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Curs 3 Engleza

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Aromatic hydrocarbons

- substances made from


carbon and hydrogen, in their
structure being one ore more
benzene nucleus.

Kekule structure

Structure based
on quantum
mechanic theory

Confirm that:
Explain:
- ration between number of C and H - equivalence of the 6 carbon
atoms is 1:1, benzene having ring with 6
atoms
atoms
- delocalization of electrons by
- in the ring exist 3 double bonds
forming an molecular orbital
- those 6 hydrogen atoms are equivalent - existence
of the aromatic
between them
character that has preference
- adition
has place with energetic
for substitutions reactions
reactions
instead of addition and
Cant explain that:
oxidation reactions.
- benzene
gives easy substitution
reactions
- is very stable at oxidation
- is not polymerizing
- exist only 3 compounds substitute: orto,
meta, para
- all bonds are equal.

Mononucleare
CH3

H3C CH CH3

CH3
CH3

benzen

toluen

orto-xilen

izopropilbenzen

Polinucleare

difenil

naftalina

antracen

Chemical properties

Reactions at nucleus

Substitutions reactions
Additions reactions
Oxidation reactions

Reactions at side chain

Substitutions reactions
Additions reactions
Oxidation reactions

I order substituents which orientates


substitution in ortho and para, for
example: -Cl, -Br, -OH, -NH2

II order substituents which orientates


subsequent substitution in meta, for
example: - NO2, -COOH, -CHO, -SO3H

Compounds with simple functions


compusi halogenati

Compusi cu grupare
functionala monovalenta

R-X

alcooli

R -OH

fenoli

Ar - OH

compusi hidroxilici

amine

R - NH 2

Compusi organici
cu functiuni
simple
Compusi cu grupare
functionala divalenta

aldehide R C
compusi carbonilici

H
cetone

R C
O

Compusi cu grupare
functionala trivalenta

acizi carboxilici

R C

O
OH

Halogenated compounds
Contain in their molecule a halogen atom combined through
covalence by a organic radical, and the general formula is R-X
where X represent halogen atom (fluorine, chlorine, bromine,
iodine).
Cl
CH3 C CH3
Cl
2,2 - diclorpropan
compus dihalogenat
geminal

CH3 CH CH2
Cl

Cl

1,2-diclorpropan
compus dihalogenat
vicinal

Chemical properties

Halogenated compounds are extremely reactive


due to polarization of the carbon-halogen bond
a. Hydrolyzing reactions
b. Reaction with alkaline cyanides
c. Reaction with ammonia
d. Reaction with hydro acids elimination
e. Reaction with magnesium

Hydroxyl compound
organic

substances that contain in


their molecule the hydroxyl group (OH) attached to an alkyl group (alcohol,
with general formula R-OH) or to an
aromatic one (fenols, with general formula
Ar-OH).
Alcohols

CH3 OH
metanol

CH3 CH2 OH
etanol

CH3 CH2 CH2 OH


propanol

Classification
after

radical nature

after

number of functional groups

after

carbon atom nature

Chemical properties
Are determine by the presence of hydroxyl
group in the alcohols structure

Reaction with alkaline metals

Esterification reaction

Elimination of intra and intermolecular water

oxidation reactions

Phenols

monohidroxilici
OH

CH3

CH3

CH3

OH

OH
fenol

polihidroxilici

orto-crezol
OH

meta-crezol

OH
para-crezol

OH

OH
OH
hidrochinona

rezorcina

Chemical properties

Reactions determine by hydroxyl group

acidity
esterification reaction

Reactions determine by aromatic


nucleus

Hydrogenation

Amines
contain in their structure amino functional groups,
-NH2, that confer an basic character.

CH3 NH2

C2H5 NH CH3

metilamina

etil-metilamina

C6H5 N

CH3

CH3
fenil-dimetilamina

alifatice
dupa natura
radicalului

R NH2

aromatice Ar

NH2

mixte R NH Ar

primare

Clasificare

R N

H
R`

secundare R N

dupa gradul
de substituire

tertiare

R`
R N

saruri cuaternare
de amoniu

R``
+

R`
R N

R``

R```

dupa numarul
gruparilor
functionale

monoamine C6H5 NH2 fenilamina


diamine
poliamine

CH2 CH2
NH2 NH2

etilendiamina

Chemical properties

Amines basicity

Alkylation reaction

Acylation reaction

Carbonyl compounds

contain in their structure an carbonyl


functional group, where a carbon atom in
sp2 hybridization type is double bond with
a oxygen atom:

C O
carbonyl group

R
C O

C O

H
aldehida

R
cetona

H
C O
H

H
C O

CH3

C O
CH3

metanal
etanal
(aldehid formic) (aldehid acetic)

CH2

propanal
(aldehid propionic)

CH3

CH3
C O
CH3
propanon
(dimetilceton)

C O
CH3

CH2
butanon
(etil-metil ceton)

Chemical properties

Aldehyds and cetones


common reactions
reactions (H2,
HCl, HCN)
Condensation reactions
(amines, phenols,
carbonyl compounds
between them)

Aldehyds common
reactions

Adition

Oxidation

reactions
(O2, [O],
Ag(NH3)2OH)

Carboxyl compounds
Have in their structure a carboxyl group
attached to a hydrocarbon radical, and the
general formula is:

R C O
OH
H C O
OH
acid metan oic
acid formic

CH3

C O
OH

acid etanoic
acid acetic

CH3

CH2

C O
OH

acid propanoic
acid propionic

saturati
dupa natura
radicalului

nesaturati
aromatici

Clasificarea
acizilor
dupa numarul
de grupari
-COOH

monocarboxilici

policarboxilici

Chemical properties

Ionization in watery solution

esterification

reaction

reaction with ammonia

Functional compounds of
organic acids
R C

R C

O
O

O
O

R C

R C

R`

O
anhidrida

ester

R C
amida

O
NH2

O
Cl

clorura acida

R C N
nitril

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