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HYDROCARBONS

Introduction Contents
Concepts: Alkanes
1. Hydrocarbons are certain organic compounds which contain Physical Properties
only two elements: Hydrogen and Carbon. Chemical Properties
Nomenclature
2. On the basis of structure, hydrocarbons are divided into Conformation
two main classes: aliphatic and aromatic. Drawing Chemical
3. Aliphatic hydrocarbons are further divided into families: Structures
alkanes, alkenes and alkynes and their cyclic analogs Cis-trans isomerism of
Alkanes
(cycloalkanes etc.)

Part I ALKANES
Concepts:
1. Alkanes have a general chemical formula of CnH2n+2.
2. Tetrahedral hybrid orbitals of Carbon are involved in bond formation.
3. The C H is sp3 s type and C C bonds are sp3 sp3 types
4. Alkanes are sometimes referred to as paraffins (L. parun affinis, meaning not enough affinity)
because alkanes have limited reactivity.
5. The most important property of alkanes is their almost lack of polarity. The electronegativity
difference between Carbon and Hydrogen is 0.4 (2.5 2.1) on the Pauling scale.
6. The only interactions between their molecules are the very weak London Dispersion forces.

A. PHYSICAL PROPERTIES OF ALKANES

a. Boiling and Melting Points

1. The boiling point of alkanes is lower than most of any type of compound with the same
molecular weight.

2. In general, both boiling point and melting points of alkanes increase with increasing
molecular weight.

Physical Properties of Some Unbranched Alkanes


Name Condensed Molecular Melting Boiling Point Density of
Structural Weight o
point ( C) (oC) liquid (g/mL
Formula (amu) at 0oC)
Methane CH4 16.0 - 182 - 164 (a gas)
Ethane CH3CH3 30.1 - 183 - 88 (a gas)
Propane CH3CH2CH3 44.1 - 190 - 42 (a gas)
Butane CH3(CH2)2CH3 58.1 - 138 0 (a gas)
Pentane CH3(CH2)3CH3 72.2 - 130 36 0.626
Hexane CH3(CH2)4CH3 86.2 - 95 69 0.659
Heptane CH3(CH2)5CH3 100.2 - 90 98 0.684
Octane CH3(CH2)6CH3 114.2 - 57 126 0.703
Nonane CH3(CH2)7CH3 128.3 - 51 151 0.718
Decane CH3(CH2)8CH3 142.3 - 30 174 0.730
Note: The density of water is 1g/mL at 4oC

3. Alkanes containing 1 to 4 Carbons are gases at room temperature.

4. Alkanes containing 5 to 17 Carbons are colorless liquids.

5. Alkanes containing 18 or more Carbons are white, waxy solids.


Example: plant waxes (apple skin wax, paraffin wax, petrolatum, Vaseline)

6. As branching in an alkane increases, the alkane molecule becomes more compact, and
its surface area decreases. As surface area decreases, London Dispersion forces act over
a smaller surface area. Hence, attraction between molecules decreases, and boiling point
decreases. Thus, the least branched isomer has the highest boiling point and the
most branched isomer has the lowest boiling point.

Note: Isomers refer to compound which have similar chemical formula but different
structural formula.

b. Solubility
1. Alkanes are non-polar, thus, they are not soluble in water.

Notes in ORGANIC CHEMISTRY LECTURE


Prepared by JMBARCELO SY 2013-2014
2. Alkanes do not dissolve in water because they do not form Hydrogen bonds with
water.

3. Alkanes, however, are soluble in each other and in non-polar organic compounds such
as toluene and diethyl ether.

c. Density
1. All liquid and solid alkanes are less dense than water, thus, they float in water.

B. CHEMICAL PROPERTIES OF ALKANES

a. Combustion

1. Oxidation of Hydrocarbons, including alkanes and cycloalkanes, is the basis for their use
as energy sources for heat and fuel.

2. The heat liberated when an alkane is oxidized to Carbon dioxide and water is called it
heat of combustion.

Equations:
CH4 + 2O2 CO2 + 2H 2O + 212
kcal/mol

CH3CH2CH3 + 5O2 3CO 2 + 4H2O + 530


kcal/mol

b. Halogenation

1. In this process, a substitution reaction happens when Chlorine or Bromine is made to


react with Methane (an alkane) in a temperature of 100oC or higher, or expose it to light.

Equation:
CH4 + Cl2 heat or light
CH3Cl + HCl

2. If halomethane is allowed to react with more halogens, further halogenations happen.

Equations:
CH3Cl + Cl2 heat
CH2Cl2 + HCl

CH2Cl2 Cl2 and heat CHCl3 Cl2 and heat CCl4

Additional Notes:
- Bromination takes place somewhat less readily than chlorination.
- Methane does not react with Iodine at all.
- With Fluorine, it reacts so vigorously that in the dark, the reaction is
controlled with great difficulty.

C. NOMENCLATURE OF ALKANES

C.1. COMMON NAMES OF STRAIGHT CHAIN ALKANES

1. Straight chain alkanes (Carbons are connected in a row) are also called as normal
alkanes, and are commonly indicated with letter n. Example: n-butane, n-pentane

2. Straight chain alkanes are named according to the number of Carbon atoms they
contain. With the exception of methane, ethane, propane and butane, the alkanes are
named based on GREEK numbers.

3. The suffix ane is added to each name to identify the molecule as an alkane.
Examples of Straight branched Alkanes

Numbe Common Name Chemical


r of Formula
Carbon
s
1 Methane CH4
2 Ethane CH3CH3
3 Propane CH3CH2CH3
4 n-butane CH3(CH2)2CH3
5 n-pentane CH3(CH2)3CH3
6 n-hexane CH3(CH2)4CH3

Notes in ORGANIC CHEMISTRY LECTURE


Prepared by JMBARCELO SY 2013-2014
7 n-heptane CH3(CH2)5CH3
8 n-octane CH3(CH2)6CH3
9 n-nonane CH3(CH2)7CH3
10 n-decane CH3(CH2)8CH3
11 Undecane CH3(CH2)9CH3
12 Dodecane CH3(CH2)10CH3
13 Tridecane CH3(CH2)11CH3
14 Tetradecane CH3(CH2)12CH3
15 Pentadecane CH3(CH2)13CH3
20 Eicosane CH3(CH2)18CH3
30 Triacontane CH3(CH2)28CH3

4. If an alkane has a terminal methyl branch (-CH3), the common name has a prefix iso-

Example: H3C-CH-CH3 is named isobutane


CH3

H3C-CH-CH2-CH3 is named isopentane


CH3

5. If an alkane has a terminal dimethyl branch, it is identified with the prefix neo-

Example:
CH3
H3C-C- CH3 is named neopentane
CH3

6. If a Hydrogen is removed from an alkane, the partial structure that remains is called and
alkyl group.

Alkyl group Name and Abbreviation


-CH3 Methyl (Me)
- CH2CH3 Ethyl (Et)
-CH2CH2CH3 Propyl (Pr)
-CH2CH2CH2CH3 Butyl (Bu)
-CH2CH2CH2CH2CH3 Pentyl or Amyl

7. The prefixes sec-(secondary), and tert-(tertiary) are used to refer to other Carbon atoms
attached to the branching Carbon atom. There are four possibilities:

H R R
R

H C R H C R R C R R C R

H H H
R
Primary Carbon Secondary Carbon Tertiary Carbon
Quaternary Carbon

Note: The symbol R is used to represent a generalized alkyl group.

Examples:

H3C-CH- is named isopropyl


CH3

H3C- CH2-CH- is named sec-butyl


CH3

CH3
H3C - C- is named tert-butyl
CH3

C.2. IUPAC NAMES OF STRAIGHT AND BRANCHED ALKANES


1. In the early times, new compounds are named from the whims of the discoverers.

2. A need for systematic naming was thus required.

3. The system of naming (nomenclature) used is devised by IUPAC means International


Union of Pure and Applied Chemistry.
Notes in ORGANIC CHEMISTRY LECTURE
Prepared by JMBARCELO SY 2013-2014
4. A chemical name typically has four parts in the IUPAC system f nomenclature:
a. Prefix answers where and what the substituents are
b. Parent answers how many carbons are present
c. Locant answers where the primary functional group is
d. Suffix answers what the primary functional groups is

5. For now, we use the IUPAC system to name branched-chain alkanes.


Steps:
1. Find the parent hydrocarbon. The parent hydrocarbon is the longest
hydrocarbon chain in the structure. The longest chain may not always be obvious. If
two chains of equal length are present, choose the one with the larger number of
branch points as the parent.

2. Number the atoms in the main chain. Begin assigning numbers at the end
nearer the branch points.

3. Identify and number the substituents. Assign a number called a locant to each
substituent to specify its point of attachment to the parent chain. If there are two
substituents on the same number, assign them both the same number.

4. Write the name as a single word. Use hyphens to separate the numbers. If two
or more different side chains are present, cite them in alphabetical order. If two or
more identical side chains are present, use the appropriate multiplier prefixes (di-,
tri-, tetra- and so forth). Dont use prefixes for alphabetizing, though.

Additional Notes:
o The prefix iso- is considered a part of an alkyl group name while the
hyphenated and italicized prefixs sec-and tert- are not. Thus,
isopropyl and isobutyl are listed alphabetically under I while sec-
butyl and tert-butyl are listed under b.

C.3. NOMENCLATURE OF CYCLOALKANES


1. Find the parent. If the number of Carbon atoms in the ring is equal to or greater than the
number in the substituent, the compound is called alkyl-substituted cycloalkane. If the
number of the Carbon atoms in the largest substituent is greater than the number in the
ring, the compound is named as cycloalkyl-substituted alkane.

2. Number the substituents and write the name. For substituted cycloalkanes, start at the
point of attachment and number around the ring. If two or more substituents are present,
begin numbering at the group that has alphabetical priority and proceed around the ring so
as to give the second substituent the lowest number.

D. CONFORMATION OF ALKANES

Conformations refers to the different arrangements of atoms that result from bond rotation.
Conformational isomers/Conformers refer to molecules that have different arrangements due
to bond rotation.

Kinds of Conformations
1. Sawhorse Representation views the C C bonds from an oblique angle

2. Newman Projection views the C C bond directly end-on and represent the two Carbon
atoms by a circle. Bonds attached to the front Carbon are represented in lines to a dot in the
center of a circle and bonds attached to the rear Carbon are represented by lines to the
edge of the circle.

3. At any give instant, alkanes have staggered conformation. It is more favored over
eclipsed conformation.

E. DRAWING CHEMICAL STRUCTURES OF ALKANES


Drawing every atom and bond is tedious so chemists have devised a way to simplify
matters. Thus, skeletal structure is devised.

Rules:
1. Carbon atoms are not usually shown.
2. Hydrogen atoms bonded to Carbon are not shown.
3. All atoms other than Carbon and Hydrogen are shown.

F. CIS-TRANS ISOMERSIM in Cycloalkanes

Notes in ORGANIC CHEMISTRY LECTURE


Prepared by JMBARCELO SY 2013-2014
1. Stereochemical Isomers/ Stereoisomers are compounds which have atoms connected in
the same order but different in spatial orientation.

2. Stereoisomers are classified as cis- isomers and trans-isomers (cis = L. on the same
side; trans = L. across)

3. Conformation of some cycloalkanes


a. Cyclopropane, Cyclobutane and Cyclopentane
i. Cyclopropane is flat, triangular molecule, with bond angles of 60 o.
ii. Cyclobutane and cyclopentane are slightly puckered.

b. Cyclohexane
i. Cyclohexane is not flat; it is puckered into a strain-free, three dimensional
shape called a chair conformation. All C-C-C bond angles are near 109 o, all C-H
bonds are staggered. It has 6 equatorial planes and 6 axial planes.

Notes in ORGANIC CHEMISTRY LECTURE


Prepared by JMBARCELO SY 2013-2014

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