Chapter 2 - Alkanes

 Functional group - collection of atoms within a molecule that have
a characteristic chemical behavior

 The group reacts in a typical way, generally independent of the rest
of the molecule
 For example, the double bonds in simple and complex alkenes react
with bromine in the same way
 Alkenes have a C=C double bond
 Alkynes have a C≡C triple bond
 Arenes have special bonds that are represented as alternating
single and double C-C bonds in a six-membered ring
 Alkanes: Compounds with C-C single bonds and C-H bonds only (no
functional groups)
 Connecting carbons can lead to large or small molecules
 The formula for an alkane with no rings in it must be C nH2n+2 where the
number of C’s is n
 Alkanes are saturated with hydrogen (no more H’s can be added)
 They are also called aliphatic compounds
 CH = methane, C H = ethane, C H = propane
4 2 6 3 8
 The molecular formula of an alkane with more than three carbons
can give more than one structure based on different connections of
the carbons
 C (butane) = butane and isobutane
4
 C (pentane) = pentane, 2-methylbutane, and 2,2-dimethylpropane
5
 Alkanes with each C connected to no more than 2 other C’s are

straight-chain or normal alkanes
 Alkanes with one or more C connected to 3 or 4 C’s are branched-
chain alkanes
 Branched chain alkanes have the same formula as normal alkanes -
CnH2n+2 – just not linear
 Isomers that differ in how their atoms are arranged in chains are called
constitutional isomers
 They must have the same molecular formula to be isomers
 Compounds other than alkanes can be constitutional isomers of one another
 We can represent an alkane in a brief form or in many types of
extended form
 A condensed structure does not show bonds but lists all atoms,
such as
 CH3CH2CH2CH3 (butane)
 CH3(CH2)2CH3 (butane)
Structural formulas
Note the names: Parent name followed by suffix (ane)
 Alkyl group – remove one H from an alkane (constitutes
a part of a structure)
 General abbreviation “R” (for Radical, an incomplete
species or the “rest” of the molecule)
 Name: replace -ane ending of alkane with –yl ending
 -CH3 is “methyl” (from methane)
 -CH2CH3 is “ethyl” from ethane
hexyl, heptyl, octyl, nonyl, decyl
 Classified by the connection site
 a carbon at the end of a chain (primary C)
 a carbon in the middle of a chain (secondary C)
 a carbon with three carbons attached to it (tertiary C)
 Compounds are given systematic names by a process that uses
 Follows specific rules

 1) Find parent hydrocarbon chain
3,4,7 3,6,7
3,4 4,5
Begin numbering from side that affords smallest numbers

 Write compound name as single word
 Name a complex substituent as though it were a compound
itself
 Called paraffins (low affinity compounds) because they do not react
with most chemicals
 Used as oils, lubricants, waxes
 They will burn in a flame, producing carbon dioxide, water, and heat
 They react with Cl2 in the presence of light to replace H’s with Cl’s
(not controlled)
 Boiling points and melting points increase as size of alkane increases
 Dispersion forces increase as molecule size increases, resulting in higher
melting and boiling points
 Stereochemistry concerned with the 3-D aspects of molecules
  bonds are cylindrically symmetrical
 Rotation is possible around C-C bonds in open-chain molecules
H’s staggered H’s eclipsed

 Conformation - Different arrangement of atoms resulting from bond
rotation
 Conformations can be represented in 2 ways:
 We do not observe perfectly free rotation
 There is a barrier to rotation, and some conformers are more stable than
others
 Staggered- most stable: all 6 C-H bonds are as far away as possible
 Eclipsed- least stable: all 6 C-H bonds are as close as possible to each other
 What is true for ethane is also true for higher alkanes, staggered
arrangements are more favorable.
Staggered Eclipsed
Most stable Least stable

 Drawing every bond in an organic molecule can become tedious.
 Several shorthand methods have been developed to write structures.
 Condensed structures don’t have C-H or C-C single bonds shown. They
are understood.
e.g.
3 General Rules for Line-Bond Structures:
1) Carbon atoms aren’t usually shown. Instead a carbon atom
is assumed to be at each intersection of two lines (bonds)
and at the end of each line.
2) Hydrogen atoms bonded to carbon aren’t shown.
3) Atoms other than carbon and hydrogen are shown.

Carvone has the following structure. Tell how many
hydrogens are bonded to each carbon, and give the
molecular formula for carvone.
C10H14O
1
2
3
 Many organic compounds contain rings of carbon atoms
e.g.
- Prostaglandins
- Steroids
 Cycloalkanes are saturated cyclic hydrocarbons
 Have the general formula (CnH2n)
 Each ring takes away two hydrogens from CnH2n+2

1) Find the parent. # of carbons in the ring.
2) Number the substituents
3) Use smallest numbers
 Cycloalkanes are less flexible than open-chain alkanes
 Much less conformational freedom in cycloalkanes
 Because of their cyclic structure, cycloalkanes have 2 sides as viewed edge-
on
“ top” side “ bottom” side
- There are two different 1,2-dimethylcyclopropane isomers
Cis – same side trans – opposite sides

 Stereoisomerism
 Compounds which have their atoms connected in the same order but differ
in 3-D orientation
 Draw the structures of the following molecules:
 a) trans-1-Bromo-3-methylcyclohexane
 b) cis-1,2-Dimethylcyclobutane
 Solution:
 a) trans-1-Bromo-3-methylcyclohexane
 b) cis-1,2-Dimethylcyclobutane
 Rings larger than 3 atoms are not flat
 Cyclic molecules can assume nonplanar conformations to minimize angle
strain and torsional strain by ring-puckering
 Larger rings have many more possible conformations than smaller rings and
are more difficult to analyze
Angle strain – deviation of bond angles from 109.5o

Torsional strain – strain from eclipsing interactions
Angle Strain Torsional Strain
 Substituted cyclohexanes occur widely in nature
 The cyclohexane ring is free of angle strain and torsional
strain
 The conformation has alternating atoms in a common plane
and tetrahedral angles between all carbons
 This is called a chair conformation
Step 1 Draw two parallel lines, slanted downward
and slightly offset from each other. This
means that four of the cyclohexane carbons
lie in a plane.
Step 2 Place the topmost carbon atom above and

to the right of the plane of the other four, and
connect bonds.
Step 3 Place the bottom most carbon atom below

and to the left of the plane of the middle
four, and connect the bonds. Note that the
bonds to the bottom most carbon atom are
parallel to the bonds of the top most
carbon.
 The chair conformation has
two kinds of positions for
substituents on the ring:
axial positions and
equatorial positions
 Chair cyclohexane has six

axial hydrogens
perpendicular to the ring
(parallel to the ring axis)
and six equatorial
hydrogens near the plane
of the ring
 Draw two different chair conformations of trans-1,4-
dimethylcyclohexane
 Label all positions as axial or equatorial
 Solution:
trans-1,4-dimethylcyclohexane
 Methyl substituents are either both axial or both equatorial
Draw two chair conformations each for cis- and trans-
1-isopropyl-4-methylcyclohexane. Of these which is
the most stable?
cis
trans
 Chair conformations readily interconvert, resulting in the exchange of axial
and equatorial positions by a ring-flip
Draw as many compounds as you can that are alcohols with the formula,
C4H8O:
The safest approach to answer this question would be to draw out all
straight-chain isomers, then proceed next to the simplest branched
structures and so on.
1-butanol 2-butanol isobutyl alcohol tert-butyl alcohol

Draw two constitutional isomers of cis-1,2-dibromocyclopentane?
First, we need to understand what constitutional isomer
means…the #’s of atoms, and types of atoms are the
same, just the arrangement may be different. We have a
5 carbon cyclic alkane, so we can only have a case when
we have a 1,2- or a 1,3- dibromo linkage, as these links
will be symmetrical with respect to middle carbon.

Chapter 2 - Alkanes

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Chapter 2 - Alkanes

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 Functional group - collection of atoms within a molecule that have

a characteristic chemical behavior

 Alkanes with each C connected to no more than 2 other C’s are

 Follows specific rules

Begin numbering from side that affords smallest numbers

H’s staggered H’s eclipsed

Most stable Least stable

2) Hydrogen atoms bonded to carbon aren’t shown.

3) Atoms other than carbon and hydrogen are shown.

 Each ring takes away two hydrogens from CnH2n+2

Cis – same side trans – opposite sides

Angle strain – deviation of bond angles from 109.5o

Step 2 Place the topmost carbon atom above and

Step 3 Place the bottom most carbon atom below

 Chair cyclohexane has six

1-butanol 2-butanol isobutyl alcohol tert-butyl alcohol

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