Org Chem Hand Out
Org Chem Hand Out
Org Chem Hand Out
HYDROCARBONS
Alkanes
Alkanes, or saturated hydrocarbons, contain only single
covalent bonds between carbon atoms. Each of the
carbon atoms in an alkane has sp3 hybrid orbitals and is
A common method used by organic chemists to simplify All alkanes are composed of carbon and hydrogen
the drawings of larger molecules is to use a skeletal atoms, and have similar bonds, structures, and formulas;
structure (also called a line-angle structure). In this type noncyclic alkanes all have a formula of CnH2n+2. The
of structure, carbon atoms are not symbolized with a C, number of carbon atoms present in an alkane has no
but represented by each end of a line or bend in a line. limit. Greater numbers of atoms in the molecules will
Hydrogen atoms are not drawn if they are attached to a lead to stronger intermolecular attractions (dispersion
carbon. Other atoms besides carbon and hydrogen are forces) and correspondingly different physical properties
represented by their elemental symbols. Figure 20.3 of the molecules. Properties such as melting point and
shows three different ways to draw the same structure. boiling point (Table 20.1) usually change smoothly and
predictably as the number of carbon and hydrogen atoms
in the molecules change.
Naming Alkanes
1.
2.
3.
When more than one substituent is present, either on the
same carbon atom or on different carbon atoms, the
4. substituents are listed alphabetically. Because the carbon
atom numbering begins at the end closest to a
substituent, the longest chain of carbon atoms is These are complex organic molecules with long chains
numbered in such a way as to produce the lowest of carbon atoms, which contain at least one double bond
number for the substituents. The ending -o replaces -ide between carbon atoms. Unsaturated hydrocarbon
at the end of the name of an electronegative substituent molecules that contain one or more double bonds are
(in ionic compounds, the negatively charged ion ends called alkenes. Carbon atoms linked by a double bond
with -ide like chloride; in organic compounds, such are bound together by two bonds, one σ bond and one π
atoms are treated as substituents and the –o ending is bond. Double and triple bonds give rise to a different
used). The number of substituents of the same type is geometry around the carbon atom that participates in
indicated by the prefixes di- (two), tri- (three), tetra- them, leading to important differences in molecular
(four), and so on (for example, difluoro- indicates two shape and properties. The differing geometries are
fluoride substituents). responsible for the different properties of unsaturated
versus saturated fats.
We call a substituent that contains one less hydrogen
than the corresponding alkane an alkyl group. The name Ethene, C2H4, is the simplest alkene. Alkene has a
of an alkyl group is obtained by dropping the suffix -ane general formula CnH2n. Each carbon atom in ethene,
of the alkane name and adding -yl: commonly called ethylene, has a trigonal planar
structure. The second member of the series is propene
(propylene) the butene isomers follow in the series. Four
carbon atoms in the chain of butene allows for the
formation of isomers based on the position of the double
bond, as well as a new form of isomerism.
1.
2.
Naming Alkenes
1. The -ene suffix (ending) indicates an alkene or
cycloalkene.
2. The longest chain chosen for the root name must
include both carbon atoms of the double bond.
3. The root chain must be numbered from the end
nearest a double bond carbon atom. If the double
3. bond is in the center of the chain, the nearest
substituent rule is used to determine the end where
Alkenes numbering starts.
Organic compounds that contain one or more double or 4. The smaller of the two numbers designating the
triple bonds between carbon atoms are described as carbon atoms of the double bond is used as the
unsaturated. You have likely heard of unsaturated fats. double bond locator.
5. If more than one double bond is present the Let’s try this!
compound is named as a diene, triene or equivalent Name the following alkenes:
prefix indicating the number of double bonds, and
each double bond is assigned a locator number. 1.
Examples:
2.
4.
FUNCTIONAL GROUPS
Certain combinations of bonds show up repeatedly in
organic chemistry and organic chemists give those
bonding combinations specific names. It is very useful to
know the names of those specific types of bonds. With
over twenty million known organic compounds in
For the example above, the longest carbon chain existence, it would be very challenging to memorize
is 7 with the triple bond on the 3rd carbon, so this is chemical reactions for each one. Fortunately, molecules
heptyne. Start numbering on the carbon nearest to the with similar functional groups tend to undergo similar
triple bond. Indicate the location of the substituents. The reactions. A functional group is defined as an atom or
name is 2,5,6-Trimethylhept-3-yne. group of atoms within a molecule that has similar
chemical properties whenever it appears in various
compounds. Even if other parts of the molecule are quite
different, certain functional groups tend to react in
certain ways.
Alcohol Nomenclature
Alcohols with one to four carbon atoms are frequently
called by common names, in which the name of the alkyl
group is followed by the word alcohol:
For this sample, the longest chain is 5 with two
substituents. Start the number to the end nearer the
The parent chain on the sample above is butane.
Start numbering on the carbon nearest to the hydroxyl
1. Find the longest chain containing the hydroxyl group group. The location of the hydroxyl group is on the first
(OH). If there is a chain with more carbons than the carbon. There is also a substituent on the third carbon.
one containing the OH group it will be named as a Indicate the location of the substituent, then write the
substituent. parent chain and the location of the hydroxyl group,
2. Place the OH on the lowest possible number for the ending with –ol. The name is 3-Methylbutan-1-ol.
chain. With the exception of carbonyl groups such as
ketones and aldehydes, the alcohol or hydroxyl
groups have first priority for naming.
3. When naming a cyclic structure, the -OH is assumed
to be on the first carbon unless the carbonyl group is
present, in which case the later will get priority at the
first carbon. The longest carbon-carbon chain is 4, so the
4. When multiple -OH groups are on the cyclic parent chain is butane. There are two hydroxyl group
structure, number the carbons on which the -OH located on the first and third carbon. The name of the
groups reside. compound is Butane-1,3-diol.
5. Remove the final e from the parent alkane chain and
add -ol. When multiple alcohols are present use di,
tri, et.c before the ol, after the parent name. ex.
Hexan-2,3-diol.
Examples: