Organic Compounds

Organic Chemistry- study of carbon-containing compounds (except carbonates, cyanides, CO 2, CO and other ionic
compounds to which carbon is part of) in which carbon atoms are bonded to one another ( C – C), to hydrogen (C – H) as
well as to other non-metal atoms such as oxygen ( C – O ) and nitrogen (C - N).

Vital force theory:

• Organic compounds could be produced only within living systems
• Living things possessed a vital force as a result of their origin
Friedrich Wohler:
Synthesized urea( an organic component of the urine of mammals using an inorganic material

Types of molecular orbitals: (refer to p227 of your chemistry 1 textbook)

1. Sigma molecular orbital, σ – head to head overlap or end-to-end overlap of orbitals
•
Ex. between 2 s orbitals: s - s
•
Between s-orbital and any p-orbital: s-px; s-py; s-pz
•
Between 2 px orbitals: Px – Px

2. Pi molecular orbital, π – side-to-side overlap of two p-orbitals

▪
Are generally weaker than sigma bonds

▪
Example: py – py ; pz - pz
The Central Themes of Valence Bond (VB) Theory
Basic Principle
A covalent bond forms when the orbitals of two atoms overlap and are occupied by a pair of electrons that have the
highest probability of being located between the nuclei

Basic Principle
A covalent bond forms when the orbitals of two atoms overlap and are occupied by a pair of electrons that have the
highest probability of being located between the nuclei.

Three Central Themes

A set of overlapping orbitals has a maximum of two electrons that must have opposite spins.
The greater the orbital overlap, the stronger (more stable) the bond.
The valence atomic orbitals in a molecule are different from those in isolated atoms (hybridization).

HYBRIDIZATION- combining of two or more orbitals of nearly equal energy within the same atom into
orbitals of equal energy.
o Introduced by Linus Pauling
o (refer to p226 – 233 of your chemistry 1 textbook)

Types of hybrid orbitals:

1) 𝒔𝒑𝟑 – s orbital mixing with 3 p orbitals in the same subshell

• central atom forms 4 equivalent bonds with terminal atoms

• characteristic of single bonds; tetrahedrally shaped
2) 𝒔𝒑𝟐 – mixing one s orbital with two p orbitals

• characteristic of double bonds; trigonally shaped

Each C is sp hybridized and has two

unhybridized p orbitals.

3) sp – mixing of one s-orbital with 1 p-orbital

• characteristic of triple bonds; linearly shaped

The number of hybrid orbitals obtained equals the number of atomic orbitals mixed.

Depicting organic compounds

Molecular formula: shows the number of each type of atom that is present in the molecule of the compound
Structural formula: shows the details of the bonding present in the molecule,i.e, which atoms are connected to which
other atom
• full or expanded structural formula: all atoms and bonds are indicated
 • condensed structural formula: an abbreviated form, shows no bonds, shows all C-C bonds but no C-H bonds

• line structural formula/line angle formula:

- use lines to show the structure of the compound
- C atoms are present at the intersection of two or more lines and whenever a line begins or not
- H atoms bonded to C are not shown but all atoms other than C & H are shown

Hydrocarbons: organic compounds that contain only H and C atoms

Alkanes:
• General formula : CnH2n+2
• Contain single bonds between C atoms
• C atoms are saturated with H atoms
Alkyl Groups – have one less hydrogen than the corresponding alkane.
• CH3 is methyl – one less H than methane, CH4

IUPAC SYSTEM of Naming Organic Compounds

The name of any organic compound is comprised of three portions:

LOCANT + PREFIX + ROOT/PARENT + SUFFIX
The root name of the compound is determined from the number of C atoms in the longest continuous chain.
Locant - where are the substituents and functional groups
The suffix indicates the type of organic compound, and is placed after the root.
The suffix for an alkane is –ane.
The prefix identifies any groups attached to the main chain.

Naming Branched Hydrocarbon Chains

Step 1: Find the longest continuous chain of carbons.

All bonds in the chain of carbons are single bonds so ending is… ane.

There are 7 continuous carbons, so the parent chain is heptane.

Step 2: Number the carbons in the main sequence starting with the end that will give the attached groups the
smallest #.

This chain is numbered from right to left because there is a substituent closest to the right.

Step 3 : Add numbers to the names of the groups to identify their positions on the chain.
these numbers become prefixes to the parent chain.

2- methyl, 3 - methyl, 4 - ethyl

Step 4: Use prefixes to indicate the appearance of a group more than once in the structure.
di – twice tri – three times tetra – four times

• This chain has 2 methyl groups so dimethyl is used.

Step 5: List the alkyl groups in alphabetical order. Nb: don’t use these prefixes for alphabetizing

Step 6: Use punctuation

➢ use commas to separate numbers

➢ hyphens to separate numbers with words.

IUPAC Name: 4-ethyl-2,3-dimethylheptane

Cycloalkanes:

➢ cyclic structures of rearranged straight chain hydrocarbon compounds where the ends meet at a common point
forming a ring.
➢ General formula : 𝑪𝒏 𝑯𝟐𝒏
Cyclobutane
Cyclopropane
Draw the structure and give the correct name

2,2-Dimethyl-6-ethylheptane

Correct IUPAC Name: 2,2,6-trimethyloctane

2-methylcyclohexane

Correct IUPAC Name: 1-methylcyclohexane

Isomers:( refer to page 234 – 239 of your gen chem 1 texbook)

• compounds having the same molecular formula but different structures
stereoisomers:
✓ same MF,same order of attachment of atoms in their molecules, but a different three-dimensional orientation of
their atoms in space

Constitutional or structural isomers

✓ the same molecular formula but a different arrangement of the bonded atoms.
✓ Structural isomers are different compounds and have different properties

The Constitutional Isomers of C4H10 and C5H12

ALKENES:
• General formula : 𝐶𝑛 𝐻2𝑛
• Series of unsaturated hydrocarbons characterized by the presence of at least one double bond between 2 C
atoms which is indicated in the nomenclature by the suffix “ene”
• To name an alkene, the root name is determined by the number of C atoms in the longest chain that also contains
the double bond.
• The C chain is numbered from the end closest to the double bond.
• The suffix for alkenes is –ene.

ethene (IUPAC Name) ethylene (common name)

𝑀𝑜𝑙𝑒𝑐𝑢𝑙𝑎𝑟 𝐹𝑜𝑟𝑚𝑢𝑙𝑎 ∶ 𝐶2 𝐻2

This is 1-butene, because the double bond is between the 1st and 2nd carbon from the
end

1-pentene

(the double bond is between C-1 and C-2 from the left end)

2- pentene

(the double bonds is closer to the right end, so numbering is from right to left thus
the double bond is between C-2 and C-3 from the right end)

3,4-dimethyl-2-pentene ( old rule)

3,4-dimethylpent-2-ene ( new rule)

1,3-cyclobutadiene

cyclobuta-1,3-diene

Alkenes may exist as geometric or cis-trans isomers, which differ in the orientation of the groups attached to the double
bond.
ALKYNES
• hydrocarbon that contains at least one CΞC triple bond
• Alkynes have the general formula CnH2n-2 and they are also considered unsaturated carbons
• Alkynes are named in the same way as alkenes, using the suffix –yne.

4—chloro-6,6-diiodo-7-methyl-2-nonyne

4-chloro-6,6-diiodo-methylnon-2-yne

6-methyl-3-octyne 6-methyloct-3-yne
Sample Problems: Give the systematic name for each of the following

(f)

Aromatic hydrocarbons: benzene & benzene compounds

• class of compounds that contain six-membered benzene-like rings with three double bonds

Bromobenzene nitrobenzene propylbenzene

Disubstituted benzenes are named using one of the prefixes ortho (o),meta (m), or para (p). An ortho-disubstituted
benzene has its two substituents in a 1,2 relationship on the ring, a meta-disubstituted benzene has its two
substituents in a 1,3 relationship, and a para-disubstituted benzene has its substituents in a 1,4 relationship

➢ benzenes with more than two substituents are named by choosing a point of attachment as carbon 1 and
numbering the substituents on the ring so that the second substituent has as low a number as possible

Polycyclic Aromatic Compounds

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