UNIT TWO

Organic compounds

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 Introduction
What are Organic Compounds?
• Organic compounds are a large class of chemical compounds in which one
or more carbon atoms are covalently paired with other elements atoms, most
commonly hydrogen, oxygen, or nitrogen.
• Organic compounds are ubiquitous and are part of your life.
- You are a carbon-based life form: DNA, proteins, neurotransmitters, etc.
- Food is primarily based on organic molecules: starch, orange juice
contains vitamins, and coffee contains caffeine and sugar
- Clothes and shoes that you wear are made of organic molecules and dyes
- Medications, vitamins, and herbal supplements are organic molecules
- The paper that is in front of you is made of cellulose
-Your phone that rings in class contains plastics and other polymers
• Others include drugs, colourants, soap and detergents. 2
 Classification of Organic Compounds
 Organic compounds contains only two elements, hydrogen and carbon,
are known as hydrocarbons.
 Hydrocarbons are classified in to two major parts

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 Functional groups
• Functional groups: are groups of atoms in the compounds that determine the physical
and chemical properties of the compound it self .
• For example:
-C-C single bond …..alkanes -COOH ……. Carboxylic acids
-C=C double bond …..alkene -COOR………Esters
-OH…….alcohol -CONH2 …….amides
-CHO ……Aldehydes -CNH2 ……….amine
-COR……. Ketone

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 Nomenclature of Organic compounds
IUPAC Nomenclature
 To give IUPAC Nomenclature for a given organic molecule
1. identify the “family” that your molecule belongs to…
2. So, check for functional groups…
3. If there are none, then your molecule is simply an alkane…
 The name for any organic molecule consists of three basic part Prefixes-Parent-Suffix
Each part of the name has a purpose.
• Suffixes on the end of the name of an organic molecule tell you what major family the
molecule belongs to
Example: The suffix for an alkane is “-ane, ‘’ene’’ for alkene, ‘’yne’’ for alkyne, ‘’ol’’ for
alcohol etc…

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 Cont…
• The “parent” part of the name tells how many carbons are in the main chain of
the molecule.
The parent is named based on the number of carbons
• 1 carbon = “meth” So a one-carbon alkane is called methane
• 2 carbons = “eth” So a two carbon alkane is called ethane.
• 3 carbons = “prop” So a three carbon alkane is called propane.
• 4 carbons = “but” So a four carbon alkane is called butane.
• 5 carbons = “pent”

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 Cont’….
• 6 carbons = “hex”
• 7 carbons = “hept”
• 8 carbons = “oct”
• 9 carbons = “non”
• 10 carbons = “dec
One more thing – If we have two or more chains that are the same length,
the parent is the one with the most prefixes
• Prefixes are the bits and pieces that are attached to the main chain (parent) of
the molecule

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 Cont’….
In general, the rules for IUPAC nomenclature include:
• Step 1: Find the main chain
• Step 2: Number the main chain
• Step 3: Identify all prefixes and their position numbers
• Step 4: Write the full name: Prefixes-Parent-Suffix
The most common prefixes we have in organic molecules are those little fragments of
carbon pieces attached to the main chains.
• The carbon fragments are called “alkyl groups”. They all end in “-yl” to indicate they
are fragments of a bigger molecule
• Alkyl groups are named similarly to alkanes, based on the number of carbons in the
fragment.
• A fragment of methane, CH4, would be CH3- , This fragment is called “methyl” where
“meth” stands for one carbon and “yl” stands for fragment (alkyl group).
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 Cont’….
• There are two possible names for three-carbon alkyl (substituent)
n-propyl & Isopropyl

There are four possible names for four-carbon alkyl (substituent)

• n-butyl , sec-butyl Isobutyl tert-butyl”

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 What alkyl groups do you see?

• There are two groups attached to the ring below. What are
they?

• The group in red has two carbons and is an ethyl group.

• The group in blue has four carbons. Three in a row and the extra attached at the
middle carbon. Its an isobutyl group.
 What alkyl groups do you see?

• There’s two groups attached to the ring below. What are they?

• The group in red has three carbons attached at the middle carbon and is an isopropyl group.
• The group in blue has four carbons, in a row, attached at one of the middle carbons. It’s a sec-butyl group
 1. Alkanes (Saturated Hydrocarbons)

• Contain carbon-carbon single bond. They are tetrahedral in shape.

• alkanes have a general formula CnH2n+2 (n = 1, 2, 3…), the simplest
Alkane is methane.
• Each consecutive member differs only by one – CH2 group. Thus they form a
Homologous series

Example
Methane (CH4) ethane (C2H6)

propane (C3H8) Butane (C4H10)

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 Nomenclature of Alkanes
• Long chain hydrocarbons can be named by the IUPAC rules.
Rule – 1: Find the longest continuous chain atoms in the skeletal structure &
name the compound as alkane with this number of carbon atoms.
Molecular Melting Boiling State
Name Formula Point (oC) Point (oC) at 25oC
methane CH4 -182.5 -164 gas
The names of
ethane C2H6 -183.3 -88.6 gas
the straight
propane C3H8 -189.7 -42.1 gas
chain butane C4H10 -138.4 -0.5 gas
hydrocarbons pentane C5H12 -129.7 36.1 liquid
hexane C6H14 -95 68.9 liquid
heptane C7H16 -90.6 98.4 liquid
octane C8H18 -56.8 124.7 liquid
nonane C9H20 -51 150.8 liquid
decane C10H22 -29.7 174.1 liquid
undecane C11H24 -24.6 195.9 liquid
dodecane C12H26 -9.6 216.3 liquid
eicosane C20H42 36.8 343 solid
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triacontane C30H62 65.8 449.7 solid
Rule- 2 : Name the substituents on the chain, substituents derived from alkanes
are named by replacing the-ane ending with –yl.
• Example: The substituent derived from methane is methyl (CH3-)
Rule- 3: Number the longest chain starting at the end nearest to the first substitute
• specify the number of carbon atoms on which the substituents are located
Rule- 4 : Use the prefixes di-,tri-, and tetra- to describe substituents that arte found two,
three of four times respectively on the same chain.
Rule- 5 : Arrange the names of the substituents in alphabetical order.

Example

Is named as 4-ethyl- 2,2,7-trimethyl octane

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 2. Cycloalkanes
Nomenclature
Step 1 Find the parent hydrocarbon.
• The parent name is determined by the number of carbons in the largest ring (e.g., cycloalkane
such as cyclohexane).
• In the case where the ring is attached to a chain containing more carbons, the ring is
considered to be a substituent on the chain.
• When two rings are attached to each other, the larger ring is the parent and the smaller is a
cycloalkyl substituent.
Step 2 Number the substituents.
• The carbons of the ring are numbered such that the substituents are given the lowest possible
numbers.

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 Examples 1

Methyl cyclopentane

2-cyclopropylbutane 3-cyclobutyl-1-cyclopropylpentane

Example 2

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 Alkene Nomenclature
• An alkene contains at least one double bond (termed as unsaturated
hydrocarbon).

• Alkenes have the general formula CnH2n,(n>2)

Example-
an alkene with 10 carbons (n = 10) will have 2(10) = 20
hydrogen, or the molecular formula C10H20

• each double bond contributes one degree of unsaturation.

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 To name alkenes
• Find the longest chain containing the double bond(Change the ‘ane’ suffix of corresponding alkane in to
ene).
• Number the chain, giving the double bond the lowest possible number

Example

• For cycloalkenes, begin numbering at the double bond and proceed through the double bond in the
direction to generate the lowest number

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 Assign stereochemistry using cis-trans- designation
• alkenes have been named using cis- and trans- to represent stereochemistry around the
double bond

Rules for assigning cis-trans designations

• if the same groups are on the same side of the double bond, the molecule is cis; if they are
found on opposite sides, the molecule is trans.

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 4. Alkynes

• Have a general form of R–C≡C–R . where R- is alkyl group

• Have the general formula of CnH2n-2 where n= 2,3,4,…..
• They are isomeric with cyclo alkenes, two double bonds, a ring plus a double bond, or
two rings. Example, C5H8- represents

Nomenclature of Alkynes
• Drop the "ane" ending and add the "yne" ending.
• The rest of the rules are similar with alkanes and alkenes.

6-Chloro-5-ethyl-4-methyl-2-heptyne

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 4. Alcohols

• The hydroxyl group (—OH) is found in the alcohol and phenol functional
groups. Alcohols have a general form of R-OH ; where R= alkyl group & -OH=
functional group
Alcohols – Nomenclature
(1) Prefix : Take the alkane name that corresponds to the number of carbon atoms
and remove the final e from the name.
(2) Position number : Count the number of carbon atoms from the nearest chain
end
to where the hydroxyl group, -OH, is attached.
(3) Suffix : Finally the suffix ol is added to denote an alcohol.
ethanol
Example: or
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 Classification of Alcohols
Alcohols are classified as primary (1°), secondary (2°) or tertiary (3°), which refers to the
carbon bearing the hydroxyl group

Examples: CH3CH2OH or

or

Propane-2-ol

or

2-methylpropan-2-ol 22
A. Dehydration
Some reactions of alcohols
Dehydration to alkenes: Heating alcohols in concentrated sulfuric acid (H2SO4) at 180°C
removes the OH group and a H from an adjacent carbon to produce an alkene with water as a
by-product. Since water is “removed” from the alcohol, this reaction is known as a
dehydration reaction (or an elimination reaction). Example: CH3CH2OH → CH2=CH2 + H2O
CH3CH2OH + CH3CH2OH → ?
• Water is a much better leaving group than HO-.
• Reactivity: 3° < 2° << 1°
B. Combustion: ethanol burns with oxygen to form carbon dioxide and water as product.
Example CH3CH2OH + 3O2(g) → 2CO2 + 3H2O
C. Esterification: an ester is formed by reacting an alcohol with a carboxylic acid
Example: CH3CH2OH + CH3COOH → CH3COOCH2CH3 + H2O
D. Oxidation: An oxidation reaction occurs when a molecule loses electrons. This is usually
manifested as an increase in the number of oxygen atoms or a decrease in the number of
hydrogen atoms. This reaction depends up on the number of hydrogen.
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Some common oxidizing agents include potassium permanganate (KMnO4), chromic acid
 Cont…
• R2CHOH + [O] → R2C=O + H2O
• Where [O] = oxidation
• Primary and secondary alcohols can be oxidized to produce compounds containing the
carbonyl group (a carbon-oxygen double bond, C=O)
• Primary alcohols are oxidized first to aldehydes, but the aldehydes are then usually
oxidized into carboxylic acids depending on oxidizing agents.
Example: CH3CH2OH + [O] → CH3COH → CH3COOH
• Secondary alcohols are oxidized to ketones, which cannot be oxidized any further
Example CH3CHOHCH3 + [O] → CH3COCH3
Tertiary alcohols cannot be oxidized because by definition, there is no hydrogen on the
alcoholic carbon CH3
Example: CH3 C OH → No reaction
CH3
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 Aldehydes and Ketones
The carbonyl group (C=O) is found in aldehydes, ketones, and many other organic functional groups.
• The carbon and oxygen in the carbonyl group are sp2-hybridized, with bond angles of 120

Nomenclature of Aldehydes (IUPAC name)

• Select the longest carbon chain containing the carbonyl carbon.
• The -e ending of the parent alkane name is replaced by the suffix -al.
• The carbonyl carbon is always numbered “1.” (It is not necessary to include the number in the name.)
• • Name the substituents attached to the chain in the usual way.
• Examples

2-methylpentanal

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 Nomenclature of Ketones(IUPAC name)

• Select the longest carbon chain containing the carbonyl carbon.

• The -e ending of the parent alkane name is replaced by the suffix -one.
• Number the chain starting with the end closest to the ketone group (i.e., the carbonyl carbon
should have the lowest possible number).
• Name the substituents attached to the chain in the usual way.
• Examples

Acetophenone
Benzophenone 3-methylbutanone
3,4-dimethyl-2-pentanone
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 Carboxylic Acids
• Carboxylic Acids
Carbon compounds containing a carboxyl functional group, –COOH are
called carboxylic acids. The carboxyl group, consists of a carbonyl group
attached to a hydroxyl group, hence its name carboxyl.
• Carboxylic acids may be aliphatic (RCOOH) or aromatic (ArCOOH)
depending on the group, alkyl or aryl, attached to carboxylic carbon.
• Large number of carboxylic acids are found in nature. Some higher
members of aliphatic carboxylic acids (C12 – C18) known as fatty acids,
occur in natural fats. Carboxylic acids serve as starting material for
several other important organic compounds such as anhydrides, esters,
acid chlorides, amides, etc.

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 Nomenclature of Carboxylic acids
• The common names end with the suffix –ic acid and have been derived from
Latin or Greek names of their natural sources.
For example, formic acid (HCOOH) was first obtained from red ants
(Latin: formica means ant), acetic acid (CH3COOH) from vinegar (Latin:
acetum, means vinegar), butyric acid (CH3CH2CH2COOH) from rancid
butter (Latin: butyrum, means butter).
• In the IUPAC system, aliphatic carboxylic acids are named by
replacing the ending –e in the name of the corresponding alkane with –
oic acid.
• In numbering the carbon chain, the carboxylic carbon is numbered one.
Example CH3CH2CH2COOH (CH3)2CHCOOH
Butanoic acid 2-Methylpropanoic acid
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 6. ETHERS
• An ether molecule has an oxygen atom connected to two alkyl units through carbon-oxygen
single bonds.

• The following are NOT examples of ethers.

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 Cyclic Ethers
• Cyclic ethers which have 3 atoms forming a ring (one oxygen atom, two carbon
atoms) are called epoxides or oxiranes.
examples

• These are also sometimes referred to as alkene oxides

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 7. Alkyl Halides
• The alkyl halides have the general form

• The simplest common alkyl halides are chloroform and carbon tetrachloride.

• An important class of alkyl halides are the chlorofluorocarbons(CFCs) which

have been used in air conditioners, etc., as refrigerants.

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 7. Amines
What are amines?
• The easiest way to think of amines is as near relatives of ammonia, NH 3.
• In amines, the hydrogen atoms in the ammonia have been replaced one at a time by
hydrocarbon groups.
Classification of amines
Primary amines
• Only one of the hydrogen atoms in the ammonia molecule has been replaced by alkyl group
(R-group).
• The formula of the primary amine will be RNH2 where "R" is an alkyl group.

Examples

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Secondary amines
• two of the Hs in an NH3 molecule have been replaced by alkyl groups.
Example

Tertiary amines
• all of the H-s in an NH3 molecule have been replaced by alkyl groups
Example

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 Nomenclature of amines

• Naming amines can be quite confusing because there are so many variations on the
names.
• For example, the simplest amine, CH3NH2, can be called

• the simplest way of naming the compound is to use the "amino" form.
Example

• For simple secondary and tertiary amines, the first way of naming is commonly used.
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 Aromatic hydrocarbons
1. Aromatic hydrocarbons
 The term aromatic is derived from the word ‘aroma’ meaning pleasant smell, which was
originally used to describe naturally occurring compounds with pleasant smells.
 They are a group of hydrocarbons characterized by the presence of a benzene ring or
related structures
 All aromatic hydrocarbons are composed solely of carbon atoms and hydrogen atoms in
various arrangements.
 Part of them apart from other hydrocarbons is the presence in their molecular structures
of at least one benzene ring.
 Arene: a term used to describe aromatic compounds
 Ar-: a symbol for an aromatic group derived by removing H from an arene. Toluene,
and naphthalene are examples of arenes. 35
 Structure of Benzene
• Benzene is the simplest (primary) aromatic hydrocarbon. Its molecular formula is C 6H6

• It consists of six carbon atoms linked together with conjugated single and double bonds.
• Experimentally the benzene molecule is a completely symmetrical .

• All carbons are SP2 hybridized carbon with delocalization of Pi-elctrons.

• Cyclic planar with bond angle of 1200

• The bonds in benzene are neither single nor double but have an intermediate character between
those of single and double bonds.
 All the carbon-carbon bonds (C-C bond) in the molecule are same in length and nature.
 Delocalized electrons are not confined between two adjacent bonding atoms. The 6 -electron
are delocalized over 6 carbon atoms.

 Its structure is
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 Nomenclature of benzene derivatives
• Nomenclature of mono substituted benzene derivatives
Br CH2CH3
NO2

bromobenzene ethylbenzene (1-methylethyl)benzene nitrobenzene

(isopropylbenzene)

Large number of non-systematic names that can serve as the parent name

O H O OH
CH3 OH OCH3 NH2

benzene toluene phenol anisole aniline styrene benzaldehyde benzoic acid

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 Nomenclature of poly substituted benzene
• When only two substituents are attached to a benzene ring, they can be
named by the common nomenclature using
ortho (o-) (1-2 placement),
meta (m-) (1-3 placement) or
para (p-)(1-4 placement).

• Multiple substituents on a benzene ring are numbered to give these

substituents the lowest possible numbers.

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 Exercise
Give the IUPAC names of the following compound
A) B) C) D)

Br

Br
C2H5
H3C CH2

C2H5 CH3
Br C2H5 CH3

E) F)

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