Year 11: Carbon Chemistry Research

Assignment Sarah Morris

What are structural and condensed structural formulae?
Structural formulas are formulas that are used to show the bonding of atoms to one another
with lines that can then extend to branches to allow for further groups. However, they
usually take a lot of time and space to write out and only show the molecules as being 2
dimensional. Without models, the representation of the molecules will be 2 dimensional,
but with condensed structural formulas, the same representation can be made more
practical. This form is completely text form and omits the need for sketching.
1
In condensed
structural formulae, each carbon atom is written with the atom bonded to it written beside
it. For repeated groups, brackets may be used to condense even further.
2
To use brackets to
depict branching, look to the left of the bracket to see what atom its attached to.
3


4


What is a hydrocarbon?
A hydrocarbon is a molecule of hydrogen and carbon atoms. They can be described as pure
or impure and are the main focus of organic chemistry. If pure, the hydrocarbon contains
only carbon and hydrogen whilst the impure contain other elements eg chlorine, sulphur

1
http://www.masterorganicchemistry.com/2011/06/20/deciphering-what-the-brackets-mean/ accessed -
12/06/13
2
http://dl.clackamas.edu/ch106-01/condense.htm Clackamas Community College
2001, 2003 Clackamas Community College, Hal Bender accessed -12/06
3
http://www.masterorganicchemistry.com/2011/06/20/deciphering-what-the-brackets-mean/ accessed -
12/06
4
http://www.masterorganicchemistry.com/2011/06/20/deciphering-what-the-brackets-mean/ accessed -
12/06
etc. They are named according to the arrangement and amount of atoms.
5
They can form
many different shapes and can be either saturated or unsaturated according to bonding
trends. Hydrocarbons are known for their use as being fossil fuels and their uses are based
on their structure.
Prefixes for naming straight-chain hydrocarbons which include up
to ten carbon atoms:
6

meth C
1

eth C
2

prop C
3

but C
4

pent C
5

hex C
6

hept C
7

oct C
8

non C
9

dec C
10


What is a homologous family?
Homologous means written the same. Taking the three simplest types of hydrocarbon,
alkanes, alkenes and alkynes we can write a general formula to represent the whole family
(or homologous series).
7
Physical and chemical properties like boiling point are similar
between members of a homologous family. For example, as the boiling point of a
homologous family increase, so do the number of carbon atoms. A homologous series have

5
http://www.wisegeek.org/what-is-a-hydrocarbon.htm Written By: Daniel Liden. Edited By: Bronwyn
HarrisCopyright Protected: 2003-2013 Conjecture Corporation accessed 12/06

6
http://www.ausetute.com.au/namsanes.html -AUS-e-TUTE n.d. Chemistry Tutorial : Naming Straight Chain
Alkanes viewed 12 June 2013 http://www.ausetute.com.au/namsanes.html

7
http://answers.yahoo.com/question/index?qid=20080324101259AAOONbh unknown author. Accessed
12/06/13

a general formula and similar chemical and physical properties because they have the same
functional group.
8

The homologous families. Alkanes and alkenes. What are they?
Alkanes are saturated hydrocarbons (no double bonds or more). They can vary in structure
and size and this atomic structure is what defines the alkane so they can be named. For
example:
butane, pentylcyclohexane,
cyclopropane
2,2-dimethylpropane, 2,2,3-trimethylbutane

Alkenes are unsaturated with a double bond between carbon atoms. Alkenes can also vary
in structure which allows identification. For example:
9

pent-1-ene, 3-ethylpent-1-ene, cyclobuta-
1,3-diene
or buta-1,3-diene, cyclohexene



8
http://www.docbrown.info/page06/FunctionalGroups.htm unknown author. Accessed 12/06/13

9
http://www.docbrown.info/page06/FunctionalGroups.htm#ALKANE unknown author. Accessed 12/06/13

What is an isomer?

An isomer is a compound that has the same formula as another compound, but with a
different arrangement. This therefore leads to different properties. This different
arrangement does not include a change in structure caused from molecule rotation or
movement around certain bonds.
10

IUPAC rules for naming alkanes:
1. Choose the correct ending: -ane, -ene, or -yne
2. Determine the longest carbon chain. Where a double or triple bond is present,
choose the longest chain that includes this bond. If there is a cyclic structure
present, the longest chain starts and stops within the cyclic structure.
3. Assign numbers to each C of the parent chain. For alkenes and alkynes the first
carbon of the multiple bond should have the smallest number. For alkanes the first
branch (or first point of difference) should have the lowest #. Carbons in a multiple
bond must be numbered consecutively.
4. Attach a prefix that corresponds to the number of carbons in the parent chain. Add
cyclo- to the prefix if it is a cyclic structure.
5. Determine the correct name for each branch (alkyl groups include methyl, ethyl,
propyl, etc.)
6. Attach the name of the branches alphabetically, along with their carbon position, to
the front of the parent chain name. Separate numbers from letters with hyphens
(e.g. 4-ethyl-2-methyldecane)
7. When two or more branches are identical, use prefixes (di-, tri-, etc.) (e.g. 2,4-
dimethylhexane). Numbers are separated with commas. Prefixes are ignored when
determining alphabetical order. (e.g. 2,3,5-trimethyl-4-propylheptane)
8. When identical groups are on the same carbon, repeat the number of this carbon in
the name. (e.g. 2,2-dimethylhexane)


10
http://www.chemguide.co.uk/basicorg/isomerism/structural.html - Jim Clark 2000 (modified November
2012) Accessed 12/06/13

Alkanes - saturated hydrocarbons
The names of the straight chain saturated hydrocarbons for up to a 12 carbon chain
are shown below. The names of the substituents formed by the removal of one
hydrogen from the end of the chain is obtained by changing the suffix -ane to -yl.
Number of Carbons Name
1 methane
2 ethane
3 propane
4 butane
5 pentane
6 hexane
7 heptane
8 octane
9 nonane
10 decane
11 undecane
12 dodecane
1. Identify the longest carbon chain. This chain is called the parent chain.
2. Identify all of the substituents (groups appending from the parent chain).
3. Number the carbons of the parent chain from the end that gives the
substituents the lowest numbers. When compairing a series of numbers, the
series that is the "lowest" is the one which contains the lowest number at the
occasion of the first difference. If two or more side chains are in equivalent
positions, assign the lowest number to the one which will come first in the
name.
4. If the same substituent occurs more than once, the location of each point on
which the substituent occurs is given. In addition, the number of times the
substituent group occurs is indicated by a prefix (di, tri, tetra, etc.).
5. If there are two or more different substituents they are listed in alphabetical
order using the base name (ignore the prefixes). The only prefix which is used
when putting the substituents in alphabetical order is iso as in isopropyl or
isobutyl. The prefixes sec- and tert- are not used in determining alphabetical
order except when compared with each other.
6. If chains of equal length are competing for selection as the parent chain, then
the choice goes in series to:
a) the chain which has the greatest number of side chains.
b) the chain whose substituents have the lowest- numbers.
c) the chain having the greatest number of carbon atoms in the smaller side
chain.
d)the chain having the least branched side chains.
7. A cyclic (ring) hydrocarbon is designated by the prefix cyclo- which appears
directly in front of the base name.
In summary, the name of the compound is written out with the substituents in
alphabetical order followed by the base name (derived from the number of carbons
in the parent chain). Commas are used between numbers and dashes are used
between letters and numbers. There are no spaces in the name.
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Examples:
IUPAC rules for naming alkenes and position isomers:

Alkenes are identified by double bonds. Double bonds in hydrocarbons are indicated by
replacing the suffix ane with -ene. If there is more than one double bond, the suffix is
expanded to include a prefix that indicates the number of double bonds present (-adiene, -
atriene, etc.). Triple bonds are named in a similar way using the suffix -yne. The position of
the multiple bond(s) within the parent chain is(are) indicated by placing the number(s) of
the first carbon of the multiple bond(s) directly in front of the base name.
1. The parent chain is numbered so that the multiple bonds have the lowest numbers
(double and triple bonds have priority over alkyl and halo substituents).
2. When both double and triple bonds are present, numbers as low as possible are
given to double and triple bonds even though this may at times give "-yne" a lower
number than "-ene". When there is a choice in numbering, the double bonds are
given the lowest numbers.
3. When both double and triple bonds are present, the -en suffix follows the parent
chain directly and the -yne suffix follows the -en suffix (notice that the e is left off, -
en instead of -ene). The location of the double bond(s) is(are) indicated before the

11
Powerpoint on nomenclature. Unknown author. Accessed 13/06/13
parent name as before, and the location of the triple bond(s) is(are) indicated
between the -en and -yne suffixes. See below for examples.
4. For a branched unsaturated acyclic hydrocarbon, the parent chain is the longest
carbon chain that contains the maximum number of double and triple bonds. If
there are two or more chains competing for selection as the parent chain (chain with
the most multiple bonds), the choice goes to (1) the chain with the greatest number
of carbon atoms, (2) the # of carbon atoms being equal, the chain containing the
maximum number of double bonds.
5. If there is a choice in numbering not previously covered, the parent chain is
numbered to give the substituents the lowest number at thefirst point of
difference.
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Examples:



What are Alkyl groups? How are these groups named that include
one or two carbon atoms?
The most common alkyl groups are discussed on this page. (They are also shown in example
11 in your workbook.) I would like to point out the similarities among these alkyl groups and
the alkanes we discussed earlier.



12
http://butane.chem.uiuc.edu/cyerkes/Chem104A_BFA05/Genchemref/nomenclature_rules.html
unknown author. accessed 12/06/13



Methyl Group
Methane has one carbon and four
hydrogens. The methyl group also has one
carbon but only three hydrogens. In place of
the fourth hydrogen, there is a bond to
something else.
methyl
H
|
H-C-
|
H

Ethyl Group
Ethane has two carbons and six hydrogens. If
any one of those hydrogens is removed and
replaced with a bond to something else, you
end up with an ethyl group.
ethyl
H H
| |
H-C-C-
| |
H H

Propyl Groups
Propane has three carbons and
eight hydrogens. If one of the
six endhydrogens is replaced by a
bond to something else, you end up
with anormal propyl group. If one
of the two middle hydrogens is
replaced by a bond to something
else, you end up with
an isopropyl group.
n-propyl
or simply
propyl
H H H
| | |
H-C-C-C-
| | |
H H H

isopropyl
H H H
| | |
H-C-C-C-H
| | |
H H






Butyl Groups
The next set of alkyl groups contains four carbons. That is why they are called butyl groups.
There are four types of butyl groups each with a different combination of carbon chain and
bonding point.
The first one is a straight chain with an H
missing from the end and is called a normal
butyl group (or n-butyl group).

n-butyl
or
butyl

The next one is iso-butyl (usually
spelled isobutyl). It has a branched chain at
the end opposite where it attaches to
something else.

iso-butyl
or
isobutyl

There is also a secondary-butyl which is
often referred to as sec-butyl. Its structural
arrangement is shown here.

sec-butyl

Also, tertiary-butyl (also called tert-
butyl or t-butyl) has a fourth kind of
arrangement as shown.
13


tert-butyl
or
t-butyl



The halogen is treated as a substituent on an alkane chain. The halo- substituent is
considered of equal rank with an alkyl substituent in the numbering of the parent chain. The
halogens are represented as:
14



13
http://dl.clackamas.cc.or.us/ch106-01/alkyl1.htm Clackamas Community College
2001, 2003 Clackamas Community College, Hal Bender accessed 12/06
14
http://butane.chem.uiuc.edu/cyerkes/Chem104A_BFA05/Genchemref/nomenclature_rules.html unknown
author accessed 12/06

F fluoro-
Cl chloro-
Br bromo-
I iodo-


IUPAC rules for naming branched alkanes and alkenes:
Examples of the IUPAC Rules in Practice
The following two cases provide examples of monosubstituted cycloalkanes.

In the first case, on the left, we see a seven-carbon ring bearing a C
4
H
9
substituent group.
Earlier this substituent was identified as the tert-butyl group, so a name based on the
cycloheptane root is easily written. In the second case, on the right, a four-carbon ring is
attached to a branched six-carbon alkyl group. This C
6
H
13
group could be named "isohexyl",
but a better approach is to name this compound as a disubstituted pentane. The four-
membered ring substituent is called a cyclobutyl group.
15

Here is a simple list of rules to follow. Some examples are given at the end of the list.
1. Identify the longest carbon chain. This chain is called the parent chain.
2. Identify all of the substituents (groups appending from the parent chain).
3. Number the carbons of the parent chain from the end that gives the substituents the
lowest numbers. When compairing a series of numbers, the series that is the
"lowest" is the one which contains the lowest number at the occasion of the first
difference. If two or more side chains are in equivalent positions, assign the lowest
number to the one which will come first in the name.
4. If the same substituent occurs more than once, the location of each point on which
the substituent occurs is given. In addition, the number of times the substituent
group occurs is indicated by a prefix (di, tri, tetra, etc.).
5. If there are two or more different substituents they are listed in alphabetical order
using the base name (ignore the prefixes). The only prefix which is used when
putting the substituents in alphabetical order is iso as in isopropyl or isobutyl. The

15
https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/nomexmp1.htm#exp1 author unknown
accessed 13/06

prefixes sec- and tert- are not used in determining alphabetical order except when
compared with each other.
6. If chains of equal length are competing for selection as the parent chain, then the
choice goes in series to:
a) the chain which has the greatest number of side chains.
b) the chain whose substituents have the lowest- numbers.
c) the chain having the greatest number of carbon atoms in the smaller side chain.
d)the chain having the least branched side chains.
7. A cyclic (ring) hydrocarbon is designated by the prefix cyclo- which appears directly
in front of the base name.
In summary, the name of the compound is written out with the substituents in alphabetical
order followed by the base name (derived from the number of carbons in the parent chain).
Commas are used between numbers and dashes are used between letters and numbers.
There are no spaces in the name.
16




16
http://butane.chem.uiuc.edu/cyerkes/Chem104A_BFA05/Genchemref/nomenclature_rules.html accessed
12/06/13. Author unknown

What are cyclic alkanes and alkenes? IUPAC rules used for naming
these:
For a branched unsaturated cyclic hydrocarbon, the parent chain is considered the chain
with the most double and triple bonds. So if two chains have the same number of bonds the
chain with the most double and triple becomes the parent chain.
A cyclic hydrocarbon has a similar naming system as a non-cyclic hydrocarbon. Cyclo-
hydrocarbons with double bonds are classed as cycloalkenes, and triple bonds as
cycloaklynes. However there are differences:



Because all the carbons in a cyclic hydrocarbon ring are equal, you don't need to use a
number if your cyclic hydrocarbon only has one constituent.
If the alkyl group attached to the cyclic hydrocarbon is larger or more complex than the ring,
then the cyclic hydrocarbon may become a substituent instead of the parent chain.
If two substituents are on the ring, they're numbered in alphabetical order. The first
(alphabetically) substituent is 1; the next is numbered going counterclockwise or clockwise -
whichever results in a lower number for the second substituent.
If more than two substituents are on the ring, the first one alphabetically is said to be
attached to the first carbon. The others are numbered counterclockwise or clockwise -
whichever results in the lowest numbers.
Like non-cyclic hydrocarbons, the final molecule is named in alphabetical order, excluding
prefixes like di-, tri- and tetra-.
Source material; contains practice problems
Wikipedia on IUPAC nomenclature
Official IUPAC literature on naming compounds Published by Advanced Chemistry
Development, Inc.
17




17
http://www.wikihow.com/Name-a-Hydrocarbon-Chain-Using-the-IUPAC-Method


Halogen derivatives of the above. Haloalkeanes and haloalkenes
HALOGENOALKANES (HALOALKANES)
C-X halogen functional group where X = F fluoro, Cl chloro.., Br bromo or I iodo
X is named as a prefix substituent in any type of organic molecule from alkanes to carboxylic
acids.
chloromethane, bromoethane, dichlorodifluoromethane
1-bromo-1-chlorobutane, iodocyclohexane
1,2-dibromocyclopentane, chloromethylbenzene
and C
n
H
2n-1
X for saturated cyclohalogenoalkanes (n=3,4,5 etc. with one C-X bond)
A sub-CLASSIFICATION based on structural differences, which can have chemical
consequences on e.g. rate of reaction or products formed in a reaction.
o Halogenoalkanes are classified according to the atoms/groups attached to
the carbon of the halogen atom X.
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18
http://www.docbrown.info/page06/FunctionalGroups.htm#ALKANE unknown author. Accessed 12/06/13
What is an alkanol? IUPAC rules for naming these:
Alkanols must include a hydroxyl OH group to a minimum of one carbon atom in the parent
chain. With the hydroxyl attached directly to the benzene ring, the hydrocarbon can be
classed as a phenol. The primary suffix name is ..ol for alcohol and so for the longest carbon
chain (alkanol) the names are based on: 1 carbon, methanol; 2 carbons, ethanol; 3 carbons,
propanol; 4 carbons, butanol. After these 4 preserved 'old trivial' names, the name is
'numerically' systematic e.g. 5 carbons, pentanol; 6 hexanol, 7 heptanol, 8 octanol etc.
The positions of the substituent alkyl (or other) groups are denoted by using the
lowest possible numbers for the associated carbon atoms in the main chain.
If there is more than one 'type' of substituent e.g. using the prefixes: methyl and
ethyl.. etc., they are written out in alphabetical order (di, tri are ignored in using this
rule).
Alcohols are classified according to the atoms/groups attached to the carbon of the
hydroxy group
19

STEPS
(1) Identify that the carbon compound is an ester, that is, it has the group: -COO- .
(2) Count the number of carbons in the carbon chain that does NOT contain the C=O
and identify the appropriate stem. This part is derived from the alkanol.
(3) Attach the ending yl to the stem. This forms the first part of the name.
(4) Count the number of carbons in the carbon chain that DOES contain the COO and
identify the appropriate stem name. This part is derived from the alkanoic acid.
(5) Attach the ending anoate to the acid stem. This forms the second part of the name.
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- Sarah Morris

19
http://www.docbrown.info/page06/DFalcether.htm unknown author. Accessed 13/06/13

20
http://www.raci.org.au/document/item/1012 unknown author. Accessed 13/06/13