INTRODUCTION

The teaching of applied sciences, and especially Chemistry, which is

based on the scientific method, plays a very important role in the studies
of General Secondary Education, since the future and definitive
orientation will depend on the way in which its study is approached. of
the student who begins to strengthen his aspirations.
How this learning is prepared, the foundation of the basic principles and
the enthusiasm that is managed to develop, will depend on the definitive
modeling of the professional future, which as a student, has an open
brain and always eager to all those
speculations and superior ideas.
If the student is shown in his teaching the usefulness that the subject
has for the different activities of his daily work, he will be stimulated and
eager to know more, it will have an impact on better academic
performance and, above all, in defining his profession. future.
In order to comply with these principles, this work was designed, which
aims to provide the content of the subject ORGANIC CHEMISTRY or
CARBON CHEMISTRY, in a simple, but complete way and above all so
that students can identify the usefulness it has for life. It presents the
theoretical part of the different topics indicated in the current program
for the subject by the Ministry of Popular Power for Education, as well as
examples of the uses of organic compounds and exercises that allow the
theoretical content to be consolidated.

Page 2
 INDEX

CONTENT PAGE
Yo 31
Yo 31
Yo 37
Yo 38
origin 44
Figure 10 44
a) ÍH CH,CH COOH HOCH,CH,COOH 58
b)CH,OCH, CH.COOH CHSCHCHCOOH 58
Always avoid excess 79

Page 3
 QUANTUM MECHANICS

In 1926, the theory known as quantum mechanics came to light,

whose development in a more useful form for the chemist is due to
Erwin Schrödinger, from the University of Zurich. He developed
mathematical expressions to describe the movement of an electron as a
function of its energy. These mathematical expressions are known as
the wave equation , since they are based on the concept that the
electron not only has particle properties but also wave properties. The
different solutions to a wave equation are called wave functions , and
each of them corresponds to an electron.
Except for the simplest systems, the mathematics involved in obtaining
solutions is so time consuming that it is only possible to obtain
approximate solutions. Still, quantum mechanics provides answers that
agree so well with the facts that it is accepted today as the most fruitful
tool for achieving an understanding of atomic and molecular structure.
A simple way used by this theory is the definition of quantum numbers
, which are used to describe the location of the electrons within the atom
and these have a relationship between them. These are four:
a) Principal quantum number (n): Indicates the energy level
where the electron is located within the atom, it takes positive
integer values that range from the 1st until the 7th
(in the
present). Remember which energy levels are related to the
periods of the periodic table. The energy levels are:

LEVEL ELECTRONS
K=1 2
L=2 8
M=3 18
N=4 32
O=5 32
P=6 18
Q=7 8
b) Secondary quantum number (l): Indicates the
sublevel
energy (subshell) where the electron is located and is related to
the main quantum number, since it takes values ranging from 0

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 to (n - 1), that is, if the electron has n = 3, it indicates that l will
take the values 0, 1 and 2.
The combination of these two quantum numbers indicates the remps or
orbitals of the electron.

SUB-LEVEL REMPE
l=0 yes
l=1 p
l=2 d
l=3 F

c) ) Magnetic quantum number (m): Point out

the
magnetic orientation of the rempes, its values are from l to
-l, that is, if l = 3 the values of m will be -3; -2; - 1; 0; 1;
2; 3. In the case of the first two levels K (1) and L (2)
their relationship is:

l m REMPES
0 0 1s
1 0 2s
1 -1 2p x
1 0 2py
1 1 2p z

This means that the rempe (orbital) 1s has quantum numbers l = 0; m =

0.
Remember: The existing Rempes in sublevel s is s , for sublevel p the
rempes will be px, py, pz.

d)Spin quantum number (s): It indicates the rotation of

the electrons on their own axis, the Pauli Exclusion
Principle establishes that in a spin there can only be two
electrons, for this reason there are only two values which
are ½ and -½.

The theory of Quantum Mechanics uses these numbers to indicate the

location of electrons within the atom through wave functions , that is,

Page 5
each wave function represents a solution to the wave equation and
corresponds to an electron, described in the following way
V(n,l,m,s) .

Examples:
1.-We have the wave function
V(1,0,0,½) this means that the

electron is located in level 1 = K, sublevel = s, rempe s.

Note : When two electrons are found in a wave, two wave
functions must be indicated.

2.- An electron is located in a 3p x type rempe, it indicates

what its wave function is.
This electron is located at an energy level 3 = M, sublevel 1
(by px) and with orientation x = -1, therefore the function will be:
V(3,1,-1,½)

Electronic configuration

It is the distribution of the electrons of an atom or element in the

different energy levels and sublevels.
We can carry out the electronic configuration using the rempes (atomic
orbitals) but at the level of knowledge that interests us we will only carry
it out with the first two levels, that is, up to element No. 10 of the
periodic table.

2 2 1 1
Example: For the element Z = 6 it will be: 1s 2s 2p x 2p y 2p
z

Observe that two p- type remps have one electron and the other none,
this is due to a rule known as Hung's Rule which states that a remp
cannot be filled when there are others of the same energy, if they
are not all found first. semi-occupied (with one electron). In the
previous case, the rempes p have the same energy, which is the reason
why none of them are filled, since the number of electrons to be
distributed in these rempes is 2.

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 Chemical bond

It originates when two atoms combine or join through their electrons, for
which both must have semi-occupied electrons, these can be combined
by sharing or transferring electrons.

Types of Chemical Bonds

LINKS
CHEMICALS

IONIC METALLIC COVALENT

Yo-----------------1
Compounds Solids ----------------------1
Inorganic Metallic SIMPLE DOUB TRIPLE
(-) LE
When they are formed by sharing electrons, the bond created is called
Covalent , and can be of three types:
a) Simple or simple (-): It is when it is formed by sharing a pair
of electrons, one from each atom.
a) Double (=): It originates for the
sharing of two peers of
electrons, two electrons from each atom.
b) Triple (≡): It originates sharing
three peers of
electrons, three electrons from each atom.
When the chemical bond is a product of the transfer of electrons, it is
called Ionic , which is characteristic of inorganic compounds.

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 Hybridization

It is the combination of pure rempes (orbitals) to produce more stable

rempes, that is, lower energy. There are three types:
a) Sp hybridization: This is when a pure rempe s and another
pure p are combined.
b)Sp 2 hybridization : This is when a pure rempe s is combined with
two pure rempes p .
c) Sp 3 hybridization : A pure rempe s is combined with the three pure
rempe p .

HYBRIDIZATION

2 3
Sp Sp Sp

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 Taken from The World of Chemistry

Characteristics of each type of Hybridization

Hybridization Shape Angle Links or Links n

Covalent Bonds
Geometric
sp linear 180º 2 2 one single one
triple
sp 2 Triangular 120º 3 1 two singles one
double
sp 3 Tetrahedral 109º28' 4 0 four singles

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 Sigma (o) bonds

They are those that are formed from the following combinations of
rempes:
a) Pure rempes s.
b) Rempes cigars and p.
c) Rempes pure s with any of the hybrids.
d) Rempes hybrids with each other.
e) Linear p-remps.
When a rempe can form a sigma bond, but they are occupied, they are
called antibonding sigma bonds and are noted as *
EITHER * . The electrons that form these types of bonds are called sigma
electrons. Single covalent bonds are of this type, in double and triple
bonds there is always one of these.

Pi (T) Links

They are those formed by the combination of parallel pure p remps ( p y

and p z ) and the electrons that originate them are called pi electrons.

These form double and triple covalent bonds, in each case there is
always a sigma bond ((5).

Important

Simple covalent bonds are formed by one bond, double covalents

by one a and one n, and triple covalent bonds by one a and two
n.

EXERCISES

1 .- Point out the wave functions for the electrons located in

energy levels 1, 2, 3 and 4.

2 .- Of the following functions, indicate which ones are wrong.

Justify your answer.
to)
V (1,1,1,½) b) V (2,1,1,-½) c) V (1,2,1,-½) d) V (5,3,1,½) e)
V(0,2,1,-½)

Page 10
 3 .- Why do atomic orbitals have a maximum capacity of two
electrons?

4 .- For elements Z = 3; Z = 5 and Z = 8 write the electronic

configuration by rempes and indicate the wave function for the electrons
with the highest energy content.

5 .- Justify why the following rempes or orbitals cannot exist,

a) 2d b) 3f c) 1p

6 .- Determine the wave function for two electrons that are

located in energy sublevel 3 and that are not located in the same
rhythm.

7 .- Indicates the configuration electronics of an element

whose
electron with maximum energy has a wave function
V(4,1,1,-½) .

8 .- During the spectral investigation of an atom, a chemist found

that the highest energy electron is located in a region of magnetic
orientation 0. What is the position of the element in the periodic table?

9 .- Indicates the electronic configuration of carbon Z = 6 using

the different types of hybridization.

10 .- Point out the reason why compounds that contain oxygen or

nitrogen do not have a tetrahedral geometric shape on them even
though they hybridize sp 3 . What is the geometric shape they present?

CARBON CHEMISTRY OR ORGANIC CHEMISTRY

INTRODUCTION

Chemistry is one of the sciences that is related to all the processes of

our lives, from the biological metabolism of living beings to each of the
simplest activities and phenomena that we experience. One of its
branches that is of great importance is ORGANIC CHEMISTRY , which
is characterized by presenting the element carbon (C) as a fundamental

Page 11
element in each of its compounds.
Because it presents carbon as a fundamental element in all compounds,
it is also known as Carbon Chemistry . This is divided into families such
as: a) Hydrocarbons. b) Derivatives
Halogenated. c) Alcohols. d) Amines. e) Aldehydes. f) Ketones. g)
Carboxylic Acids. h) Ethers. i) Amides, etc.
It is important to know the characteristics of carbon. Its electronic
configuration by rempes is 1s 2 2s 2 2p x 1 2p y 1 2p z , which would
indicate that it can only form two chemical bonds, according to what was
stated above in relation to chemical bonds (they are formed in atoms
with rempes semi-occupied), but the reality is that it always forms four
chemical bonds, which it can do, since it hybridizes in three possible
ways, giving rise to different families of organic compounds.
a) When HE hybridizes sp , his setting
2 1 1 1 1
will be: 1s 2sp 2sp 2p and 2p z in which case it forms two type O
bonds and two type T bonds, that is, one single covalent and the other
triple covalent.
b) When hybridizes sp 2 his setting is:
2 2 1 2 1 2 1 1
1s (2sp ) (2sp ) (2sp ) 2p z in which case it forms 3 o
bonds and one T , that is, two single covalent bonds and another double
covalent bond.
c)When hybridizes sp 3 su setting is:
2 3 1 3 1 3 1 3 1
1s (2sp ) (2sp ) (2sp ) (2sp ) which indicates that the
four bonds formed are of type o , that is, they are all single covalent.
Because of the way carbon hybridizes, there are so many organic
compounds.

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 DIFFERENCE BETWEEN INORGANIC COMPOUNDS AND
THE ORGANICS

PROPERTY INORGANIC ORGANIC

Composition Basically c andH, but

All known elements P, S, O, N and halogens can
exist.

Generally liquid
Physical state Solid, liquid and and
gas gaseous, but, some are

Page
13
 solids.

Chemical bond Ionic and covalent Generally covalent

Density Greater than or Smaller, but close to 1

equal to 1

High Low
Melting and
boiling point

Water solubility
T=
Generally slightly soluble
environment Soluble
(ambient) Very soluble
Somewhat soluble
T = Greater
amb.

They do not
Side reactions They always exist
present

Reaction
In one step Generally several steps.
mechanism

Types of structures used in Organic Chemistry

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14
Structure can be defined as the way of indicating the unions of the
elements in a compound, which can be:
a) Developed structure : It is the one that presents all the
chemical bonds that form the compound.
b) Semi-developed structure: It is the one that indicates only
some of the chemical bonds that constitute the compound.
c) Molecular formula: It shows us the elements that make up
the compound and how many atoms of each exist in it.

ORGANIC NOMENCLATURE

BASIC RULES

Nomenclature means naming or formulating chemical compounds.

There are rules that are useful for any of the families of organic
compounds and which we will proceed to mention below.
1 .- The main chain : is one that has the following
characteristics:
a) It is the one with the highest number of carbons.
b) It is the most linear or straight possible.
c) It presents the greatest or total number of functional groups
(what characterizes a family) and, above all, the most important
functional group.
To name it, the following prefixes are used according to the amount of
carbon it has:
met = 1 C; et = 2 C; prop = 3C; but = 4C; pent = 5 C

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15
 hex = 6C; hept = 7 C; oct = 8 C; non = 9 C; dec = 10 C
undec = 11 C; dudec = 12 C; tridec = 13 C, etc.
Ending the name with the characteristic suffix of the family
corresponding to the compound.

2 .- The radicals (substituents) or secondary chains : they

are all the carbon chains that are not included within the main chain,
they are named indicating first the quantity prefix and then the suffixes
il (when all their chemical bonds are simple), enil (if they present a
double bond) and inil (if they present a triple bond).
Example: Methyl (-CH 3 ); ethyl (-CH 2 CH
3 ); et enyl (-CH=CH 2 );
et inyl (-C ≡ CH).

3 .- When a radical or functional group is repeated several times in

a compound, the following prefixes are used to indicate them:
say = 2 times. tri = 3 times. tetra = 4 times
penta = 5 times. hexa = 6 times. hepta = 7 times. etc

4 .- To indicate the radicals in the names of the compounds, they

must be arranged in alphabetical order, without taking into
consideration the quantity prefixes.

5 .- To name the compound, the carbon chain must be numbered

starting from the end or carbon closest to a more voluminous radical or
functional group of greater importance, this in the case of open chain
compounds, since if they are closed chain Carbon No. 1 will be the one
with the largest radical or most important functional group.

6 .- To indicate the radicals or functional groups in the name of

the compound, the number(s) of the carbon(s) of the main chain where
it is located is indicated. If it appears several times they must appear

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16
 7 as many numbers as times it is repeated and they must be
separated by a comma.

8 .- Between number and word there must be a hyphen (-).

9 .- The functional and radical groups are arranged in the name of

the compound in alphabetical order, but the compound will bear the
name of the most important family that exists in the structure of the
compound. Any other rule will be established with the corresponding
family.

Example of some most commonly used radicals

a) Radicals that use the prefix iso : are those that have a methyl
on the penultimate carbon of their linear chain.

Yo....................................................................................................................................31
Yo....................................................................................................................................31
Yo.......................................................................................................................................37
Yo.......................................................................................................................................38
origin........................................................................................................................44
Figure 10..................................................................................................................44
a) ÍH CH,CH COOH HOCH,CH,COOH.................................................................58
b)CH,OCH, CH.COOH CHSCHCHCOOH.............................................................58
Always avoid excess..............................................................................................................79

isopropyl isohexyl

Important
Note that to name them, all the carbons that exist in the
structure are counted, and carbon number one in the linear chain
is the one attached to the main chain.

b) Radicals that use the prefix sec are those that have a branched
methyl on the first carbon of their linear chain.

1 2 3 4 5 1 2 3
- CH 2
CHCH 3
/
CH 3
secbutyl
Page
17
 -CH 2 CH 2 CH 2 CHCH 3 /
CH 3
sechexil

HYDROCARBONS

They are organic compounds that have only the elements carbon and
hydrogen in their structure. A clear example of this type of organic
compounds is petroleum .
Hydrocarbons are classified as follows:

a) Aliphatic : These are those that have an open carbon chain,

that is, the chain begins at one carbon and ends at another different
carbon. These in turn can be:
a.1.- Saturated : They are those in which all their carbons have
3
sp hybridization, which indicates the maximum amount of hydrogens
allowed (four), causing all chemical bonds to be simple.
a.2.- Unsaturated: These are those that have double chemical
bonds in their structure, carbons with sp 2 hybridization or triple bonds
where the carbons have sp hybridization.
b) Alicyclics : These are those that have a closed main carbon
chain, that is, the chain begins at one carbon and ends at the same
carbon. These can also be saturated and unsaturated.
c) Aromatics : They are six-carbon closed chain compounds that
have three alternating double bonds and three single bonds.

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18
 NOMENCLATURE OF ALIPHATIC HYDROCARBONS

Aliphatic hydrocarbons are classified into families that are:

1 .- Alkanes: They are saturated hydrocarbons. To name them,
the suffix ano is used after the prefix corresponding to the number of
carbons that the main chain has. The general formula is:
CnH2n + 2
Example:
a) methane (CH 4 )
met = a single carbon in the main chain anus = suffix
corresponding to the family.

b) propane ( CH 3 CH 2 CH 3 )
prop = three carbons in the main chain anus = suffix
corresponding to the family
2 .- Alkynes: They are unsaturated hydrocarbons, since they
have a triple bond in their structure. To name them, the suffix ino is
used after the prefix corresponding to the number of carbons in the main
chain; the number of the carbon where the triple bond is located must
be indicated (when it is located in No. 1 it is not necessary to mention
it). Its general formula is: C n H 2n - 2
Example:
a) Ethine ( CH ≡ CH)
Et = two carbons in the main chain ino = suffix
corresponding to family 1 2 34
b) 2-but ino (CH 3 C ≡ CCH 3 )
2-but = the triple bond is located on carbon No. 2 and the
main chain has four carbons.
ino = suffix corresponding to the family

3 .- Alkenes: They are also unsaturated, because they have a

double bond in their structure. The suffix ene is used after the prefix
that indicates the number of carbons in the main chain and the number
of the carbon in which the unsaturation is located must also be indicated
(if it is in the first carbon it is not necessary). Its general formula is: C n
H 2n

Example:
a) Prop ene (CH 2 =CHCH 3 )

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19
 Prop = 3 carbons in the main chain
eno = suffix corresponding to the family

1 2 3 45
b) 2-pentene ( CH 3 CH=CHCH 2 CH 3 )
2-pent = on carbon No. 2 of the main chain the double
bond is located and the chain consists of 5 carbons. eno =
suffix corresponding to the family

EXERCISES

1 .- Name the following hydrocarbons.

a) CH 3 CH 2 CH 2 CH 2 CH 3 b) CH 3 CH=CHCH 2 CH 2 CH 2 CH 2 CH
3

c) CH 3 (CH 2 ) 4 C ≡ CCH 2 CH 3 d) CH2=CH(CH2)5CHCH2CH3

/
CH 2 CH 2 CH 3

e) CH3C=CH(CH2)2CH3 f)
CH (CH ) CH=CHCH(CH ) CH
/ /
CHCH3
CH(CH 2 ) 2 CH 3
CH3
C/H3

g
) CHΞCCH 2 (CH ) 4 CHCH 3
2
/
CH 2 CH 2 CHCH 3
/
CH 3

2.- Point out the semi-developed structure of the following

hydrocarbons.
a) 3-ethyl-6-isopropyl-2-methyl-4-secbutyl-2-octene
b) 6,6,8,8-tetramethyl-4-propyl-4-secpentyl-2-nonimo

c) 2-ethyl-4-propyl-3-hexene
d) 3,4-sietyl-5-isopropyl-2,6-dimethyloctene

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20
 e) 4,5-dimethyl-3-secbutyl-7-yne-2-octene.
f) 4-isobutyl-2,5-dimethylheptane
g) 3-ethyl-2,3,5-trimethylnonane
h) 3,6-diethyloctene
i) 2,4-dimethyl-3-isopropylheptane

CLOSED CHAIN HYDROCARBONS

They are closed-chain hydrocarbons because they are composed of

carbon and hydrogen only and their main carbon chain begins with a
carbon and ends with itself.
The families of closed chain hydrocarbons are:
a) Cycloalkanes b) Cycloalkenes c) Cycloalkynes d) Aromatics

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21
The first three families are similar to open chain hydrocarbons in terms
of their physical and chemical properties. To name them, the following
rules are followed:
a) The chain begins to be numbered by the carbon that allows the
most voluminous unsaturation or branching to be located on the
lowest carbon in number, in the case of Cycloalkanes by that
carbon that contains a branch.
b) To name them, the word Cycle is placed before the quantity
prefix and it ends using the suffix according to the family ( ano,
eno, ino ).
c) The other rules are similar to open chain.
d) The numbering direction will be in the sense of giving the
smallest number to the branches or substituents.

Example:

It is called dimethyl cyclohexane , di = has two methyl radicals.

cycle = because it is closed chain. hex = the chain has six
carbons

EXERCISES

1 .- Name the following organic compounds.

to b)
)

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22
c)
d CH
3
)
CHCH
3

H CH 2
CH 3
CH
3

a CH
n 3

CH
3

2 .- Indicates the semi-developed structure for the following

organic compounds.

a) 6 – ethyl – 4 – methyl – 4 – propylcyclohexene

b) 2 – ethyl – 3 – isobutyl – 4,4- dipropylcyclopentene
c) 2 – cyclopentyl – 1 – cyclohexylcyclohexane
d) 3,4 – dipropylcyclohexine
e) Secpentylcyclooctane

AROMATIC COMPOUNDS

They are closed-chain and unsaturated organic compounds, which,

because they are made up of carbon and hydrogen, are only
hydrocarbons. They are characterized by being made up of six (6)
carbons and those that have three pi bonds interspersed between
carbons, that is, they have three double covalent bonds interspersed
with single covalent bonds. Its fundamental or main compound is
Benzene (C 6 H 6 ) . Another definition of aromatic compounds is:
compounds formed by

Page
23
 a ring of six carbons that have alternating double and single
covalent bonds.
Benzene is represented as follows:

As the pi bonds are delocalized, the ring is obtained, which is:

Where the circle inside the hexagon represents the movement of the pi
electrons.
Aromatic radicals (when they are secondary chains)

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24
 Aromatic Derivatives

The homologs of benzene are derived from it by replacing one or more

hydrogen atoms with one or more radicals (secondary chains).

Monosubstituted derivatives

They are named as derivatives of (Phenyl) or putting the group

phenyl before
substituent to the word benzene.

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25
 Disubstituted or Bisubstituted Derivatives

They arise when two hydrogen atoms of benzene are replaced and are
named as follows:
a) If the substituents are located on the 1,2 carbons it is called
ortho (o-)
b) Yeah the substituents are in carbons 1,3 are
called
goal (m-)
c) Yeah the substituents are in the 1,4 carbons
it is called
to P-)

Exampl
e:

Polysubstituted
Derivatives
They are named after the cyclical, but placing as
hydrocarbons suffixed by the word
benzene.

Page
26
Example
s
3-bromo-5-
chloro-1-
nitrobenzene

1,3,5-
tribromobenzene

2-chloro-1,3-
dinitrobenzene

EXAMPLES OF

HYDROCARBONS
NOMENCLATURE

1) Name the
following
hydrocarbons
using IUPAC
nomenclature rules.
a)
CH 3 CH 2 CH 2 CH 3

Answer: Butane , since the carbon chain is

made up of 4 linear carbons.

b)
CH 3 CH 2 CHCH 3 │ CH 3

Answer: 2-methylbutane or isopentane . Well, the

longest carbon chain is 4 carbons, so it is a butane and has a methyl on
the second carbon, which is why it is 2-methyl, and since the radicals are
named first and finally the name of the long chain is given this first

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27
name. It is isopentane because it has the methyl in the penultimate
carbon of the longest chain and the compound has a total of 5 carbons.

c)
CH 3 (CH 2 ) 4 CH 2 CHCH 2 CH 3

│
CH 3

Answer: 3-methylnonane . Well, the longest chain has 9

carbons and carbon number 3 has a methyl radical. (remember that the
carbon chain begins to be numbered at the end closest to the branch)

d)
CH 2 CH ═ CHCH 2 (CH 2 ) 4 CH 2 CH 2 CH 2 CH 3

Answer: 2-dodec ene . The carbon chain is 12 carbons

(docec) and is an alkene (ene), since it has a double bond that is located
on the second carbon.

and)
CH 3 CH 2 CHCH 2 CH ═ CH(CH 2 ) 4 CH 3

│
CH 3 CH 2 CH 2

Answer: 9-ethyl-6-dodecene: The longest chain is 12

carbons, it has an ethyl radical at carbon 9 and a double bond at number
6 (remember that you start numbering the chain at the end closest to
the double bond because it is an alkene).

F)
CH 3 CH 2 CH 2 CH 3

│ │
CH 3 CHCHCHCH ═ CH(CH 2 ) 4 CH 3 │
CH 3 CH 2 CH 2

Answer: 9-isopropyl-8-propyl-6-dodecene . The longest

chain is 12 carbons, on carbon 9 there is an isopropyl radical, on carbon
8 there is a propyl and a double bond at number 6 (remember that the

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28
radicals are arranged in alphabetical order).

g)

Answer: Dimethylcyclohexane. It is a saturated hydrocarbon (all the

carbons of the main chain have sp 3 hybridization, that is, all its chemical
bonds are simple) with a closed chain (cycle), so it belongs to the
cycloalkane family. Because the cycle has 6 carbons, the prefix hex is
prefixed, because it has two methyl radicals it is called dimethyl , and
because it is an alkane cycle its ending is ane .
REMEMBER: Closed-chain hydrocarbons' names always
begin with cycle , then the amount of carbon they have is considered
and they are finished according to the family to which they belong , ano,
eno or ino .

h)

Answer: 1-phenyl-3-methyl-1-
propylcyclohexane. He
Cyclohexane is the main chain because it is the most branched, it is
numbered (in this case looking for the substituents to be on the lowest
carbons, so the clockwise direction is not followed) by where the phenyl
is, since It is the most important branch, the radicals are named in
alphabetical order and indicating the number of the carbon where it is
located.

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29
 Yo)

Answer: Benzene: Because it is the main hydrocarbon

aromatic (closed chain of six carbons with chemical double bonds
interspersed with single bonds)
REMEMBER: A hydrocarbon is an organic compound made
up of carbon and hydrogen only. Aromatic compounds are unsaturated
hydrocarbons, since they have double bonds that are formed with
carbons with sp 2 hybridization. Unsaturation is formed with carbons with
sp 2 or sp hybridization.

j)

Answer: Phenylbenzene. The aromatic family ends in

benzene, the radical being phenyl.
k)

2) Indicates the semideveloped structure for the following

hydrocarbons.
a) 3-methyl-1-heptine
Answer: The main chain is made up of 7 carbons on

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30
carbon 3, it has a methyl radical ending in ino and it belongs to the
family of alkynes with the triple bond on carbon number 1.

1 23 4 5 6 7
CH ≡ CCHCH 2 CH 2 CH 3 CH 3

│
CH 3

b) 4-isopropyl-5-propyl-6-dodecine
Answer: the main chain is 12 carbons, it belongs to
the alkyne family ( ino ending) with the triple bond at carbon 6, it has
an isopropyl radical at carbon 4 and another propyl at number 5.

CH 3 CHCH 3

CH 3 CH 2 CH 2 CHCHC ≡ C(CH 2 ) 4 CH 3

Yo
CH 2 CH 2 CH 3

c) 3,5-diethyl-1-octene
Answer: It belongs to the alkene family ( ene ending)
and the main chain has 8 carbons with two ethyl radicals, one on carbon
3 and another on carbon 5, the double bond is located on carbon number
1.

CH 2 CH 3
Yo
CH 2 =CHCH CH 2 CH(CH 2 ) 2 CH 3

CH 2 CH 3

d) 3-ethyl-6-methyl-5-propynyl-1-nonene
Answer: It belongs to the alkene family, with a double
bond on carbon 1, an ethyl radical on carbon 3, a methyl on carbon 6,
and a propenyl (radical with triple bond) on carbon 5. Main chain of 9
carbons.

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31
 CH 2 CH 3

Yo
CH 2 =CHCHCH 2 CH(CH 2 ) 2 CH 3

CH 2 CH 3

NOMENCLATURE OF OTHER FAMILIES OF COMPOUNDS

ORGANIC

To name the other families of organic compounds, the general rules of

organic nomenclature already studied must be taken into account and
the following table must be taken into consideration, placing the prefix or
suffix to the main chain according to the corresponding family.

FAMILY FUNCTIONAL SUFFIXES PREFIXES EXAMPLE

GROUP
Alcohols - OH ......ol Hydroxy methanol

Ethers - EITHER - dimethyl ethyl

. .illilicon ether
ether
- C = O C=O
│ - to the propanal
Aldehydes
h
.....ona Oxo propanone

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32
 Ketones 0 ketone Dimethyl
-2 ■ ketone
1 131

Carboxylic -COOH Acid........oic

propanoic acid
acids either
-COOmetal ...aotode .... Umbose
acid salts
propanoatopl
...oato of methyl
.....oil ethanoate
0 co-R
Esters
9 -C-0-Ar

....amide Propanamide

p
Amides -C-NH2

primary -NH 2 .....amine Methylamine

amines
2-chloropropane
aurochsilo methyl
-X chloride
Halogenated ....year
Alkyl Halides
Carboxylic acid EITHER EITHER
anhydride ║ ║ Anhydride….. Ethylmethyl
-C – O - C - ……..oico anhydride

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33
FAMILIES PRIORITY

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34
 FAMILY FUNCTIONAL GROUP NOMENCLATURE

─ COOH Acid -------oico

Carboxylic acids

Esters ─ COOR ---ate of -----ilo

Amide ─ CONH 2 ----amide

Acid Anhydride ─ OC ─ O ─ CO ─ --- oic anhydride

Acid Halide ─COX - - - uro de --- ilo

Aldehyde ─ CHO ---- to the

- - - ona
Ketone ─ CO ─ - - - ketone

----- nitrile
Nitrile ─C≡N cyanide ------- ilo

---- ol
Alcohols ─ OH Alcohol - - - - ilic

Mercaptene ─ SH - - - mercaptan

Amine - - - amine
─ NH 2 ─ NH ─ ─ N ─ │
------ ether ether
Ether ─ OR ─ ------ ilic

alkyl halide ─ ---ure of ---- ilo

X = Cl, Br, I

Nitro compounds ─ NO 2 ----

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35
 Alkenes ═ - - - eno

Alkynes ≡ - - - ino

Alkanes ─ - - - year

EXERCISES

1 .- Point out the semi-developed structure of the following organic

compounds.
a) p-methylphenol or methylhydroxybenzene
a) diethyl ether
b) 9,11-diethyl-3,4,6-trimethyl-7-propyl-decane
c) etherdiphenyl
d)3,6-dimethyl-5-ethyl-3- nonene (5-ethyl-3,6-dimethyl-3-
nonene)
e) 2-methyl-propanal
f) 3-pentanone
g) 4-ethyl-1-propylcyclohexane
h) 4-methyl-2-pentanol
i) cyclohexanol
j) etherdiphenyl
k) ethylphenyl ketone
l) 4-methylpentanoic acid
m) phenyl 2-methylhexanoate
n) 3-methylhexanoyl chloride
o) o-methyltoluene
p) 1-isopropyl-2,5-dimethylbenzene
q) 3(3-methyl-cyclopentyl)-2-secbutylbutyl chloride
r) Ethylmethylpropylamine
s) Ethylphenylamine
t) 3-ethylhexanethiol

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36
 u) 4-isopropyloctanamide
v) phenyl butanoate
w) 3-ethyl-2,6-diphenyl-6-propyldecanal
x) 2,3-dicyclohexyl-4-ethyl-2,6,8-trimethylundecanol
y) Cyclohexenylpropyl ketone
z) Cyclopropenylethylisohexylamine
aa) 5 –cyclopentyl-4-isobutyl.2-ene-4-chloropentene
bb) Benzyl fluoride
cc) o-methylbenzoic acid
dd) 4,5-cyclopropyl-2-phenyl-6-secpentyldecanal
ee) phenylsecoctylether
ff) 2-isopentyl-3-secdecylbenzanal

2.- Complete and name the following organic compounds.

to) C-C
Yo
C–C–C–C–C–C
Yo
C–C–C

c
c)
Yo d)
C–C–C–C-C

NH2

and) F
(©)- C = O )
C–C
Yo C-C
c

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37
 g) h) C – C – C – C = O
C – C – C – C - SH
Yo
C–C–C

i) j) C – C – C
Yo
C-C C–C C – C – C – C –C - C
II II
C–C–C–C–C–C c OH
Yo Yo
Br c

ISOMERY

Isomerism: it is a phenomenon by which several species with the

same molecular formula can arrange their atoms differently and for each
arrangement different properties correspond.

Types of Isomerism

ISOMERY TYPE
_______Yo____

STRUCTURAL STEREOISOMERY

CHAIN POSITION FUNCTION GEOMETRIC OPTICAL

1 .- Structural isomerism: corresponds to different

arrangements of atoms, and are classified as:

1.1. - Functional isomerism , when there are at least three types

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38
of atoms capable of forming more than one bond, they can generate
different functional groups (different families). (Ex. Ether isomers of
alcohols).
1.2. - Position isomerism, when the same functional group is on
different carbons of the same chain (Ex. primary and secondary
alcohols).
1.3. - Chain isomerism , when the same functional group is on a
chain with a different arrangement of its carbons. (Ex. normal chain and
branched chain alcohols).
The table indicates the structural isomers for compounds with the
molecular formula C 4 H 10 O.

Board. STRUCTURAL ISOMERS FOR C,H,o

Com Molecular Composite d pf pe Solub.

p. formula class Structure g/ml ( S C) ('C) Hz0(%)

1 C,H,0 alcohol OH 0,810 - 89,2 117,7 7,9

3
C,#,0

C#,0
alcohol

alcohol
MOH\OH
e 0,808 - 89

0,801 - 108
99,5

108
12,5

9,5

4 CH,0 alcohol -’ 0,789 25,5 82.8 00

5 C#,0 ether 0,738 38,9 3,1

6 C,M,0 ether AO- 0,714 34,6 7,5 ■

7 CH,0 ether

M 0,734 32,5

2 .-Stereoisomerism, corresponds to species that have the same

molecular formula, the same structure but differ in the spatial
relationships of one or more atoms that constitute them.
In the graphical representation of stereoisomers, it is much more
convenient to handle simplified structural formulas because this allows for
a global vision of the molecule. It is important to highlight the spatial

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39
relationships of the atoms and to do this there are several ways that obey
certain conversions. For example, a cyclic structure like cyclohexane can
be represented as a regular “lying down” hexagon and the substituents
are attached to it with vertical lines up or down (if the lines are in one
direction, the substituents will be on the same side of the ring). and in
that direction).
The hexagon can also be drawn "vertically" in which case the orientation
of the substituents is indicated with: thick lines if they point forward or
with broken lines if they are located behind the plane of the ring.
However, the bond angles of cyclohexane cause the molecule to adopt a
non-planar shape as an average structure and will resemble a “chair” or a
“boat”. In these cases the substituents will be oriented "axial" (vertical
and perpendicular to the imaginary plane that cuts the chair or boat) and
equatorial (if they are located approximately in the plane).

Figure 3. Representations of the Lrans-1. 3-cyclohexanediol

2.1.Geometric isomerism , when there is a different geometry

with respect to a double bond or the plane of a ring (Ex. Cis - trans of
alkenes). At this point it is worth differentiating the terms "Configuration"
and "Conformation".

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40
Conformation refers to different arrangements due to rotations of sigma
bonds (single bonds) both in open chains and in alicyclic structures, in
which case it is called pseudorotation. The different arrangements are
known as conformers (or rotamers: a more general term applied to open-
chain compounds). Here, only the extreme conformations are drawn. For
cyclohexane derivatives two chairs and a canister.
In some cases the energy barrier to rotate a sigma bond is sufficiently
more stable and high it that It allows individualize two either
therefore more of the molecule. Generally by media
abundant. HE achieve detect, low certain conditions
the conformers (called also isomers

Page
41
Figure 5. Conformations

Configuration refers to different arrangements of substituents on the

same carbons that give rise to geometric or configurational isomers
(stereoisomers). The cycles impose a certain molecular rigidity and, as in
olefins, "cis" isomers are defined as those that have the substituents on
the same side. In the case of cyclohexane disubstituted on carbons 1 and
2 or 1 and 4, trans isomers will be those whose substituents occupy the
axial and equatorial positions, while in the "cis" isomer both will be in the
axial or equatorial position. When the substituents are located on carbons
1 and 3, they will be cis, if both are axial or equatorial oriented.

Figure 6. Settings

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42
 Figura 6. Settings

2.2 Optical isomerism , when the spatial relationships of the

atoms that make up a structure are identical but two non-superimposable
molecules can be created, that is, one is the mirror image of the other.
As they present the same spatial relationship, their physical and chemical
behaviors are identical as long as the observed phenomenon is not
related to spatial symmetry factors such as the rotation of the plane of
polarized light (physical property) or a chemical reaction that affects
carbon. 'asymmetric' (carbon with four different substituents) with an
asymmetric reactant. Each optical isomer will react at a different rate.
These isomers are known as "enantiomers" or 'enantiomorphs' and the
configuration of a pair of enantiomers is opposite at the asymmetric
center.

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43
 Figura 7. Optical isomers with a single asymmetric carbon

COOH COOH
acid name evolactic dextrolactic acid

fermentation
of sugars origin muscle
Figure 10

When there is more than one asymmetric center in the molecule, we can
have "enantiomeric" molecular arrangements (a pair of enantiomers, if
one is the mirror image of the other, and "diastereomeric" when they
are not mirror images. They are all optical isomers and their maximum
possible number is 2 n , n = number of asymmetric carbons.
The number of optical isomers decreases depending on molecular
symmetry. A molecule with several equally substituted asymmetric
centers can present two types of optical isomers:

the
enantiomers and the "meso" ones in the latter mirror images overlap.
Meso compounds are quickly recognized if it is possible to draw a plane
of symmetry in the molecule. The existence of meso compounds implies

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44
the decrease in the number of isomers

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45
optical, because each meso pair is actually a single compound. Thus
tartaric acid with two asymmetric centers could generate 2 2 = 4
isomers, of these two are enantiomers and two are meso (therefore only
one) with which the number of isomers of tartaric acid is reduced to 3.
Meso-tartaric acid is a diastereoisomer of L-tartaric and D-tartaric, while
the last two have an enantiometric relationship with each other.

by D,L (enontiomers)

Figure 9, Optical isomers of tartaric acid

Newman projections: They are representations of molecules to be

able to see the distribution of the substituents of a main hydrocarbon
chain.
Stepped Projection Eclipsed Projection

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46
Fischer projection: They are representations of organic molecules,
useful especially in the area of biochemistry to represent asymmetric
carbons or optically active molecules.

Nature without image and without

likeness
The most efficient and best equipped laboratory that exists is
nature. It is responsible for the fact that life on Earth is
"homochiral" and that it is possible to obtain only one
enantiomer of proteins and nucleic acids. The reason for the
enantiomeric purity of many natural products has not been
determined. But it is known that those responsible for this great
specificity are enzymes.

It is unknown why all essential amino acids, those that make up

proteins, are left-handed (the molecules bend the plane of
polarized light counterclockwise) and why all fundamental
carbohydrates are right-handed (the molecules bend the plane
of light polarized clockwise). The property of deflecting the plane
of polarized light is typical of molecules whose structure is
"chiral": what does "chiral" mean? Our hands are chiral, that is,
the left hand is a mirror image of the right hand. Chiralide, which
The figure shows the similarity of the concept of chirality
comes from the Greek chiros = hands, can originate for different
for an organic molecule of an acid, as occurs with the
structural reasons, one of them is the existence of an sp 3
right and left hands.
carbon with four different substituents, as in the case of amino
acids, and for this reason this carbon is called “ chiral” or
“asymmetric”.

In the event that nature produces both enantiomers, it is responsible for producing one in a greater proportion than the other
and for differentiating them very well. This is the case with limonene, which has a lemon or orange smell depending on the
isomer considered.

Taken from the World of Chemistry

EXERCISES
1.- Indicates the structural isomers that comply with the following
molecular formulas:

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47
 a) C 5 H 12 b) C 10 H 22 c) C 8 H 18 d) C 6 H 14

e) C 5 H 10 f) C 3 H 6 g) C 6 H 12 h) C 7 H 14

2.- Represents structural isomers for the following compounds.

a) Cycloctane b) 2-phenyl-3,3-dimethyldecane
c) 1-cyclopentyl-3,3-diethylcyclohexane
d) 4-cyclopropyl-2,3-dipropyloctane

3 .- Determine the position isomers for the following molecular

formulas. The main chain should not be linear.

a) C 5 H 12 O b) C 5 H 10 O 2 c) C 7 H 16 O d) C 8

H 17 Br

4 .- The molecular formulas C 7 H 12 ; C 8 H 14 ; C 6 H 10 belong to

the cycloalkene families. Indicate 4 position isomers that comply with
the same.

5 .- Write all the positional isomers of hexachlorocyclohexane.

Which of them are capable of exhibiting optical isomerism?

6 .- Determine the isomers of function for the following molecular

formulas.

a) C 6 H 12 b) C 4 H 8 c) C 5 H 12 O d) C 6 H 12 O 2

7 .- Write all the possible structures of C 5 H 10 that contain a

double bond. Mark those that present geometric isomerism.

8 .- Indicate which of the following compounds present geometric

isomerism.

a) ethyl 1,2-dichloride b) 1,2-ethenyl bromide

c) 2-enopropanol d) 2-3-pentenyl chloride
e) Dimethylcyclobutane f) 1,3-dimethylcyclobutane

g) 2-ethyl-3-isopropylcyclcohexane

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48
 h) 4-Bromocyclopentyl chloride

9 .- Indicate which of the following compounds present optical

isomerism.

a) 2-butanol b) 2-enopropanal c) 2-hydroxypropanal

d) 3-phenyl-3-methylpentane e) p-butyl(2-
cyclopentyl)me-
tilbenzene.

10 .- Make all the isomers alternate and eclipsed through the

carbons 2 and 3of the2,3-dichloro-2,3-dimethylbutane, using
projection by Newman.

11 .-Write all the isomers structural and geometric of

the
dimethylcyclohexane. (Uses chair conformation).

12 .-The mint flavor must be mainly to activity of

the
menthol. This is one of the isomers of 2-isopropyl-5-methylcyclohexane.
Draw all the geometric isomers of this compound using chair
conformation.

13 .- What is meant by each of the following terms?

a) optical activity. b) right-handed. c) levorotatory

d)
enantiomer. e) diastereoisomer. f) compoundmeso.

PROPERTIES AND STRUCTURES

The physical properties of organic compounds give a valuable indication

about their structure and in turn the structure of a substance often tells
us the physical properties we can expect from it.

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49
 CLASSIFICATION OF ORGANIC MOLECULES

To recognize the type of molecule that an organic compound presents, it

is necessary to know if it has a Dipole Moment (
u), which is defined as “ the modulus of the vector that originates from
the attraction of electrons on the part of an atom and that indicates the
positive charge at its end and the negative charge at its tip .”
a) Polar molecules : These are those that, due to having a
difference in electronegativity between the elements that form their
chemical bonds, result in a total dipole moment in the molecule other
than zero, this means that for polarity to exist in a molecule it must
have electronegative elements. Examples: Water, Methyl chloride,
Methanol, Ethanoic acid.
b) Non-polar molecules: These are those that do not have a
dipole moment, that is, they do not present marked differences in
electronegativity between the elements that form their chemical bonds,
which is why they give rise to a dipole moment equal to zero and when
there are differences between them when adding their Individual dipole
moments do not give rise to a total dipole moment. Example: Ethane,
Methyl tetrachloride, Methanol, Benzene.

Intermolecular Forces of Organic Molecules

They are the forces that hold the molecules of a compound together.
These forces are:
1) Van der Waals forces : Their existence can be described as
follows: “ the average distribution of charges around a non-polar
molecule is symmetrical, so that there is no net dipole moment.”
However, the electrons move, so that at a given moment, this
distribution is distorted, generating a momentary dipole moment, which
will affect the electronic distribution in another molecule of the same
compound (non-polar), that is, the opposite ends of each molecule will
be attracted .” Despite these momentary dipole moments (of each
molecule), a net attraction occurs between them. These forces are very
short-range: they only act when the molecules are in intimate contact
between their surfaces.
In conclusion, these forces hold nonpolar molecules together. They are
generally weak and become stronger as the linear carbon chain

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50
increases in a compound and decrease when the compound is branched.
Example : Pentane molecules must be more closely linked than 2-
methylbutane, despite the fact that both compounds have the same
amount of carbons in their structure.
2) Dipole-Dipole Forces : It is the attraction exerted by the
positive end of a polar molecule on the negative end of another similar
molecule. As a result of this interaction, polar molecules bind more
firmly than nonpolar molecules of comparable molecular weight; This
difference will be reflected in the physical properties of the compounds.
3) Hydrogen Bridge : It is a particularly strong type of dipolar
attraction, in which a hydrogen atom acts as a bridge between two
atoms of very electronegative elements (mainly F, O, N), holding one
with a covalent bond and the other with purely electrostatic forces. This
force is much stronger than other types of dipole-dipole forces. This
bridge becomes quite important for molecules that have up to five
carbons in their chain; above this amount they continue to be important
but weaker.

PHYSICAL PROPERTIES OF ORGANIC COMPOUNDS

1) Density: It is the relationship between the mass and volume of

the compounds. Compounds with a higher molecular mass will have a
higher density, as will those with a lower volume.

d = m/v

2) Melting Point : It is the energy necessary to break the forces

that hold the molecules of a solid substance together and allow them to
pass into the liquid state, which represents a greater disorganization of
them. This energy is provided by heat. This means that the more closely
linked the molecules are, the higher their melting point will be.
3) Boiling Point : Although in liquids the molecules have greater
ease of movement than in solids, they are united by intermolecular
forces. The energy that must be supplied to the liquid to break these
forces and allow the molecules to go to a state of greater freedom (the
gaseous state) is what is called Boiling Point.

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51
 4) Solubility: When a solid or liquid dissolves, the structural units
-ions or molecules- separate from each other and the space between
them is occupied by the molecules of the solvent. This means that the
intermolecular or interionic forces that hold the solute together must be
broken, for which energy must be supplied, which is provided by the
bonds established between the solute and the solvent. For this to occur,
polar molecules must be dissolved into similar molecules and non-polar
molecules into non-polar ones. It has also been proposed that inorganic
compounds must dissolve in inorganic compounds and organic
compounds in organic ones. For an organic compound to dissolve in
water (universal solvent) it must be able to form hydrogen bonds with it.

CHEMICAL PROPERTIES OF ORGANIC COMPOUNDS

1) Acids and Bases: These words have been defined from

different points of view, here we will deal with the Bronsted-Lowry
definition, which indicates that an acid is a substance capable of giving
up protons and a base is those that accept them.
This establishes what is known as the Bronsted-Lowry conjugate pair,
for example:

- +
CH 3 COOH + NH3 CH 3 COO + NH4

Ac 1 B2 B1 Ac 2

According to this definition, the strength of an acid depends on its

tendency to give up a proton and that of a base on its tendency to
accept it. Acidity increases with electronegativity and within a group with
the size of the elements, for example, in halogens it increases as
follows: iodine; bromine; chlorine; fluorine.
For Lewis, a base is a substance that can supply a pair of electrons to
form a covalent bond and an acid will be one that can receive a pair of
electrons to form a covalent bond . This definition is fundamental for the
understanding of Organic Chemistry. The acidic or basic behavior of a
compound can be of different intensity or strength, this is determined by
the acidity constant (Ka) in the case of acids and the basicity constant
(Kb) for bases. When the Ka or Kb are large, it indicates stronger acids
or bases.

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52
 Example:
- +
CH 3 COOH + H 2 O ↔ CH 3 COO + H 3 O

Remember H 2 O (l) is not considered for the equilibrium constant .

Ka = I CH 3 COO - 11 H 3 O +
1
[ CH3COOH ]
+ OH-
CH 3 NH 2 + H2O ↔ CH 3 NH 3 +

K b = I CH 3 NH 3 + H OH - 1
[ CH3 NH2]

Another way that the degree of acidity or basicity of organic compounds

can be determined is by means of the pKa , which will measure the
strength of the compound as an acid, or the pK b , which will measure
the strength as a base.

pKa = - log Ka and pK b = - log K b

Substituents located on the carbon chain can affect the acidity or

basicity of an organic compound. Electronegative elements (F, O, N, Cl,
Br, I) when present in a compound increase the degree of acidity and
decrease the basicity. The alkyl groups (-CH 3 ;-CH 2 CH 3 ; etc.)
increase the basicity by being
electron donors and decrease the acidity of organic compounds.
2) Inductive Effect: It is the effect produced by electronegative
elements on the carbon chain of a compound, by attracting electrons
towards it. This weakens with distance. The inductive effect is important
in determining the degree of acidity or basicity of organic compounds.

RESONANCE

Resonance or Mesomerism: It is the delocalization of the pi electrons

of a compound along the carbon chain. When in a compound there are
alternating pi and sigma electrons (they are recognized by the single
and double or triple bonds), the former will remain in constant
movement along the carbon chain, which means that the compound
cannot be represented by a single structure, but by a combination of all
its structures that can represent it (known as resonance structures)

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53
and which is called a resonance hybrid. The resonance method allows
us to know, in a qualitative way, the stabilization that a molecule can
achieve by electronic delocalization. The greater the number of resonant
structures by which a chemical species can be described, the greater its
stability.

RULES FOR PERFORMING RESONANCE

1 .- As has already been said, the compound must have

alternating pi and sigma electrons. Only the pi electrons will move.
2 .- When the compound is neutral, you must begin by creating
charges, which is done by breaking a pi bond (double or triple) and
moving the electrons to the side where there is greater electron
attraction (inductive effect), in this way the carbon or element that
remains with the electrons will be negative and the other positive.
(because?).
3 .- It is recommended to move the pi electrons to the side where
they were initially made, that is, to move the negative charge.
4 . - When the compound has a charge, the movement of the pi
electrons must be towards the negative charge.
5 .- It is advisable to start the resonance at one of the ends of the
compound, whenever possible.

Examples

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54
 CONTRIBUTION OF STRUCTURES TO THE HYBRID IN
ORDER OF DECREASING IMPORTANCE

1 .- The neutral ones.

2 .- Those that have the greatest number of chemical bonds.
3 .- Those that have negative charges on electronegative
elements.
4 .- Those that have positive charges on electropositive elements.
5 .- Those that have nearby opposite charges.
6 .- Those that have equal charges far apart.

Importance of resonance

Resonance is a good measure of the stability of compounds, since when

a compound has a greater number of structures contributing to the
hybrid, it will indicate that it has lower energy, that is, it is more stable.
In the case of acids or bases, when their conjugate pair is stabilized by
resonance, it indicates that they will be stronger as an acid or base.

EXERCISES

1.- A Below are the moments dipolar of some

molecules. For each of them indicates the address
vector
dipole moment (

Page
55
 u), based on its structure

10 , 0; BF 0; HC CC1 0.44; BrCl 0.57; CC1. 0 CH 3 COOH 1.74; CH,CN 3.94; LiH
5.88; CH OH 1.69 0 0.49; CH,NO, 3.54; CHNH 1.31

2 .- Write 5 possible structures for the molecular formula C 6 H 14

(chain isomers) and name them. Sorted according to boiling point.
Justify your answer.

3 .- Relate the following organic compounds to their boiling point.

Justify your answer.
a) Heptane b) 3~methylhexane c) 2,3~dimethylpentane d)
Heptanol
b) e) Heptylamine
Tf= 120 ºC; 89 2C; 25ºC; 108ºC; 175ºC

4 .- Explain why hexylamine has a higher boiling point than

ethylmethylpropylamine.

5 .- For the following compounds, indicate which ones are soluble

in water and which ones are soluble in benzene. Justify your answer.
a) Potassium chloride. b) 2~methylbutane c) 3-Acid
ethylheptanoic
d) Methylamine e) Carbon dioxide
f) o-chloromethylbenzene g) Ethanal.
6 .- Complete the following Bronsted Lowry acid-base equilibrium
reactions.

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56
 a) C_H_NH, + CH-COOH — 6 5 2 3S
b) CH30+ 3 • Cn 3 L - O - Ch
_—
0 0
c) CH,NO, +

d) Cl,CHCOOH

7 .- In each of the following pairs of compounds, indicate which

one is stronger as an acid. Justify your answer.

a) ÍH CH,CH COOH HOCH,CH,COOH

3LL LL

b)CH,OCH, CH.COOH CHSCHCHCOOH

8.- Order the following species according to their basicity in

increasing order.

a) F; OH'; NH,; CH,' c) Cl'; SH

bl HF; H,0; NH, d) F“; Cl"; Br"; Yo

IMPORTANT

Basicity increases as the size of the atom that has the charge (-)
decreases.

9 .- Of each pair of substances, indicate which one is more acidic,

taking into account the inductive effect.
a) Methanoic acid; ethanoic acid
b) b) Cyclohexylamine; phenylamine
10 .- The value of Ka for benzoic acid is 6.3 x l0 -5 By introducing
a group - NO 2 + into the ring, the acidity varies as follows.

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57
 p-nitrobenzoic acidKa = 36 x l0 -5
m-nitrobenzoic acidKa = 32 x l0 -5
O-nitrobenzoic acidKa = 670 x l0 -5
Explain: a) Why in the three compounds the acidity exceeds that
of benzoic acid. b) Why does o-nitrobenzoic acid show the highest Ka
value?

11 .-Indicate what type of intermolecular force exists between the

molecules of the following compounds.
a) Propene b) Water c) Ammonia d)
Benzene e) Propanol f) Methane g) Acid
pentanoic.

12 .- What type of hydrogen bond is stronger? Justify your

answer.
SH---0 ; OH-----Yes

13 .- The dipole moment of NF 3 is 0.24 and for NH 3 it is 1.46.

Explain why the deference.

14 .- Write the resonance structures for the following species.

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58
 15 .- Compare the stability of each of the following pairs of
ions.

a
'0 0
w ()CH:CH-CH,; CH,-CH:CH-CH,
2 3 2

b)
3L and 33•L
0

REACTIONS OF ORGANIC COMPOUNDS

GENERAL REPRESENTATION OF AN ORGANIC REACTION

Substrate + Reagent Products

The substrate is the organic substance that is attacked by another

smaller substance called Reagent ( attacking agent) . When the two
substances are of similar size, the one that is most altered during the
chemical change is considered reactive.
There are three types of chemical changes that can occur in organic
compounds: Substitution, Addition and Elimination .

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59
 REACTIONS
ORGANIC

Of rearrangement or
SUBSTITUTIO ADDITIO ELIMINATION
transposition
N N

It changes a new is added is lost The structure is

substituent for substituent. Link substituent. Links altered
another. pi becomes sigma become of the molecule
They maintain the sigma . in pi without
links . suffer alteration in

Substitution: It is when an element or group enters the organic

substrate and produces the departure of another, which occurs by
breaking and forming sigma bonds.
Example:

CH 3 CH 3 + Cl 2 → CH 3 CH 2 Cl + HCl

FeBr 3 + HBr
+ Br
2

Addition: It is when a new element or group is incorporated into the

substrate, which occurs by breaking a pi bond ( a double or triple bond )
and forming a sigma bond.
Example:

CH 2 =CH 2 + Cl 2 → CH 2 ClCH 2 Cl

Elimination: Occurs when the substrate loses an element or group

without the entry of others. It is carried out by breaking sigma bonds
and forming one σ.

Example:

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60
 CH 3 CH 2 Cl + KOH → CH 2 =CH 2 + KCl + H 2 O (in the presence of
alcohol)

Rearrangement or transposition: Here, a molecule undergoes an

alteration in its structure without losing its original composition, that is,
its atoms are rearranged in a different way.

GENERAL ANALYSIS OF CHEMICAL REACTIONS

The basic principle of chemistry and of course organic chemistry is that

in every transformation of one molecule into another there is breaking
and/or formation of bonds. It means then that this particular event has a
capital importance to be considered in any analysis that may be carried
out related to chemical reactions.
This allows us to immediately generalize that: after examining
thousands of reactions, we reach the surprising conclusion that the
breaking of any chemical bond can apparently occur in only two ways:

a) Homolytically : When the bond is broken, each molecular

fragment remains with an odd electron. This is what happens in free
radical reactions.

*A+•B

b) Heterolytically : When the bond is broken, both electrons

remain in one of the fragments of the molecule, forming a cation (
lacking electrons ) and an anion ( with electrons ). This process occurs in
ionic or polar reactions.

A+

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61
 Types of reagents

TYPES
REAGENTS

RADICALS
NUCLEOPHILIC ELECTROPHILIC
FREE

Cl , Br , I , OH , -
- - - -
(CH 3 ) 3 N, -SCH 3
OCH 3 , -CN, CH 3 COO - H + , NH4 + , NO2 + , R + ,
NO + , SO 3

Nucleophiles: These are chemical species with negative charges, or

that can behave like Lewis bases.
Electrophilic: These are chemical species with positive charges, or that
can behave like Lewis acids.
Free radicals: They do not have an electric charge, but they have
unpaired electrons, so they are very reactive and unstable species. They
are very important intermediaries in many processes and phenomena
such as photosynthesis, pyrolysis ( decomposition of a substance into
simpler substances) , polymerization ( reaction in which
macromolecules, called polymers, are obtained from small molecular
units ), etc. .

Example:

a) Addition of hydrobromic acid to a double bond in the presence

of peroxide.

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62
 Br
Br+CC / M DC

Br Br h
DC +H C_C

b) Substitution of a hydrogen in an alkane for an “A” atom, which

can be a halogen such as chlorine or bromine.

R+ H5- CH 3 R—H + CH
3

CH 3 +AA »A—CH 3 +A
replaced
Types of mechanisms
The mechanisms will depend on the type of reagent involved in the
chemical change or the number of molecules in the determining step of
the reaction.

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63
Unimolecular Mechanism: The speed of the reaction will depend on a
single type of molecule, so the determining phase is the formation of an
intermediate, which will be an ion.

Bimolecular Mechanism: The rate of the reaction is determined by the

concentration of the substrate and the reactant; Therefore, in the
important phase, both molecules are involved; The changes are
generated simultaneously, without the formation of intermediate ions.

ELECTROPHILIC ADDITION REACTIONS

The characteristic reaction of alkenes is the addition of substances to the

double bond, according to the equation:

H,C CH 3 H 3 C CHa
\/ - H— C— C_Br
II
H,C CH 3

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64
 ek + H— Br
H 3 C CH,

The first stage of the reaction is the addition of the proton to the
nucleophilic alkene, to form the carbocation. In the second stage, the
carbocation reacts with the nucleophile.

The addition of electrophiles to alkenes makes possible the synthesis of

many classes of compounds:
H Br
H2C=CH2 4- H — Br --------- H,C-- - -CH 2

Haloalkanes

HH
H2C==CH2 + H— H --------3- CH^CH 2

to the gray hair

Br Br
H„C=CH2 4- Br— Br --------5- CHgCH2
1,2-Dihaloal gray hair

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65
 11
Br OH
. . H,O
H2C==CH2 4- Br— Br 2 9- CH CH
Hatohydrins

OH OH
HC==CH2 4- OsO 4 H2O2 -- CHgCH2
1,2-Diols

1.BH,THF H OH
H 2 C=CH 2 --------- -----=- CH—CH
2.H,O,,OH , Kl
J
“ Alcohols

1 .Hg(OAc).H,O H OH
H 2 C=CH 2 ------- ------- - CHgCH2
2 . NaBH, OH
NUCLEOPHILIC ADDITION REACTIONS

Nucleophilic addition to carbon-heteroatom double bonds

The addition reactions of a nucleophile on carbon-heteroatom double

bonds such as C=O or C=N show a wide variety. These bonds are polar (
there is a significant difference in electronegativity between the two
atoms that form them ), so that the carbon supports a partial positive
charge. This makes this atom the target of the nucleophile.

-
Nu + RR'C=O → NuRR'CO - (Nucleophilic attack)

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66
 - +
NuRR'CO +H → NuRR'C-OH (Protonation)

NUCLEOPHILIC SUBSTITUTION REACTIONS

Nucleophilic substitution is that reaction in which the attacking reagent,

the nucleophile, donates a pair of electrons to the substrate, forming a
new bond with it, displacing another nucleophile, the nucleophile, which
leaves with an electron pair. It is classified as aliphatic to distinguish it
from aromatic. The general reaction can be illustrated as follows:

Charges are not reflected in this chemical equation. The nucleophile ''Y''
can be neutral or carry a negative charge ( anion ); The ''RX'' substrate
can be neutral or carry a positive charge ( cation ). In any case, the
nucleophile ''Y'' must have a lone pair ( non-bonding pair of electrons ).
Hence all nucleophiles are Lewis bases.

Substitution reactions can occur by two mechanisms:

a) Bimolecular Nucleophilic Substitution (SN 2 )

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67
Bimolecular nucleophilic substitution reactions (SN 2 ) consist of the
attack of a group with lone pairs ( nucleophile ) to a positively polarized
carbon with loss of the leaving group. The rate of the reaction depends
on the structure of the substrate, nature of the nucleophile, leaving
group and solvent.

According to the mechanism, a carbocation is formed, which is flat, and

which can be attacked by the nucleophile with equal ease on each face
of the plane.

b) NucleophilicUnimolecular Substitution (SN 1 )

In the unimolecular nucleophilic substitution (SN 1 ) the substrate is

ionized, forming a carbocation, which is attacked in the next stage by

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68
the nucleophile. The reaction only takes place with secondary or tertiary
substrates and requires a good leaving group, although its speed does
not depend on the nucleophile.

The mechanism of a unimolecular nucleophilic substitution consists of

two steps:
Step 1 (slow): RX <====> R + + X -

++
Step 2 (quick): R Y -----> RY

The first step is a slow ionization of the substrate and is the determining
step of the reaction. This reaction requires the assistance of the solvent
since the energy necessary to break the RX bond is compensated by the
solvation of R + and X - .

The second step is the rapid reaction between the carbocation

intermediate and the nucleophile (Y).

ELIMINATION REACTIONS

a) Bimolecular elimination ( E2 )
In bimolecular elimination, the base extracts hydrogen from the carbon
adjacent to the one with the leaving group, generating alkenes. Strong
bases, good leaving groups, and anti-arrangement of hydrogen with
respect to the leaving group are required.

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69
In bimolecular elimination (E 2 ) the base removes hydrogen from the β
carbon and at the same time the leaving group is lost. It is therefore an
elementary reaction, whose kinetics are second order.

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70
The rate of the reaction depends on the concentration of the base and
the substrate.

v = k [substrate][Base]

The energy diagram has the following form:

b) Unimolecular elimination (E 1 )

The unimolecular elimination reactions proceed like SN 1 through the

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71
formation of a carbocation. They require weak bases and can lead to
carbocation rearrangement.

STUDY OF FAMILIES OF ORGANIC COMPOUNDS

PHYSICAL PROPERTIES OF ALKANES

1 .- Its boiling and melting point increases with the carbon chain
and decreases with the branches, that is, alkanes with the same amount
of carbons, but branched will have a lower boiling and melting point than
one with the same amount of carbons with a straight chain.
2 .- They are soluble in non-polar organic solvents such as
benzene.
3 .- The first four alkanes are gaseous, from five carbons to 17
carbons they are liquid and from the 18 carbon alkane onwards they are
solid.
4 .- Density increases with the amount of carbons.

SYNTHESIS OR OBTAINING ALKANES

1 .- By Hydrogenation
It occurs when alkenes react with hydrogen.
Alkene + H2—> Alkane

Example: Ethene is reacted with hydrogen.

CH 2 =CH 2 + H2- CH 3 CH 3

2 .-Wutz synthesis
It is when a halogenated derivative reacts with sodium to produce

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72
an alkane and a salt.
2R-X + 2Na 2R + 2NaX
Example: 2CH 3 Br + 2Na CH 3 CH 3 +2NaBr

3 .- Grignard synthesis
It is when a halogenated derivative reacts with magnesium to
produce an alkane and a basic salt.
R - X + Mg R - R + HOMgX (this in the presence of
H 2 O)
Example: CH 3 CH 2 Cl + Mg CH 3 CH 3 +
HOMgCl
(presence of H 2 O)

CHEMICAL PROPERTIES OF ALKANES

1 .- Halogenation: When an alkane reacts with a halogen (F 2 ,

Cl 2 , Br 2 , I 2 ).
Alkane + X2- R - X + HX
Example: CH 3 CH 3 + Br 2- CH 3 CH 2 Br + HBr

2 .- Nitration: Alkane + HO-NO 2 R-NO 2 +H2O

Example: CH 3 CH 3 + HO-NO 2 CH 3 CH 2 NO 2 +H2O

3 .- Combustion: Reaction of an alkane with oxygen.

Alkane + O2-> CO 2 + H 2 O + energy

PHYSICAL PROPERTIES OF ALKYNES

Because they are slightly polar compounds, their physical properties are

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73
similar to those of alkanes and alkenes.

SYNTHESIS OR OBTAINING ALKYNES

1 .- From calcium carbide

CaC 2 + H2O CH ≡ CH + Ca(OH) 2

2 .- Dehydrogenation of alkyne dihalides

- CHX - CHX - + 2KOH - alkyne + 2KX + H 2 O

(X = Cl, Br, I)

3 .- Dehalogenation of alkyl tetrachloride

CX 2 CX 2 + 2Zn ->alkyne + 2ZnX 2

(X = Cl, Br, I)

CHEMICAL PROPERTIES

1 .- Halogenation

Alkyne + 2X2—> CX 2 CX 2 (alkyl tetrahalide)

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74
 2 .- Hydrogenation

Alkyne + 2H2—> alkane (with Pt as catalyst)

Alkyne + H2—>alkene (with Pt as catalyst)

3 .- Hydrohalogenation

Alkyne + 2HX CH 2 X - CH 2 X (alkyl dihalide)

4 .- Combustion

Alkyne + O 2 CO2 +H 2 O + energy

PHYSICAL PROPERTIES OF ALKENES

Its physical properties are similar to those of alkanes and alkynes.

SYNTHESIS OR OBTAINING ALKENES

1 .- Dehydration

Alcohol + H 2 SO4—>Alkene + Water

2 .- Dehydrohalogenation

Alkyl halide + KOH ->Alkene + KX + Water

CHEMICAL PROPERTIES OF ALKENES

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75
1 .- Hydrogenation

Alkene + hydrogen alkane

2 .- Halogenation

Alkene + halogen Vicinal dihalide

3 .- Hydrohalogenation

Alkene + HX alkyl halide

4 .- Hydration

Alkene + Water Alcohol

5 .- Combustion

Alkene + Oxygen CO2 + Water + energy

EXERCISES

1 .- Complete the following chemical reactions.

a) ethene + bromine
b) 3-methyl-2-butene + hydrogen
c) Pentane + Chlorine
d) Butene + oxygen
e) CH 3 CH 2 OH + H 2 SO4->
f) CH 3 CH 2 Cl + 2Na

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76
 g) Heptene + Water

PHYSICAL PROPERTIES OF AROMATIC COMPOUNDS

Aromatic compounds are benzene and those substances that are

similar to it in their chemical behavior . Aromatic hydrocarbons are
characterized by their tendency toward ionic substitution. Where the
benzene ring acts as a base, since it is an electronic source.

CHEMICAL PROPERTIES OF AROMATIC COMPOUNDS

1.- Nitration.

ArH + HNO 3 → ArNO 2 +H 2 O (In the presence of H 2 SO 4 )

2.- Sulfonation.

ArH + H 2 SO 4 → ArHSO 3 + H 2 O (In the presence of SO 3 )

3 .- Halogenation.

ArH + Cl 2 → ArCl+ HCl (In the presence of Fe)

ArH + Br 2 → ArBr + HBr (In the presence of Fe)

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77
 4 .- Rental of Friedel – Crafts.

ArH + RCl → ArR + HCl (In the presence of AlCl 3 )

5 .-Friedel acylation – Crafts.

ArH + RCOCl → ArCOR + HCl (In the presence of AlCl 3 )

USES OF AROMATIC COMPOUNDS

As synthetic sweeteners, such as Saccharin. In medicine as tranquilizers,

Diazepam (Valium) is an example.

PHYSICAL PROPERTIES OF ALCOHOLS

Alcohols contain the hydroxyl functional group (-OH) which is very polar
and because it has a hydrogen bonded to oxygen, which is a very
electronegative element, it allows the formation of hydrogen bonds.
Their boiling point increases with the amount of carbon and decreases
with the branches, but higher than hydrocarbons with a similar amount
of carbon.
Lower alcohols ( up to five carbons for primary alcohols ) are soluble in
water, forming a hydrogen bond with it.
Alcohols behave as weak acids or bases depending on the medium in
which they are found.

As a base it acts as follows:

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78
 + X-
R – OH + H – X → R – O H 2 +

When the medium is aqueous they behave like acids:

- +
R – OH + H 2 O → RO + H3O

SYNTHESIS OR OBTAINING ALCOHOLS

There are two main ways to obtain simple alcohols:

the
hydration of alkenes , obtained by cracking petroleum , and the
fermentation of carbohydrates .

Hydration of Alkenes

Alkenes can be easily converted to alcohols by the addition of water or

sulfuric acid,

CH 3 -CH=CH 2 +H 2 SO 4 → CH -CH-CH
3 3 +H 2 O
→ CH 3 -CH-CH 3 + H 2 SO 4
│ │
BEAR 3 H OH

Carbohydrate Fermentation

The fermentation of sugars with yeast, the oldest process used by man,
remains of enormous importance in the preparation of ethyl alcohol (
ethanol ) and certain other alcohols.

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79
 Other methods of obtaining alcohols

a) Oxymercuration - demercuration.

R 2 C=CR 2 + Hg(OAC) 2 →R 2 COH-CHR 2 (Marconikov

Guidance)

b) Hydroboration - oxidation.

R 2 C=CR 2 + (BH 3 ) 2 → R 2 CH-COHR 2 + B(OH) 3

The orientation of this reaction is anti-Marconikov

c) Grignard synthesis.

It is the most important method in the preparation of alcohols.

\│
+2 X-
C = O + RMgX → - C –OMgX → R - C – OH + Mg +
⁄ │
R

RMgX = Grignard reagent

d) Hydrolysis of alkyl halides.

R – X + OH - (OH 2 O) → R – OH + X - (or HX)

NOTE: Cholesterol, is the substance that is deposited on the walls of the

arteries and is the main constituent of gallstones, it is an alcohol of the

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80
type known as sterol .

REACTION OF ALCOHOLS

a) Reaction with hydrogen halide.

R – OH + HX → R – X + H 2 O

The reactivity of HX is HI >HBr>HCl

b) Dehydration.

RCH- COHR → RC=CR + H 2 O (presence of H 2 SO 4 or H 3

PO 4 )

Alcohol reactivity: 3º > 2º > 1º

c) Formation of Esters.

R – OH + H 2 SO 4 → R – OSO 2 H+H 2 O

R – OH + HNO 3 → R – ONO 2 + H 2 O

d) Oxidation.

R – OH + Oxidant → Aldehyde or Ketone + Oxidant + H 2 O

Primary alcohols produce aldehydes, secondary alcohols produce

ketones, and tertiary alcohols do not oxidize easily.

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81
 Oxidizers:
Potassium permanganate in water (KMnO 4 + H 2 O)
Mixture of permanganate and sulfuric acid (KMnO 4 + H 2 SO 4 )
Potassium dichromate in water (K 2 Cr 2 O 4 + H 2 O)
Chromosulfuric mixture (K 2 Cr 2 O 4 + H 2 SO 4 )
Cupric oxide (CuO)

USES OF ALCOHOLS

Methanol is the simplest alcohol, it is used in the manufacture of resins,

plastics, solvents, as a fuel additive, anticorrosive, preparation of acetic
acid, cleaners, antifreeze and recently in the manufacture of batteries.
In October 2003, Toshiba announced the creation of the smallest
rechargeable portable battery on the market, made from methanol. It is
also usually used illegally in the production of adulterated alcoholic
beverages, which are very dangerous, since methanol is toxic to
humans. In low doses it can cause blindness and in high doses death.
Ethanol or ethyl alcohol is used in the manufacture of alcoholic
beverages, as a base substance in the production of acetaldehyde or
ethanal, acetic acid, ethyl chloride and butadiene. Mixed with methanol
it is used as fuel. It is also used as antifreeze, in the manufacture of
perfumes, celluloid lacquers and explosives.

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 L —2 , — p
Design of a chemical breathalyzer
A breathalyzer is a device designed to determine an individual's alcohol
intake. It is based on the oxidation reaction of alcohols using an acid solution
of potassium dichromate. During the reaction, color changes ranging from
brown to green will be observed, as a result of the change in the oxidation
states of chromium.
With the help of your teacher, design a breathalyzer with the materials
mentioned below: a U-shaped glass tube, a straight glass tube, two glass
tubes bent at right angles, a plastic bag and wick. Also, ethanol, potassium
dichromate and sulfuric acid.

Taken from the World of Chemistry

Always avoid excess

Ethanol is a substance that is quickly absorbed in the human body because it is soluble in water in any proportion. Within
minutes of being ingested, it passes into the bloodstream and reaches all parts of our body, including the brain. It is a drug
classified as an antidepressant, as it suppresses feelings of
fear and tension. Abuse in consumption causes serious
diseases such as liver cirrhosis and degeneration of the
central nervous system. Ethanol can be purchased as
lower-cost “denatured alcohol,” which is a mixture of
ethanol and methanol. The cost of methanol is lower than
that of pure ethanol, which is why unscrupulous traders
often use it illegally in the bottling of alcoholic beverages.
In March 2003, in the United Kingdom, an alert was issued
regarding the contamination of an alcoholic beverage by
methanol, which was immediately withdrawn from the
market after severe cases of poisoning were detected.

Taken from the World of

Chemistry
PHYSICAL PROPERTIES OF
ETHERS

The presence of the electronegative oxygen atom causes the ethers to

have a slight polarity, which causes their boiling points to be a little

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83
higher than similar alkanes. This polarization of the C – O bond is lower
than in alcohols, due to the substitution of H by an alkyl group (radical
R), which causes their boiling points to be lower than isomeric alcohols.
Its solubility in water is similar to that of alcohols, the reason is the
formation of hydrogen bonds. Ethers behave like Lewis bases.

SYNTHESIS OR OBTAINING ETHERS

a) Dehydration of alcohols.
This method only serves to obtain symmetrical ethers from primary
alcohols, which is why it is little used. It occurs catalyzed by H 2 SO 4 and
at temperatures between 130º C and 140 ºC.

R – OH + HO – R → R – O – R + H 2 O

b) Williamson synthesis.
The reaction involves the displacement of the halide ion, coming from an
alkyl halide, by the alkoxide ion, which originates from the reaction
between an alcohol and a strong base such as sodium hydride (NaH) or
silver oxide (Ag). 2O ).

R – OH + NaH or Ag O → R – O - Na + + H 2
2

alkoxide
R–O- Na ++ R –X→R–O–R'+
'
NaX
Alkoxide halide
I rent

USES OF ETHERS

They are used as solvents in chemistry laboratories, especially for organic

compounds. In the industry to obtain low temperatures when mixed with
dry ice. In some cases they are used as anesthetics, but it is not highly
recommended because it produces side effects on the respiratory system
and kidneys.

PHYSICAL PROPERTIES OF ALDEHYDES AND KETONES

-C=O

The carbonyl group H polarized converts aldehydes and

Ketones are essentially polar, so they have higher boiling points than
non-polar compounds of similar molecular weight. They cannot be linked
intermolecularly by hydrogen bonds, so their boiling points are lower than

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comparable alcohols and carboxylic acids.
Lower aldehydes and ketones are soluble in water, up to those with five
carbons, probably due to the formation of hydrogen bonds with water.
Methanal is gaseous, from compounds with two carbons and up to
twelve, its physical state is liquid, the rest are in a solid state.

SYNTHESIS OR OBTAINING ALDEHYDES AND KETONES

a) Oxidation of alcohols.
When primary alcohols are oxidized, an aldehyde is obtained; if
secondary alcohols are oxidized, a ketone is obtained. The oxidizing
agent is potassium dichromate (K 2 Cr 2 O 4 ).

RCH2OH → RCHO (presence of K 2 Cr 2 O 4 )

Alcohol 1st Aldehyde

RCHOHR ' → RCOR '

(presence of K 2 Cr 2 O 4 )
2nd alcohol Ketone

There are other methods such as: Reduction of acid chlorides

(Rosenmund Reduction) and Friedel and Crafts Acylation, which will not
be studied in this course.
REACTION OF ALDEHYDES AND KETONES
a) Oxidation.
Aldehydes are easily oxidized to carboxylic acids; not so with ketones.
This reaction is what most distinguishes aldehydes from ketones. The
oxidizing agents are: Ag(NH 3 ) 2 + , KMnO 4 , K 2 Cr 2 O 4.

RCHO or ArCHO → RCOOH or ArCOOH

b) Reduction to alcohols.
Aldehydes are reduced to primary alcohols and ketones to secondary
alcohols, the reducing agent is: LiAlH 4 .
RCOR ' → RCOHR '

RCHO → RCOH

c) Reduction to hydrocarbons.

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85
Aldehydes and ketones can be reduced to hydrocarbons by the action of
(a) amalgamated zinc (ZnHg) and concentrated hydrochloric acid
(Clemmensen reduction) or (b) with hydrazine (NH 2 NH 2 ) and a strong
base, such as KOH ( Wolff-Kishner reduction).
ZnHg, HCl
11
' '
RCOR ------------ → RCH 2 R

d) Addition of Grignard reagent.

RCOR ' + R '' MgX → RCOMgXR ' + H 2 O → RCOHR '

RCHO + R ' MgX → RCHOMgX + H 2 O → RCHOH

There are other reactions of aldehydes and ketones that will not be
studied in this course.

USES OF ALDEHYDES AND KETONES

Methanal or formaldehyde: Used as an insecticide, fumigation
agent and antiseptic. Other uses are: manufacturing of synthetic resins,
disinfectant of closed spaces, in medicine for the disinfection of the
clothing of surgeons and patients.
Ethanal or acetaldehyde: Used in the manufacture of mirrors, to
prevent mold from stored fruits and as a disinfectant or antiseptic in
medicine.
Acetone or propanone: Its main use is as a solvent for organic
substances, also in the manufacture of lacquers and colors, in the
preparation of chloroform and iodoform.
PHYSICAL PROPERTIES OF CARBOXYLIC ACIDS

Their structures suggest that carboxylic acids are polar. Small aliphatic
acids up to nine carbon (nonanoic acid) are liquid, intermediate-sized
acids are oily, and larger acids are crystalline solids. The odor of the
inferior ones progresses from the strong and irritating of formic and
acetic to the openly unpleasant of butanoic, pentanoic and decanoic acid;
the superior ones have very little odor due to their low volatility.
The solubility in water is high up to the four-carbon (butanoic acid),
moderate for the pentanoic acid and very low for those greater than this.
The branches decrease the solubility in water. Most carboxylic acids are

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86
soluble in less polar solvents, such as: ether, alcohol, benzene, etc.
The boiling point increases proportionally with the molecular weight and
is higher than that of alcohols of similar molecular weight. This is because
the carboxylic acid molecules are held together not by one hydrogen
bond but by two.
SYNTHESIS OR OBTAINING CARBOXYLIC ACIDS
a) Oxidation.
The oxidation of primary alcohols, aldehydes, substituted benzenes or
some alkenes results in the production of carboxylic acids. Primary
alcohols are treated with CrO 3 or Na 2 Cr 2 O 7 in an acidic medium,
aldehydes are oxidized with CrO 3 in an acidic medium and in the
presence of silver ions. To oxidize substituted benzenes and some
alkenes, KMnO 4 or sodium dichromate in an aqueous medium is used as
an oxidant.
R – OH → RCOOH (Na 2 Cr 2 O 7 and H 2 SO 4 )

b) Carbonation of the Grignard Reagent.

+
RX + Mg → RMgX + CO 2 → RCOOMgX + H → RCOOH
c) Hydrolysis of Nitriles.
R–C≡N+H 2 O → R – COOH + NH 3

(in the presence of an acid or a base)

It can also be an aromatic. (Ar – C ≡ N)

REACTION OF CARBOXYLIC ACIDS

The reactions of carboxylic acids give rise to the families derived from
them.
a) Salt formation.
- +
RCOOH ↔ RCOO +H

CH 3 COOH + Zn ↔ (CH 3 COO) 2 Zn + H 2

b) Conversion into functional derivatives.

RCOOH → RCOOZ (Z = - Cl, - OR ' , - NH 2 )

c) Conversion into esters.

RCOOH+ R ' OH ↔ RCOOR ' + H 2 O (presence of acid)

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 d) Conversion to amide.

RCOOH + SOCl 2 → RCOOCl + NH 3 → RCOONH 2 + HCl

PHYSICAL PROPERTIES OF THE FAMILIES DERIVED FROM THE

CARBOXYLIC ACIDS

The possibility of forming hydrogen bonds and their relative strength

determines the boiling points of carboxylic acid derivatives, for similar
molecular weights.
Amides are solid at room temperature, as they have high boiling points,
which is due to the formation of very strong hydrogen bonds between the
NH 2 group and the carbonyl oxygen. In contrast, esters do not form
these bridges, which indicates that they have low boiling points.
Small molecules are soluble in water, and as the molecular weight
increases it decreases. Esters are soluble in alcohol and ether.
The low molecular weight esters are volatile and have a sweet and
pleasant odor, while the higher ones are solid, colorless and greasy in
appearance.
Halides are toxic, especially chlorine.
SYNTHESIS OR OBTAINING ESTERS
a) Esterification.
RCOOH+ R ' OH → RCOOR ' + H2O

b) Esterification from an acid anhydride. RCOOCOR ' +

+
R''OH →
RCOOR ' ' R'COOH

REACTION OF ESTERS

a) Hydrolysis.

RCOOR ' + H 2 O → RCOOH + R ' OH (presence of H 2 SO 4 )

b) Alcohollysis.

RCOOR ' + R ''

OH → RCOOR ''
+ R ' OH (presence of H 2 SO 4 )

SYNTHESIS OR OBTAINING ANHYDRIDES

Dehydration of two molecules of carboxylic acids.

RCOOH + R ' COOH → RCOOCOR '

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88
REACTION OF ANHYDRIDES

a) Hydrolysis.

RCOOCOR ' + H 2 O → RCOOH + R ' OH (presence of H 2 SO 4 )

b) Alcohollysis.

RCOOR ' +R ''

OH → RCOOR ''
+ R ' OH (presence of

H 2 SO 4 )

SYNTHESIS OR OBTAINING ACID HALIDE

RCOOH+ PCl 3 → RCOCl + H 3 PO 4

REACTION OF ACID HALIDES

a) Hydrolysis.

RCOCl + H 2 O → RCOOH + HCl

b) Alcohollysis.

RCOCl + R ' OH → RCOOR ' + HCl

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 n-ra,anuaruep-p*rnE,aa7a-TNIry-TAETpyMq-7HHIMNIMGHNFMALTGGLRGFIHTETIPMMMSN-MTMH. AN-.
!.NS-i1 MFEFAN-TTHTVLLINMGG3-: v'u. Yo."': ! ■.

The structure of acetominothene, a widely

used analgesic, contains a carbonyl function
that, when linked to a nitrogen atom, is
called an amide. In addition, it has an -OH
group linked directly to an aromatic ring and
this new function is known as phenol.

Taken from the World of

Chemistry

PHYSICAL PROPERTIES OF AMINES

Amines are polar, and primary and secondary amines can form hydrogen
bonds between themselves and with water, but weaker than that of
alcohols and therefore with a lower boiling point than analogous
oxygenated compounds. The boiling points of tertiary amines are lower
than that of primary and secondary amines of similar molecular weights.
They have an unpleasant odor, such as that of cadaverine, an amine
present in decomposed meat and which is responsible for the putrid
smell.

Cadaverine = H 2 N(CH 2 ) 5 NH 2 = 1,5-pentadiamine

SYNTHESIS OR OBTAINING AMINES

a) Alkylation of ammonia.
RCl + NH 3 → RNH 2 + HCl

b) Nitrile Reduction.

R – CN + 2H 2 → RNH 2

REACTION OF AMINES
a) Reaction with nitrous acid.
RNH 2 + HNO 2 → R-OH + N 2 T+H 2 O
b) Bromination.
RNH 2 + Br 2 → RBr + HBr

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90
 Exercises

1) Synthesize the following compound meeting the indicated

characteristics.
1) 3 – methyl – 1,2 – dichlorobutane by halogenation
alkenes.
2) 3 – methyl – 2 – chlorobutane by alkane halogenation
3) 3,3 – dimethylpentanol by alkene hydration
4) propene from alcohol dehydration
5) 2 – butanol by Grignard synthesis
6) Ethanoic acid by oxidation of alcohol.
7) Ethylmethyl ether by Williamson synthesis
8) 3-Methylbutanoic acid by oxidation of alcohol.
9) Tip for dehalogenation.
10) 4,4 – dimethylpentane by dehalogenation.

2) Formulate, complete and name the organic products of the

following chemical reactions.
1) Cyclopropane + hydrochloric acid
2) 2 – cyclopentylpentane + Baeyer's reagent
3) 3 – ethyl – 2 – pentene + hydrochloric acid (in
presence of hydrogen peroxide)
4) 2 – methylpropanal + hydrocyanic acid
5) Acid 2 – methylpropanoic acid + Magnesium
6) Ethanoic acid + isopropyl alcohol
7) 2 – methylbutane + chlorine
8) 3,4 – dimethyl – 2 – heptene + hydrochloric acid
9) 2 – methylhexanal + hydrocyanic acid
10) Propanoic acid + propyl alcohol
REFERENCES

- Bolívar Díaz Miguel A. ORGANIC CHEMISTRY II year E. M.D.

Q. Editorial School News 2000. Caracas Venezuela. 2010
- Celsi Santiago A., Iacoblicci Alberto D. CHEMISTRY

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 ELEMENTAL MOSERNA, Organic Part . Editorial Kapelusz, SA
Senillosa – Argentina. 1957.
- Polar Foundation. THE WORLD OF CHEMISTRY . Last News .
- K. Peter C. Vollhardt. ORGANIC CHEMISTRY . Editions
Omega S. TO. Barcelona. Spain. 1994
- Morrison Robert Thonton; Boyd Robert Nelson. ORGANIC
CHEMISTRY. Inter-American Educational Fund, S. TO. Third
edition. AND. OR. TO. 1973.
- Rodríguez María del Pilar. CHEMISTRY 2 Diversified cycle.
Salesian Publishing House. First edition. Caracas Venezuela.
2001.
- Requena, Liney. LET'S STUDY ORGANIC CHEMISTRY . Eneva
Editions. Caracas Venezuela. 2001
- Chemistry 2. Santillana Editorial. Caracas Venezuela. 2008.
- WWW. CHEMICAORGANICA.ORG.
- WWW. WIKIPEDIA, THE FREE ENCYCLOPEDIA.

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