Organic Chemistry

What is Organic Chemistry?

 The study of carbon and most carbon
compounds

 “The chemistry of life”

 … but includes far more compounds than
those made by living things.
Bonding of Carbon Atoms
 Carbon can form so many compounds
because carbon atoms easily form
covalent bonds with other carbon atoms

 Can be single, double, or triple covalent bonds

Bonding of Carbon Atoms
 Lewis Dot Diagram of Carbon in ground
state

 Lewis dot diagram of bonded carbon atom

 Enables four covalent bonds
 Tetrahedral shape
 Angles are actually 109.50
Some Terminology
 Organic compounds containing only single
bonds are said to be saturated.

 Organic compounds containing one or

more double or triple bonds are called
unsaturated compounds.
More Terminology
 Hydrocarbons - organic compounds that
contain only hydrogen and carbon atoms

 Homologous series - group of related

compounds in which each member differs from
the one before by one additional unit.
 Alkanes
 Alkenes
 Alkynes
Chemistry Humor
 According to a chemist, why is the
world so diverse?

 Because it's made up of alkynes of

people.
Alkanes
 All single bonds between carbon atoms

 Therefore, all saturated.

 As the number of carbon atoms in this

homologous series increases, so does the
boiling point

 Names end with “-ane”

Alkanes
 Methane - Natural gas
 Ethane - Also natural gas
 Propane - outdoor grills/home heating
 Butane - lighters
 Pentane, Hexane, Heptane, Octane, Nonane,
Decane - all found in gasoline
 Candle wax - 20 or more carbon atoms
 Road Tar - 40 or more carbon atoms
General Formula For Alkanes
 Each successive carbon adds two more
hydrogen atoms
 Let’s develop a general formula for
alkanes…

 CnH2n+2
Alkenes
 Each member of alkene series contains one
double covalent bond

 Names are same as for alkanes, except change

ending to “-ene”.

 Ethene - (common name “ethylene”)

 Unsaturated
Alkenes
 Let’s develop a general formula for
“alkenes”….

 CnH2n
Alkynes
 Contain one triple bond between carbon atoms

 Names are same as for alkanes, except change

ending to “-yne”.

 Ethyne (common name “acetylene” - used in

welding torches)
Alkynes
 Let’s develop a general formula for alkynes

 CnH2n-2

 Pull out Reference Tables…

 Table P - Organic Prefixes
 Table Q - homologous series & general formulas
Let’s Keep some terms straight…
 Molecular formula - represents the actual atoms
in a molecule
 Reminder - empirical formula is the simplest integer
ratio in which atoms combine in a compound.

 Structural Formula - attempts to show the kinds

and numbers of atoms, but also the bonding
patterns and approximate shapes
 Condensed structural formulas
Let’s Keep some terms straight…
 Ball-and-stick model

 Space-filling model (very similar to

“molecular shape” model)
Isomers
 Starting with butane there’s more than one
way to combine the carbon and hydrogen
atoms.

 When a molecular formula can be

represented by more than one structural
arrangement, the compounds are called
isomers of one another.
Isomers
 Even though they have the same
molecular formula, isomers have different
chemical and physical properties.
 Different boiling points
 Different reactivities

 As the number of carbon atoms increases,

so does the number of possible isomers.
Naming Organic Compounds
 When carbon atoms in one continuous
chain, called a “straight chain” hydrocarbon
 Also called “normal form”

 The letter “n-” precedes the name of

straight chain hydrocarbons
Naming Organic Compounds
 Compounds with branched chains must be
given different names because they have
different chemical and physical properties.

 Naming rules are governed by IUPAC

(International Union of Pure and Applied
Chemistry)
Naming Organic Compounds
 Step 1 - Find the longest continuous chain
of carbon atoms
 The compound will be named based on its
longest chain.

 For example, if the longest chain is 6, then

the compound will be named as a hexane.
Naming Organic Compounds
 Step 2 - Identify attached Alkyl Groups
 An alkyl group contains one less hydrogen than an
alkane with the same number of carbon atoms

 Step 3 - Assign numbers to the carbon atoms in

the longest chain.
 They must be numbered from the end that will give the
lowest number for the attached group.
Naming Organic Compounds
 Step 4 - Name the compound by stating
the location of the attached chain, the alkyl
group, then the main branch name
Naming Organic Compounds
 Some additional naming info…
 If there is more than one of the same type of
group attached to the parent chain, then a
prefix is used
 di- means two; tri- means three; tetra- means four

 Commas are used to indicate the specific

carbon to which each group is attached
Functional Groups
 Functional Groups - are atoms or groups
of atoms that replace hydrogen in a
hydrocarbon, and give the compound
distinctive chemical and physical
properties.
Organic Acids
 Organic Acids are a homologous series

 Functional group is carboxyl group (-COOH)

 Name comes from corresponding hydrocarbon, but

replace ending “-e” with “-oic acid”

 Ethanoic acid (common name “acetic acid”, which is

found in vinegar)
Organic Acids
 Most organic compounds are nonelectrolytes,
but organic acids are weak electrolytes.

 Reference Table R
Alcohols
 Alcohols - organic compounds where one
hydrogen of a hydrocarbon is replaced by an -
OH group (called a hydroxyl group)

 The -OH group resembles the hydroxide ion, but

it isn’t the same. It doesn’t form hydroxide ion in
water.

 Therefore, alcohols are nonelectrolytes

Alcohols
 The hydroxyl group is polar, though, which
allows alcohols to dissolve in water.

 Name by changing corresponding alkane

ending “-e” to “-ol”
Esters
 Esters are organic compounds whose type
formula is R-CO-ORI

 Part comes from an organic acid, and the RI

part comes from an alcohol

 Esters have strong, fragrant odors.

Esterification
 Esterification - The organic reaction
between an organic acid and an alcohol to
produce an ester plus water.

 Esters are named by using the alkyl name

of the alcohol followed by the acid group
modified to end in “-oate”.
More About Alcohols
 There are several different types of
alcohols

 Type depends on number of hydroxyl groups

 Type depends on the position of each hydroxyl

group on the chain
Alcohols
 Alcohols are primary, secondary, or tertiary
based on whether the hydroxyl group is attached
to a primary, secondary, or tertiary carbon atom.
 Primary carbon - attached to only one other carbon
atom
 Secondary Carbon - attached to two other carbon
atoms
 Tertiary Carbon - attached to three other carbon atoms
Alcohols
 Primary Alcohol - has a hydroxyl group attached
to primary carbon

 Secondary Alcohol - hydroxyl group attached to

secondary carbon

 Tertiary Alcohol - hydroxy group attached to

tertiary alcohol
Alcohols
 Monohydroxy alcohols - have one hydroxyl group

 Dihydroxy alcohols - two hydroxyl groups

 1,2 ethanediol

 Trihydroxy Alcohols- three hydroxyl groups

 1,2,3 propanetriol
Organic Halides (“Halocarbons”)
 When a halogen (F, Cl, Br, or I) replaces a
hydrogen on an alkane, the compound is
called an organic halide (or halocarbon).

 The functional group is the attached halogen.

 Named by citing the location of the halogen

attached to the chain.
Ethers
 Series of organic compounds in which two
carbon chains are joined together by an
oxygen atom bonded between two carbon
atoms.

 Named using alkyl group names followed

by “ether”.
Amines
 Amines are formed when one of the
hydrogens of ammonia is replaced by an
alkyl group.

 Named by taking the alkane name and

change the ending “-e” to “-amine”, and
number the alkane chain to show the
location of the amine group.
Carbonyl Group
 When an oxygen is bound to a carbon by a
double bond, it is called a carbonyl group.

 Overhead “Functional Groups of Organic

Compounds”
Aldehydes
 Aldehydes are organic compounds in which the
carbonyl group is on the end carbon

 Named by substituting “-al” for the final “-e” of the

corresponding alkane name.

 Methanal’s common name is “formaldehyde”

Ketones
 Ketones formed when carbonyl group is attached to an
interior carbon atom that is attached to two other carbon
atoms.

 Named by replacing final “-e” of corresponding alkane

name with “-one”

 Propanone’s common name is “acetone” - nail polish

remover.

 Ketones are often used as solvents (because both polar

and nonpolar
Amino Acids
 Amino acids contain the carboxylic group (-
COOH) and an amine.
 The amine group is attached to the carbon
adjacent to the acid group.
 Amino acids are the building blocks of protein.
 The body must take in (ingest) 10 essential
amino acids, because the body can’t produce
them. The remaining amino acids can be
synthesized.
Amides
 Amides are compounds formed by
combination of two amino acids.
 Look at Figure 11-15 page 166.
 Also called a “peptide bond”.
 Additional amino acids can be linked,
forming “polypeptides”, and eventually,
proteins.
Saponification
 The name of the organic reaction that
makes soap.

 An ester reacts with an inorganic base to

produce an alcohol and soap.
Polymerization
 Polymers - organic compounds made up
of chains of smaller units covalently
bonded together
 The formation of these large polymer
molecules is called polymerization
Polymerization
 Each individual unit is called a monomer.

 Synthetic Plastics (nylon, rayon,

polyethylene, etc..) are polymers
Polymerization
 Two General Types of Polymerization Reactions
 Addition Polymerization - involves the joining of
monomers of unsaturated compounds

 Condensation Polymerization - result from the bonding

of monomers by removing water from hydroxyl groups
and joining the monomers by an ester or ether linkage.
Addition Polymerization
 An addition reaction is one in which two or more
molecules join together to give a single product. During
the polymerisation of ethene, thousands of ethene
molecules join together to make poly(ethene) - commonly
called polyethylene.

 The number of molecules joining up is very variable, but is in the region of 2000 to
20000.
Addition Polymerization
 The mechanism

 The over-all process is known as free radical addition.

 Chain initiation

 The chain is initiated by free radicals, Ra, produced by reaction between some of the ethene and
the oxygen initiator.

 Chain propagation

 Each time a free radical hits an ethene molecule a new longer free radical is formed.

 etc
Substitution Reactions
 A substitution reaction involves the
replacement of one or more of the
hydrogen atoms in a saturated
hydrocarbon with another atom or group.

CH4 + Cl2  CH3Cl + HCl

Substitution Reactions
 If a mixture of methane and chlorine is
exposed to a flame, it explodes - producing
carbon and hydrogen chloride. This isn't a
very useful reaction!

 So how does the substitution reaction

occur without an explosion?
Substitution Reaction
 The mechanism involves a chain reaction.

 The chain is initiated (started) by UV light breaking a chlorine

molecule into free radicals.

Cl2  2Cl•

 By the way, this is an example of a photochemical

reaction.
Substitution Reaction
 Chain propagation reactions - these are the reactions
that keep the chain going…

CH4 + Cl• CH3• + HCl

CH3• + Cl2  CH3Cl + CL•

▪ The chain terminates when one of these reactions

occurs…
2Cl•  Cl2
CH3• + Cl•  CH3Cl
CH3• + CH3•  CH3CH3
Addition Reactions
 Addition Reactions involve adding one or
more atoms at a double or triple bond.

C2H4 + Cl2  C2H4Cl2

Or
C2H4 + H2  C2H6
Fermentation
 Fermentation is a chemical process in
which yeast cell secrete enzymes
(zymase) and break sugar chains into
carbon dioxide and water
C6H12O6  2C2H5OH + 2CO2