Organic Compounds and the

Atomic Properties of Carbon

15-1
 Organic Compounds and the Atomic Properties of Carbon

The Special Nature of Carbon and the Characteristics of Organic

Molecules

The Structures and Classes of Hydrocarbons

Some Important Classes of Organic Reactions

Properties and Reactivities of Common Functional Groups

15-2
 Bonding Properties of Carbon

• Carbon forms covalent bonds in all its elemental forms

and compounds.
– The ground state electron configuration of C is [He]2s22p2; the
formation of carbon ions is therefore energetically unfavorable.
– C has an electronegativity of 2.5, which is midway between that
of most metals and nonmetals. C prefers to share electrons.
• Carbon exhibits catenation, the ability to bond to itself
and form stable chain, ring, and branched compounds.
– The small size of the C atom allows it to form short, strong
bonds.
– The tetrahedral shape of the C atom allows catenation.

15-3
 The position of carbon in the periodic table.

15-4
 Comparison of Carbon and Silicon

• As atomic size increases down the group, bonds

between identical atoms become longer and weaker.
– A C–C bond is much stronger than a Si–Si bond.
• The bond energies of a C–C bond, a C–O bond, and a
C–Cl bond are very similar.
– C compounds can undergo a variety of reactions and remain
stable, while Si compounds cannot.
• Si has low energy d orbitals available for reaction,
allowing Si compounds to be more reactive than C
compounds.

15-5
 Diversity and Reactivity of Organic Molecules

• Many organic compounds contain heteroatoms, atoms

other than C and H.
– The most common of these are O, N, and the halogens.
• Most reactions involve the interaction of electron rich
area in one molecule with an electron poor site in
another.
– C–C bonds and C–H bonds tend to be unreactive.
– Bonds between C and a heteroatom are usually polar, creating
an imbalance in electron density and providing a site for
reactions to occur.

15-6
 Heteroatoms and different bonding arrangements lead to great
chemical diversity.
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

15-7
 Carbon Skeletons

Each C atom can form a maximum of 4 bonds.

Groups joined by a single bond can rotate, so there are
often several different arrangements of a given carbon
skeleton that are equivalent:

15-8
 Some five-carbon skeletons.

15-9
 Drawing Carbon Skeletons

Each C atom can form a maximum of four bonds.

These may be four single bonds, OR one double and two single bonds,
OR one triple and one single bond.

The arrangement of C atoms determines the skeleton, so a

straight chain and a bent chain represent the same
skeleton.

Groups joined by a single bond can rotate freely, so a

branch pointing down is the same as one point up.

15-10
 Adding the H-atom skin to the C-atom skeleton.

A C atom single-bonded to one A C atom single-bonded to two

other atom gets three H atoms. other atoms gets two H atoms.

A C atom single-bonded to three

other atoms gets one H atom. A C atom single-bonded to four other atoms
is already fully bonded (no H atoms).

15-11
 continued

A double-bonded C atom is
treated as if it were bonded to
two other atoms.

A double- and single-bonded C

atom or a triple-bonded C atom is
treated as if it were bonded to three
other atoms.

15-12
 Sample Problem Drawing Hydrocarbons

PROBLEM: Draw structures that have different atom arrangements

for hydrocarbons with
(a) Six C atoms, no multiple bonds, and no rings
(b) Four C atoms, one double bond, and no rings
(c) Four C atoms, no multiple bonds, and one ring

PLAN: In each case, we draw the longest carbon chain first and
then work down to smaller chains with branches at
different points along them. Then we add H atoms to give
each C a total of four bonds.

15-13
 Sample Problem

(a) Six carbons, no rings

15-14
 Sample Problem

(b) Four C atoms, one double bond, and no rings

15-15
 Sample Problem

(c) Compounds with four C atoms and one ring

15-16
 Alkanes

Hydrocarbons contain only C and H.

Alkanes are hydrocarbons that contain only single bonds
and are referred to as saturated hydrocarbons.
The general formula for an alkane is CnH2n+2, where n is
any positive integer.

Alkanes comprise a homologous series, a group of

compounds in which each member differs from the next by
a –CH2– group.

15-17
 Naming Organic Compounds
The name of any organic compound is comprised of three
portions:
PREFIX + ROOT + SUFFIX

The root name of the compound is determined from the

number of C atoms in the longest continuous chain.

The suffix indicates the type of organic compound, and is

placed after the root.
The suffix for an alkane is –ane.

The prefix identifies any groups attached to the main

chain.

15-18
 Table Numerical Roots for Carbon Chains and Branches

Roots Number of C
Atoms
meth- 1
eth- 2
prop- 3
but- 4
pent- 5
hex- 6
hept- 7
oct- 8
non- 9
dec- 10
undec- 11
dodec- 12

15-19
 Rules for Naming an Organic Compound

15-20
 Ways of depicting the alkane 3-ethyl-2-methylhexane.

15-21
 Depicting cycloalkanes.

Cyclobutane
Cyclopropane

15-22
 Depicting cycloalkanes.

Cyclopentane Cyclohexane

15-23
 Constitutional Isomers

Constitutional or structural isomers have the same

molecular formula but a different arrangement of the
bonded atoms.

A straight-chain alkane may have many branched

structural isomers.

Structural isomers are different compounds and have

different properties.
If the isomers contain the same functional groups, their properties
will still be similar.

15-24
 The Constitutional Isomers of C4H10 and C5H12

15-25
Formulas, molar masses (in g/mol), structures, and boiling points (at 1
atm pressure) of the first 10 unbranched alkanes.

Alkanes are nonpolar and their physical properties are

determined by the dispersion forces between their molecules.

15-26
 Alkenes

A hydrocarbon that contains at least one C=C bond is

called an alkene.

Alkenes are unsaturated and have the general formula

CnH2n.

To name an alkene, the root name is determined by the

number of C atoms in the longest chain that also
contains the double bond.
The C chain is numbered from the end closest to the double bond.
The suffix for alkenes is –ene.

15-27
 Geometric Isomers

The double bond of an alkene restricts rotation, so that

the relative positions of the atoms attached to the double
bond are fixed.
Alkenes may exist as geometric or cis-trans isomers,
which differ in the orientation of the groups attached to
the double bond.

Geometric isomers have different physical properties.

15-28
 The Geometric Isomers of 2-Butene

15-29
 Alkynes

An alkyne is a hydrocarbon that contains at least one

CΞC triple bond.

Alkynes have the general formula CnH2n-2 and they are

also considred unsaturated carbons.

Alkynes are named in the same way as alkenes, using

the suffix –yne.

15-30
 Sample Problem Naming Alkanes, Alkenes, and Alkynes

PROBLEM: Give the systematic name for each of the following,

indicate the chiral center in part (d), and draw two
geometric isomers for part (e).

PLAN: For (a) to (c), we find the longest continuous chain (root) and
add the suffix –ane because there are only single bonds. Then
we name the branches, numbering the C chain from the end
closest to the first branch. For (d) and (e) the longest chain must
include the double bond.

15-31
 Sample Problem

SOLUTION:

2,3-dimethylbutane
3,4-dimethylhexane

1-ethyl-2-methylcyclopentane

15-32
 Sample Problem

3-methyl-1-pentene

cis-2,3-dimethyl-3-hexene trans-2,3-dimethyl-3-hexene

15-33
 Figure Representations of benzene.
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

Resonance forms
Resonance hybrid shows the
having alternating single
delocalized electrons as either
and double bonds.
an unbroken or a dashed circle.

Benzene is an aromatic hydrocarbon.

15-34
 methylbenzene 1,2-dimethylbenzene 1,3-dimethylbenzene
(toluene) (o-xylene) (m-xylene)
bp = 110.6°C bp = 144.4°C bp = 139.1°C

1,4-dimethylbenzene 2,4,6-trinitromethylbenzene
(p-xylene) (trinitrotoluene, TNT)
bp = 138.3°C
15-35
 Functional Groups
Organic compounds are classified according to their
functional groups, a group of atoms bonded in a
particular way.

The functional groups in a compound determine both its

physical properties and its chemical reactivity.
Functional groups affect the polarity of a compound, and therefore
determine the intermolecular forces it exhibits.
Functional groups define the regions of high and low electron density in
a compound, thus determining its reactivity.

15-36
 Important Functional Groups in Organic Compounds

15-37
 Important Functional Groups in Organic Compounds

15-38
 Alcohols

The alcohol functional group consists of a carbon bonded

to an –OH group.

Alcohols are named by replacing the –e at the end of the

parent hydrocarbon name with the suffix –ol.

Alcohols have high melting and boiling points since they

can form hydrogen bonds between their molecules.

15-39
 Haloalkanes

Haloalkanes or alkyl halides contain a halogen atom

bonded to carbon.

Haloalkanes are named by identifying the halogen with a

prefix on the hydrocarbon name. The C bearing the
halogen must be numbered.

15-40
 Amines

The amine functional group contains a N atom.

The systematic name for an amine is formed by dropping

the final –e of the alkane and adding the suffix –amine.

Common names that use the name of the alkyl group

followed by the suffix –amine are also widely used.

15-41
 General structures of amines.

Amines are classified according to the number of R groups directly

attached to the N atom.

15-42
 Alkenes
Alkenes contain the C=C double bond:

Alkenes typically undergo addition reactions.

The electron-rich double bond is readily attracted to the partially
positive H atoms of H3O+ ions and hydrohalic acids.

15-43
 Aldehydes and Ketones

Aldehydes and ketones both contain the carbonyl

group, C=O.

R and R′ indicate
hydrocarbon groups.

Aldehydes are named by replacing the final –e of the

alkane name with the suffix –al.
Ketones have the suffix –one and the position of the
carbonyl must always be indicated.

15-44
 Some common aldehydes and ketones.

Methanal (formaldehyde) Used

to make resins in plywood, Benzaldehyde
dishware, countertops; Artificial almond
biological preservative flavoring

Ethanal (acetaldehyde) 2-Propanone (acetone) 2-Butanone

Narcotic product of ethanol Solvent for fat, rubber, plastic, (methyl ethyl ketone)
metabolism; used to make varnish, lacquer; chemical Important solvent
perfumes, flavors, plastics, feedstock
other chemicals

15-45
 The polar carbonyl group.

The C=O bond is electron rich and is also highly polar. It

readily undergoes addition reactions, and the electron-poor C
atom attracts electron-rich groups.

15-46
 Carboxylic Acids

Carboxylic acids contain the functional group –COOH, or

Carboxylic acids are named by replacing the –e of the

alkane with the suffix –oic acid.

Carboxylic acids are weak acids in water, and react with

strong bases:

15-47
 Some molecules with the carboxylic acid functional group.

Methanoic acid (formic acid) Butanoic acid (butyric acid)

An irritating component of ant and Odor of rancid butter; suspected
bee stings component of monkey sex
attractant

Benzoic acid
Calorimetric standard; used in
preserving food, dyeing fabric, Octadecanoic acid (stearic acid)
curing tobacco Found in animal fats; used in making
candles and soaps
15-48
 Esters

The ester group is formed by the reaction of an alcohol and a

carboxylic acid.

Esterification is a dehydration-condensation reaction.

Ester groups occur commonly in lipids, which are formed by

the esterification of fatty acids.

15-49
 Figure 15.23 Some lipid molecules with the ester functional group.

Cetyl palmitate
The most common
lipid in whale
blubber

Tristearin Typical dietary fat

used as an energy store in
animals
Lecithin Phospholipid found in all cell
membranes

15-50
 Saponification

Ester hydrolysis can be carried out using either aqueous

acid or aqueous base. When base is used the process is
called saponification.
This is the process used to make soaps from lipids.

15-51
 Amides

An amide contains the functional group:

Amides, like esters, can be hydrolyzed to give a

carboxylic acid and an amine.

The peptide bond, which links amino acids in a protein,

is an amide group.

15-52
 Some molecules with the amide functional group.

Acetaminophen
Active ingredient in nonaspirin
pain relievers; used to make dyes
and photographic chemicals

N,N-Dimethylmethanamide
Lysergic acid diethylamide (LSD-25)
(dimethylformamide)
A potent hallucinogen
Major organic solvent; used in
production of synthetic fibers

15-53
 Functional Groups with Triple Bonds

Alkynes contain the electron rich –CΞC– group, which

readily undergoes addition reactions:

Nitriles contain the group –CΞN and are made by a

substution reaction of an alkyl halide with CN- (cyanide):

15-54
 Sample Problem Recognizing Functional Groups

PROBLEM: Circle and name the functional groups in the following molecules:

PLAN: identify the various functional groups.

SOLUTION:
carboxylic acid alcohol
ester ketone

2° amine
aromatic ring alkene
haloalkane
aromatic ring

15-55