Power Point to Accompany

Principles and Applications of

Inorganic, Organic, and Biological
Chemistry
Denniston, Topping, and Caret
4th ed
Chapter 11

Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
11-1
Organic Chemistry-History
Historically - compounds from living
systems (plants and animals)
A “vital force”, ie. life was thought to be
necessary to make organic chemicals.
In 1828 Wohler synthesized urea from
purely inorganic chemicals.
Urea, found in urine, was definitely an
organic compound!
O
KCNO + NH4Cl H2N C NH2+ KCl
urea
11-2
Modern Organic Chemistry
The Study of Carbon Compounds
(some exceptions: for example
carbonates, carbon dioxide, etc.)
Biochemistry is now the field that
studies chemicals of life.

11-3
Examples of Organic Chemicals
Foods Plastics
Carbohydrates Pharmaceuticals
Fats Detergents and
Proteins Soaps
Clothing Pesticides
silk, linen, wool, Gasoline and oils
cotton, Dacron, Water purification
Nylon, Orlon,
etc.
11-4
11.1 Why is Carbon Unique?
1. Forms four covalent bonds
2. Bonds covalently to: H, O, N, P, S, and
all other nonmetals (except noble
gases)
3. Carbon atoms join to form:
a. Chains and b. Rings H2
C
CH3CH2CH2CH3 H2C CH2
H2C CH2
11-5
Why is carbon unique?: 2
4. Carbon can form H2C CH2
multiple bonds to
H2C O
itself, oxygen, and
nitrogen. H2C NH
double bonds
HC CH
HC N
triple bonds
11-6
Why is Carbon Unique?: 3
4. Many carbon compounds exist in the
form of isomers.
Isomers are compounds with the same
molecular formula but different
structures.
An isomer example: A, B, and C all are
C4H10 but have different structures. See
the next slide!

11-7
Why is Carbon Unique?: 3b
Isomer Examples. All C4H8

CH3CH2CH CH2 A
CH3CH CH CH3 B
CH2 CH2
C
CH2 CH2
11-8
Organic vs Inorganic: Differences
Organic Inorganic
Bonding Covalent Ionic
Physical State Gas/liquid Solids common
(room temp) common
Melting points Tend to be low Tend to be very
high
Sol. In water Tend to be Much higher
insoluble percent soluble
Conductivity Nonconductors Conduct in soln.
and molten
11-9
Families of Compounds: Hydrocarbons
Hydrocarbons contain only carbon and
hydrogen.
They are nonpolar molecules and
consequently are not soluble in water
but are soluble in typical nonpolar
organic solvents like toluene or
pentane.
Hydrocarbons are constructed of chains
or rings of carbon atoms with sufficient
hydrogens to fulfill carbons need for
four bonds.
11-10
 Hydrocarbons

Aliphatics Aromatics
Structures Based On:
Chains and Benzene ring
nonbenzenoid
rings
11-11
 Hydrocarbons

Aliphatics Aromatics

Alkanes and cycloalkanes

Alkenes and cycloalkenes
Alkynes and cycloalkynes
11-12
Functional groups
Alkanes are CH3 CH3 ethane
compounds that CH3 CH2 CH3
contain only propane-
carbon-carbon and burned in a barbecue grill
carbon-hydrogen CH2 CH2
single bonds.
CH2 CH2

For example: CH2 CH2

cyclohexane-a ring alkane

11-13
Alkanes are sometimes referred to as
paraffins, a word derived from the Latin
parum affi nis, meaning “slight affinity.”
This term aptly describes their behavior, for
alkanes show little chemical affinity for
other substances and are inert to most
laboratory reagents. They do, however,
react under appropriate conditions with
oxygen, chlorine, and a few other
substances.

11-14
Functional groups-2
alkenes have a H2C CH2
carbon-carbon ethene: basis of
polyethylene plastics
double bond H H
CH2 C C H
CH3 CH2 C C
alkynes have a CH2 CH2
H
CH2 CH2
carbon-carbon triple CH2 CH2 CH2
CH2
bond CH2 female silkworm moth
OH sex attractant

HC CH
acetylene-welding gas
in oxyacetylene torch
11-15
Functional groups-3
alcohols have the general
formula: CH3CH2 OH
ROH (R is a carbon ethanol,
group) drinking alcohol

ethers have the general CH3 CH2 O CH2 CH3

formulas: diethyl ether, a general
R-O-R, Ar-O-R, Ar-O-Ar anesthetic
Ar is also a carbon OH
group but is
“aromatic” aromatic ring
phenols have the general
phenol-an early topical
formula: anesthetic
Ar-OH (aromatic only!)
11-16
Functional groups-4
aldehydes have the O
aldehyde carbonyl
general formula R1 C H O
2-
R1 may be H or H C CH CH2OPO3
any carbon OH
glyceraldehyde-3-phosphate
group from glucose metabolism
ketones have the O ketone carbonyl
general formula R1 C R2
neither R1 nor R2 O O
can be H CH3C CH2 C O
acetoacetate ion, product
of fat metabolism
11-17
Functional groups-5
acid groups
carboxylic acids have the O
general formula O CH2 C OH
R1 C OH HO C CO2H condensed
CH C OH formula
R1 may be carbon or H 2
O
esters have the general citric acid, found in fruits
formula O O ester carbonyl
R1 C O R2 C O CH
3
R1 may be carbon or H
but R2 cannot be H or OH
it would be an acid! methyl salicylate
oil of wintergreen

11-18
Functional groups-6
acid chlorides have the O O
general formula O
ClC CH2CH2CH2CH2C Cl
R1 C Cl pivaloyl chloride-
used to make nylon
R1 is usually carbon
anhydrides have the O O
general formula CH3C O C CH3
O O acetic anhydride-
used to transfer
R1 C O C R2 an acetyl group
R1 usually is the
same as R2 and
neither is H
11-19
Functional groups-7
amines have one of these
general formulas Tryptophan- an
essential amino O
R2 R2 acid
CH2 CH C OH
R1 NH2 R1 NH R1 N R3
N NH2
R groups may be alkyl
O
or aromatic amine nitrogens
amides have the general N C CH3
formula O
R2 amide bond
R1 C N
R3 acetaminophen-the
HO analgesic found in
All Rs may be carbon or Tylenol (Reg)
H
11-20
Functional Groups-8
thiols (mercaptans) have
the general formula
COOH
R1 SH H C CH2 SH
R1 is any carbon NH2 cysteine, an
group amino acid
disulfides have the cystine-anfound
aminoinacid
general formula important in
R S S R 3-D structure of proteins.
COOH COOH
R is any carbon H C CH2 S S CH2 C H
group
Rs may be different NH2 NH2
11-21
Test: Identify the groups 1-9
O O
1 an amine 2. 3.
CH3 CH C OH CH3 C
2 a carboxylic acid 1. NH2 O CH3

3 an ester 4.
CH2 CH CH CH2 5. O
4 an alkene H C
CH3 CH OH
5 an aldehyde O
7. C HO CH 6.
6 an alcohol CH2 CH OH
7 a ketone CH2
HO CH
8. CH2
8 a thiol CH2 SH OH
9 an anhydride O 9. O
CH3 C O C CH3 11-22
11.2 Alkanes, CnH2n+2
The title shows the general formula for a
chain alkane.
The first ten alkanes are:
methane CH4 hexane C6H12
ethane C 2 H6 heptane C7H16
propane C3H8 octane C8H18
butane C4H10 nonane C9H20
pentane C5H12 decane C10 H22
11-23
Lewis vs Condensed Formulas
The Lewis dot
and condensed H
formulas for H C H CH4
H
methane.
The Lewis dot HH
and condensed H C C H CH3 CH3
formulas for HH
ethane .
11-24
Drawing Methane and Ethane
H H H
in plane H
C C
H H 109.5 o
behind plane H
H in front of plane H H
Staggered form of ethane

11-25
Lewis vs Condensed Formulas-2
Lewis dot vs condensed formulas: propane.
Terminal carbons condense to CH3 with the
hydrogens usually to the right of the carbon.
Interior carbons condense to CH2 .

H H H
H C C C H CH3CH2CH3
H H H
11-26
Lewis vs Condensed Formulas-3
A branch or substituent on a chain may
be condensed into the chain usually
after the carbon from which it branches.
H
HCH
H H H H
H C C C C C H
H H Cl H H
CH3CH(CH3)CHClCH2CH3 11-27
IUPAC Names
The IUPAC (International Union of Pure
and Applied Chemistry) is
responsible for chemistry names.
Before learning the IUPAC rules for
naming alkanes, the names and
structures of eight alkyl groups must
be learned.
These alkyl groups are historical names
accepted by the IUPAC and integrated
into modern nomenclature.

11-28
Alkyl Groups
H H
H C H H C or CH3
H H
An alkyl group is an alkane with one
hydrogen atom removed. It is named by
replacing the ane of the alkane name
with -yl.
Methane becomes a methyl group.
11-29
Alkyl Groups-2
All six hydrogens on ethane are
equivalent. Removing one H
generates the ethyl group.
HH CH3 CH2
HCCH CH2 CH3
HH C2H5
11-30
Alkyl Groups-3
Propane: removal of a hydrogen generates
two different propyl groups depending on
whether an end or center H is removed.

CH3 CH2 CH3

CH3CH2CH2 CH3CH CH3

n-propyl isopropyl
11-31
Alkyl Groups-4a
n-butane gives two butyl groups
depending on whether an end (1o)
or interior (2o) H is removed.
CH3 CH2 CH2 CH3

CH3 CH2 CH2 CH2 CH3 CH CH2 CH3

n-butyl sec-butyl
11-32
Alkyl Groups-4b
Isobutane gives two butyl groups
depending on whether a 10 or 30 H is
removed. CH 3
CH3 CH CH3
CH3 1 C o CH3
CH3 CH CH2 CH3 C CH3
3o C
isobutyl t-butyl
11-33
IUPAC Names for Alkanes-1
1. The base or parent name for an
alkane is determined by the longest
chain of carbon atoms in the formula.
Note: the longest chain may bend and
twist. It is seldom horizontal!
Any carbon groups not part of the
base chain are called branches or
substituents.
These carbon groups are also called
alkyl groups.
11-34
IUPAC Names for Alkanes-1a
Rules 1 applied. Find the longest chain
in each molecule. (Click for answer.)
A=7 B=8
A CH3
CH2CH2CH CH2CH3
B CH3
CH2
CH3CH2CH2 CH2
CH3
CH3CH2CH CH2CH CH3
11-35
IUPAC Names for Alkanes-2
2. Number the carbon atoms in the chain
starting from the end with the first
branch. If both branches are equally
from the ends, continue until a point of
difference occurs.

11-36
IUPAC Names for Alkanes-2a
Number the carbon atoms correctly.
Left: first branch is on carbon 3.
Right: first branch is on carbon 3 (From
top) not carbon 4 (If from right).
1 CH3
6 7 8
CH3 2 CH2 CH2CH2CH3
4
5 CH2CH2CH CH2CH3 CH3CH CH2CH CH2CH3
3 2 1 3 4 5
6 CH
2
this branch would be on C-4
7 CH3 if you started at correct C-8.
11-37
IUPAC Names for Alkanes-3
3. Prefix the branches/substituents
in alphabetical order before the
base/stem name (longest chain).
Halogens usually come first.
Indicate the position of the branch
on the main chain by prefixing its
name with the carbon number to
which it is attached. Separate
numbers and letters with a
hyphen.
11-38
IUPAC Names for Alkanes-3a
Name
CH3
CH2 CH3
CH3 CH2 CH CH2 CH CH3
4-ethyl-2-methylhexane

11-39
IUPAC Names for Alkanes-3b
Hyphenated and number prefixes are not
considered when alphabetizing groups.
Name the compound below.
5-sec-butyl-4-isopropylnonane

CH3
CH3 CH CH2 CH3
CH CH CH CH2 CH2 CH2 CH3
CH3 CH2 CH2 CH3
11-40
IUPAC Names for Alkanes-4
When a branch/substituent occurs more
than once, prefix the name with di, tri,
tetra,etc. Then prefix the number to
the name with a separate number for
each occurance. Separate numbers
with commas.
eg. 3,4-dimethyl or 4,4,6-triethyl

11-41
IUPAC Names for Alkanes-4a

Name
CH3 CH2CH3
CH3CH CH CH2CH CH2CH3
CH3
5-ethyl-2,3-dimethylheptane
ethyl>dimethyl

11-42
Test: IUPAC Names
Name
CH3 CH3CH CH3
CH2 CH2
CH3C CH2CH2C CH2CH3
CH3 CH2CH2CH2CH3
6-ethyl-6-isobutyl-3,3-dimethyldecane

11-43
Constitutional/Structural Isomers
Constitutional/Structural Isomers differ
in how atoms are connected. The two
isomers of butane are shown below.
The carbon atoms are connected in
different patterns. CH 3
CH3 CH2 CH2 CH3 CH3 CH CH3
butane Isobutane
Bp –0.4 oC Bp –12 oC
Mp –139 oC Mp –145 oC
11-44
11.3 Cycloalkanes
Cycloalkanes have two less hydrogens than
the corresponding chain alkane.
Hexane=C6H14; cyclohexane=C6H12
To name cycloalkanes, prefix cyclo to the
name of the corresponding alkane.
Place substituents in alphabetical order
before the base name as for alkanes.
For multiple substituents, use the lowest
possible set of numbers. A single
substituent requires no number.
11-45
Cycloalkanes-cont.
H H Cl H
H
C C C C
C H
H H
H H
H H
CH3
H H H C C C C
H H H H H H
H H
C C C C C C
H H H H H H
Cl
or or CH3

1-chloro-3-
Cyclopropane cyclohexane methyl-
cyclohexane11-46
Cis-trans Isomers in Cycloalkanes
Two groups may be on the same side (cis) of
the imagined plane of the cycloring or they
may be on the opposite side (trans). The
two isomers are referred to geometric or
cis-trans isomers. E. g.
Cl Cl cis-1-chloro-3-methylcyclohexane
CH3
trans-1-chloro-3-
CH3 methylcyclohexane
Cl Cl Cl cis-1,4-dichlorolcyclohexane
trans-1,4-dichlorocyclohexane
Cl 11-47
11.4 Conformations of Alkanes
Conformations differ only in rotation about
carbon-carbon single bonds. Two
conformations of butane are shown below.
The first (staggered form) is more stable
because it allows hydrogens to be farther
apart and thus the atoms are less crowded.

Insert Fig 11.6

11-48
Two conformations of Cyclohexane
Chair form Boat form
(more stable) E=equitorial
A A A=axial H H
E A E H H H H
E
A E
E E H H H H
A A
H H

11-49
11.5 Reactions of Alkanes
All alkanes undergo:
Combustion to carbon dioxide and water
Halogenation to haloalkanes
2 C2H6 + 7 O2 4 CO2 + 6 H2O
heat or
CH3CH3 + Cl2 light CH3CH2Cl +HCl
H Br
H + Br2 heat or H
light
+HBr
11-50
Lipids
any of a class of organic compounds that are
fatty acids or their derivatives and are insoluble
in water but soluble in organic solvents. They
include many natural oils, waxes, and steroids

11-51
Lipids can serve a diverse range of functions within a cell,
including:
Storage of energy for long-term use (e.g. triglycerides)
Hormonal roles (e.g. steroids such as estrogen and
testosterone)
Insulation – both thermal (triglycerides) and electrical
(sphingolipids)
Protection of internal organs (e.g. triglycerides and waxes)
Structural components of cells (e.g. phospholipids and
cholesterol)

Mnemonic: SHIPS
11-52
Types of Lipids
Triglycerides:  Function as a long-term energy source in animals
(fats) and plants (oils)
Phospholipids:  Structural component of cell membranes
Steroids:  Act as hormones in plants and animals, and is a
structural component of animal cell membranes (cholesterol)
Waxes:  Act as a protective layer against water loss in plant
leaves and animal skin
Carotenoids:  Light-absorbing accessory pigment in plants
(involved in photosynthesis)
Glycolipids:  Complexes of carbohydrate and lipid that function
as cell receptor and cell re

11-53
Example of lipids

11-54
 The End
Organic Introduction
Saturated Hydrocarbons

11-55
11-56