curs 3 engleza

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Aromatic hydrocarbons - substances made from carbon and hydrogen, in their structure being one ore more benzene nucleus.

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Curs 3 Engleza

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Page 1: Curs 3 Engleza

Aromatic hydrocarbons

- substances made from carbon and hydrogen, in their structure being one ore more benzene nucleus.

Page 2: Curs 3 Engleza
Page 3: Curs 3 Engleza

Kekule structure Structure based

on quantum mechanic theory

Confirm that:- ration between number of C and H

atoms is 1:1, benzene having ring with 6 atoms

- in the ring exist 3 double bonds - those 6 hydrogen atoms are equivalent

between them- adition has place with energetic

reactions Can’t explain that: - 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.

Explain:- equivalence of the 6 carbon

atoms - delocalization of electrons by

forming an molecular orbital- existence of the aromatic

character that has preference for substitutions reactions instead of addition and oxidation reactions.

Page 4: Curs 3 Engleza

CH3 CH3

CH3

CH CH3H3C

benzen toluen orto-xilen izopropilbenzen

difenil naftalina antracen

Mononucleare

Polinucleare

Page 5: Curs 3 Engleza

Chemical properties

Reactions at nucleus Substitutions reactions Additions reactions Oxidation reactions

Reactions at side chain Substitutions reactions Additions reactions Oxidation reactions

Page 6: Curs 3 Engleza

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

Page 7: Curs 3 Engleza

Compounds with simple functions

Compusi cu grupare functionala monovalenta

compusi halogenati R-X

compusi hidroxilici

alcooli R -OH

fenoli Ar - OH

amine R - NH 2

Compusi organici cu functiuni simple

Compusi cu grupare functionala divalenta compusi carbonilici

aldehide

cetone

R CO

H

R C R

O

Compusi cu grupare functionala trivalenta

acizi carboxilici R CO

OH

Page 8: Curs 3 Engleza

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).

CH3 C CH3

Cl

Cl

CH3 CH CH2

Cl Cl

2,2 - diclorpropan 1,2-diclorpropancompus dihalogenat compus dihalogenat geminal vicinal

Page 9: Curs 3 Engleza

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

Page 10: Curs 3 Engleza
Page 11: Curs 3 Engleza

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).

CH3 OH CH3 CH2 OH CH3 CH2 CH2 OHmetanol etanol propanol

Alcohols

Page 12: Curs 3 Engleza

Classification

after radical nature

after number of functional groups

after carbon atom nature

Page 13: Curs 3 Engleza

Chemical properties

Reaction with alkaline metals

Esterification reaction

Elimination of intra and intermolecular water

oxidation reactions

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

Page 14: Curs 3 Engleza

monohidroxilici

polihidroxilici

Phenols

OH

OH

CH3

OH

CH3

fenol orto-crezol meta-crezol para-crezol

CH3

OH

OH

OH

OH

OH

hidrochinona rezorcina

Page 15: Curs 3 Engleza

Chemical properties

Reactions determine by hydroxyl group acidity esterification reaction

Reactions determine by aromatic nucleus

Hydrogenation

Page 16: Curs 3 Engleza

Amines

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

CH3 NH2 C2H5 NH CH3 C6H5 NCH3

CH3

metilamina etil-metilamina fenil-dimetilamina

Page 17: Curs 3 Engleza

Clasificare

dupa naturaradicalului

alifatice

aromatice

mixte

dupa gradul de substituire

primare

secundare

tertiare

saruri cuaternarede amoniu

R NH

H

R NR`

H

R NR`

R``

R N

R`

R```

R``

+

dupa numarul gruparilorfunctionale

monoamine

diamine

poliamine

C6H5 NH2 fenilamina

CH2 CH2

NH2 NH2

etilendiamina

R NH2

Ar NH2

R NH Ar

Page 18: Curs 3 Engleza

Chemical properties

Amines basicity

Alkylation reaction

Acylation reaction

Page 19: Curs 3 Engleza

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:

carbonyl group

C O

Page 20: Curs 3 Engleza

C O

H

R

C O

R

R

aldehida cetona

C O

H

CH3

C O

H

CH2CH3

C O

H

Hmetanal etanal propanal

(aldehidă formică) (aldehidă acetică) (aldehidă propionică)

C OCH2CH3

CH3

C OCH3

CH3

propanonă butanonă (dimetilcetonă) (etil-metil cetonă)

Page 21: Curs 3 Engleza

Chemical properties Aldehyds and cetones

common reactions

Adition reactions (H2, HCl, HCN)

Condensation reactions (amines, phenols, carbonyl compounds between them)

Aldehyds common reactions

Oxidation reactions

(O2, [O],

Ag(NH3)2OH)

Page 22: Curs 3 Engleza

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

R C O

OHH C O

OH

C O

OH

CH3 C O

OH

CH2CH3

acid metan oic acid etanoic acid propanoicacid formic acid acetic acid propionic

Page 23: Curs 3 Engleza

Clasificareaacizilor

dupa naturaradicalului

saturati

nesaturati

aromatici

dupa numarulde grupari-COOH

monocarboxilici

policarboxilici

Page 24: Curs 3 Engleza

Chemical properties

Ionization in watery solution

esterification reaction

reaction with ammonia

Page 25: Curs 3 Engleza

Functional compounds of organic acids

R CO

O R`

R CO

O

OCR

R CO

Cl

R CO

NH2

R C N

ester anhidrida clorura acida

amida nitril