Organic Chemistry 1

prof. Dr. Fakhri Elabbar

‫غير معتمدة علي" مرجع معين‬

What is organic chemistry?
• study of carbon, the compounds it makes, and
the reactions it undergoes
• over 16 million carbon-containing compounds
are known
• because the C-C single bond (348 kJ mol-1) and
the C-H bond (412 kJ mol-1) are strong, carbon
compounds are stable
• carbon can form chains and rings
Homologous series/compounds
• related compounds that have the same
functional group (groups of atoms found within
molecules that are involved in the chemical reactions
characteristic of those molecules)
• differ from each other by a CH2 unit
• can be represented by a general formula
– examples:
• CnH2n+2 (alkanes)
• have similar chemical properties
• have physical properties that vary in a regular
manner as the number of carbon atoms
increases
– Example: the alkanes
Trends in boiling points of members of a
homologous series
• melting point and
boiling point increase Alkane Formula Boiling
with more carbon Pt./oC
atoms
methane CH4 -162.0
• Why?
– intermolecular forces
increase ethane C2H6 -88.6
– adding a CH2 adds
propane C3H8 -42.2
more electrons
• this increases the
butane C4H10 -0.5
• Van der Waal’s forces
 Intermolecular Forces (van der Waals Forces)
• The forces that act between molecules are not as
strong as those between ions, but they account for the
fact that even completely nonpolar molecules can exist
in liquid and solid states.
These intermolecular forces, collectively called van der
Waals forces, are all electrical in nature. We will focus
our attention on three types:
• 1. Dipole–dipole forces
• 2. Hydrogen bonds
• 3. Dispersion forces
Dipole–Dipole Forces

• Most organic molecules have a permanent

dipole moment resulting from a nonuniform
distribution of the bonding electrons . dipole–
dipole attractions cause the molecules to
orient themselves so that the positive end of
one molecule is directed toward the negative
end of another
Hydrogen Bonds
• Very strong dipole–dipole attractions occur
between hydrogen atoms bonded to small,
strongly electronegative atoms (O, N, or F)
and nonbonding electron pairs on other
electronegative atoms. This type of
intermolecular force is called a hydrogen
bond.
Dispersion Forces
• 1. The relative surface area of the molecules involved.
The larger the surface area, the larger is the overall attraction between molecules
caused by dispersion forces
• 2. The relative polarizability of electrons of the atoms involved.
By polarizability we mean how easily the electrons respond to a changing electric field.
Elecronegativity
• Relative ability of an atom to attract electrons
in a chemical bond

Types of covalent bonds

* Non-polar covalent: equal sharing of electrons
* Polar covalent: unequal sharing of electrons
Example: + -
H-Cl and H-Cl

F F F H
Empirical, molecular & structural formulas
structural formula
• unambiguously shows how the atoms are
bonded together

• can use condensed structural formulas

– bonds are omitted, repeated groups put
together, side chains put in brackets
• CH3CH2CH2CH2CH2CH3
– or even CH3(CH2)4CH3
• CH3CH(CH3)CH3
condensed
skeletal formula
– not accepted in the IB for answers but often
used in questions
– every “corner” represents a carbon
– hydrogens are implied
Alkanes
Structural formulas for the isomers of non-
cyclic alkanes up to C6 (10.1.5)
• hydrocarbon chains where all the bonds between
carbons are SINGLE bonds
• CnH2n+2
• draw out and write the structural formulas for
all isomers that can be formed by:
– CH4
– C2H6
Richard Thornley 10.1.5
– C3H8 2:54
– C4H10
– C5H12
– C6H14
Naming the isomers (IUPAC) of non-cyclic
alkanes

1. Determine the longest carbon chain

– Use the prefix to denote the number carbons

1 Meth-
2 Eth-
3 Prop-
4 But-
5 Pent-
6 Hex-
3. use the suffix “-ane” to indicate that the substance
is an alkane

4. number the carbons in the chain consecutively,

starting at the end closest to a substituent
(groups attached to the main chain/most busy
end)
5. name and number the location of each substituent
– the name of the substituent will be written before the main
chain and will end with “–yl” (or just memorize the below)
• CH3 is methyl
• C2H5 is ethyl
• C3H7 is propyl
And with 2 or more side chains:
5. use prefixes di-, tri-, tetra-, to indicate when there
are multiple side chains of the same type
6. use commas to separate numbers and hyphens to
separate numbers or letters.
7. name the side chains in alphabetical order
 Naming Branches as “Groups”
Naming Branches as Groups

Group Formula Prefix Suffix Name Abbreviation Structure

H
–CH3 meth- -yl methyl –Me C H

H
H H

–C2H5 eth- -yl ethyl C C H

–Et
H H

H H

C C CH3 or
–C3H7 prop- -yl propyl –Pr
H H

H3C C CH3 or
–C3H7 iso-prop- -yl iso-propyl –iPr

H H H
–C4H9 but- -yl butyl –Bu C C C CH3 or
H H H
 Naming Branches as “Groups”
Other Groups We May Encounter

Group Formula Name Structure Group Formula Name Structure

–C4H9 iso-butyl –F fluoro –F

–C4H9 sec-butyl –Cl chloro –Cl

–C4H9 tert-butyl –Br bromo –Br

–C5H11 neo-pentyl –I iodo –I

• How about C5H12? The isomers are:

Pentane 2-methyl-butane 2,2-dimethyl propane

 Structural Isomers
How many structural isomers – compounds with the same chemical formula but different
connectivity – are there with the formula C7H16?
IUPAC Name CH3 IUPAC Name
2 4 6 4
2
heptane 2,2-dimethylpentane
1 3 5 7 1 CH3 3 5

CH3 CH3
4 6 3
2 2-methylhexane 2 4 2,3-dimethylpentane
1 3 5 1 5
CH3

2 4 6 CH3 CH3
3
3-methylhexane
1 5 2 4 2,4-dimethylpentane
CH3 1 3 5

CH3 2 CH3 4
2 6 3,3-dimethylpentane
4 4-methylhexane 1 3 5
1 3 5 CH3

2 4
CH3 3
–
2 3 –
6 3-ethylpentane
1 5
6 5 4 –
4 2 3-methylhexane
1
–
1 –
3 5– 1 CH3
2
3-methylhexane
3 –4
2 4 4 6 2-ethylpentane
H3C –2 5
2,2,3-Trimethyl-butane 3
– –
5
1 3 –
1
 Nomenclature Practice
Name this compound

CH3
H3C1 CH3 9 carbons = nonane
2 3 4 5
6
Cl
7
8
H3C9

Step #1: For a branched hydrocarbon, the longest

continuous chain of carbon atoms gives the root name
for the hydrocarbon
 Nomenclature Practice
Name this compound

CH3
9 carbons = nonane
H3C1 CH3
2 3 4 5
6 CH3 = methyl
Cl
7
8 chlorine = chloro

H3C9

Step #2: When alkane groups appear as substituents, they are named
by dropping the -ane and adding -yl.
 Nomenclature Practice
Name this compound

CH3
9 carbons = nonane
H3C1 CH3
2 3 4 5
6 CH3 = methyl
Cl
7
8 chlorine = chloro

H3C9

1 9 NOT 9 1

Step #3: The positions of substituent groups are

specified by numbering the longest chain of carbon
atoms sequentially, starting at the end closest to the
branching.
 Nomenclature Practice
Name this compound

CH3
9 carbons = nonane
H3C1 CH3
2 3 4 5
6 CH3 = methyl
Cl
7
8 chlorine = chloro

H3C9

2-chloro-3,6-dimethylnonane

Step #4: The location and name of each substituent are

followed by the root alkane name. The substituents are
listed in alphabetical order (irrespective of any prefix),
and the prefixes di-, tri-, etc. are used to indicate
multiple identical substituents.
 Rules for Naming Alkanes

1. Find the parent carbon chain and add the suffix.

It does not matter if the chain is straight or it bends.

If there are two chains of equal length, pick the chain with greater
number of substituents.
2. Number the atoms in the carbon chain to give the first substituent the
lowest number.
If the first substituent is the same distance from both ends, number the
chain to give the second substituent the lower number.
When numbering a carbon chain results in the same numbers from either
end of the chain, assign the lower number alphabetically to the first
substituent.
3. Name and number the substituents.
• Name the substituents as alkyl groups.
• Every carbon belongs to either the longest chain or a substituent, not
both.
• Each substituent needs its own number
• If two or more identical substituents are bonded to the longest chain,
use prefixes to indicate how many: di- for two groups, tri- for three
groups, tetra- for four groups, and so forth.
4. Combine substituent names and numbers + parent and suffix.
• Precede the name of the parent by the names of the substituents.
• Alphabetize the names of the substituents, ignoring all prefixes except iso, as
in isopropyl and isobutyl.
• Precede the name of each substituent by the number that indicates its
location.
• Separate numbers by commas and separate numbers from letters by hyphens.
The name of an alkane is a single word, with no spaces after hyphens and
commas.
Alkenes
Structural formulas for the isomers of the straight
chain alkenes up to C6
• alkenes have a double bond between two or more of
the carbons
• CnH2n
• draw out and write the structural formulas for all
isomers that can be formed by each
– C2H4
– C3H6 Richard Thornley 10.1.7 (1:37)
– C4H8
– C5H10
– C6H12
Naming the isomers (IUPAC) of straight chain
alkenes
1. suffix changes to “-ene”
2. when there are 4 or more carbon atoms in a
chain, the location of the double bond is
indicated by a number
3. begin counting the carbons closest to the end
with the C=C bond
– numbering the location of the double
bond(s) takes precedence over the location
of any substituents

1-butene 2-butene
but-1-ene but-2-ene
Naming Practice

CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

choose the correct ending

ene
 CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

determine the longest carbon chain with

the double bond
ene
 CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

assign numbers to each carbon

ene
 CH2 CH2 CH3
1 5 6
CH3 CH2 C CH2 C CH3
2 3 4
CH3

assign numbers to each carbon

ene
 CH2 CH2 CH3
1 5 6
CH3 CH2 C CH2 C CH3
2 3 4
CH3

attach prefix (according to # of carbons)

1-hexene
ene
 CH2 CH2 CH3
ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
determine name for side chains
1-hexene
 CH2 CH2 CH3
ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
attach name of branches alphabetically
2-ethyl-4-methyl-4-methyl-1-hexene
 CH2 CH2 CH3
ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
group similar branches
2-ethyl-4-methyl-4-methyl-1-hexene
 CH2 CH2 CH3
ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
group similar branches
2-ethyl-4,4-dimethyl-1-hexene
or 2-ethyl-4,4-dimethyl hex-1-ene
CH3 CH CH2 CH3 CH3
propene CH3 CH CH C CH3

CH3 CH CH CH3
2,4-dimethyl-2-pentene
2-butene 2,4-dimethyl pent-2-tene
 CH3 CH3

CH2 CH C CH2 CH3 CH3 C CH CH2

CH3 CH2 CH3

a) 3,3-dimethyl-1-pentene b) same

CH 3

CH 3 C C CH CH CH3

CH3
c) 4,5 dimethyl-2-hexene
 • Alkynes
H H

ethyne

3,3,4-triethylhex-1-yne

4-(tert-butyl)-4-ethyl-5,5-dimethylhex-2-yne