Chem 102 Institute of Agriculture and Life Sciences

Organic Chemistry DOSCST, Mati City, Davao Oriental

Chapter 1
INTRODUCTION TO ORGANIC CHEMISTRY

Organic Compounds

- Compounds made from carbon [C] atoms

- Have one or more C atoms
- Have many hydrogen [H] atoms
- May also contain oxygen, sulfur, nitrogen and halogens (fluorine [F], chlorine [Cl], bromine [Br],
iodine [I])

Properties of Organic Compounds

Typical organic compounds

- Contain carbon.
- Have covalent bonds.
Oil (organic) and water (inorganic)
- Have low melting points.
- Have low boiling points.
- Are flammable.
- Are soluble in nonpolar solvents.
- Are not soluble in water. Copyright © 2007 by Pearson Education, Inc.
Publishing as Benjamin Cummings

Organic vs Inorganic
• Propane, C3H8, is an organic compound used as a fuel.
• NaCl, salt, is an inorganic compound composed of Na= and Cl-
ions.

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Cummings

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Chem 102 Institute of Agriculture and Life Sciences
Organic Chemistry DOSCST, Mati City, Davao Oriental

Comparing Organic and Inorganic Compounds

Table 1 Some Properties of Organic and Inorganic Compounds

Property Organic Example: C3H8 Inorganic Example: NaCl
Bonding Mostly covalent Covalent Many are Ionic
ionic; some
covalent
Polarity of bonds Nonpolar, unless Nonpolar Most are ionic Ionic
a more or polar
electronegative covalent, few
atom is present are nonpolar
covalent
Melting point Usually low -188oC Usually high 801oC
Boiling point Usually low -42oC Usually high 1413oC
Flammability High Burns in air Low Does not burn
in air
Solubility in water Not soluble, No Most are Yes
unless a polar soluble, unless
group is present nonpolar
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Writing Formulas for Carbon Compounds

In carbon compounds
• Carbon has 4 valence electrons and hydrogen has 1.

• To achieve an octet, C forms four bonds.

CH4, methane

Tetrahedral Structure of Carbon

• Valence Shell Electron Pair Repulsion Theory (VSEPR) predicts that a carbon atom with four single,
covalent bonds, has a tetrahedral shape.

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Chem 102 Institute of Agriculture and Life Sciences
Organic Chemistry DOSCST, Mati City, Davao Oriental

Copyright © 2007 by Pearson Education, Inc. Publishing

as Benjamin Cummings

Organic Compounds with More Carbon Atoms

In organic molecules with more carbon atoms,

• Valence electrons are shared.
• Covalent bonds form between carbon and carbon atoms.
• Covalent bonds form between carbon and hydrogen atoms

ethane, CH3 – CH3

Tetrahedral Structure of Carbon

• In molecules with two or more carbon atoms, each carbon atom with four single bonds has a
tetrahedral shape.

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Cummings

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Chem 102 Institute of Agriculture and Life Sciences
Organic Chemistry DOSCST, Mati City, Davao Oriental

Alkanes

Names of Alkanes

The names of alkanes

• Are determined by the IUPAC (International Union of Pure and Applied Chemistry) system
• Use a prefix to indicate the number of carbons in a chain
• End in –ane

IUPAC Names for Alkanes

Table 2. IUPAC Names for the First Ten Continuous-Chain Alkanes

#of Carbon Molecular
Prefix Name Condensed Structural Formula
Atoms Formula
1 Meth Methane CH4 CH4
2 Eth Ethane C2H6 CH3CH3
3 Prop Propane C3H8 CH3CH2CH3
4 But Butane C4H10 CH3CH2CH2CH3
5 Pent Pentane C5H12 CH3CH2CH2CH2CH3
6 Hex Hexane C6H14 CH3CH2CH2CH2CH2CH3
7 Hept Heptane C7H16 CH3CH2CH2CH2CH2CH2CH3
8 Oct Octane C8H18 CH3CH2CH2CH2CH2CH2CH2CH3
9 Non Nonane C9H20 CH3CH2CH2CH2CH2CH2CH2CH2CH3
10 Dec Decane C10H22 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3

Structural Formulas

Alkanes are written with structural formulas that are

• Expanded to show each bond.
• Condensed to show each carbon atom and its attached hydrogen atoms

Writing Structural Formulas

Carbon atoms in a chain
• Maintain tetrahedral shape
• Are connected in a zig-zag pattern
• Are drawn as 2-dimensional
• Can be written in several conformations.

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Chem 102 Institute of Agriculture and Life Sciences
Organic Chemistry DOSCST, Mati City, Davao Oriental

Expanded and Condensed Structures

Table 3. Writing Structural Formulas for Some Alkanes

Alkanes Methane Ethane Propane
Molecular formula CH3 C2H6 C3H8
Structural formulas

• Expanded

CH3 – CH2 – CH3

• Condensed CH4 CH3 – CH3

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Line-Bond Formulas

• Because each C atom has a tetrahedral arrangement, the order of atoms is not a straight line, but
a zigzag pattern.
• A line-bond formula abbreviates the C atoms and shows only the zigzag pattern of bonds from C
atom to C atom.

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Conformations

The groups attached to a C-C single bond

• Rotate around the bond
• Give different relative arrangements called conformations

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Chem 102 Institute of Agriculture and Life Sciences
Organic Chemistry DOSCST, Mati City, Davao Oriental

Conformations of Butane

• Rotation of the end CH3– provides different conformations for butane.

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Some Structures for Butane

Table 4. Some Structural Formulas for Butane, C4H10

Expanded Structural Formula for Butane

Condensed Structural Formulas that Represent Butane

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Hexane has Six Carbon Atoms

Hexane
• Is an alkane with 6 C atoms in a continuous chain.
• Has a zigzag look because each C atom is at the center of a tetrahedron.
• Is represented by a ball-and-stick model

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Chem 102 Institute of Agriculture and Life Sciences
Organic Chemistry DOSCST, Mati City, Davao Oriental

Cycloalkanes
• Are cyclic alkanes.
• Have 2H fewer that the open chain.
• Are named by using the prefix cyclo- before the name of the alkane chain with the same number
of carbon atoms.

Cycloalkanes
The structural formulas of cycloalkanes are usually represented by geometric figures,

Cyclopropane

Cyclobutane

Cyclopentane

Cyclohexane

ALKANES WITH SUBSTITUTENTS

Isomers of Butane

Isomers
• Have the same molecular formula
• Have different atom arrangements.
• Of butane (C4H10) consist of a straight chain and a branched chain each with 4 C atoms

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Chem 102 Institute of Agriculture and Life Sciences
Organic Chemistry DOSCST, Mati City, Davao Oriental

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Alkyl Groups

Alkyl groups are

• Alkanes that are missing one H.
• Stubstitutents attached to carbon chains.
• Named with a –yl ending.

Naming Substituents

In the IUPAC system,

• A C branch is named as an alkyl group.
• Halogen atoms are names as halo.

Table 5. Names and Formulas of Some Common Substituents

Substituent Name
CH3– Methyl
CH3– CH2– Ethyl
CH3 –CH2–CH2– Propyl
CH3–CH–CH2– Isopropyl
F– , Cl– . Br– , I– Fluoro, chloro, bromo, iodo
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Chem 102 Institute of Agriculture and Life Sciences
Organic Chemistry DOSCST, Mati City, Davao Oriental

Alkanes with Alkyl Groups

CH3
methylpropane CH3 CH CH3
methyl groups
CH3 CH3
2,4-dimethylpentane CH3 CH CH2 CH CH3

Naming Alkanes with Substituents

Guide to Naming Alkanes

Step 1. Write the alkane name of the longest continuous chain of carbon atoms.
Step 2. Number the carbon atoms starting from the end nearest a substituent.
Step 3. Give the location and name of each substituent (alphabetical order) as a prefix to the name of
the main chain.

Example:
Give the name of
CH3 CH CH CH3

CH3 CH3

Step 1. Longest chain is butane.

1 2 3 4
CH3 CH CH CH3

CH3 CH3
Step 2. Number chain.

Step 3. Locate substituents and name. 2,3-dimethylbutane

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Chem 102 Institute of Agriculture and Life Sciences
Organic Chemistry DOSCST, Mati City, Davao Oriental

Drawing Alkane Structures

Guide to Drawing Alkane Formulas

Step 1. Draw the main chain of carbon atoms.

Step 2. Number the chain and place the substituents on the carbons indicated by the numbers.
Step 3. Add the correct number of hydrogen atoms to give four bonds to each carbon atom.

Example: Draw the structural formula of 2,4-dimethylhexane.

Location of branches Two CH3– groups 6 carbon main chain

on main chain attached with single C-C bonds

Naming Cycloalkanes with Substituents

The name of a substituent is placed in front of the cycloalkane name.

methylcyclobutane CH3

Number ring with two substituents. Br

1-bromo-2-chlorocyclopentane Cl

Properties of Alkanes

The properties of alkanes include being

• Nonpolar
• Insoluble in water
• Less dense than water.
• Flammable in air.

Alkanes with 1-4 carbon atoms are

• Methane, ethane, propane, and butane.
• Gases at room temperature.
• Used as heating fuels.

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Chem 102 Institute of Agriculture and Life Sciences
Organic Chemistry DOSCST, Mati City, Davao Oriental

Alkanes with 5-8 carbon atoms are

• Liquids at room temperature.
• Pentane, hexane, heptane and octane.
• Very volatile
• Used to make gasoline.

Alkanes with 9-17 carbon atoms are

• Are liquids at room temperature.
• Have higher boiling points.
• Are found in kerosene, diesel, and jet fuels.

Alkanes with 18 or more carbon atoms are

• Have high molar masses.
• Are waxy solids at room temperature.
• Used in waxy coatings of fruits and vegetables.

Boiling Points of Pentanes

Boiling points of alkanes
• Are lowest of organic compounds.
• Increase with larger molecules due to increased dispersion forces.
• Decrease for branched alkanes.
• Increase for cycloalkanes

Table 6. Comparison of Boiling Points of Alkanes and Cycloalkanes with Five Carbons
Formula Name Boiling Point oC
Cycloalkanes

Cyclopentane 49

CH3
Methylcyclobutane 36.3

Continuous chain
CH3–CH2–CH2–CH2–CH3 Pentane 36
Branched chains
CH3
2-methylbutane 28
CH3 CH CH2 CH3
CH3

CH3 C CH3 Dimethylpropane 10

CH3

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Chem 102 Institute of Agriculture and Life Sciences
Organic Chemistry DOSCST, Mati City, Davao Oriental

Crude Oil

The hydrocarbons in crude oil are

• Separated by boiling points.
• Heated to higher temperatures to produce
gases that can be removed and cooled.

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Classification of Carbon Atoms

The classification of carbon atoms indicates the number of carbon atoms attached.
• A primary carbon (1o) bonds to one carbon atom.
• A secondary carbon (2o) bonds to two carbon atoms.
• A tertiary carbon (3o) bonds to three carbon atoms.

1o
CH3

CH3 – CH2 – CH2 – CH3 CH3 – CH – CH3

1o 2o 2o 1o 1o 3o 1o

Combustion of Alkanes
Alkanes
• Undergo combustion by reaction with oxygen to produce
carbon dioxide, water, and energy.
• Are typically not very reactive due to strong C-C single
bonds.

Alkane + O2 à CO2 + H2O + energy

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Balancing A Combustion Equation

Write the equation

C5H12 + O2 à CO2 + H2O

Balance C
C5H12 + O2 à 5CO2 + H2O

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Chem 102 Institute of Agriculture and Life Sciences
Organic Chemistry DOSCST, Mati City, Davao Oriental

Balance H
C5H12 + O2 à CO2 + 6H2O

Balance O with O2
C5H12 + 8O2 à 5CO2 + 6H2O The equation is now balanced.

Functional Groups

Elements in Organic Compounds

In organic molecules, C atoms form bonds

• Mostly with H and other C atoms.
• Sometimes atoms of O, N, S, and halogens F, Cl, and Br.

Table 7. Covalent Bonds for Elements in Organic Compounds

Element Group Covalent Bonds Structure of Atoms
H 1 1 H–

C 4 4 C

..
N 5 3
N

O 6 2
..
O
..
.. .
F, Cl, Br, I 7 1 X
.. .
(X = F, Cl, Br, I)
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Functional Groups

Functional Groups are

• A characteristic feature of organic molecules that behave in a predictable way.
• Composed of an atom or group of atoms.
• Groups that replace a H in the corresponding alkane.
• A way to classify families of organic compouds.

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Chem 102 Institute of Agriculture and Life Sciences
Organic Chemistry DOSCST, Mati City, Davao Oriental

Table 8. Classification of Organic Compounds

Class Example Functional Group Characteristic

Alkane
H3C CH3 C C Carbon-carbon single bond

Alkene H2 C CH 2 C C Carbon-carbon double bond

Alkyne HC CH C C Carbon-carbon triple bond

H
C C
C C H C C H
Aromatic Six-atom ring
C C C C
C H C H
H
Haloalkane CH 3 Cl F, Cl , Br , I One of more halogen atoms

Alcohol CH3 CH2 OH OH Hydroxyl group (–OH)

Ether H3 C O CH3 O Oxygen atom bonded to two carbons

Thiol CH3 SH SH A –SH group bonded to carbon

O O
Carbonyl group (carbon-oxygen
Aldehyde
double bond) with –H
CH3 C H C H
O O Carbonyl group (carbon-oxygen
Ketone
double bond) between carbon atoms
CH3 C CH3 C
O O
Carboxylic Carboxyl group (carbon-Oxygen
acid double bonds and –OH)
CH3 C O H C O H
O O Carboxyl group with –H replaced by a
Ester
carbon
CH3 C O CH3 C O

Nitrogen atom with one or more

Amine CH3 NH2
..N
carbon groups

Amide
O O
Carbonyl group bonded to nitrogen
CH3 C NH2 C NH2
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Chem 102 Institute of Agriculture and Life Sciences
Organic Chemistry DOSCST, Mati City, Davao Oriental

Functional Groups in Everyday Items

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UNSATURATED HYDROCARBONS
Alkenes and Alkynes

Unsaturated Hydrocarbons
• Have fewer hydrogen atoms attached to the carbon chain than alkanes.
• Are alkenes with double bonds.
• Are alkynes with triple bonds.

Bond Angles in Alkenes and Alkynes

According to VSEPR theory:

• Three groups in a double bond are bonded at 120o angles.
• Alkenes are flat because the atoms in a double bond lie in the same plane.
• The groups attached to a triple bond are at 180o angles.

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Chem 102 Institute of Agriculture and Life Sciences
Organic Chemistry DOSCST, Mati City, Davao Oriental

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Naming Alkenes

The names of alkenes

• Use the corresponding alkane name.
• Change the ending to -ene.

Alkene IUPAC Common

H2C=CH2 ethene ethylene

H2C=CH–CH3 propene propylene

Cyclohexene

Ethene (ethylene)
• Is an alkene C2H4.
• Has two carbon atoms connected by a double bond.
• Has two H atoms bonded to each C atom.
• Is flat with all the C and H atoms in the same plane.
• Is used to accelerated the ripening of fruits.

Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Naming Alkynes

The names of alkynes

• Use the corresponding alkane name.
• Change the ending to -yne.

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Chem 102 Institute of Agriculture and Life Sciences
Organic Chemistry DOSCST, Mati City, Davao Oriental

Alkyne IUPAC Common

HC≡CH ethyne acetylene

HC≡C-CH3 propyne

Guide to Naming Alkenes and Alkynes

Step 1 Name the longest carbon chain with a double or triple bond.

Step 2 Number the carbon chain starting from the end nearest a double or triple bond.

Step 3 Give the location and name of each substituent (alphabetical order) as a prefix to the name.

Naming Alkenes

Write the IUPAC name for CH2=CH–CH–CH2–CH3 and CH3–CH=CH–CH3.

Step 1 Name the longest carbon chain. Butene

Step 2 Number the chain from the double bond.

CH2=CH–CH2–CH3 1-butene

1 2 3 4

CH3–CH=CH–CH3 2-butene

Comparing Names of Alkanes, Alkenes, and Alkynes

Table 9. Comparison of Names for Alkanes, Alkenes, and Alkynes

Alkane Alkene Alkyne

H3C–CH3 H2C=CH2 HC≡CH
CH3–CH2–CH3 CH3–CH=CH2 CH3–C≡CH

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Organic Chemistry DOSCST, Mati City, Davao Oriental

Naming Alkenes with Substituents

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