MBS 322: ORGANIC

CHEMISTRY
CHAPTER 2: ALKANES- THE NATURE OF ORGANIC COMPOUNDS
LEARNING OBJECTIVES
1. familiarize the structure of some common functional groups;
2. illustrate isomeric structures of alkanes and alkyl groups;
3. identify the carbon atoms in primary, secondary, tertiary and
quaternary molecules;
4. name the branched chain alkanes ;
5. illustrate the structure from a given name of alkane;
6. explain the conformations of ethane based on the rotation of carbon-
carbon bond; and
7. illustrate chemical or structures of an alkane.
IDENTIFY THE FOLLOWING CONCEPTS BEING DESCRIBED.
CHOOSE YOUR ANSWER INSIDE THE BOX BELOW.
_______________1. It is an atom or group of atoms within a larger
molecule that has a characteristic chemical activity
_______________2. A saturated hydrocarbons having the general
formula of CnH2n+2.
_______________3. It is a compound that have the same chemical
formula but different structures.
_______________4. A specific bond that lies in a belt around the ring
equator
_______________5. These are directed up and down, parallel to the ring
axis.

Equatorial Bonds Axial Bonds Isomers Cycloalkane

Alkane Functional Group
 ANALYZE THIS ARTICLE (SW #1)

Article: Cholesterol and Heart Disease

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Guide Question:
➢ What do you think is the connection of this article to Alkanes?
 LESSON 1: FUNCTIONAL GROUPS
 Functional group is a group of atoms within a
molecule that has a characteristic chemical
behavior. Chemically a given functional group
behaves almost the same way in every
molecule it’s a part of it. For example, compare
ethylene, a plant hormone that causes fruit to
ripen, with menthane a much more
complicated molecule found in pepper mint
oil. Both substances contain a carbon-carbon
double bond functional group. And both
therefore react with Br2 in the same way to give
products in which a Br atom has added to
each of the double bond carbons.
SOME OF THE
FUNCTIONAL
GROUPS
SOME OF THE
FUNCTIONAL
GROUPS
CARBON-CARBON
MULTIPLE BONDS ALKANES- Single Bond

ALKENES- Double Bond

ALKYNES- Triple Bond

ARENES- Alternating Double and Single

Bonds
CARBON SINGLY BONDED TO AN
ELECTRONEGATIVE ATOM
 ALKYL HALIDES- Have a carbon atom bonded to Halogen (--X)
 ALCOHOL- Have a carbon atom bonded to the oxygen of a hydroxyl
group (-- OH)
 ETHERS- Have two carbon atoms bonded to the same oxygen
 ORGANOPHOSPHATES- Have a carbon atom bonded to the oxygen
of a phosphate group ( _ OPO32- )
 AMINES- Have a carbon atom bonded to a nitrogen
 THIOLS- Have a carbon atom bonded to the sulfur of an (--SH) group
 SULFIDES- Have a carbon atoms bonded to the same sulfur
 DISULFIDES- Have a carbon atoms bonded to two sulfurs that are
joined together
 Carbonyl groups are present in the great majority of organic compounds and in practically all
CARBON-0XYGEN biological molecules. These compounds behave similarly in many respects but differ
depending on the identity of the atoms bonded to the carbonyl-group carbon.
DOUBLE BOND ALDEHYDES- Have at least one hydrogen bonded to the C=O

(CARBONYL
GROUPS) KETONES- Have to carbons bonded to the C=O

CARBOXYLIC ACID- Have one carbon and one –OH group bonded to the C=O

Note: The carbonyl carbon atom ESTERS- Have one carbon and one ether-like oxygen bonded to the C=O
bears a partial positive charge
(δ+), and the oxygen bears a AMIDES- Have one carbon and one nitrogen bonded to the C=O
partial negative charge (δ-).

ACID CHLORIDES- Have one carbon and one Chlorine bonded to the C=O
LESSON 2: ALKANES AND ALKYL GROUP: ISOMERS

Alkanes (Methane,
Ethane, and Propane, ALKYL group
Butane, Pentane)
 Alkanes are often described as saturated
ALKANES hydrocarbons. Hydrocarbons because they contain
only carbon and hydrogen atoms; saturated because
they have only C—C and C—H single bonds and thus
contain the maximum possible number of hydrogens
per carbon. They have a general formula CnH2n+2,
where n is any integer. Alkanes are also called
aliphatic compounds a word derived from the Greek
aleiphas, meaning fat.

Alkanes in which the carbons form a continuous

chain with no branches are called straight chain
alkanes. The names of the four smallest straight-
chain alkanes have historical roots, but the others
are based on Greek numbers.
NOMENCLATURE
AND PHYSICAL
PROPERTIES OF
STRAIGHT-CHAIN
ALKANES
 The family of alkanes shown in the table is an
example of a homologous series. A homologous
series (homos is Greek for “the same as”) is a family
of compounds in which each member differs from
the one before it in the series by one methylene
(CH2) group. The members of a homologous series
are called homologues.

It follows the general formula of CnH2n+2, where n is

any positive integer, so if an alkane has one carbon,
it must have four hydrogens; if it has two carbons, it
must have six hydrogens; and so on.
ARRANGEMENT
OF METHANE,
ETHANE AND
PROPANE
  Both structures fulfill the requirement that each carbon forms
four bonds and each hydrogen forms one bond.
 Compounds such as butane and isobutane that have the same
molecular formula but differ in the way the atoms are
connected are called constitutional isomers—their molecules
have different constitutions. In fact, isobutane got its name
because it is an isomer of butane. The structural unit consisting
of a carbon bonded to a hydrogen and two CH3 groups, which
occurs in isobutane, has come to be called “iso.” Thus, the
name isobutane tells you that the compound is a four-carbon
STRUCTURES OF alkane with an iso structural unit.
BUTANE
STRUCTURES OF
PENTANE

 Pentane is the straight-

chain alkane. Isopentane,
as its name indicates, has
an iso structural unit and
five carbons. We cannot
name the other branched-
chain alkane without
defining a name for a new
structural unit.
 If a hydrogen atom is removed from an alkane, the partial
structure that remains is called an alkyl group. Alkyl groups are
named by replacing the -ane ending of the parent alkane with an
-yl ending. For example, removal of a hydrogen atom from
methane, CH4, generates a methyl group, _CH3, and removal of a
hydrogen atom from ethane, CH3CH3, generates an ethyl group, _
CH2CH3. Similarly, removal of a hydrogen atom from the end
carbon of any n-alkane gives the series of n-alkyl groups
ALKYL GROUP
N-ALKYL GROUPS (3-
COMMON ALKYL
GROUPS)

 These are generated by

removing a hydrogen from
an end carbon, branched
alkyl groups are generated
by removing a hydrogen
atom from an internal
carbon.
N-ALKYL GROUPS
(4-COMMON ALKYL
GROUPS)

 These are generated by

removing a hydrogen from
an end carbon, branched
alkyl groups are generated
by removing a hydrogen
atom from an internal
carbon.
 The symbol R is used here and throughout this text to represent a
generalized alkyl group. The R group can be methyl, ethyl, or any of a
multitude of others. You might think of R as representing the Rest of the
molecule, which isn’t specified.
FOUR
POSSIBILITIES OF
BRANCHING
CARBON ATOM
 The system of naming (nomenclature) we’ll use in this module is that
devised by the International Union of Pure and Applied Chemistry
(IUPAC, usually spoken as eye-you-pack). This method of
nomenclature is called systematic nomenclature or sometimes called
as IUPAC nomenclature.
A chemical name typically has four parts in the IUPAC system of
nomenclature: prefix, parent, locant, and suffix. The prefix specifies the
location and identity of various substituent groups in the molecule, the
parent selects a main part of the molecule and tells how many carbon
atoms are in that part, the locant gives the location of the primary
functional group, and the suffix identifies the primary functional group.
NOMENCLATURE
The IUPAC rules have been continually revised by the commission since
OF ALKANES then. A name such as isobutane—a nonsystematic name—is called a
common name. Common names are shown in red and systematic
(IUPAC) names in blue
 1. Determine the number of carbons in the longest continuous
carbon chain. The longest continuous chain is not always in a
straight line; sometimes you must “turn a corner” to obtain the
longest continuous chain. This chain is called the parent
hydrocarbon. The name that indicates the number of carbons in
the parent hydrocarbon becomes the alkane’s “last name.” For
example, a parent hydrocarbon with eight carbons is called
octane.
STEPS IN NAMING
ALKANES
 2. The name of any alkyl substituent that is attached to the parent
hydrocarbon is placed in front of the name of the parent
hydrocarbon, together with a number to designate the carbon to
which the alkyl substituent is attached. The carbons in the parent
chain are numbered in the direction that gives the substituent as
low a number as possible. The substituent’s name and the name of
the parent hydrocarbon are joined into one word, preceded by a
hyphen that connects the substituent’s number with its name.
STEPS IN NAMING
ALKANES
Note: Only systematic names
have numbers; common
names never contain
numbers.
 3. If more than one substituent is attached to the parent
hydrocarbon, the chain is numbered in the direction that
produces a name containing the lowest of the possible numbers.
The substituents are listed in alphabetical order, with each
substituent preceded by the appropriate number. In the following
example, the correct name contains a 3 as its lowest number,
whereas the incorrect name contains a 4 as its lowest number:

STEPS IN NAMING
ALKANES
STEPS IN NAMING
ALKANES
 If two or more substituents are the
same, the prefixes “di,” “tri,” and
“tetra” are used to indicate how
many identical substituents the
compound has. The numbers
indicating the locations of the
identical substituents are listed
together, separated by commas.
There are no spaces on either
side of a comma. There must be
as many numbers in a name as
there are substituents. The
prefixes “di,” “tri,” “tetra,” “sec,”
and “tert” are ignored in
alphabetizing substituents.
 4. When numbering in either direction leads to the same lowest
number for one of the substituents, the chain is numbered in the
direction that gives the lowest possible number to one of the
remaining substituents.

STEPS IN NAMING
ALKANES
 5. If the same substituent numbers are obtained in both directions,
the first group listed receives the lower number.

STEPS IN NAMING
ALKANES
 6. Systematic names for branched substituents are obtained by
numbering the alkyl substituent starting at the carbon attached to
the parent hydrocarbon. This means that the carbon attached to
the parent hydrocarbon is always the number-1 carbon of the
substituent. In a compound such as 4-(1-methylethyl) octane, the
substituent name is in parentheses; the number inside the
parentheses indicates a position on the substituent, whereas the
number outside the parentheses indicates a position on the parent
hydrocarbon. (If a prefix such as “di” is part of a branch name, it is
STEPS IN NAMING included in the alphabetization.)

ALKANES
STEPS IN NAMING
ALKANES

 If the substituent has a

common name, the
common name can be
used instead of the
parenthetical name
STEPS IN NAMING
ALKANES

 If the substituent does not

have a common name, the
parenthetical name must
be used
 7. If a compound has two or more chains of the same length, the
parent hydrocarbon is the chain with the greatest number of
substituents.

STEPS IN NAMING
ALKANES
CONFIRMATION OF
ETHANE
 The different arrangements
of atoms that result from
bond rotation are called
conformations, and
molecules that have
different arrangements are
called conformational
isomers, or conformers.
Unlike constitutional
isomers, however, different
conformers can’t usually be
isolated because they
interconvert too rapidly.
  A sawhorse representation views the C—C bond from an
oblique angle and indicates spatial relationships by showing all
the C--H bonds.
 A Newman projection views the C—C bond directly end-on
and represents the two carbon atoms by a circle. Bonds
attached to the front carbon are represented by lines to a dot
in the center of the circle, and bonds attached to the rear
SAWHORSE carbon are represented by lines to the edge of the circle.
REPRESENTATION
VS. NEWMAN
PROJECTION
DRAWING
CHEMICAL
STRUCTURES

 Skeletal structures of Alkane

 For further clarifications watch video presentations on how to name
alkanes as well as the 3D structure of alkanes and alkyl groups.

➢ Video Presentation 1:
https://www.youtube.com/watch?v=TYU_JluleME
➢ Video Presentation 2:
https://www.youtube.com/watch?v=QzDli_Llo9A
➢ Video Presentation 3:
https://www.youtube.com/watch?v=EyDYaER0PWM
ANSWER THE FOLLOWING

 Lesson 1 (10 points)

 Lesson 2 (2 and 3)- 14 points

 Lesson 3 (1 and 2)-26 points

 Lesson 5 (#1-a-d)- 8 points