Organic Chem

Organic compounds are now defined as compounds that are based on

carbon. They usually contain carbon-carbon and carbon-hydrogen bonds.

Carbon Atom:
Properties of carbon:
- Carbon can form 4 bonds due to having 4 valence electrons, carbon can bond to many
other types of atoms, such as hydrogen, oxygen, and nitrogen.
- Carbon can form strong single, double, or triple bonds with itself.
- Molecules that contain carbon-carbon bonds are saturated (all carbon atoms are bonded
to the maximum # of other atoms:4), bonds containing double triple carbon atoms are
unsaturated.
- Due to the unique bonding properties, carbon can create a variety of structures,
including chains, rings, sheets and other shapes in a variety of sizes.
 1.2 Hydrocarbons
Hydrocarbons are composed entirely of carbon and hydrogen atoms, and are widely
used as fuels. Gasoline, propane, and natural gas. They contain only carbon and
hydrogen atoms, hydrocarbons are nonpolar compounds

Classification of Hydrocarbons:
- Aliphatic hydrocarbons contain carbon atoms that are bonded in one or more chains
and rings. The carbon atoms have single, double, or triple bonds. Aliphatic hydrocarbons
include straight chain and cyclic alkanes, alkenes, and alkynes.

- Aromatic hydrocarbon is a hydrocarbon based on the aromatic benzene group.

Benzene is the simplest aromatic compound. Its bonding arrangement results in special
molecular stability

Alkanes, Alkenes, and Alkynes

- An alkane is a hydrocarbon that has only single bonds, Alkanes that do not contain rings
have the formula CnH2n + 2.
- An alkane in the shape of a ring is called a cycloalkane, which has the formula CnH2n.
- An alkene is a compound that has at least one double bond; straight-chain alkenes with
one double bond have the same formulary as cycloalkane.
- In a double carbon-carbon bond, one pair of electrons form a single bond and the other
pair creates an additional weaker bond. These weaker bonds react faster than the
electrons in the single bond. As a result carbon-carbon double bonds are more
reactive than single carbon-carbon bonds.
- Functional groups help to determine the physical and chemical properties of compounds.
For example, the reactive double bond is the functional group for an alkene.
- An alkyne is a compound that has at least one triple bond. A straight chain alkyne with
one triple bond has the formula CnH2n − 2. Triple bonds are even more reactive than
double bonds. The functional group for an alkyne is the triple bond

Naming organic compounds:

prefix + root + suffix

The root of a compound’s name indicates the number of carbon atoms in

the main (parent) chain or ring.
The suffix indicates the type of compound, according to the functional groups present. The
prefix indicates the name and location of each branch and functional group on the main carbon
chain. Most organic compounds have branches, called alkyl groups, attached to the main
chain. An alkyl group is obtained by removing one hydrogen atom from an alkane.

How to name Hydrocarbons:

1) Find the Root: Identify the longest chain or ring in the hydrocarbon. If the hydrocarbon
is an alkene or an alkyne, make sure that you include any multiple bonds in the main
chain. Count the number of carbon atoms in the main chain to obtain the root
2) Find the suffix: If the hydrocarbon is an alkane, use the suffix -ane. Use -ene if the
hydrocarbon is an alkene. Use -yne if the hydrocarbon is an alkyne. If more than one
double or triple bond is present, use the prefix di- (2) or tri- (3) before the suffix to
indicate the number of multiple bonds.
3) Give a position number to every carbon atom in the main chain. Start from the end that
gives you the lowest possible position number for the double or triple bond, if there is
one. If there is no double or triple bond, number the compound so that the branches
have the lowest possible position numbers
4) Find the prefix: Name each branch as an alkyl group, and give it a position number. If
more than one branch is present, write the names of the branches in alphabetical order.
Put the position number of any double or triple bonds after the position numbers and
names of the branches, just before the root.
5) Put the name together: prefix + root + suffix.
Aromatic Compounds:
- Benzene is a cyclic compound with the equivalent of three double bonds and three
single bonds.
- The electrons that form the double bonds in benzene are spread out and shared over
the whole molecule. Thus, benzene actually has six identical bonds, each one half-way
between a single and a double bond. These bonds are much more stable than ordinary
double bonds and do not react in the same way. Molecules with this type of special
electron sharing are called aromatic compounds.

Naming an Aromatic Hydrocarbon:

1. Number the carbons in the benzene ring. If more than one type of branch is attached to
the ring, start numbering at the carbon with the highest priority (or most complex) group.
(See the Problem Tip.)
2. Name any branches that are attached to the benzene ring. Give these branches
position numbers. If only one branch is attached to a benzene ring, you do not need to
include a position number.
3. Place the branch numbers and names as a prefix before the root, benzene
4. When a benzene ring has only two branches, the prefixes ortho-,
meta-, and para- are sometimes used instead of numbers.

Functional Groups:
Physical Properties and Forces Between Molecules:
- Hydrogen bonding is a strong intermolecular attraction between the hydrogen atom from
an NH, OH, or FH group on one molecule,and a nitrogen, oxygen, or fluorine atom on
another molecule.
- The attractive forces between polar molecules are called dipole-dipole interactions.
These forces cause polar molecules to cling to each other.
- Dispersion forces are attractive forces that occur between all covalent molecules. These
forces are usually very weak for small molecules, but they strengthen as the size of the
molecule increases.
- Molecules that can form hydrogen bonds with themselves have a higher boiling point
than similar molecules that cannot form hydrogen bonds with themselves. For example,
alcohols can form hydrogen bonds, but alkanes cannot. Therefore, alcohols have higher
boiling points than alkanes.
- Polar molecules usually have a higher boiling point than similar non-polar molecules.
Also, polar molecules that can form hydrogen bonds have an even higher boiling point
than polar molecules that cannot form hydrogen bonds. For example, ethanol. Polar
molecules with a large non-polar hydrocarbon part are less polar than polar molecules
with a smaller non-polar hydrocarbon part. For example, octanol,
CH3CH2CH2CH2CH2CH2CH2CH2OH, is less polar than ethanol, CH3CH2OH. The
larger it is the less soluble it becomes.
- A molecule with a greater number of carbon atoms usually has a higher boiling point
than the same type of molecule with fewer carbon atoms.

Alcohols:
- Contains the OH functional group.
- Depending on the position of the hydroxyl group, an alcohol can be primary, secondary.
Or tertiary.
Naming Alcohols:
- Step 1 Locate the longest chain that contains an OH group attached to one of the
carbon atoms. Name the parent alkane.
- Step 2 Replace the -e at the end of the
name of the parent alkane with -ol.
- Step 3 Add a position number before the
root of the name to indicate the location of
the OH group. (Remember to number the
main chain of the hydrocarbon so that the
hydroxyl group has the lowest possible
position number.) If there is more than one
OH group, leave the -e in the name of the
parent alkane, and put the appropriate
prefix (di-, tri-, or tetra-) before the suffix -ol.
- Step 4 Name and number any other branches on the main chain. Add the name of these
branches to the prefix.
- Step 5 Put the name together: prefix + root + suffix.

Physical Properties of Alcohols:

Physical Properties of Alcohols:
- Hydroxyl group is very polar, making smaller alcohols polar also.
- Small alcohols such as methanol and ethanol can be mixed in all proportions (miscible)
with water.
- As the chain grows longer, the non-polar characteristics take the place of the polarity of
the hydroxyl group and the alcohol becomes less soluble in water.
- Hydroxyl groups also allow the alcohols to hydrogen bond with one another, making the
boiling point of pure alcohols much higher than those of the corresponding alkanes.
- All straight chain alcohols, containing less than 12 carbon atoms are liquids at room
temp.

Haloalkanes: a hydrocarbon derivative that contains at least one halogen atom

- Not found in the living system but are artificial.
- Trichloromethane, commonly known as chloroform, was once used as an anesthetic. It is
no longer used as such because it is now considered a possible carcinogen. Another
familiar group of haloalkanes, chlorofluorocarbons (CFCs), were once used as
refrigerants and as propellants in spray cans

Physical Properties of Haloalkanes:

- only the smallest haloalkanes
(fluoromethane, chloromethane,
bromomethane, and iodomethane) are
slightly soluble in water
- All other haloalkanes are insoluble
in water.
- The boiling point differs from
alkanes with the same number of carbon
atoms.
Aldehydes:
- Aldehydes, as well as several other hydrocarbon
derivatives, contain a carbonyl functional group.
- A carbonyl group (>C=O) is a functional group containing a
carbon atom that is double bonded to an oxygen atom.
- Carbonyl groups are components of several different
functional groups. In aldehydes, a carbonyl group is part of
a larger functional group that also contains a hydrogen
atom bonded to the carbon atom. Called a formyl group
(-CHO)
- an aldehyde is a hydrocarbon derivative that contains a
formyl group, this group is always found at the end of a
hydrocarbon chain.

● carbonyl group a functional group in which a carbon atom

is double bonded to an oxygen atom
● formyl group a functional group in which a carbon atom is double bonded to an oxygen
atom and single bonded to a hydrogen atom
● Aldehyde a hydrocarbon derivative that contains a formyl group

Physical Properties:
- The carbonyl group of
aldehydes is very polar but the
carbon-hydrogen bonds are not.
aldehydes do not hydrogen bond with
one another but they can hydrogen bond
with water. the strength of the attraction
among aldehyde molecules is not as
strong as that between alcohol molecules
- The boiling points of aldehydes are lower than those of alcohols having the same
number of carbon atoms. Only methanal (formaldehyde) is a gas at room
temperature
 - Aldehydes from three to 14 carbons long are liquids at room temperature, while
those with carbon chains of 15 carbon atoms or longer are waxy solids.
- The small aldehydes having one through four carbon atoms are soluble in water
and those with five through seven carbon atoms are slightly soluble in water.
When the carbon chain gets longer than seven carbon atoms, the insoluble
nature of the hydrocarbon chain overcomes the solubility of the polar carbonyl
group and the aldehydes are insoluble in water.
- The shooter the worse it smells, as the chain gets large the odor becomes more
pleasant.

Ketones: a hydrocarbon derivative that contains a carbonyl group that is bonded to two
carbon atoms or carbon chains
- Acetone is the most common name for the ketone, propanone. It dissolves many
compounds that are insoluble in water, it is used to remove nail polish, ink, removing
stickers etc.
- The smell of acetone may also indicate the presence of a serious health condition.
Breath that smells like acetone can be a sign of a dangerous
condition known as diabetic ketoacidosis. This condition occurs
when a diabetic individual is unable to produce enough insulin to
utilize glucose as a fuel source for the body. Instead, the body
burns fatty acids. Ketones, a by–product of fatty acid metabolism,
produce the scent of acetone on the breath. If not treated
immediately, diabetic ketoacidosis can cause a diabetic coma and
death.
- A ketone, like an aldehyde, contains a carbonyl group (>C=O).
Unlike aldehydes, the carbon atom in the carbonyl group of a
ketone is bonded to two carbon atoms or carbon chains.
Physical properties of Ketones:
- Contains a carbonyl group that is very polar, but no hydrogen atoms bonded to strongly
electronegative atoms.
- They are able to hydrogen bond with water molecules,
- Therefore they are very similar to aldehydes as they have similar boiling points and
solubilities
- Carbon chains of 16 carbon atoms or longer are waxy solids at room temp, all smaller
are liquids.

Carboxylic Acids: a hydrocarbon derivative that contains a carboxyl group

- Carboxylic acids are found in many foods, including oil and vinegar (acetic acid) salad
dressings, oranges (citric acid), and tamarinds (tartaric acid).
- carboxyl group a functional group made up of a carbonyl group with a hydroxyl group
attached to it

Naming and Drawing:

Physical properties:
- The presence of both a >C=O group and the −OH group make the
carboxyl group very polar, allowing carboxylic acid molecules to form
hydrogen bonds with one another. Thus, the boiling points of
carboxylic acids are much higher than those of other hydrocarbons
- Short-chain carboxylic acids are liquids at standard temperature while
those with longer chains are waxy solids. The polarity of the carboxyl
group makes the small carboxylic acids soluble in water. In fact,
carboxylic acids with one to four carbon atoms are completely miscible with water. Those
with chain lengths of five to nine carbon atoms are less soluble in water, while those with
chains longer than ten carbon atoms are insoluble in water.
- Carboxylic acids are also weak acids and thus turn litmus paper red. As weak acids, they
conduct electric current.

Esters: a hydrocarbon derivative that contains a functional group with a carbon atom
double bonded to one oxygen atom and single bonded to another
- The general formula for an ester is RCOOR. The symbol R represents
any hydrocarbon or just a hydrogen atom. The symbol R represents a
hydrocarbon and, therefore, it must contain at least one carbon atom.

Naming and Drawing:

Physical Properties:
- The presence of the >C=O group makes esters somewhat polar but without an −OH
group, ester molecules cannot form hydrogen bonds with one another. Therefore, the
boiling points are lower than the corresponding alcohols and carboxylic acids
- The smaller esters are liquids at standard temperature while the longer chain esters are
waxy solids. Esters with four or fewer carbon atoms are soluble in water while larger
esters are insoluble

Ethers: a hydrocarbon derivative in which an oxygen atom is single bonded to two

carbon atoms
- Started for diesel engines in extreme cold weatherIt is also used as
an aerosol propellant, solvent, and plasticiser.
- An ether is a hydrocarbon derivative in which an oxygen atom is
single bonded to two carbon atoms. The functional group can be
written as –O–. The general formula for all ethers can be expressed
as R–O–R9, where R and R9 are alkyl groups.

Name and Drawing:

Physical properties:
- The bond angle formed by the C–O bonds in ethers makes them slightly polar. If the
bonds formed a straight line, the two bond dipoles would cancel each other
- ether molecules cannot form hydrogen bonds with one another, the attraction between
them is small. As a result, ethers with a total of two or three carbon atoms are gaseous
at room temperature while larger ethers are liquids.
- Ethers can form hydrogen bonds with water molecules. Thus, ethers with two or three
carbon atoms are soluble in water. Straight chain ethers with a total of four to six carbon
atoms are slightly soluble while all larger ethers are insoluble in water.

Amines: a hydrocarbon derivative that contains a nitrogen atom bonded to at least one
carbon atom, although it may be bonded to up to three
- practical uses, such as corrosion inhibitors in boilers, antioxidants in roofing asphalt,
flotation agents in mining, and many more
- When you are in a dangerous situation, a complex amine, adrenaline, is released into
your blood. Once in your blood, adrenaline increases your heartbeat and respiration and
helps to release more glucose into your bloodstream.
- An amine is a hydrocarbon derivative that contains a nitrogen atom bonded to at least
one carbon atom, although it may be bonded to up to three. Chemists separate amines
into three categories depending on the number of carbon atoms bonded to the nitrogen
atom.

Naming and Drawing:

 Physical properties:
- The N-H bonds in primary and
secondary amines are very polar.
However, tertiary amines do not have
N-H bonds. Thus, primary and
secondary amines can hydrogen bond
with themselves and with one another
but tertiary amines cannot.
- primary and secondary amines
have relatively high boiling points
compared to ethers and alkanes of a
similar size. As well, they have higher
boiling points than tertiary amines with
the same number of carbon atoms
- All amines can hydrogen bond
with water. Therefore, the smaller
amines are very soluble in water.

Amides: a hydrocarbon derivative that contains a carbonyl group bonded to a nitrogen atom
- Penicillin is also an amide but it is very complex. It contains several other functional
groups in addition to an amide group. Another amide, commonly called
dimethylformamide, is a very commonly used organic solvent in industry.
- Amides are hydrocarbon derivatives containing the functional group, –CON–, which is a
carbonyl group bonded to a nitrogen atom. One, or both, of the hydrogen atoms on the
nitrogen atom can be replaced by alkyl groups. Similar to the case of amines, such
replacements result in secondary and tertiary amides
 - You can think of them as the product of a reaction between a carboxylic acid and
ammonia or a primary or secondary amine, as shown in Figure 1.41. If R9 and R99 are
hydrogen atoms, the blue reactant is ammonia. If either R9 or R99 are alkyl groups, it is
an amine.

Naming and Drawing Amides:

Physical properties:
- Amides have a polar carbonyl group and primary
and secondary amides have at least one –NH
group. Therefore, they can form strong hydrogen
bonds among themselves. Consequently, their
boiling points are much higher than those of other
hydrocarbon derivatives of similar size.
- From the melting and boiling points, ethanamide is a solid at room
temperature, ethanoic acid is a liquid, and ethanamine is a gas. The polarity and
potential for forming hydrogen bonds makes a tremendous difference in the physical
properties of the compounds. In general comparison, the order of the hydrocarbon
derivatives of similar size in terms of their polarity, from greatest to least is:
amide > acid > alcohol > ketone ≅ aldehyde > amine > ester > ether > alkane
- Because amides can form hydrogen bonds with water, the small amides are very soluble
in water.

Types of Organic Reactions

Addition Reactions: reactions in which atoms are added to a carbon-carbon double or
triple bond.
Alkenes and alkynes characteristically undergo addition reactions in which atoms are
added to a double or triple bond, as shown in Figure 2.2. To recognize an addition reaction,
check whether the carbon atoms in the product(s) are bonded to more atoms than the carbon
atoms in the organic reactant

- In a typical addition reaction, a small molecule is added to

an alkene or alkyne. The small molecule is usually one of
the following: H2O (ℓ) (when the bonds of water break in a
reaction, it is often written, HOH), H2, HX, or X2 (where X
= F, Br, Cl, or I). The reaction results in one major product
or two products that are isomers of each other
- In an alkyne, a maximum of four bonding electrons can be
rearranged to form bonds with three new atoms, leaving a
single bond between the two carbon atoms.
- When alkenes and alkynes that contain more than two
carbon atoms react with a small molecule, more than one
product might form.
Elimination Reactions: reaction in which atoms are removed from an organic molecule
to form a double bond
In an elimination reaction, atoms are removed from an organic molecule and a double
bond forms between the two carbon atoms from which the atoms were removed, as shown in
Figure 2.5. This type of reaction can be envisioned as the reverse of an additional reaction. One
reactant usually loses two atoms, and two products are formed. A double bond is formed in the
organic product. To recognize an elimination reaction, determine whether the carbon atoms in
the organic product are bonded to fewer atoms than were the carbon atoms in the organic
reactant.

The equation below illustrates an example of how alcohols can undergo elimination
reactions to form alkenes when they are heated in the presence of a strong acid, such as
sulfuric acid (H2SO4(aq)). The strong acid acts as a catalyst to speed up the reaction. A small,
stable molecule, such as H2O(ℓ), is formed as a second product.

Substitution Reactions:
In a substitution reaction, a hydrogen atom or a functional group is replaced by a different
functional group, as shown in Figure 2.6. To recognize this type of reaction, look for the
following two features:
• two compounds react to form two different compounds
• carbon atoms are bonded to the same number of atoms in the product as in the reactant

Alcohols and haloalkanes commonly undergo substitution reactions. When an alcohol

reacts with an acid that contains a halogen, such as hydrogen chloride or hydrogen bromide,
the halogen atom is substituted for the hydroxyl group of the alcohol, as shown in the equation
below. A haloalkane is produced.
Condensation Reactions: Reaction in which two molecules combine to form a larger
molecule, producing a small, stable molecule, usually water, as a second product or functional
group.
an example of a condensation reaction. The carboxylic acid and the amine are the large
molecules that combine. The resulting amide is the larger molecule and water is the small
molecule.

The symbols R1, R2, and R3 represent R groups of three different amino acids. The
carboxyl group on one amino acid reacts with the amino group on another amino acid. The
process continues and makes very long chains of amino acids to make a protein. The red boxes
around atoms in the reactants show which atoms are removed and form the water molecules.
The blue boxes around atoms in the products show the newly formed amide groups that link the
amino acids together. In polymers, these groups are called amide linkages. When the polymer is
a protein, the amide linkages are called peptide bonds.
Esterification Reactions: reaction of a carboxylic acid with an alcohol to form an ester
and water; a specific type of condensation reaction
An esterification reaction is a special type of condensation reaction in which a carboxylic
acid reacts with an alcohol to form an ester and water. This reaction is shown in Figure 2.10.
The chemical formula for sulfuric acid over the arrow indicates that the reaction is catalyzed by a
strong acid.

The equation below shows the esterification reaction that is used to form the cherry
flavour compound. Benzoic acid (a carboxyl acid) combines with ethanol (an alcohol) to form
ethyl benzoate (an ester) and water.

Hydrolysis Reactions: reaction in which a molecule is broken apart by adding the

hydroxyl group from a water molecule to one side of a bond and the hydrogen atom of a water
molecule to the other side of the bond.
A hydrolysis reaction is essentially the reverse of a condensation reaction. The term
hydrolysis means to “break apart using water.” The compounds that are formed by condensation
reactions can be broken down by hydrolysis reactions. The hydroxyl group in a water molecule
is added to one side of a bond such as an ester bond or an amide bond and the hydrogen atom
of the water molecule is added to the other side of the bond and the bond is broken. The
diagram in Figure 2.12 represents a simplified version of the process of hydrolysis.

This reaction appears to be the opposite of the reaction shown in Figure 2.10 for forming
an ester. Both the condensation reaction and the hydrolysis reaction are catalyzed by an acid.
So, the reactions are reversible, as shown in the equation below. A double arrow can be drawn
to represent a reversible reaction.
Oxidation and Reduction Reactions: a reaction in which a carbon atom forms more
bonds to oxygen atoms or fewer bonds to hydrogen atoms
In organic chemistry, oxidation is defined as a reaction in which a carbon atom forms
more bonds to oxygen, O, or fewer bonds to hydrogen, H. An oxidation that involves the
formation of double C2O bonds may also be classified as an elimination reaction. For example,
alcohols can be oxidized to produce aldehydes and ketones. Oxidation occurs when an organic
compound reacts with an oxidizing agent. Common oxidizing agents include acidified potassium
permanganate, KMnO4, acidified potassium dichromate,
K2Cr2O7,
and ozone, O3. The symbol [O] is used to symbolize an oxidizing agent, as shown below. Note
that equations for the oxidation of organic compounds are often left unbalanced. The purpose of
the equation is to show the changes in the organic reactant only

Reduction: a reaction in which a carbon atom forms fewer bonds to oxygen atoms or more
bonds to hydrogen atoms
In organic chemistry, reduction is defined as a reaction in which a carbon atom forms
fewer bonds to oxygen, O, or more bonds to hydrogen, H. Often, a C O bond or C C double
bond is reduced to a single bond by reduction. A reduction that transforms double C C or C O
bonds to single bonds may also be classified as an additional reaction. Aldehydes, ketones, and
carboxylic acids can be reduced to become alcohols. Alkenes and alkynes can be reduced by
the addition of H2 to become alkane.

To identify a reduction, count and compare the number of C2H and C2O bonds in both
the reactant and the product. Try it for the following example.