Org Chem Hand Out

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INTRODUCTION TO ORGANIC CHEMISTRY bonded to four other atoms, each of which is either

carbon or hydrogen. The Lewis structures and models of


All living things on earth are formed mostly of methane, ethane, and pentane are illustrated in Figure
carbon compounds. The prevalence of carbon 20.2. Carbon chains are usually drawn as straight lines in
compounds in living things has led to the epithet Lewis structures, but one has to remember that Lewis
“carbon-based” life. The truth is we know of no other structures are not intended to indicate the geometry of
kind of life. Early chemists regarded substances isolated molecules. Notice that the carbon atoms in the structural
from organisms (plants and animals) as a different type models (the ball-and stick and space-filling models) of
of matter that could not be synthesized artificially, and the pentane molecule do not lie in a straight line.
these substances were thus known as organic Because of the sp3 hybridization, the bond angles in
compounds. The widespread belief called vitalism held carbon chains are close to 109.5°, giving such chains in
that organic compounds were formed by a vital force an alkane a zigzag shape.
present only in living organisms. The German chemist The structures of alkanes and other organic molecules
Friedrich Wohler was one of the early chemists to refute may also be represented in a less detailed manner by
this aspect of vitalism, when, in 1828, he reported the condensed structural formulas (or simply, condensed
synthesis of urea, a component of many body fluids, formulas). Instead of the usual format for chemical
from nonliving materials. Since then, it has been formulas in which each element symbol appears just
recognized that organic molecules obey the same natural once, a condensed formula is written to suggest the
laws as inorganic substances, and the category of organic bonding in the molecule. These formulas have the
compounds has evolved to include both natural and appearance of a Lewis structure from which most or all
synthetic compounds that contain carbon. Some carbon- of the bond symbols have been removed. Condensed
containing compounds are not classified as organic, for structural formulas for ethane and pentane are shown
example, carbonates and cyanides, and simple oxides, at the bottom of Figure 20.2, and several additional
such as CO and CO2. Although a single, precise examples are provided in the exercises at the end of this
definition has yet to be identified by the chemistry chapter.
community, most agree that a defining trait of organic
molecules is the presence of carbon as the principal
element, bonded to hydrogen and other carbon atoms.

Today, organic compounds are key components


of plastics, soaps, perfumes, sweeteners, fabrics,
pharmaceuticals, and many other substances that we use
every day. The value to us of organic compounds
ensures that organic chemistry is an important discipline
within the general field of chemistry. In this chapter, we
discuss why the element carbon gives rise to a vast
number and variety of compounds, how those
compounds are classified, and the role of organic
compounds in representative biological and industrial
settings.

HYDROCARBONS

The simplest organic compounds contain only


the elements carbon and hydrogen, and are called
hydrocarbons. Even though they are composed of only
two types of atoms, there is a wide variety of
hydrocarbons because they may consist of varying
lengths of chains, branched chains, and rings of carbon
atoms, or combinations of these structures. In addition,
hydrocarbons may differ in the types of carbon-carbon
bonds present in their molecules. Many hydrocarbons
are found in plants, animals, and their fossils; other
hydrocarbons have been prepared in the laboratory. We
use hydrocarbons every day, mainly as fuels, such as
natural gas, acetylene, propane, butane, and the principal
components of gasoline, diesel fuel, and heating oil. The
familiar plastics polyethylene, polypropylene, and
polystyrene are also hydrocarbons. We can distinguish
several types of hydrocarbons by differences in the
bonding between carbon atoms. This leads to differences
in geometries and in the hybridization of the carbon
orbitals.

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

The International Union of Pure and Applied Chemistry


(IUPAC) has devised a system of nomenclature that
begins with the names of the alkanes and can be adjusted
from there to account for more complicated structures.

The nomenclature for alkanes is based on two rules:

1. To name an alkane, first identify the longest chain of


carbon atoms in its structure. A two-carbon chain is
called ethane; a three-carbon chain, propane; and a
four-carbon chain, butane. Longer chains are named
as follows: pentane (five-carbon chain), hexane (6),
heptane (7), octane (8), nonane (9), and decane (10).
2. Add prefixes to the name of the longest chain to
indicate the positions and names of substituents.
Substituents are branches or functional groups that
replace hydrogen atoms on a chain. The position of a
Let’s try this!
substituent or branch is identified by the number of
Draw the skeletal structures for these two molecules: the carbon atom it is bonded to in the chain. We
number the carbon atoms in the chain by counting
from the end of the chain nearest the substituents.
Multiple substituents are named individually and
placed in alphabetical order at the front of the name.

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.

The name of an alkene is derived from the name of the


alkane with the same number of carbon atoms. The
presence of the double bond is signified by replacing the
suffix -ane with the suffix -ene. The location of the
double bond is identified by naming the smaller of the
numbers of the carbon atoms participating in the double
bond:

Let’s try this!


Name the following alkanes:

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.

This alkene will be named based on the rules of


naming alkanes. The only difference is that the position
3.
of the double bond must be specified.

The longest Carbon chain is 5, so the parent is


pentene. However, the double bond must be specified.
The position of the double bond is on the 2nd carbon,
therefore, the name of the alkene above is pent-2-ene.
4.

If there is/are double bond/s present, it must be


included in the parent chain. For the alkene above, the 5.
longest chain is 6, but the double bond is not included,
so, this will be 5. The double bond is located in the first
carbon. On the 2nd carbon, there is a substituent having 2
carbons (ethyl). Indicate first the position of the
substituent, write the prefix of the parent, indicate the
position, then write –ene. This alkene will be named as
2-ethylpent-1-ene. Alkynes
Hydrocarbon molecules with one or more triple bonds
are called alkynes; they make up another series of
unsaturated hydrocarbons. Two carbon atoms joined by
a triple bond are bound together by one σ bond and two
In this condensed structure sample of an alkene,
π bonds. The sphybridized carbons involved in the triple
the longest chain is 6 wherein the double bond is
bond have bond angles of 180°, giving these types of
position on the 2nd carbon. Therefore, the name of the
bonds a linear, rod-like shape.
alkene is hex-2-ene.
The simplest member of the alkyne series is ethyne,
C2H2, commonly called acetylene. The Lewis structure
for ethyne, a linear molecule, is:

The IUPAC nomenclature for alkynes is similar to that


In this sample, the longest carbon chain is 6,
for alkenes except that the suffix -yne is used to indicate
with a substituent. In assigning the numbers, prioritize
a triple bond in the chain. For example, CH3CH2C≡CH
the double bond. However, if the double bond is in the
is called but-1-yne.
middle part and there is a substituent, start numbering
where the substituent will receive the smallest number
Naming Alkynes
possible. The example above will be named as 2-
1. Find the longest carbon chain that includes both
methylhex-3-ene.
carbons of the triple bond.
2. Number the carbon of the longest chain starting at
the end closest to the triple bond.
3. In case there is a double bond, numbering of the
hydrocarbon chain starts from the end nearer the first
If there are more than 1 double bonds, assign the multiple bonds, whether double or triples. If there is
numbers for each carbon where the double bonds will a choice in numbering, double bonds receive lower
receive the least number possible. In this sample, the numbers than triple bonds.
name of the alkene is pent-1,3-diene. 4. After numbering the longest chain with the lowest
number assigned to the alkyne, label each of the
substituents at its corresponding carbon. While
writing out the name of the molecule, arrange the Let’s try this!
substituents in alphabetical order. If there are more Name the following alkynes.
than one of the same substituent use the prefixes di, 1.
tri, and tetra for two, three, and four substituents
respectively. These prefixes are not taken into
account in the alphabetical order.
2.
Examples:

For this alkyne, the longest carbon chain is 4, so


it is a butyne with the first carbon having a triple bond.
Start numbering with the carbon having the triple bond.
3.
Indicate the location or number of the substituent. The
name of the alkyne above is 3-Methylbut-1-yne.

4.

For this example, the longest chain is 6, which


has a triple bond on the second carbon (hexyne). Start 5.
numbering on the carbon nearest to the triple bond.
Indicate also the position of the substituents. The name
for this alkyne is 4,4,5-Trimethylhex-2-yne.

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.

We've already looked at alkanes, but they are


generally unreactive. We primarily use alkanes as a
For this example, the longest chain of carbon is nine. source of energy when they are combusted. While the
The triple bond is located on the 3rd carbon. Substituents majority of functional groups involve atoms other than
are on the 5th and on the 6th carbon. The name for this carbon and hydrogen, we will also look at some that
compound is 5,6-Dimethylnon-3-yne. include only carbon and hydrogen. Some of the most
common functional groups are presented in the
following sections.

Organic molecules vary greatly in size and when


focusing on functional groups, we want to direct our
attention to the atoms involved in the functional group.
As a result, the abbreviation R is used in some examples.
For the last example, there are both double and triple
The letter R is used in molecular structures to represent
bond on the compound. Start numbering on the carbon the “Rest of the molecule”. It consists of a group of
with the nearest multiple bond. In this case, triple bond carbon and hydrogen atoms of any size. It is used as an
is nearest to the terminal carbon. The longest chain is 7.
abbreviation since a group of carbon and hydrogen
There are no substituents. The name for this organic atoms does not affect the functionality of the compound.
compound is hept-3-en-1-yne. In some molecules, you will see R, R’, or R’’ which
indicates that the R groups in the molecule can be
different from one another. For example, R might be –
CH2CH3 while R’ is –CH2CH2CH2CH3.
Alkyl Halides halogen. Indicate the positions of the substituents
The alkyl halides, also known as haloalkanes, considering the alphabetical order in naming the
are a group of chemical compounds comprised of an compound. The IUPAC nomenclature of the compound
alkane with one or more hydrogens replaced by a is 3-Ethyl-2-iodopentane.
halogen atom (Group 17 atom). There is a fairly large
distinction between the structural and physical properties
of haloalkanes and the structural and physical properties
of alkanes.
Haloalkanes are found in fire extinguishers,
refrigerants, propellants, solvents, and medications. They
are also a significant source of pollution and their use For this sample, the carbon-carbon bonds
has been reduced or eliminated in some products. formed a ring, resulting to a cycloalkane with three
Chlorofluorocarbons (CFCs) were used as refrigerants in substituents. Start numbering on the carbon with
air-conditioners but were found to be a major cause of attached fluorine atom with an alkyl substituents near it
the depletion of the ozone layer. Research and so that the fluorine atoms will receive 1 and 4
development of alternatives began in the 1970s. respectively while the alkyl substituent will receive 2.
Hydrochlorofluorocarbons (HCFCs) have been used for Consider the alphabetical order in numbering the
many years since they cause less damage to the ozone compound. The IUPAC name for this compound is 1,4-
layer, but many countries agreed to eliminate HCFCs by Difluoro-2-methylcyclopentane.
2020.

Steps in naming Alkyl Halides


1. Identify and name the longest carbon chain
containing the halogen atoms.
2. Identify and name each halogen atom present in the
For the skeleton structure of the organic
molecule:
compound above, the longest carbon-carbon chain is 7.
Symbol of Name of "Halo" Prefix to There are three substituents. The distance of the
Element Element use branches varies where in an alkyl group is nearer than
F fluorine fluoro the halogens in the terminal carbon. Start numbering
near the alkyl group so all the substituents will receive
Cl chlorine chloro
the numbers 2, 4 and 5 respectively. Indicate the position
Br bromine bromo of the substituents. The IUPAC nomenclature for this
I iodine iodo organic compound is 4-Bromo-5-chloro-2-
methylheptane.
3. If more than one type of halogen atom is present,
assign the numbers to which the substituents
including the halogens will receive the lowest
number possible. If a substituent and halogen are on
the same position, prioritize the halogen, if not,
assign the lowest possible numbers to the substituent For the example above, the compound is
nearest to the first carbon. composed of a5-carbon ring with halogen. Another thing
4. If more than one atom of the same halogen element is that there is a triple bond so it is an alkyne. Start
is present, modify the halo prefix using the numbering on the triple bond where the substituents can
appropriate multiplier prefix. receive the lowest numbers possible. The name for this
5. Assemble the name. compound is 3-Bromo-4-chlorocyclopent-1-yne.
6. Rules on multiple bonds will be applied.
Alcohol
Examples: An alcohol is an organic compound with a hydroxyl
(OH) functional group on an aliphatic carbon atom.
Because OH is the functional group of all alcohols, we
often represent alcohols by the general formula ROH,
where R is an alkyl group. Alcohols are common in
nature. Most people are familiar with ethyl alcohol
For this example, the longest chain is 4 with two (ethanol), the active ingredient in alcoholic beverages,
substituents (chlorine and methyl). Start number to the but this compound is only one of a family of organic
end nearer the halogen. Indicate the position of the compounds known as alcohols. The family also includes
substituents. Consider the alphabetical order in naming such familiar substances as cholesterol and the
the compound. The IUPAC nomenclature for this carbohydrates. Methanol (CH3OH) and ethanol
organic compound is 2-chloro-3-methylbutane. (CH3CH2OH) are the first two members of the
homologous series of alcohols.

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: The sample above contains a triple bond, a


substituent and a hydroxyl group. The longest chain is 8.
Start numbering on the carbon nearest to the hydroxyl
group since it will be prioritized than the triple bond.
The name for the compound is 5-Methyloct-6-en-3-ol.
The skeleton structure above is composed of 6-
carbon ring with two hydroxyl group. Start numbering Aldehydes
on the first carbon where the two hydroxyl group will An aldehyde is a common functional group in
receive the smallest possible number. The name of the organic chemistry. Britannica states that aldehydes can
compound is Cyclohexane-1,2-diol. be found in perfume fragrances as well as natural and
synthetic hormones. In an aldehyde, a carbonyl group is
single-bonded to a hydrogen atom. A carbonyl is a
carbon that is double bonded to an oxygen atom. The
The structure above shows a chain of 3 carbons carbonyl carbon is also bonded to another hydrogen
with a double bond. For this, the name of the parent atom or a carbon/hydrogen chain, typically known as an
chain is propene. Start numbering where the hydroxyl R group.
group will receive the smallest possible number. Indicate Aldehydes contain the carbonyl group.
the position of the double bond. The name for the Aldehydes are considered the most important functional
compound is Prop-2-en-1-ol. group. They are often called the formyl or methanoyl
group. Aldehydes derive their name from
the dehydration of alcohols. Aldehydes contain the
carbonyl group bonded to at least one hydrogen atom.

For this sample, the longest carbon chain is 7 Aldehyde Nomenclature


with a double bond. Start numbering where the hydroxyl
(OH) group will receive the smallest possible number. The IUPAC system of nomenclature assigns a
The name for the compound is Hept-6-en-1-ol. characteristic suffix -al to aldehydes. For example,
H2C=O is methanal, more commonly called
formaldehyde. Since an aldehyde carbonyl group must
always lie at the end of a carbon chain, it is always is
given the #1 location position in numbering and it is not
necessary to include it in the name. There are several
simple carbonyl containing compounds which have
The sample above shows butane with a common names which are retained by IUPAC.
substituent bonded with a hydroxyl group. Start
numbering where the hydroxyl group will receive the 1. Aldehydes take their name from their parent alkane
smallest possible value. State the location of the chains. The -e is removed from the end and is
substituent, write the root of the parent name then replaced with -al.
indicate the location of the hydroxyl group then write – 2. The aldehyde functional group is given the 1
ol. The name for the compound is 3-Methylbutan-1-ol. numbering location and this number is not included
in the name.
3. For the common name of aldehydes start with the
common parent chain name and add the suffix -
aldehyde. Substituent positions are shown with
Greek letters.
4. When the -CHO functional group is attached to a
ring the suffix -carbaldehyde is added, and the
carbon attached to that group is C1.

Examples:

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