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Unit 3
Unit 3
ALKANES
Chem211E Organic Chemistry
Engr. KBDimalanta
1. Alkanes and • Alkanes are aliphatic hydrocarbons having only C–C
Cycloalkanes and C–H 𝜎 bonds.
3. Physical Properties Secondary carbon (2° C) Carbon bonded to two other C atoms
of Alkanes
5. Lipids
1. Alkanes and
EXAMPLES:
Cycloalkanes
3. Physical Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
1.1a Acyclic Alkanes (≤ 𝟓 C Atoms)
1. Alkanes and ➢ All C atoms in an alkane are surrounded by four
Cycloalkanes groups, making them 𝑠𝑝3 hybridized and tetrahedral,
with bond angles = 109.5°.
2. Nomenclature and
Conformations Acyclic Formula Lewis Molecular Ball&Stick
Alkane (𝑪𝒏 𝑯𝟐𝒏+𝟐 ) Structure Geometry Model
3. Physical Properties 𝑪𝟏 𝑯𝟐(𝟏)+𝟐
of Alkanes = 𝑪𝑯𝟒
4. Oxidation of 𝑪𝟐 𝑯𝟐(𝟐)+𝟐
Alkanes = 𝑪𝟐 𝑯𝟔
5. Lipids 𝑪𝟑 𝑯𝟐(𝟑)+𝟐
= 𝑪𝟑 𝑯𝟖
1.1a Acyclic Alkanes (≤ 𝟓 C Atoms)
1. Alkanes and • The structures can be drawn straight/with a bend.
Cycloalkanes E.g. These structures are equivalent because the same number of
carbons are represented.
2. Nomenclature and
Conformations
3. Physical Properties
of Alkanes
• Two alkanes may have different structures but the
4. Oxidation of
same molecular formula (isomers). Constitutional
Alkanes • isomers differ in the way the atoms are connected to
each other.
5. Lipids
1.1a Acyclic Alkanes (≤ 𝟓 C Atoms)
1. Alkanes and
Cycloalkanes
2. Nomenclature and
Conformations
3. Physical Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
1.1b Acyclic Alkanes (↑≥ 𝟓 C Atoms)
1. Alkanes and • The max. no. of possible constitutional isomers ↑
Cycloalkanes dramatically as the number of C-atoms in the alkane ↑.
• A group of compounds that differ by only a methylene
2. Nomenclature and
Conformations
group (𝐶𝐻2) is called a homologous series.
No. of C Molecular Formula Name Constitutional
3. Physical Properties atoms Isomers
of Alkanes 3 𝑪𝟑 𝑯𝟖 Propane ---
4 𝑪𝟒 𝑯𝟏𝟎 Butane 2
4. Oxidation of
Alkanes
6 𝑪𝟔 𝑯𝟏𝟒 Hexane 5
8 𝑪𝟖 𝑯𝟏𝟖 Octane 18
5. Lipids 10 𝑪𝟏𝟎 𝑯𝟐𝟐 Decane 75
20 𝑪𝟐𝟎 𝑯𝟒𝟐 Eicosane 366,319
1.2 Cycloalkanes
1. Alkanes and • Cycloalkanes have molecular formula 𝐶𝑛𝐻2𝑛 and
Cycloalkanes contain C-atoms arranged in a ring/rings.
• Simple cycloalkanes are named by adding the prefix
2. Nomenclature and
Conformations
cyclo- to the name of the acyclic alkane having the
same number of carbons. Cycloalkanes are most
3. Physical Properties often drawn in skeletal representations
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
1. Alkanes and The nomenclature of organic compounds can be done
Cycloalkanes three ways:
1. Systematic : The systematic name follows the
2. Nomenclature and accepted rules of nomenclature and indicates the
Conformations
compound’s chemical structure. It is also known as
3. Physical Properties
(International Union of Pure and Applied Chemistry)
of Alkanes IUPAC name.
2. Generic : This is the official, internationally approved
4. Oxidation of name for the compound.
Alkanes
3. Trade : The name for a compound may be assigned
by the company that manufactures it. Trade names
5. Lipids
are often “catchy” and easy to remember.
1. Alkanes and Generally, the name of organic molecules has 3 parts:
Cycloalkanes ✓ The parent name indicates the number of carbons in
the longest continuous carbon chain in the molecule.
2. Nomenclature and ✓ The suffix indicates what functional group is present.
Conformations
✓ The prefix reveals the identity, location, and number of
3. Physical Properties
substituents attached to the carbon chain.
of Alkanes
• ALL alkane names end in the suffix -ane, and the
4. Oxidation of syllable preceding the suffix identifies the number of
Alkanes
C-atoms in the chain. → One C atom: meth-, two C
atoms: eth-, three C atoms: prop-, four C atoms: but-.
5. Lipids
• Alkanes with more than four carbons use Greek roots
in the prefixes.
1. Alkanes and ILLUSTRATION:
Cycloalkanes
2. Nomenclature and
Conformations
3. Physical Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
2.1 How to Name Substituents
1. Alkanes and • Carbon substituents bonded to a long carbon chain
Cycloalkanes are called alkyl groups. → formed from the removal
of one H from an alkane.
2. Nomenclature and • To name an alkyl group, change the -ane suffix to -yl.
Conformations
3. Physical Properties
• Naming three- and four-carbon alkyl groups is
of Alkanes dependent on the parent hydrocarbon containing
more than one type of H atom. The prefix iso- is
4. Oxidation of formed by removal of a 1°H. The prefix sec- (short for
Alkanes
secondary) is formed by removal of a 2°H. The prefix
tert- (short for tertiary) is formed by removal of a 3°H.
5. Lipids
2.1 How to Name Substituents
1. Alkanes and ILLUSTRATION:
Cycloalkanes
• For propane
2. Nomenclature and
Conformations
4. Oxidation of
Alkanes
4. Oxidation of
Alkanes
5. Lipids
2.2 Naming Acyclic Alkanes
1. Alkanes and Step [1] Find the parent carbon chain and add the suffix.
Cycloalkanes
3. Physical Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
2.2 Naming Acyclic Alkanes
1. Alkanes and Step [1] Find the parent carbon chain and add the suffix.
Cycloalkanes
3. Physical Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
2.2 Naming Acyclic Alkanes
1. Alkanes and Step [2] Number the atoms in the Carbon chain.
Cycloalkanes
3. Physical Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
2.2 Naming Acyclic Alkanes
1. Alkanes and Step [2] Number the atoms in the Carbon chain.
Cycloalkanes
4. Oxidation of
Alkanes
5. Lipids
2.2 Naming Acyclic Alkanes
1. Alkanes and Step [2] Number the atoms in the Carbon chain.
Cycloalkanes
4. Oxidation of
Alkanes
5. Lipids
2.2 Naming Acyclic Alkanes
1. Alkanes and Step [3] Name the substituents.
Cycloalkanes • Consideration 1: Name the substituents as alkyl groups,
and use the numbers from Step 2 to designate their
2. Nomenclature and location.
Conformations
3. Physical Properties
of Alkanes
2. Nomenclature and
Conformations
3. Physical Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
2.2 Naming Acyclic Alkanes
1. Alkanes and ILLUSTRATIONS:
Cycloalkanes
2. Nomenclature and
Conformations
3. Physical Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
2.2 Naming Acyclic Alkanes
1. Alkanes and EXAMPLES:
Cycloalkanes
1. Give the IUPAC name on the compound represented
by the structure below:
2. Nomenclature and
Conformations ANS:
5-tert-butyl-3-methylnonane
3. Physical Properties
of Alkanes
5. Lipids ANS:
2.3 Naming Cycloalkanes
1. Alkanes and • The rules are the same as in acyclic alkanes →but the
Cycloalkanes cyclo- immediately precedes the name of the parent.
2. Nomenclature and
Conformations
5. Lipids
2.3 Naming Cycloalkanes
1. Alkanes and Step [2] Name and number the substituents.
Cycloalkanes • Consideration 1: No number is needed to indicate the
location of a single substituent.
2. Nomenclature and
Conformations
5. Lipids
2.3 Naming Cycloalkanes
1. Alkanes and Step [2] Name and number the substituents.
Cycloalkanes
• Consideration 3: With two different substituents, number
2. Nomenclature and the ring to assign the lower number to the substituents
Conformations
alphabetically.
3. Physical Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
2.3 Naming Cycloalkanes
1. Alkanes and ❖If the number of carbons in the ring ≥ number of
Cycloalkanes carbons in the longest chain, the compound is named
as a cycloalkane.
2. Nomenclature and
Conformations
3. Physical Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
2.3 Naming Cycloalkanes
1. Alkanes and ILLUSTRATIONS:
Cycloalkanes
2. Nomenclature and
Conformations
3. Physical Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
1. Alkanes and • Alkanes contain only nonpolar C-C and C-H bonds
Cycloalkanes → they exhibit only weak van der Waals forces.
4. Oxidation of
Alkanes
5. Lipids
1. Alkanes and 1. BOILING POINT (cont.)
Cycloalkanes ➢ BP ↑ as the number of C ↑ because of increased
surface area.
2. Nomenclature and
Conformations
3. Physical
Properties
of Alkanes
➢ The BP of isomers ↓ with branching because of
decreased surface area.
4. Oxidation of
Alkanes
5. Lipids
1. Alkanes and 2. MELTING POINT
Cycloalkanes ➢ Alkanes have low MPs compared to more polar
compounds of comparable size.
2. Nomenclature and
Conformations
3. Physical
Properties
of Alkanes
➢ MP ↑ as the number of C ↑ because of increased
4. Oxidation of surface area.
Alkanes
5. Lipids
1. Alkanes and 2. MELTING POINT (cont.)
Cycloalkanes ➢ MP ↑ with increasing symmetry.
2. Nomenclature and
Conformations
3. Physical
Properties
of Alkanes
3. SOLUBILITY
4. Oxidation of
Alkanes ➢Alkanes are soluble in organic solvents.
➢Alkanes are insoluble in water.
5. Lipids
1. Alkanes and There are three types of strain in organic molecules:
Cycloalkanes 1. Torsional strain : caused by eclipsing interactions
2. Steric strain : strain produced when atoms are forced
2. Nomenclature and
Conformations
too close to one another
3. Angle strain : strain produced when bond angles
3. Physical deviate from 109.5° (for 𝑠𝑝3 hybridized atoms)
Properties
of Alkanes
➢ Besides torsional and steric strain, the conformations
4. Oxidation of of cycloalkanes are also affected by angle strain. There
Alkanes
is an increase in energy when tetrahedral bond angles
deviate from the optimum angle of 109.5°.
5. Lipids
1. Alkanes and • Baeyer strain theory: cycloalkanes were originally
Cycloalkanes thought to be flat rings, with the bond angles between
carbon atoms determined by the size of the ring.
2. Nomenclature and → It was assumed that rings with bond angles so
Conformations
different from the tetrahedral bond angle would be
3. Physical
very strained and highly reactive.
Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
1. Alkanes and • Cycloalkanes with more than three C atoms in the ring
Cycloalkanes are NOT flat molecules. → They are puckered to reduce
both angle and torsional strain.
2. Nomenclature and • 3 and 4 C-rings still possess considerable angle strain, but
Conformations
puckering reduces the internal bond angles in larger rings,
thus reducing angle strain.
3. Physical
Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
1. Alkanes and ILLUSTRATIONS:
Cycloalkanes
2. Nomenclature and
Conformations
3. Physical
Properties
of Alkanes • Tetrahedrane : 4 three-membered rings bonded together
3. Physical
Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
1. Alkanes and Each C in cyclohexane has two diff. kinds of H-atoms:
Cycloalkanes • Axial hydrogens - located above and below the ring
(along a perpendicular axis).
2. Nomenclature and • Equatorial hydrogens - located in the plane of the
Conformations
ring (around the equator).
3. Physical
Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
1. Alkanes and
• The bonds in cyclohexane twist and bend → however, the
Cycloalkanes movement of the bonds are more restricted. Ring-flipping
is a conformational change that involves a 2-step process.
2. Nomenclature and
Conformations
3. Physical
Properties
of Alkanes
4. Oxidation of
➢ The up Cs become down Cs; and the down Cs become up
Alkanes Cs. → Cyclohexane exists as two diff. chair conformations
of equal stability, which rapidly interconvert into each other
5. Lipids at room temp.
1. Alkanes and
• Axial and equatorial H atoms are interconverted during a ring
Cycloalkanes flip.
2. Nomenclature and
Conformations
3. Physical
Properties
of Alkanes • The chair forms of cyclohexane are 30 kJ/mol more stable
than the boat forms. The boat conformation is destabilized
4. Oxidation of
by torsional strain:
Alkanes → The H atoms on the 4 C atoms in the plane are eclipsed.
→ There is steric strain because two H-atoms at either end
5. Lipids of the boat—the flagpole hydrogens—are forced close to
each other.
1. Alkanes and • A functional group contains a heteroatom or a 𝜋 bond
Cycloalkanes and constitutes the reactive part of a molecule.
➢ Alkanes are the only family of organic molecules that
2. Nomenclature and
Conformations
have no reactive site → alkanes undergo few reactions.
In fact, alkanes are inert to reaction unless forcing
3. Physical Properties conditions are used.
of Alkanes
Oxidation and Reduction Reactions
4. Oxidation of
• Oxidation is the loss of electrons.
Alkanes • Reduction is the gaining of electrons.
5. Lipids
→ Oxidation and reduction are opposite processes. When
one component is oxidized, the other is reduced.
1. Alkanes and • To determine if an organic compound undergoes
Cycloalkanes oxidation or reduction → concentrate on the C atoms of
the starting material vs. the C atoms of the product.
2. Nomenclature and • Compare the relative number of 𝐶−𝐻 and 𝐶−𝑍 bonds (𝑍 =
Conformations
𝑎𝑛𝑦 𝑒𝑙𝑒𝑚𝑒𝑛𝑡 𝑚𝑜𝑟𝑒 𝑒𝑙𝑒𝑐𝑡𝑟𝑜𝑛𝑒𝑔𝑎𝑡𝑖𝑣𝑒 𝑡ℎ𝑎𝑛 𝐶)
3. Physical Properties
of Alkanes
➢ Compounds that contain many 𝐶−𝐻 bonds and few 𝐶−𝑍
bonds are said to be in a reduced state.
4. Oxidation of
Alkanes ➢ Compounds that contain few 𝐶−𝐻 bonds and more 𝐶−𝑍
bonds are in a more oxidized state.
5. Lipids
(e.g. 𝐶𝐻4 is highly reduced, while 𝐶𝑂2 is highly oxidized).
1. Alkanes and Oxidation and reduction can be defined in complementary
Cycloalkanes ways:
• Oxidation results in an increase in the no. of 𝐶−𝑍 bonds; or
2. Nomenclature and • Oxidation results in a decrease in the no. of 𝐶−𝐻 bonds.
Conformations
4. Oxidation of
➢ Because Z is more electronegative than C, replacing
Alkanes 𝐶−𝐻 bonds with 𝐶−𝑍 bonds decreases the electron
density around 𝐶 (loss of electron density = oxidation).
5. Lipids
1. Alkanes and The figure shows the trends in oxidation and reduction
Cycloalkanes reactions. The symbol [𝑂] indicates an oxidation reaction
while [𝐻] indicates a reduction reaction.
2. Nomenclature and
Conformations
3. Physical Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
1. Alkanes and • Alkanes undergo combustion: they burn in the
Cycloalkanes presence of 𝑂2 to form 𝐶𝑂2 and 𝐻2 𝑂.
• In complete combustion: every C-H and C-C bond in the
2. Nomenclature and starting material is converted to a C-O bond in the
Conformations
product.
3. Physical Properties
• Combustion of alkanes in the form of natural gas,
of Alkanes gasoline, or heating oil releases energy in the form of
heat. Combustion requires a spark or a flame to initiate
4. Oxidation of the reaction. → Gasoline which is composed largely of
Alkanes
alkanes, can be safely handled and stored, but the
presence of a spark/flame causes immediate and violent
5. Lipids
combustion.
1. Alkanes and
Cycloalkanes
2. Nomenclature and
Conformations
3. Physical Properties
of Alkanes
4. Oxidation of EXAMPLE:
Alkanes
Draw the products of each combustion reaction.
5. Lipids
? ?
1. Alkanes and • Lipids are biomolecules whose properties resemble
Cycloalkanes those of alkanes and other hydrocarbons.
• They are composed of many nonpolar 𝐶−𝐻 and 𝐶−𝐶
2. Nomenclature and
Conformations bonds, and have few polar functional groups.
• Unlike other biomolecules, lipids are characterized by a
3. Physical Properties specific physical property, NOT by the presence of a
of Alkanes
particular functional group.
4. Oxidation of ➢ Lipids have varied sizes and shapes, and a diverse
Alkanes number of functional groups. The unifying feature for
lipids is their solubility. Lipids are biomolecules that
5. Lipids are soluble in organic solvents and insoluble in water.
1. Alkanes and
Cycloalkanes
2. Nomenclature and
Conformations
3. Physical Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
❖Waxes : lipids having two long alkyl chains joined by a single
1. Alkanes and oxygen-containing functional group. Because of their many
Cycloalkanes
𝐶−𝐶 and 𝐶−𝐻 bonds, waxes are hydrophobic. They form a
protective coating on the feathers of birds to make them water
2. Nomenclature and
Conformations
repellent, and on leaves to prevent water evaporation. Bees
secrete 𝐶𝐻3 (𝐶𝐻2 )14 𝐶𝑂𝑂(𝐶𝐻2 )29 𝐶𝐻3 , a wax that forms the
3. Physical Properties
honeycombs in which they lay eggs.
of Alkanes
❖PGF2α` belongs to a class of lipids called prostaglandins.
Prostaglandins contain many 𝐶−𝐶 and 𝐶−𝐻 bonds and a
4. Oxidation of
Alkanes
single --COOH group (carboxy group). Prostaglandins
possess a wide range of biological activities: inflammation,
blood-platelet aggregation, uterine contractions, etc.
5. Lipids
Nonsteroidal anti-inflammatory drugs such as ibuprofen
operate by blocking the synthesis of prostaglandins.
1. Alkanes and
❖Cholesterol is a member of the steroid family, a group of
Cycloalkanes lipids having four rings joined together. Because it has just
one polar -𝑂𝐻 group, cholesterol is insoluble in the aqueous
2. Nomenclature and medium of the blood. It is synthesized in the liver and
Conformations transported to other cells by binding to water-soluble organic
molecules. Elevated cholesterol levels can lead to coronary
3. Physical Properties artery disease.
of Alkanes
• The nonpolar HC skeleton of cholesterol is embedded in
the nonpolar interior of the cell membrane. Its rigid carbon
4. Oxidation of
Alkanes
skeleton stiffens the fluid lipid bilayer, giving it strength.
• Cholesterol’s polar -OH group is oriented toward the
5. Lipids
aqueous media inside and outside the cell.
1. Alkanes and
• Lipids have a high energy content, meaning that much
Cycloalkanes energy is released when they are metabolized.
2. Nomenclature and • Lipids are composed mainly of 𝐶−𝐶 and 𝐶−𝐻 bonds
Conformations
3. Physical Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids
-- End of Presentation --
1. Alkanes and EXAMPLE
Cycloalkanes Draw the products of each combustion/metabolism
reaction.
2. Nomenclature and
Conformations
3. Physical Properties
of Alkanes
4. Oxidation of
Alkanes
5. Lipids