GENERAL

INFORMATION
OF
ORGANIC
CHEMISTRY

Jan 10, 2016

USAMVB TIMISOARA
Facultatea de Medicin Veterinar

Chemical bonding in organic compounds

Organogenic elements (C, H, N, O, S, halogens) makes
covalent bonding, carbon atom participate in this bondings with
orbitals in hybrid state.
For carbon atom the are three
orbitals type : sp, sp2, sp3
Orbitals sp type type s
orbital and type p orbital, hybrid
orbitals obtained have 1800 angle
between them, having an
intermediary energy between
orbital s and orbital p.

Jan 10, 2016

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Orbitals type sp2

are coplanar,
with 120 angle
between them,
at hybridization
participate with
one orbital s
and
two
orbitals p.

Jan 10, 2016

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Orbitals type sp3 has

place for transition of one
electron from orbital 2s
into orbital 2p and then
hybridization of one orbital
s and three orbitals p. At
this type of hybridization
orbitals, in space, have
10928` angle as if carbon
atom nucleus would be in
the
centre
of
one
tetrahedron and hybrid
orbitals
are
oriented
through tetrahedron tops.

Jan 10, 2016

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Compui nesaturai

Compui
saturai

Covalent bonding can be done between atoms from the

same type or different atoms and can be simple, duble
or triple.
Carbon atom can participate
C

C H

C N

C N

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C O

C O

at
simple bonding only in sp3
hybridization state, forming sigma
type bonding ()

Double bonding is made between four

electrons or two doublets electronic
bonding, one sigma () and the other pi
(), participation of carbon atom is
possible only if is in hybridation state sp2.

When between two atoms, is set in common three

electrons from each part, it will result three double
electronic bonding : one sigma type () and two pi
N type () which corresponding to one triple bonding
making. Carbon atom participate at this bonding type
adopting sp hybridization.

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Carbon atoms bonding

Carbon atom property to make bonds in

carbon chain (chains of carbon atoms)
determine existing of chemical structures
at organic molecules.

Jan 10, 2016

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7C
C

C C

C C
5 4

catena liniar

6C

C8

C
3

C
2

5,7,8 - C primar
4 - C secundar
1,3,6 - C tertiar
2 -C cuaternar
C
1

catena ramificat

C C

C C

C C

C
caten ciclic

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caten ciclic cu ramificatii

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Isomers = organic compounds that have the same

molecular formula but different structural formulas.
There can be different isomeric types: catena
isomeric, function isomeric, geometric isomeric,
optic isomeric, etc.
Molecular formula : C3H6O

H H
H C

C O

C C H

H O H

H H H
aldehid propionic
Jan 10, 2016

H C

dimetilceton

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Hydrocarbons are compounds that have in structure only carbon

and hydrogen atoms.
HYDROCARBONS
HYDROCARBONS

aliphatic
aliphatic
saturate
saturate

aromatic
aromatic
nosaturate
nosaturate

mononuclear
mononuclear

alkanes
alkanes

alkenes
alkenes

cycloalkanes
cycloalkanes

alkadyenes
alkadyenes

polinuclear
polinuclear

alkynes
alkynes
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Alkanes CnH 2n+2

Hydrocarbons that contain only single
bonds between C and H atoms.

n=1
n=2
n=3
n=4
n=5
n=6
n=7
n=8
n=9
n = 10
Jan 10, 2016

CH4
C2H6
C3H8
C4H10
C5H12
C6H14
C7H16
C8H18
C9H20
C10H22

metan
etan
propan
butan
pentan
hexan
heptan
octan
nonan
decan

CH4
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3

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CH3
CH2 CH3
(CH2)2 CH3
(CH2)3 CH3
(CH2)4 CH3
(CH2)5 CH3
(CH2)6 CH3
(CH2)7 CH3
(CH2)8 CH3
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Radicals
Radicals nomenclature is made from alkane
name from which it comes, where suffix ane
is replace with:
yl if contains one less hydrogen
ylen if will remain two free valence
yn if radical is trivalent (three free valences)
CH4

CH3

CH2

CH

metan

metil

metilen

metin

Jan 10, 2016

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Isomerism
Is due to chain branching and is named chain
isomerism
CH3 CH2 CH2 CH3

CH3 CH CH3
CH3

normal butan

izobutan

For alkanes with more than four carbon atoms can be

written isomers obtain through changing places of
carbon atoms in chain.

Jan 10, 2016

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Isomers nomenclature

is established the longest linear chain;

is numbered all the carbon atoms, in such way as
lateral chain to have the position with the lowest number. In
isoalkanes with multiple-strand chain, designation of base
chain has to be done in such way that the index sum, that
indicates position of branching, has to be minimum.
is named lateral chain radicals, by indicating, at the
beginning, their position by number. Radicals are indicated by
prefix: di-, tri-, tetra-.
is adding at the end, the alkane number with stable
linear chain.
CH3
4 3
5
6
2 1
CH3 CH2 CH CH2 C CH3
CH2
CH3
Jan 10, 2016

CH3
4-etil-2,2-dimetil hexan
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Chemical properties

Substitution, dehydrogenation, oxidation reactions

C-H bond rupture;
Thermic decomposition, isomerization, burning
reactions C-C bond rupture.

1. Substitution reaction
Is the reaction where one or more hydrogen atoms are replaced with atoms or atoms
groups from reactant.

+ Cl2 , h
+ Cl2 , h
+ Cl2 , h
+ Cl2 , h
CHCl
CH
Cl
CH3Cl
3
CH4
2 2
HCl
- HCl
HCl
HCl
cloroform
clorura de
clorura de
metan
metilen
metil

Jan 10, 2016

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CCl4
tetraclorura
de carbon

2. Oxidation reaction
Under oxygen action, alkanes can suffer complete oxidation (burnings) or
incomplete oxidation (oxidation).

C2H6
etan

oxidare

CH3OH
metanol
CH3CH2OH
etanol
CH3CHO
aldehida acetic

Burnings or complete oxidation

leads to CO2 and H2O development,
being always associate with high heat
releasing Q, this makes alkanes to be
used like compustibles.

CH3COOH
acid acetic

3. Thermic decomposition
Take place at high temperatures and can be done only by dehydrogenation
reactions (C-H bond rupture) or by cracare reactions (C-C bond rupture), resulting
small saturated or non-saturated hydrocarbons molecules.

Jan 10, 2016

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Alkenes
CnH 2n
Contain in their molecules one double covalent bond between two
carbon atoms.

C2H4
C3H8
C4H10

eten
CH2 CH2
propen CH2 CH CH3
buten
CH2 CH CH2 CH3

In chain structure enter sp3 hybridized carbon atoms (they participate at simple
bonds) and sp2 hybridized carbon atoms (participate at double bonds).

Jan 10, 2016

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Click mouse to repeat

one p orbital

three sp2 orbitals

Jan 10, 2016

pi

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sigma
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Isomerism
chain isomerism - due to carbon chain branching
position isomerism - due to position of the double chain bonding
geometrical or cis-trans isomerism datorat rigiditii dublei legturi

CH3
H

C C

CH3
H

cis-2-buten

H
C C
CH3

CH3
H

trans-2-buten

Towards datum plan (plan determinate by pi - bonds) substituents can exist of the
same part of the double chain plan (cis isomer) or on the both parts of the double
chain plan (trans isomer).
Jan 10, 2016

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Chemical properties
Presence of the double bond offers high reactivity to alkene molecule.
Alkenes gives: addition reactions, oxidation reactions and polymerization reactions

a. Addition reactions

C C

+ H2

C C

A B

A B

R CH2 CH3
alcan

+ Cl2
R CH CH2
alchen

R CH CH2
Cl

+ H OSO3H

Cl

derivat dihalogenat

R CH CH3
OSO3H

+ H2O
- H2SO4

sulfat acid de alchil

+ HCl

R CH CH3
Cl
derivat monohalogenat

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R CH CH3
OH

Regula lui
Markovnikov

alcool

At addition of haloids acids at

non-symmetrical
alkenes,
halogen atoms are fixed at
carbon
atom
poorest
in
hydrogen, combined at double
chain.

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a. Oxidation reactions
soft - bond from double
bond is detach (oxidation
with
potassium
permanganate in liquid
medium or less basic);

KMnO4
Na2CO3
R CH CH2
alchen

+ [O]
KMnO4
H2SO4

energetic - double bond

is broking, with chain
reducing ( oxidation with
potassium permanganate in
liquid medium of sulfuric
acid).

Jan 10, 2016

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R CH CH2
OH OH
1,2-diol

R COOH + CO2
acid

Alkynes
CnH2n-2
Containing in their molecule a triple covalent bond between two carbon
atoms.
etin
HC CH

Triple bond is made from on sigma bond

and two pi bonds (), which induce to
molecules a non saturate character
more accentuate than double bond.

propin

CH C

CH3

CH C

CH2 CH3 butin

Presence of triple bond in alkynes determine existence of position

isomers, different by the place the take in the triple bond.

Jan 10, 2016

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Chemical properties
1.Addition reactions
Addition of hydrogen and halogens

Acids addition
CH CH
acetilena

CH2

+ HCl

Cl
clorura de vinil

HgCl2 / 170C

CH2

+ CH3COOH
Zn(CH3COO)2 / 200C
+ HCN
CuCl2 + NH4Cl / 80C

OH

CH

Water addition

Jan 10, 2016

+
CH
acetilena

CH

CH

O CO CH3
acetat de vinil
CH2

CH

CN
acrilonitril
H2SO4
HgSO4

CH3

CH2

C O
H
acetaldehida

CH OH
alcool vinilic

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2.Oxidation reactions
With weak oxidant agents (KMnO4) is forming oxalic acid.
CH
CH

+ 4 [O]

KMnO4

COOH
COOH

At energetic oxidation of acetylene results high heat quantity

C2H2 + O 2

CO 2 + H2O + Q

3.Substitution reactions
CH

+ Na

CH
acetilena

150C

CH

200C

+ Na
-1/2 H2
-1/2 H2 C -Na+
acetilura
monosodica

Jan 10, 2016

: Na
C: Na
acetilura
C

disodica

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Due to fact the acetylene

molecule is polar weak,
having a weak acid character,
will lose easily a proton in
reactions with metals or with
substances that have basic
character.

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