PART II: ORGANIC CHEMISTRY

Organic Chemistry is the study of carbon and its compounds.

Historical Development
The practice of organic chemistry has been going on since the prehistoric times. The ancient
Romans, Egyptians, and Phoenicians used dyes which were pure compounds isolated from plant and animal
resources. They converted animal fat into soap and fermented sugars yielding alcohol.
Organic chemistry started in the part of the 18 th century when there was a determined effort to
isolate pure organic compounds. At that time, materials were classified as organic (those derived from
living resources) and inorganic (those coming from minerals).

Scientists
Torbern Bergman (1735-1784)
Michel Eugene Chevreul (1786-1889)
Friedrich Wohler (1800-1882)
Contribution
He was the first person to express the difference between
organic and inorganic substances.
He started to study soaps from fats and alkalis. He made
possible to make chemical change in fats to produce new
substances.
He found it possible to convert salt ammonium cyanate, an
inorganic compound, into urea, an organic compound isolated
from urine.

William Henry Perkin (1838-1907)
Marcellin Berthelot (1827-1907)
Friedrich August Kekule ( 1829-1896)
Archibald Scott Couper ( 1831-1892)
Joseph Achille Le Bel (1874-1930)
Jacobus Henricus van’t Hoff (1852-1911)
He was able to manufacture the organic dye from aniline
(Perkin’s mauve).
He was able to synthesize numerous hydrocarbons proving
that organic compounds can be formed by ordinary methods
of chemical manipulation.
They were the first to recognize that in all organic
compounds, carbon has four affinity units said to be
tetravalent.
He proposed that the four bonds of carbon are not randomly
oriented but have a specific special orientation.

ORGANIC COMPOUNDS
 Principally made up of carbon
 May be linked with other carbon atoms or with H, S, N, and some halogens
 May form single, double or triple bonds
 Most come from coal, natural gas, and petroleum
 Some come from plant sources

Properties of Organic Compounds

1. they have low densities
2. they have low boiling and melting points
3. they generally dissolve in non-polar solvents or in solvents with low polarity (alcohols)
4. their viscosity may be increased by the ability of functional groups to form H-bonds

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 Hydrocarbons

Aliphatic Alicyclic Aromatic

Unsaturated Saturated

Alkynes Alkanes

Alkenes Branched Chain

Geometric Isomers Continuous chain

Stereoisomers

Aliphatic Hydrocarbons
a. Saturated
 Carbon atoms joined by single bonds
 alkanes
b. Unsaturated
 Carbon atoms joined by either double or triple bonds
 Alkenes, alkynes
 Does not contain the maximum number of hydrogen in their structure

ALKANES
 CnH2n + 2
 Sometimes called the paraffin series due to lack of affinity or reactivity
 Physical states:
o Gases at room temperature (cycloalkanes and less than 5 carbons)
o Liquids (5 – 17 carbons)
o Waxy solids (larger alkanes)
 Melting and boiling points increase with increasing molecular weights
 Colorless, odorless and tasteless
 Generally soluble in non-polar solvents
 Less dense than water

# of C atoms Name Molecular Formula

1 Methane CH4
2 Ethane C2H6
3 Propane C3H8
4 Butane C4H10
5 Pentane C5H12
6 Hexane C6H14
7 Heptane C7H16
8 Octane C8H18
9 Nonane C9H20
10 Decane C10H22

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 Alkyl group Molecular formula Halogen Alkyl Molecular formula
Methyl -CH3 group
Ethyl -C2H5 Bromo -Br
Propyl -C3H7
Chloro -Cl
Butyl -C4H9
Amyl/Pentyl -C5H11 Fluoro -F
Hexyl -C6H13
Iodo -I
Heptyl -C7H15
Octyl -C8H17
Nonyl -C9H19
Decyl -C10H21

Naming Alkanes
 n-alkane (normal alkane)
o straight chain alkane
 iso-alkane
o one carbon atom is attached to the second carbon atom in the chain
 neo-alkane
o indicates a new molecule
Isomers
 compounds with the same molecular formulas with different structures
 methane, ethane and propane – 1 isomer
 butane – 2 isomers
 hexane – 5 isomers
 octane – 18 isomers
 decane – 75 isomers

Steps in naming the alkane isomers

1. The longest continuous chain of carbon atoms determines the base name of the molecule. The base
name corresponds to the number of carbon atoms in this chain
2. The locations of other groups of atoms attached to the base chain are identified by counting carbon
atoms from either the left or from the right. The direction selected is the one that results in the
smallest numbers for attachment locations.
3. The hydrocarbon groups attached to the base chain are named from the number of carbons in the
group by changing the alkane affix “-ane” to “-yl”.
4. The prefixes ‘di-“, “tri-“ and so on are used to indicate if a particular hydrocarbon group appears on
the main chain more than once.

Examples:
a. n-hexane b. 2-methylpentane
CH3-CH2-CH2-CH2-CH2-CH3 CH3-CH2-CH2-CH-CH3
|
   CH3 

c. 2,2-dimethylbutane d. 3-methylhexane
CH3
CH3-CH2-CH2-CH-CH3
    |
           |
   CH3-C-CH-CH3
              CH2
   |
           |
   CH
              CH3
e. 1-chloro-2, 3-dimethylbutane f. 3-ethyl-2-methylpentane

CH3     CH3
|   |
CH3-CH-CH-CH2-Cl CH2
   |     |
CH3 CH3-CH2-CH-CH-CH3
|
87 CH3
Naming Cycloalkanes or Alicyclic
 Cycloalkanes are cyclic hydrocarbons (closed rings or chains) with single bonds
 CnH2n

cycloalkane Molecular formula

Cycloprapane C3H6
Cyclobutane C4H8
Cyclopentane C5H10
Cyclohexane C6H12
Cycloheptane C7H14
Cyclooctane C8H16
Cyclononane C9H18
Cyclodecane C10H20

Steps in naming cycloalkanes

1. If the cycloalkane has a greater number of carbons than any alkyl substituent, then use it as the
parent chain. If the alkyl chain has a greater number of carbons, then use the alkyl chain as the
parent and the cycloalkane as the cycloalkyl substituent.
2. When numbering, start with the substituted carbon so as to contain the lowest number.
3. When two or more different substituents are present, number according to alphabetical order (but
still sum up to the least number).
Examples:
a. cyclohexane b. 1-ethyl-3-methyl-2-propylcyclopentane

c. 1,5-dichloro-3-methylcyclooctane d. 1,1,2-trichlorocyclopropane

e. 3-butyl-1,1-dimethyl-5-propylcyclohexane f. 1-bromo-2-chloro-3-methylcyclobutane

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ALKENES
 CnH2n
 Double bond
 Alkenes are also called OLEFINS because they form oily liquids on reaction with chlorine gas.

# of C atoms Name Molecular Formula

2 Ethene C2H4
3 Propene C3H6
4 Butene C4H8
5 Pentene C5H10
6 Hexene C6H12
7 Heptene C7H14
8 Octene C8H16
9 Nonene C9H18
10 Decene C10H20

Steps in naming of Alkenes

1. Select the longest chain containing the double bond.
2. Number from the terminal carbon nearest the double bond.
3. Specify position (carbon number) where the double bond is found.
4. Identify and specify the position of the substitiuents.
5. The suffix “ene’ is used in the final name.

Examples
a) 2-hexene b) 2-methyl-1-pentene

c) 3-chloro-4-methyl-1-pentene d) 2,5-dimethyl-2-heptene

Cl  CH3 CH3

|  | |
CH3-CH-CH-CH=CH2 CH3CH2CHCH2CH=CCH3
|       
CH3  

e) 2-methyl-1,3-butadiene f) 3-methylcyclopentene

CH3
|
CH2=CCH=CH2

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ALKYNES
 CnH2n-2
 triple bond

# of C atoms Name Molecular Formula

2 Ethyne C2H2
3 Propyne C3H4
4 Butyne C4H6
5 Pentyne C5H8
6 Hexyne C6H10
7 Heptyne C7H12
8 Octyne C8H14
9 Nonyne C9H16
10 Decyne C10H18

Steps in Naming Alkynes

1. Find the longest continuous chain of carbons which contains the triple bond.
2. Number the carbons in the parent chain so that the triple bond has the lower possible number.
3. Determine the names and location of the substituents.
4. List the substituent groups alphabetically in the final name.
5. The suffix “yne” is used in the name.

Examples:
a) 1-butyne b) 2-butyne

c) 2-hexyne

Acetylene Methyl acetylene Dimethyl Acetylene

Aromatic Compounds
 refer to the class of compounds that contain benzene-like, six-membered rings with three double
bonds

BENZENE
 most common and more stable aromatic hydrocarbon
 CnH2n-6
 August Kekule (1865) – formulated the structure 1,3,5-cyclohexatriene

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Derivatives of Benzene
1. Ortho – when two groups are attached to two adjacent carbon atoms

ortho-dichlorobenzene
o-dichlorobenzene
1,2-dichlorobenzene
2. Para – when two groups are in opposite carbon atoms

para-dichlorobenzene
p-dichlorobenzene
1,4-dichlorobenzene

3. Meta – when two groups are attached to any alternate carbon atoms

meta-dichlorobenzene
m-dichlorobenzene
1,3-dichlorobenzene

Common Names of Some Aromatic Compounds (monosubstituted aromatic compounds)

Formula Name Formula Name

Toluene Benzaldehyde
methylbenzene Benzene carboxaldehyde
(bp 111°C) (bp 178 °C)

Phenol Benzoic Acid

hydroxybenzene Benzene carboxylic acid
(mp 43 °C) (mp 122 °C)

CN
Aniline
aminobenzene Benzonitrile
(bp 184 °C) (bp 191 °C)

COCH3
ortho-xylene
Acetophenone ortho-dimethylbenzene
(mp 21 °C) (bp 144 °C)

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Naming Aromatic Hydrocarbons
a) chlorobenzene b) nitrobenzene

                       
c) o-bromochlorobenzene d) p-bromochlorobenzene

e) m-chlorophenol f) 1,2,5-trichlorobenzene

Functional Organic Compounds

 Special group of atoms acting as a single atom

1. Organic Alcohols
 Class of organic compounds containing the hydroxyl group –OH attached to a carbon atom
 R-OH where R (alkyl group): CnH2n + 1 OH (hydroxyl group)

Classifications of Alcohols (according to number of functional group)

a. monohydric (1 OH group)
b. dihydric (2 OH group)
c. trihydric or triol (3 OH group)

Classification of Alcohols (according to attachment of functional group)

a. primary alcohols – the OH group is attached to a primary carbon/terminal carbon
b. secondary alcohols – the OH group is attached to a secondary carbon atom (carbon is attached to 2
other carbon atoms)
c. tertiary alcohols – the OH group is attached to a tertiary carbon atom (carbon attached to 3 other
carbon atoms)

Naming Alcohols
1. Name the longest carbon chain containing –OH groups.
2. Number the chain so that carbon atoms with –OH groups attached have the smallest numbers.
3. Locate, name, and alphabetize (ignore sec-, t-, and –OH) all attached groups.
4. Collect all groups with the same name and add appropriate prefix.
5. Put name together and change the ending on the main chain. Add the numbers for the –OH groups
immediately before the main chain name.
Number of -OH groups Ending
1 Drop -e, add -ol
2 Add -diol
3 Add -triol

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Examples:
a) IUPAC name: ethanol b) IUPAC name: 2-propanol
Common name: ethyl alcohol Common name: isopropyl alcohol

CH3CH2OH OH
l
CH3CHCH3

c) IN: 1,2-ethanediol d) IN: 1,2,3-propanetriol

CN: ethylene glycol CN: glycerol

H OH HO H OH
|| | | |
H-C-C-H H-C-C-C-H
|| | | |
H OH H OH H

e) cyclobutanol f) 1,4-cyclohexanediol

Aromatic Alcohols
 have their –OH attached to a side chain
 fragrant odor, are colorless liquids, used in soaps, cosmetics and perfumes

IN: phenylmethanol
CN: benzyl alcohol

Phenols
 have their –OH attached directly to the ring
 strong aromatic odors, are corrosive, antiseptic, used in the manufacture of plastic, dyes and
explosives

phenol 1-phenylethanol

2. Aldehydes
 R-CHO where: R (hydrogen, all alkyl, or an aryl radical) -CHO (formyl group)
-CO (carbonyl group)

Naming Aldehydes
1. Identify the longest continuous chain of carbons with the formyl carbon as part of the chain.
2. Number the carbon chain so that the formyl carbon is always number one.
3. Locate and identify alphabetically the branched groups by prefixing the carbon number it is attached
to. If more than one of the same type of branched group is involved use the prefixes di for 2, tri for
three, etc.

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4. After identifying the name, number and location of each branched group, use the alkane name that
represents the number of carbons in the continuous chain.
5. Change the "e" ending and replace it with -al.

Examples:
a) IN: ethanal b) IN: propanal
CN: acetaldehyde CN: propionaldehyde

O O
ll ll
CH3 CH CH3 CH2CH

CH3CHO CH3CH2CHO

c) IN: 2-methylbutanal d) IN: 2-methylpropanal

CN: 2-methylbutyraldehyde CN: 2-methylpropionaldehyde

e) IN: benzaldehyde
CN: benzenecarbaldehyde

3. Ketones
 R-CO-R where: R (alkyl group) -CO (carbonyl group)

Naming Ketones
1. Identify the longest continuous chain of carbons with the carbonyl carbon as part of the chain.
2. Number the carbon chain so that the carbonyl carbon is always number one.
3. After identifying the name, number and location of each branched group, use the alkane name that
represents the number of carbons in the continuous chain.
4. Change the "e" ending and replace it with -one.

Examples:
a) IN: propanone b) IN: 2-butanone
CN: acetone

c) 3-pentanone d) 3,4-dimethyl-2-heptanone

H     CH3 CH3 H  H  H

|     |   |  |  |  |
H-C--C--C---C--C--C--C-H
|  ||  |   |  |  |  |
H  O  H   H  H  H  H

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4. Carboxylic Acids
 R-COOH where: R (hydrocarbon group) -COOH (carboxyl group)
 Are weak acids
 Have high boiling temperature
 Have strong, unpleasant odor

Naming Carboxylic acids

1. Identify the longest continuous chain of carbons with the carboxyl carbon as part of the chain.
2. Number the carbon chain so that the carboxyl carbon is always number one.
3. After identifying the name, number and location of each branched group, use the alkane name that
represents the number of carbons in the continuous chain.
4. Change the "e" ending and replace it with –oic acid or –oate for straight chain.
5. Affix carboxylic acid for cycloalkanes.

Examples:
a) IN: methanoic acid b) IN: propanoic acid
CN: formic acid CN: propionic acid

c) IN: ethanoic acid d) IN: 2-chloropropanoic acid

CN: acetic acid

e) IN: 3-chlorobutanoic acid f) IN: 3-methylpentanoic acid

g) IN: ethanedioic acid h) IN: propanedioic acid

CN: oxalic acid CN: malonic acid

5. Esters
 R-COO-R’ where: R (hydrocarbon group) -COO (carboxylate group)
 Have distinctive fruity odor
 Have low boiling temperature
 Formed from the reaction of an acid and a base (saponification)

Naming Esters
1. The parent chain must contain the carboxylate group.
2. Name of alkyl group is given first, the suffix changed to –yl
3. Next, name of the carboxylic acid (suffix –oate)

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Examples:

a) IN: methyl methanoate b) IN: methyl ethanoate

CN: methyl formate CN: methyl acetate

c) IN: methyl propanoate d) IN: methyl butanoate

CN: methyl propionate CN: methyl butyrate

e) IN: propylpentanoate
CN: propylvalerate

6. Ethers
 R-O-R’ where: R (hydrocarbon group)

Naming Ethers
1. Name the alkyl group alphabetically followed by the word “ether”; or
2. Add the prefix –oxy- to the smaller hydrocarbon group and joining it to the alkane name of the larger
hydrocarbon group

Examples:

a) IN: ethoxyethane b) IN: methoxyethane

CN: diethyl ether CN: ethyl methyl ether

CH3CH2OCH2CH3 CH3–CH2–O–CH3

c) IN: 2-methoxybutane d) IN: methoxycyclopentane

CN: 2-butyl methyl ether CN: cyclopentyl methyl ether

e) IN: 2-(1-propoxy) pentane

CN: 2-pentyl 1-propyl ether

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7. Acid Amide
 R-CO-NH2 where: R (hydrocarbon group) -NH2 (amino group)

Naming Acid Amides

IUPAC name:
1. Name the parent chain.
2. Then, the suffix –amide is attached to it

Common name:
1. Give the trivial root
2. Then the suffix –amide is attached to it
Examples:

a) IN: methanamide b) IN: ethanamide

CN: formamide CN: acetamide

c) IN: propanamide d) IN: butanamide

CN: propionamide CN: butyramide

e) IN: pentanamide
CN: valeramide

8. Amines
 Nitrogen-containing compounds

Naming Amines
IUPAC name:
1. The word amino is stated first.
2. The parent chain is named next.

Common name:
1. The parent chain is named first, the suffix is changed to –yl
2. Then the word “amine” is added.

Examples:

a) IN: aminoethane b) IN: 2-aminobutane

CN: methylamine CN: butylamine

H    H   H  H   H
|    |   |   |   |
H-C-N-H H-C-C-C-C-H
  |   |  |   |   |   |
H   H H   N   H   H
/ \   
H  H   
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 c) IN: 1-aminopropane d) IN: 2-aminopropane
CN: propylamine CN: isopropylamine

H   H   H    H H   H   H

     |   |   |    / |   |   |
H-C-C-C-N H-C-C-C-H
     |    |   |    \ |   |   |
     H   H   H     H H   N   H
/ \
H  H

e) IN: N-ethyl-1-aminopropane
CN: ethylpropylamine

H   H       H   H   H

|   |       |   |   |
H - C - C - N - C - C - C - H
|   |   |   |   |   |
H   H   H   H   H   H

9. Thiols
 R-SH where: -SH (mercapto group)

Naming Thiols
IUPAC name:
1. Name the parent hydrocarbon chain
2. Then affix the suffix –thiol

Common name:
1. Name the alkyl group attached to the –SH and add the word “ mercaptan”

Examples:

a) IN: ethanethiol b) IN: benzenthiol

CN: ethyl mercaptan CN: benzyl mercaptan

c) IN: 2-methyl-1-propanethiol d) IN: 2-propanethiol

CN: isobutyl mercaptan CN: isopropyl mercaptan

CH3
|
CH3CHCH2 – SH CH3CH(SH)CH3

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10. Acid Anhydrides
 RCO-O-OCR'

Naming Acid Anhydrides

IUPAC name:
1. Name the parent hydrocarbon chain
2. Change the “e” of the parent alkane name with –oic
3. Then affix the word “anhydride”

Common name:
1. Give the trivial root
2. Then affix the word “anhydride”

Examples:

a) IN: propanoic anhydride b) IN: ethanoic propanoic anhydride

CN: propionic anhydride CN: acetic propionic anhydride

c) IN: benzoic ethanoic anhydride d) IN: ethanoic anhydride

CN: acetic anhydride

e) IN: butanedioic acid

CN: succinic acid

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11. Acid/Acyl Halides
 R-CO-X where: R (hydrocarbon group) -X (halogen)

Naming Acid/Acyl Halides

IUPAC name:
1. Name the parent hydrocarbon chain
2. Change the “e” of the parent alkane name with –oyl
3. The halogen is named next with its suffix changed to -ide

Common name:
1. Give the trivial root and the suffix is changed to –yl
2. The halogen is named next with its suffix changed to -ide

Examples:

a) IN: ethanoyl chloride b) IN: propanoyl chloride

CN: acetyl chloride CN: pripionyl chloride

c) IN: butanoyl chloride d) IN: pentanoyl chloride

CN: butyryl chloride CN: valeryl chloride

100