanone
CH3
3,3-dimethylbutanal
73
CH3
A. 3-Methylpentanal
Br O
CH3CH2CHCH2CH
B. 2,3-Dibromopropanal
Br-CH2CHCH
O
C. 3-Methyl-2-butanone
CH3CHCCH3
CH3
74
CH
3CH
2OH
Primary
alcohol
CH3CHCH3
OH
Oxidation
CH3C
acetaldehyde
ethanal
CH3CCH3 acetone
propanone
O
Secondary alcohol
75
CH3 COH
CH3COOH
carboxyl group
General formula
RCOOH
76
Common
prefix ic acid
methanoic acid
CH3COOH
ethanoic acid
CH3CH2COOH
propanoic acid
formic acid
acetic acid
propionic acid
butyric acid
77
78
CH3
|
CH3CHCOOH
2-methylpropanoic acid;
79
Esterification
O
CH3C OH
Carboxylic acid
H OCH2CH3
Alcohol
O
CH3C OCH2CH3
H2O
Ester
80
Esters
In ester, the H in the carboxyl group is
replaced with an alkyl group
CH3 CO CH3
CH3
CH3COO
ester group
Naming Esters
The parent alcohol is named first with a yl
ending
Change the oic ending of the parent acid to
ate
acid
alcohol
O
methyl
CH3 CO CH3
Ethanoate
methyl ethanoate (IUPAC)
(acetate)
methyl acetate (common)
82
Amines
Organic compounds of nitrogen N;
derivatives of ammonia
Classified as primary, secondary, tertiary
CH3
CH3
CH3NH2
CH3NH
CH3N CH3
Primary
Secondary
one N-C
bond
two N-C
bonds
Tertiary
three N-C
bonds
83
Naming Amines
IUPAC aminoalkane
Common alkylamine
CH3CH2NH2
aminoethane
(ethylamine)
NH2
N H2
|
CH3CHCH3
2-aminopropane
(isopropylamine)
Aniline
84
Organic Reactions
In general, we look at what occurs and try to
learn how it happens
Common patterns describe the changes
Addition reactions two molecules combine
85
Organic Reactions
Substitution Reactions parts from
two molecules exchange
86
Exercise
87
22.5 Polymers
Poly= many; mers=parts
89
Types of Polymerization
Addition Polymerization: monomers
add together to form the polymer,
with no other products.
( Polyethylene and Teflon)
Condensation Polymerization: A
small molecule, such as water, is
formed for each extension of the
polymer chain. (Nylon)
90
Addition Polymerization
H
H
C C
H
H
H H
H C C
OH H
A species with
an unpaired
electron such as
hydroxyl free radical
OH
The polymerization process
Is initiated by a free radical
H
H
C C
H
H
H H
H C C
H H H H
H C C C C
OH H H H
OH H
Condensation Polymerization
Formation of Nylon
H
O
O
N (CH2)6 N
C (CH2)4 C
H
H
H O
O H
Adipic acid
Hexamethylendiamine
Diamine
H
H
Dicarboxylic acid
H O
O
(CH2)6 N C (CH2)4 C
O H
Dimer
+ H2O
Nylon
H
(
H O
O
(CH2)6 N C (CH2)4 C )n
93