Review of the

Organic Compounds

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 What is organic compound?

Organic compound
- any of a large class of chemical compounds in
which one or more atoms of carbon are
covalently linked to atoms of other elements,
most commonly hydrogen, oxygen, or nitrogen

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15-3 Source: https://www.slideshare.net/saisukesaiful/introduction-of-organic-chemistry
 Figure 15.1 The position of carbon in the periodic table.

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 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:

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 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.

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 Table 15.1 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

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 Figure 15.6 Depicting cycloalkanes.

Cyclobutane
Cyclopropane

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 Figure 15.6 Depicting cycloalkanes.

Cyclopentane Cyclohexane

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 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.

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 Alkenes

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.

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 Aromatic Hydrocarbons

Benzene is an aromatic hydrocarbon and is a resonance

hybrid. Its  bond electrons are delocalized.

Aromatic compounds are unusually stable and although

they contain double bonds they undergo substitution rather
than addition reactions.

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 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.

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 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.

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 Table 15.5 Important Functional Groups in Organic Compounds

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 Table 15.5 Important Functional Groups in Organic Compounds

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 Table 15.5 Important Functional Groups in Organic Compounds

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 Table 15.5 Important Functional Groups in Organic Compounds

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 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.

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 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.

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 Figure 15.18 Some biomolecules with the amine functional group.

Lysine (1° amine) Adenine (1° amine)

amino acid found component of
in proteins nucleic acids

Epinephrine (adrenaline;
2° amine) Cocaine (3° amine)
neurotransmitter in brain brain stimulant;
; hormone released widely abused drug
during stress

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 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.

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 Figure 15.20 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) Solvent 2-Butanone

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

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 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:

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 Figure 15.22 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
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 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.

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 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

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 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.

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 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.

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 Figure 15.24 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

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 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

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

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