• Organic chemistry is the study of the compounds of carbon, all of which

have covalent bonds.

• Carbon atoms can bond to each other to form open-chain compounds, or

cyclic (ring) compounds.

• Both types can also have branches of C atoms.

• Saturated compounds have C’s bonded to each other by single bonds, C-C;

unsaturated compounds have C’s joined by multiple bonds.

• Cyclic compounds having at least one atom in the ring other than C (a

heteroatom) are called heterocyclics.

• The heteroatoms are usually oxygen (0),nitrogen (N), or sulhr (S).

• The compounds of carbon are the central substances of which all

living things on this planet are made.

1) DNA: the giant molecules that contain all the genetic information

for a given species.

2) proteins: blood, muscle, and skin.

3) enzymes: catalyze the reactions that occur in our bodies.

4) furnish the energy that sustains life.

• Billion years ago most of the carbon atoms on the earth existed as

CH4:
1) CH4, H2O, NH3, H2 were the main components of the primordial atmosphere.

2) Electrical discharges and other forms of highly energetic radiation caused

these simple compounds to fragment into highly reactive pieces which combine

into more complex compounds such as amino acids, formaldehyde, hydrogen

cyanide, purines, and pyrimidines.

3) Amino acids reacted with each other to form the first protein.

4) Formaldehyde reacted with each other to become sugars, and some of these

sugars, together with inorganic phosphates, combined with purines and

pyrimidines to become simple molecules of ribonucleic acids (RNAs) and

DNA.
4. We live in an Age of Organic Chemistry:
1) clothing: natural or synthetic substance.
2) household items:
3) automobiles:
4) medicines:
5) pesticides:
5. Pollutions:
1) insecticides:
2) PCBs:
3) dioxins:
4) CFCs:
 TYPES OF BONDS
TYPES OF BONDS
• An ionic bond is an attractive force between oppositely charged ions.

• Ionic compounds are generally inorganic; have high melting and boiling points due to
the strong electrostatic forces attracting the oppositely charged ions; are soluble in
water and insoluble in organic solvents; are hard to burn; involve reactions that are rapid
and simple; also bonds between like elements are rare, with isomerism being unusual.

• Covalent bonds are formed by the sharing of pairs of electrons.

• Covalent compounds, on the other hand, are commonly organic; have relatively low
melting and boiling points because of weak intermolecular forces; are soluble in organic
solvents and insoluble in water; bum readily and are thus susceptible to oxidation
because they are less stable to heat, usually decomposing at temperatures above 700°C;
involve reactions that are slow and complex, often needing higher temperatures and/or
catalysts, yielding mixtures of products; also, honds between carbon atoms are typical,
 TYPES OF BONDS
• Electronegativity is a measure of the ability of an atom to attract electrons

FORMAL CHARGE
• The formal charge on a covalently bonded atom equals the number of valence
electrons of the unbonded atom (the Group number) minus the number of electrons
assigned to the atom in its bonded state.

• The assigned number is one half the number of shared electrons plus the total
number of unshared electrons.

Bond order = ½ [(Number of bonding electrons) – (Number of anti-bonding electrons)

 TYPES OF BONDS
• The compounds we encounter in chemistry are made up of elements combined
in different proportions.

• Elements are made up of atoms. An atom (Fig. 1.1) consists of a dense, positively
charged nucleus containing protons and neutrons and a surrounding cloud of
electrons.

• The elements commonly found in organic molecules are carbon, hydrogen, nitrogen,
oxygen, phosphorus, and sulfur, as well as the halogens: fluorine, chlorine, bromine,
and iodine.

• Isotopes:- the existence of atoms of the same element that have different masses.

• Although all the nuclei of all atoms of the same element will have the same
number of protons, some atoms of the same element may have different masses
because they have different numbers of neutrons. Such atoms are called
isotopes.
 TYPES OF BONDS
 Isomers: The Importance of Structural Formulas

• These chemists frequently found examples of different compounds that have

the same molecular formula. Such compounds are called isomers.

• Constitutional isomers are different compounds that have the same molecular
formula but differ in the sequence in which their atoms are bonded, that is, in
their connectivity.

• Constitutional isomers usually have different physical properties (e.g., melting

point, boiling point, and density) and different chemical properties (reactivity).

 Resonance theory. This theory states that whenever a molecule or ion can be
represented by two or more Lewis structures that differ only in the positions of
the electrons.
 Atomic and Molecular Structure
Quantum Mechanics and Atomic Structure

• Each wave function (c) corresponds to a different energy state for an electron.

• Each energy state is a sublevel where one or two electrons can reside.

• The energy associated with the state of an electron can be calculated from the
wave function.

• The relative probability of finding an electron in a given region of space can be

calculated from the wave function.

• The solution to a wave function can be positive, negative, or zero .

 Atomic and Molecular Structure
Quantum Mechanics and Atomic Structure

• The phase sign of a wave equation indicates whether the solution is positive or
negative when calculated for a given point in space relative to the nucleus.

• Wave functions, whether they are for sound waves, lake waves, or the energy of an
electron, have the possibility of constructive interference and destructive
interference.

• Constructive interference occurs when wave functions with the same phase sign
interact. There is a reinforcing effect and the amplitude of the wave function
increases.

• Destructive interference occurs when wave functions with opposite phase signs
interact. There is a subtractive effect and the amplitude of the wave function goes
to zero or changes sign.
Atomic and Molecular Structure
 Atomic and Molecular Structure
 A physical interpretation related to the electron wave function was put forth by Max
Born in 1926, as follows.

 The square of a wave function (Ψ2) for a particular x,y,z location expresses the
probability of finding an electron at that location in space.

 If the value of Ψ2 is large in a unit volume of space, the probability of finding an

electron in that volume is high—we say that the electron probability density is
large.

 Conversely, if Ψ2 for some other volume of space is small, the probability of finding
an electron there is low.* This leads to the general definition of an orbital and, by
extension, to the familiar shapes of atomic orbitals.

• An orbital is a region of space where the probability of finding an electron is high.

• Atomic orbitals are plots of Ψ2 in three dimensions. These plots generate the
familiar s,p, and d orbital shapes.
 Atomic and Molecular Structure
Three principles are used to distribute electrons in orbitals.

1. “Aufbau” or building-up principle. Orbitals are filled in order of increasing

energy: Is, 2s,2p,3s, 3p, 4s, 3d, 4p, 5s,4d, 5p, 6s, 4f, 5d, 6p, etc.

2. Pauli exclusion principle. No more than two electrons can occupy an orbital and
then only if they have opposite spins.

3. Hund’s rule. One electron is placed in each equal-energyorbital so that the

electronshave parallel spins, before pairing occurs. (Substances with unpaired
electrons are paramagnetic-they are attracted to a magnetic field.)
 Atomic and Molecular Structure
• According to the Heisenberg uncertainty principle, we cannot simultaneously
know the position and momentum of an electron.

• A covalent bond forms by overlap (fusion) of two AO’s-one from each atom.

• This overlap produces a new orbital, called a molecular orbital (MO), which embraces both
atoms. The interaction of two AO’s can produce two kinds of MO’s.

• If orbitals with like signs overlap, a bonding MO results which has a high electron density
between the atoms and therefore has a lower energy (greater stability) than the individual
AO’s.

• If AO’s of unlike signs overlap, an antiboding MO* results which has a node (site of zero
electron density) between the atoms and therefore has a higher energy than the individual
AO’s. Asterisk indicates antibonding.
• What we have just described has its counterpart in a mathematical treatment called the LCAO (linear
combination of atomic orbitals) method. In the LCAO treatment, wave functions for the atomic orbitals
are combined in a linear fashion (by addition or subtraction) in order to obtain new wave functions for
the molecular orbitals.
 Atomic and Molecular Structure
• Orbital hybridization, in its simplest terms, is nothing more than a mathematical approach that involves
the combining of individual wave functions for s and p orbitals to obtain wave functions for new orbitals.

• The new orbitals have, in varying proportions, the properties of the original orbitals taken separately.
These new orbitals are called hybrid atomic orbitals.

• According to quantum mechanics, the electronic configuration of a carbon atom in its lowest energy
state—called the ground state.

• Wave functions for the 2s, 2px, 2py, and 2pz orbitals of ground state carbon are mixed to form four new
and equivalent 2sp3 hybrid orbitals.

• The designation sp3 signifies that the hybrid orbital has one part s orbital character
and three parts p orbital character.

• The mathematical result is that the four 2sp3 orbitals are oriented at angles of 109.5° with respect to each
other. This is precisely the orientation of the four hydrogen atoms of methane. Each H C H 99 bond angle
is 109.5°.
• The Structure of Ethene (Ethylene): sp2 Hybridization

• Carbon–carbon double bonds are comprised of sp2-hybridized carbon atoms.

• The mathematical mixing of orbitals that furnish the sp2 orbitals for our model can be visualized in the
way shown in Fig. 1.21.

• The 2s orbital is mathematically mixed (or hybridized) with two of the 2p orbitals. (The hybridization
procedure applies only to the orbitals, not to the electrons.)

• One 2p orbital is left unhybridized. One electron is then placed in each of the sp2 hybrid orbitals and one
electron remains in the 2p orbital.

• The three sp2 orbitals that result from hybridization are directed toward the corners of hybridized is
perpendicular to the plane of the triangle formed by the hybrid sp2 orbitals.

a regular triangle (with angles of 120° between them). The carbon p orbital that is not
 Development of the Science of Organic Chemistry

 The science of organic chemistry began to flower with the demise of a nineteenth
century theory called vitalism.

 According to vitalism, organic compounds were only those that came from living
organisms, and only living things could synthesize organic compounds through
intervention of a vital force.

⇒ the study of compounds extracted from living organisms

⇒such compounds needed “vital force” to create them

 Inorganic compounds were considered those compounds that came from nonliving
sources.

 Friedrich Wöhler, however, discovered in 1828 that an organic compound called

urea (a constituent of urine) could be made by evaporating an aqueous solution of
the inorganic compound ammonium cyanate.
With this discovery, the synthesis of an organic compound, began the

evolution of organic chemistry as a scientific discipline.

• Exceptions:
– oxides of carbon (CO2, CO)
– carbonates,bicarbonates(NaHCO3,CaCO3)
– cyanides (NaCN, etc)

One C with no H, or with metal

Properties of Organic Compounds:-
1. Covalently bonded
2. Low Melting Points
3. Non-electrolytes
4. Nonpolar
5. React slower than inorganic compounds
6. Require high activation energies
7. Insoluble in water ~ generally
• Organic (Benzene) • Inorganic (NaCl)
– Low melting pts – High melting pts
– Low boiling pts – High boiling pts
– Low solubility in water – Soluble in water
– Highly flammable – Nonflammable
– Nonconductive – Conductive
– Covalent bonds – Ionic bonds
 1.4. Hydrocarbons
Compounds containing only Carbon and hydrogen
Alkanes C C Alkenes C C
CnH2n+2 CnH2n
H H H
H H H H H
H C C C C C H
H C C C C C H
H H H H H
H H H H H

Alkynes C C Aromatics H
CnH2n-2 H C H
H H H C C
H C C C C C H C C
H C H
H H H
H
1.5. Functional Groups
1.5. Functional Groups
 1.5. Functional Group
 a structural unit in a molecule responsible for its characteristic
chemical behavior and its spectroscopic characteristics.

• A functional group is an atom or a group of atoms with characteristic

chemical and physical properties. It is the reactive part of a molecule.

• Organic compounds having only C—C and C—H bonds are called
Hydrocarbons. There are four classes of hydrocarbons: alkanes,
alkenes, akynes and aromatics. Alkanes are saturated structures and
the others contain unsaturations.

• Many organic molecules contain Heteroatoms, these are atoms other

than carbon or hydrogen.
 1.5. Functional Groups
Functional Groups:
• Heteroatoms and  bonds confer reactivity on a particular
molecule.
Heteroatoms have lone pairs and create electron-deficient
sites on carbon.
 Bonds are easily broken in chemical reactions. A  bond
makes a molecule a base and a nucleophile.

Don’t think that the C—C and C—H bonds are unimportant. They
form the carbon backbone or skeleton to which the functional group is
attached. 28
 1.5. Functional Groups
• A functional group determines all of the following properties of a
molecule:
 Bonding and shape
 Chemical reactivity
 Type and strength of intermolecular forces
 Physical properties
 Nomenclature
 1.5. Functional Groups
Intermolecular Forces:
• Intermolecular forces are interactions that exist between
molecules. Functional groups determine the type and
strength of these interactions.
• There are several types of intermolecular interactions.
• Ionic compounds contain
oppositely charged particles held
together by extremely strong
electrostatic inter-actions. These
ionic inter-actions are much
stronger than the intermolecular
forces present between covalent
molecules.
30
 1.5. Functional Groups
Intermolecular Forces:

• Covalent compounds are composed of discrete molecules.

• The nature of the forces between molecules depends on the

functional group present. There are three different types of
interactions, shown below in order of increasing strength:

 van der Waals forces (London forces)

 dipole-dipole interactions

 hydrogen bonding

31
 Functional Groups
Intermolecular Forces: van der Waals Forces
• van der Waals forces are also known as London forces.
• They are weak interactions caused by momentary changes in electron
density in a molecule.
• They are the only attractive forces present in nonpolar compounds.

Even though CH4 has no net

dipole, at any one instant its
electron density may not be
completely symmetrical,
resulting in a temporary
dipole. This can induce a
temporary dipole in another
molecule. The weak
interactions of this type
constitutes van der Waals
forces. 32
 Functional Groups
Intermolecular Forces: van der Waals Forces
• All compounds exhibit van der Waals forces.
• The surface area of a molecule determines the strength of the van der
Waals interactions between molecules. The larger the surface area, the
larger the attractive force between two molecules, and the stronger the
intermolecular forces.

Figure 3.1 Surface area and van der Waals forces

33
 Functional Groups
Intermolecular Forces: van der Waals Forces
• van der Waals forces are also affected by polarizability.
• Polarizability is a measure of how the electron cloud around an atom
responds to changes in its electronic environment.

Larger atoms, like iodine,

which have more loosely held
valence electrons, are more
polarizable than smaller atoms
like fluorine, which have more
tightly held electrons. Thus,
two F2 molecules have little
attractive force between them
since the electrons are tightly
held and temporary dipoles
are difficult to induce.

34
 Functional Groups
Intermolecular Forces: Dipole-Dipole Interactions
• Dipole—dipole interactions are the attractive forces between the
permanent dipoles of two polar molecules.
• Consider acetone (below). The dipoles in adjacent molecules align so
that the partial positive and partial negative charges are in close
proximity. These attractive forces caused by permanent dipoles are
much stronger than weak van der Waals forces.

35
 Functional Groups

Intermolecular Forces: Hydrogen Bonding

• Hydrogen bonding typically occurs when a hydrogen atom

bonded to O, N, or F, is electrostatically attracted to a lone
pair of electrons on an O, N, or F atom in another molecule.

36
 Functional Groups
Intermolecular Forces: Summary
Note: as the polarity of an organic molecule increases, so does
the strength of its intermolecular forces.

37
 Functional Groups
Physical Properties: Solubility
• The nonpolar part of a molecule that is not attracted to
H2O is said to be hydrophobic.
• The polar part of a molecule that can hydrogen bond to
H2O is said to be hydrophilic.
• In cholesterol, for example, the hydroxy group is
hydrophilic, whereas the carbon skeleton is
hydrophobic.
Figure 3.5
Solubility
summary

38
Properties of Alkanes

• Alkanes are insoluble in water but soluble in nonpolar organic solvents.

• Because alkanes are generally less dense than water, they float on its surface.

• Low-molecular-weight alkanes are volatile and must be handled with care because
their vapors are flammable.

• Mixtures of alkane vapors and air can explode when ignited by a single spark.

• Mineral oil, petroleum jelly, and paraffin wax are mixtures of higher alkanes. All are
harmless to body tissue and are used in numerous food and medical applications.

• Odorless or mild odor, colorless, tasteless, nontoxic

• Nonpolar, insoluble in water but soluble in nonpolar organic solvents, less dense
than water

• Flammable, otherwise not very reactive

• A primary carbon has one other C directly bonded to it.
• A secondary carbon is directly bonded to two other C’s.
• A tertiary carbon is directly bonded to three other C’s.
• Multivalent atoms are 1º, 2º, or 3º by bonding to C’s.
• Univalent atom or group not really 1º, 2º, or 3º on its own - ID
depends on type of carbon it is bonded to.

Chapter 2 42
 Reactions of Alkanes
Combustion
• The reaction of an alkane with oxygen is called combustion, an oxidation reaction that
commonly takes place in a controlled manner in an engine or furnace.

• Carbon dioxide and water are the products of complete combustion of any hydrocarbon, and a
large amount of heat is released.

• When hydrocarbon combustion is incomplete, carbon monoxide and carbon-containing soot

are among the products.

Halogenation
• Halogenation is the replacement of an alkane hydrogen by a chlorine or bromine initiated by
heat or light.
• Halogenation is used to prepare a number of key industrial solvents, as well as other
molecules that are used for the preparation of other larger organic molecules.
• In a halogenation reaction, only one H at a time is replaced. If allowed to react for a long
enough time, all H’s will be replaced with halogens.
• A cycloalkane is an alkane that contains a ring of carbon atoms.

• To form a closed ring requires an additional C–C bond and the loss of 2 H atoms.

• The general formula for cycloalkanes is CnH2n.

• Compounds of ring sizes from 3 through 30 and beyond have been prepared in the laboratory.

• The C–C–C bond angles in cyclopropane are 60°, and the bond angles in cyclobutane are
90°, much less than the ideal 109.5° tetrahedral angle.

• These compounds are less stable and more reactive than other cycloalkanes.
Nomenclature of Branched-Chain Alkanes

1. Locate the longest continuous chain of carbon atoms; this chain determines the parent name

for the alkane

2. Number the longest chain beginning with the end of the chain nearer the substituent.

3. Use the numbers obtained by application of rule 2 to designate the location of the substituent

group.

4. When two or more substituents are present, give each substituent a number corresponding to

its location on the longest chain.

5. When two substituents are present on the same carbon atom, use that number twice:

6. When two or more substituents are identical, indicate this by the use of the prefixes di-, tri-,

tetra-, and so on.

7. When two chains of equal length compete for selection as the parent chain, choose the chain

with the greater number of substituents:

• Refinery and tank storage facilities, like this one in Texas,
are needed to change the hydrocarbons of crude oil to many
different petroleum products. The classes and properties of
hydrocarbons form one topic of study in organic chemistry.
Bicyclic Compounds:

We name compounds containing two fused or bridged rings as bicycloalkanes, and we use the name of the

alkane corresponding to the total number of carbon atoms in the rings as the parent name. The following

compound, for example, contains seven carbon atoms and is, therefore, a bicycloheptane. The carbon atoms

common to both rings are called bridgeheads, and each bond, or each chain of atoms, connecting the

bridgehead atoms is called a bridge:

Then we interpose an expression in brackets within the name that denotes the number of carbon atoms in

each bridge (in order of decreasing length). Fused rings have zero carbons in the bridge. For example,
If substituents are present, we number the bridged ring system beginning at one bridgehead, proceeding first

along the longest bridge to the other bridgehead, then along the next longest bridge back to the first

bridgehead. The shortest bridge is numbered last:

At room temperature (25°C) and 1 atm pressure the first four members of the
homologous series of unbranched alkanes are gases, the C5—C17 unbranched alkanes
(pentane to heptadecane) are liquids, and the unbranched alkanes with 18 and more
carbon atoms are solids.
Boiling Points The boiling points of the unbranched alkanes show a regular increase
with increasing molecular weight in the homologous series of straight-chain alkanes.
Branching of the alkane chain, however, lowers the boiling point.
• With unbranched alkanes, as molecular weight increases, so too do molecular size
and, even more importantly, molecular surface area.
• With increasing surface area, the dispersion forces between molecules increase;
therefore, more energy (a higher temperature) is required to separate molecules from
one another and produce boiling.
• Chain branching, on the other hand, makes a molecule more compact, reducing its
surface area and with it the strength of the dispersion forces operating between it and
adjacent molecules; this has the effect of lowering the boiling point.
Density:- As a class, the alkanes and cycloalkanes are the least dense of all groups of
organic compounds. All alkanes and cycloalkanes have densities considerably less than
1.00 g mL-1 (the density of water at 4°C). As a result, petroleum (a mixture of
hydrocarbons rich in alkanes) floats on water.
Solubility:- Alkanes and cycloalkanes are almost totally insoluble in water because of
their very low polarity and their inability to form hydrogen bonds. Liquid alkanes and
cycloalkanes are soluble in one another, and they generally dissolve in solvents of low
polarity. Good solvents for them are benzene, carbon tetrachloride, chloroform, and
other hydrocarbons.
 Cyclic Alkanes. . . CnH2n
• Cycloalkanes
– Smaller than five carbons, very reactive.
– Rings of carbon atoms.
– Isomers
• Structural isomers generally have different properties:
– different melting points
– different boiling points
– often different chemical reactivity
• Cis: both substituents are on the same side of the ring.
• Trans: substituents are on opposite sides of the ring.
 Reactions of Alkanes. . . .
• Combustion: react with oxygen produce
carbon dioxide and water
• Substitution: halogen atoms replace hydrogen
atoms
• Dehydrogenation reactions:hydrogen removed
forms double bond there unsaturated
hydrocarbon is the product
 Alkenes. . .
• 1. Root hydrocarbon (longest chain containing double bond)
name ends in –ene.
• 2. More than three carbon atoms, the location of the double
bond is indicated by the lowest numbered carbon atom in the
bond. If equidistant: begin at end closer to substituent group.
– CH2=CHCH2CH3 1-butene
– CH3CH=CHCH3 2- butene
• 3. More than one double bond
– Indicate the position of each and use –diene, triene, tetraene.
..
 Cycloalkenes. . .
• Name same as alkenes.
• Number so double bond is between C1 and C2
and the first substituent has the lowest
number possible.
– Alkenes can also add to each other in an addition
reaction to form long chains of carbon compounds.
this is called polymerization
 Practice. . .write the skeletal formula
and name.
• CH2=CHCH(CH3)C(CH3)(CH3)CH3
• CH3CH2CH=C(CH3)CH2CH3
• CH3CH=CHCH(CH3)CH=CHCH(CH3)CH3
 2-methyl-1,5-hexadiene
 3-ethyl-2,2dimethyl-3-heptene
 2,3,3-trimethyl-1,4,6-octatriene
 4-tert-butyl-2-methylheptane
 3,4-diisopropyl-2,5-dimethyl-3-hexene
 Alkynes. . .
• Unsaturated hydrocarbons contain atleast one triple
carbon-carbon bond.
• -yne replaces –ane.
• Begin numbering chain at end closest to triple bond.
• More than one bond: -diynes, -triynes.
• Double and triple bonds: -enynes
– Start numbering from end nearer first bond. (if there is a
choice. Usually double bonds get lower numbers than
triple.)
 Practice. . .

• CH3CH(CH3)C CCH(CH3)CH3
• CH CC(CH3)(CH3)CH3
• CH3CH=CHCH=CHC CCH3
• CH3CH2C(CH3)(CH3)C CCH2CH2CH3
 Reactions of Alkenes and Alkynes. . .
• Addition reactions: double bond broken and new bonds
formed to atoms added.
– Hydrogenation reactions: addition of hydrogen atoms
– Halogenation: addition of a halogen
• Elimination:one reactant splits apart to give two products.
• Substitutions: two reactants exchange parts to give two new
products.
• Rearrangement:one reactant undergoes a reorganization of
bonds and atoms to give a new product.
 Aromatic Hydrocarbons. . .
Benzene and its structural relatives

• Monosubstituted benzene: named as other

hydrocarbons, with benzene as parent name.
– If substituent larger than ring (six carbons) : benzene
becomes substituent group called phenyl.
• Disubstituted benzene: ortho:1,2 meta-1,3 para-
1,4
• More than two: number the position of each
substituent group.
 Hydrocarbon derivatives. . .
– The atom or group of atoms that are added to the hydrocarbon are
called functional groups.
• Functional groups usually have multiple bonds or lone pairs of
electrons that make them very reactive.
Alcohols:
Presence of an –OH (hydroxyl group).
• ROH is an alcohol and ArOH is a phenol
– Nomenclature: replace final -e of parent hydrocarbon with –ol.
• (parent: longest chain containing –OH)
– Position of –OH specified by number.
• Number is lowest of substituent groups.
– Classified by: number of hydrocarbon fragmennts bonded to
carbon where –OH group is attached.
• R,R’,R”represent the hydrocarbon fragments.
 Alcohols
• Polar
• Higher boiling points than expected from molecular weights.
• Intermolecular attractions. –OH extensive hydrogen bonding.
• CH3C(OH)(CH3)CH2CH2CH3
• 2methyl-2-pentanol
• CH3CH(OH)CH2CH(OH)CH(CH3)2
• 5-methyl-2,4-hexanediol
 Alcohols
Nomenclature of Alcohols :-
Alcohols
 Practice. . .

• 2-ethyl-2-buten-1-ol
• 3-cyclohexen-1-ol
• trans-3-chlorocycloheptanol
• 1,4-pentanedio
l CH3
4,4-dimethylcyclohexanol
OH
CH3

CH2CH2C(OH)(CH3)2

2-methyl-4-phenyl-2-butanol
Four different alcohols.
The IUPAC name is given
above each structural
formula, and the common
name is given below.
The OH group is polar and short chain
alcohols are soluble in both non-polar
alkanes and water.
If an alcohol contains two OH groups it
is a diol (sometimes called a glycol).
An alcohol with three OH groups is
called a triol (sometimes called a glycerol).
Common
examples of
alcohols with one,
two, and three
hydroxyl groups
per molecule.
The IUPAC name
is given above
each structural
formula, and the
common name is
given below.
Preparation of Alcohols:-
Preparation of Alcohols:-
 Aldehydes. . .

• Nomenclature: remove –e replace with –al.

• Longest chain as base name,must contain the carbonyl group.

Aldehyde carbon assigned number 1, when subtituent
positions are listed in the name.

• Bonded to at least one hydrogen atom.

• Number indicates position of carbonyl group.

• -CHO group attached to a ring, suffix -carbaldehyde.

 Practice. . .
• CH3CHO
• Ethanal
CHO
• CH3CH2CHO Benzene carbaldehyde
• Propanal
• CH3CH(CH3)CH2CH(CH2CH3)CHO
• 2-ethyl-4-methylpentanal

CHO

Cyclohexanecarbaldehyde
 Ketones. . .
• Contain carbonyl group bonded to two carbon atoms
• Final –e replaced with -one.
• Longest chain with ketone group is the parent.
• Numbering begins at the end nearest the carbonyl
carbon.
• If ketones is the substituent group, -acyl is used and
the name ending –yl is attached.
 Practice. . .
• OHCCH2CH2CH2CHO
• Pentanedial
• CH3CH2CH(CH3)CH(CH2CH2CH3)COCH3
• 4-methyl-3propyl-2-hexanone
• CH3CH=CHCH2CH2CHO
• 4-hexenal
• 3-methylbutanal
• 3-methyl-3-butenal
• 4-chloro-2-pentanone
 Carboxylic Acids. . .
• Two systems:
• Derived from open chain alkanes:
– Carboxyl carbon is always C1.
– Replace terminal –e of alkane with –oic acid.
– -COOH group bonded to a ring, the suffix –carboxylic acid is used.
– The carboxylic acid carbon is attached to C1 and is not itself numbered
in this system.
– Organic acids are those
PREPARATION OF CARBOXYLIC ACIDS
1. Oxidation of 1o Alcohols, Aldehydes, and Arenes

2. Oxidative Cleavage of Alkenes and Alkynes

cids that are derived from living organisms, usually from metabolism, but
sometimes as a defense mechanism.
– Long chain organic acids are known as fatty acids.
 Practice. . .
• CH3CH(CH3)CH2CH2COOH
• 4-methylpentanoic acid
• HOOCCH2CH(CH2CH3)CH2CH2CH(CH3)CH2COOH
• 3-ethyl-6-methyloctanedioic acid
• (CH3)2CHCH2COOH
• 3-methylbutanoic acid
• CH3CHBrCH2CH2COOH
• 4-bromopentanoic acid
• CH3CH=CHCH=CHCOOH
• 2,4-hexadienoic acid
• CH3CH2CH(COOH)CHCH2CH2CH3
• 2-ethylpentanoic acid
 Practice. . .

COOH

3-bromocyclohexanecarboxylic acid

Br

COOH

1-cyclopentenecarboxylic acid

 Strong hydrogen bonding has a noticeable effects on boiling points.

Much higher than corresponding alcohols.
 ESTERS
– Esters are condensation products of carboxylic acids
with the removal of water (also called a dehydration
synthesis).
• These red ants, like other ants, make the simplest of the
organic acids, formic acid. The sting of bees, ants, and some
plants contains formic acid, along with some other irritating
materials. Formic acid is HCOOH.
 Organic Compounds of Life
– Living organisms have to be able to:
• Exchange matter and energy with their surroundings.
• Transform matter and energy into different forms.
• Respond to changes in their environment.
• Grow.
• Reproduce.
– All of these changes are due to large organic compounds called
macromolecules.
• A macromolecule is a combination of many smaller similar molecules
polymerized into a chain structure.
– In living organisms there are three main types of macromolecules which
control all activities and determine what an organism will do and become.
• Proteins.
• Carbohydrates
• Nucleic acids.
 Organic Compounds of Life
– The basic unit of life is the cell.
• The cell makes up all living organisms that we know of.
• Cells are in turn made of macromolecules that form inside the
cell.
• Other macromolecules control the formation of these
macromolecules.
– Metabolism is the breaking down or building up of
macromolecules.
• Generally, breaking down macromolecules releases energy
that the organism can use as an energy source.
• The building up of macromolecules requires energy, that is
obtained from breaking down macromolecules.
 Organic Compounds of Life
• Dehydration to alkene
• Oxidation to aldehyde, ketone
• Substitution to form alkyl halide
• Reduction to alkane
• Esterification
• Tosylation
• Williamson synthesis of ether
 Structure and classification of amines
• This is an important difference in
the way that 1o, 2o, and
3o classification is given.
tert-butanol tert-butylamine
Methylamine Trimethylamine Methylpropylamine
a 3o alcohol a 1o amine

Methylphenylamine Cyclohexyldimethylamine

• The –NH2 group of a primary amine can be thought of as an “amino”

group. Thus secondary and tertiary amines possess substituted amino
groups.

amino group Monosubstituted Disubstituted

1o amino group amino group
2o 3o
 Nomenclature for amines
• The IUPAC system for naming amines is as follows:
– Select the longest carbon chain bound to the nitrogen as the
parent chain
– Name the chain by changing the alkane name for this chain:
drop the “e” and add “amine”
– Number the chain to give the nitrogen the lowest numbering
– The number and identity of other substituents (including any on
the main chain) are indicated at the beginning of the amine name
(some are attached to N)

1-Butanamine

2-Butanamine
 Structure and classification of amines
• For di- and trisubstituted amines, the non-parent chains are indicated as N-bonded:

N,N-Dimethyl-1-propanamine
N-Ethyl-N-methyl-2-butanamine

• For diamines, the molecule is named as an “alkane-diamine” with NH2 groups

numbered.

1,4-Butanediamine

• And for cases where NH2-substituted alcohols or other compound cases are
involved, the NH2-group is called an “amino” substituent.

3-Aminobutanoic acid
4-Amino-4-chloro-2-pentanone
 Nomenclature of Amides
• Aromatic amines involve an amine-type nitrogen
bound to an aromatic ring. The simplest case for
these is aniline.

Aniline 3-Bromo-2-chloroaniline

Aniline N-Ethyl-N-methylaniline 3,N-Dimethylaniline

 Nomenclature of Amides
• IUPAC system for naming amides:
– Like esters, amides are made using carboxylic acids. The portion
that comes from the carboxylic acid is named as a carboxylic acid
first, before dropping the “-oic acid” from the name and adding “-
amide”
– Substituents attached to the nitrogen are prefixed with “N-” to
indicate their position; other substituents on the parent chain are
named as part of the parent chain (unlike for amines)

Ethanoic acid Methyl ethanoate Ethanamide

(carboxylic acid) (ester) (amide)

Propanamide N-Methylbutnamide
N,N-Diethyl-3-methylbutanamide
 Benzamide N,N-Dimethylbenzamide
N,N,3,5-Tetramethylbenzamide

• Urea is one of the simplest amides, formed by reaction

between CO2 and ammonia in a series of metabolic
reactions.
• Acetominophen is an aromatic amide Urea

• Barbiturates derive from barbituric acid (sedatives/tranquilizers) are cyclic amides, made
from urea and malonic acid:

2H2O

Urea
Pentanedioic acid
Malonic acid
Barbituric acid

Methanamide
N-Methylmethanamide N,N-Dimethylmethanamide
 100 oC
H2O
catalyst

• Reactions that make esters from carboxylic acids and alcohols are called esterification
reactions.
• Reactions that make amides from carboxylic acids and amines (or ammonia) are called
amidification reactions.
• Thus amidification reactions are condensation reactions.

Amide hydrolysis

heat
amide carboxylic acid amine
(derivative?) (derivative?)