![Page 1: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/1.jpg)
Funções e nomenclatura
• Generalidades
• Nomenclatura
http://www.chem.uiuc.edu/GenChemReferences/nomenclature_rules.html
![Page 2: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/2.jpg)
Funções orgânicas• Hidrocarbonetos
• Saturados: CnH2n+2
• Insaturados: CnH2n CnH2n-2
• Lineares ou Cíclicos
• Haletos de alquila: R-X
• Álcoois: R-OH
• Éteres: R1-O-R2
• Aminas: R-NH2 R1-NH-R2 R1-N(R3)-R2
• Aromáticos: Ph-R
• Fenóis: Ph-OH
![Page 3: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/3.jpg)
Grupo funcional Prefixo Sufíxo
ácidos carboxílicos nenhum Ácido -óico
aldeídos nenhum -al
cetonas nenhum -ona
álcoois hidróxi- -ol
aminas amino- -amina
éteres alcóxi- -éter
fluoreto fluoro- nenhum
cloreto cloro- nenhum
brometo bromo- nenhum
iodeto iodo- nenhum
![Page 4: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/4.jpg)
![Page 5: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/5.jpg)
![Page 6: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/6.jpg)
Haletos de alquila
![Page 7: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/7.jpg)
Chapter 6
A. Nomenclatura
1. IUPAC (International Union of Pure and Applied Chemistry)Acrescente: fluoro-cloro-bromo-iodo-
Ao nome do alcano
exemplos:
CH3 CH
CH3
CH
Cl
CH2CH3
2-methyl-3-chlorohexane
I
Br
trans-1-bromo-3-iodocyclobutane2-metil-3-cloro-hexano
trans-1-bromo-3-iodociclobutano
![Page 8: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/8.jpg)
Nomenclatura IUPAC
• Name as haloalkane.
• Choose the longest carbon chain, even if the halogen is not bonded to any of those C’s.
• Use lowest possible numbers for position.
CH3 CH CH2CH3
Cl CH3(CH2)2CH(CH2)2CH3
CH2CH2Br
2-chlorobutane 4-(2-bromoethyl)heptane
![Page 9: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/9.jpg)
9
2. Nomes usuais
CH3Cl
CH Cl
CH3
CH3
CH3CH2Cl
CH2Cl2
CHCl3
CCl4
methyl chloride
ethyl chloride
i-propyl chloride
methylene chloride
chloroform
carbon tetrachloride
3. Nomes especiais
C
X
X
C C
X X
geminal dihalide
vicinal dihalide
Cloreto de metila
Cloreto de etila
Cloreto de iso-propila
Cloreto de metileno
Clorofórmio
Tetracloreto de carbono
![Page 10: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/10.jpg)
Usos dos haletos de alquila
• Solventes – desengraxantes e líquido para lavagem a seco
• Reagentes para síntese de outros compostos
• Anestésicos: Halotano é CF3CHClBr– CHCl3 (usado antigamente, é tóxico e carcinogênico)
• Freons, chlorofluorocarbons or CFC’s– Freon 12, CF2Cl2, now replaced with Freon 22, CF2CHCl, not
as harmful to ozone layer.
• Praguicidas - DDT banned in U.S. (1972) and Sweden (1970).
=>
![Page 11: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/11.jpg)
B. Industrial usesa. solvents: CH2Cl2, CHCl3, CCl4b. refridgerents:
CF2Cl2 - Freon-12 (eats O3)HCF2Cl - Freon-22 (destroyed at
lower altitudes)c. pesticides: DDT •introduced 1939
•banned 1972 (Rachel Carson)
Cl C
Cl
Cl
CH
Cl
Cl
Dichlorodiphenyltrichloroethane
DDT
![Page 12: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/12.jpg)
Chapter 6 12
chlordane -termites•banned 1995
ClCl
Cl
Cl
H
H
H H
Cl
Cl
Cl
Cl
capacitors, etc.PCB (polychlo-rinated biphenyl)•banned 1985
ClCl
Cl
Cl Cl Cl Cl
ClCl
Cl
![Page 13: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/13.jpg)
Chapter 6 13
d. AnestheticsCHCl3 - chloroform carcinogenicCH3CH2Cl - ethyl chloride topical useCF3CHBr-Cl - halothane - general
e. polymers
H
H
Cl
H
F
F
F
F
* C
H
H
C
Cl
H
C
H
H
C
Cl
H
*
* C
F
F
C
F
F
C
F
F
C
F
F
*
polyvinyl chloride(PVC)
teflon
![Page 14: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/14.jpg)
Classes de Haletos• Alkyl: Halogen, X, is directly
bonded to sp3 carbon.
• Also characterized as 1o, 2o, 3o
• Vinyl: X is bonded to sp2 carbon of alkene.
• Aryl: X is bonded to sp2 carbon on benzene ring. Examples:
C
H
H
H
C
H
H
Br
alkyl halide
C C
H
H
H
Cl
vinyl halide
I
aryl halide
=>
![Page 15: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/15.jpg)
Di-haletos
• Di-haleto geminal : two halogen atoms are bonded to the same carbon
• Di-haleto vicinal: two halogen atoms are bonded to adjacent carbons.
C
H
H
H
C
H
Br
Br
geminal dihalide
C
H
H
Br
C
H
H
Br
vicinal dihalide
=>
![Page 16: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/16.jpg)
Systematic Common Names
• Name as alkyl halide.
• Useful only for small alkyl groups.
• Name these:
CH3 CH CH2CH3
Cl
(CH3)3CBr
CH3 CH
CH3
CH2F =>
![Page 17: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/17.jpg)
“Trivial” Names
• CH2X2 called methylene halide.
• CHX3 is a haloform.
• CX4 is carbon tetrahalide.
• Examples: – CH2Cl2 is methylene chloride
– CHCl3 is chloroform
– CCl4 is carbon tetrachloride.
=>
![Page 18: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/18.jpg)
• Substâncias comuns
O
O O
O
O
H3C OH C2H5 OH
Metanol Etanol
Éter
Éter etílico
Éter dietílico
Oxirano
THF
Tetra-hidrofurano
1,4-Dioxano
![Page 19: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/19.jpg)
Nomenclatura de éteres
• Os grupos ligados ao oxigênio são listados em ordem alfabética
– Allyl ethyl ether
– Éter alil etílico
• Grupos:
– RO: groupo alcóxi
O
OMe
5-Methoxy-hept-1-ene
5-metóxi-hept-1-eno
![Page 20: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/20.jpg)
Nomenclature of Ethers, Epoxides, and Sulfides
![Page 21: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/21.jpg)
name as alkoxy derivatives of alkanes
CH3OCH2 CH3
methoxyethane
CH3CH2OCH2 CH3
ethoxyethane
CH3CH2OCH2CH2CH2Cl
1-chloro-3-ethoxypropane
Substitutive IUPAC Names of Ethers
![Page 22: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/22.jpg)
name the groups attached to oxygen in alphabetical order as separate words; "ether" is the
last word
CH3OCH2 CH3
ethyl methyl ether
CH3CH2OCH2 CH3
diethyl ether
CH3CH2OCH2CH2CH2Cl
3-chloropropyl ethyl ether
Functional Class IUPAC Names of Ethers
![Page 23: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/23.jpg)
16-5
name as alkylthio derivatives of alkanes
CH3SCH2 CH3
methylthioethane
CH3CH2SCH2 CH3
ethylthioethane
(methylthio)cyclopentane
Substitutive IUPAC Names of Sulfides
SCH3
![Page 24: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/24.jpg)
cyclopentyl methyl sulfide
analogous to ethers, but replace “ether” as lastword in the name by “sulfide.”
CH3SCH2 CH3
ethyl methyl sulfide
CH3CH2SCH2 CH3
diethyl sulfide
Functional Class IUPAC Names of Sulfides
SCH3
![Page 25: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/25.jpg)
Oxirane
(Ethylene oxide)
Oxetane Oxolane
(tetrahydrofuran)
Oxane
(tetrahydropyran)
1,4-Dioxane
Names of Cyclic Ethers
O O O
O
O
O
![Page 26: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/26.jpg)
Moléculas contendo a função éter
Estricnina(produto natural)
Propanolol(fármaco)
Poliéter (polímero)
Generalidades
![Page 27: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/27.jpg)
Nomenclatura de éteres
1,2-dimetoxietano
Nomenclatura IUPAC
CH3CHCH2CH2CH3
OCH3
1-etóxi-4-metilbenzeno
O
O
O
Oxaciclopentano (nomenclatura de substituição)
1,4-dioxaciclo-hexano (nomenclatura de substituição)
CH3CH2O CH3
2-metóxipentano
CH3OCH2CH2OCH3
![Page 28: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/28.jpg)
éter etil metílico
Nomenclatura usual
CH3CH2OCH3
O
O
O
CH3CH2OCH2CH3éter dietílico
tetra-hidrofurano
1,4-dioxano
óxido de etilenoO
![Page 29: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/29.jpg)
McMurry Organic Chemistry 6th edition Ch 15 (c) 2003
29
Aromatic Compounds
• Aromatic was used to described some fragrant compounds in early 19th century – Not correct: later they are grouped by chemical behavior
(unsaturated compounds that undergo substitution rather than addition)
• Current: distinguished from aliphatic compounds by electronic configuration
![Page 30: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/30.jpg)
McMurry Organic Chemistry 6th edition Ch 15 (c) 2003
30
Sources of Aromatic Hydrocarbons
• From high temperature distillation of coal tar
• Heating petroleum at high temperature and pressure over a catalyst
![Page 31: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/31.jpg)
Naming Aromatic Compounds
➢Vários nomes usuais (tolueno = metilbenzeno; anilina = aminobenzeno)
➢Benzenos monossubstituidos: nomes sistemáticos como hidrocarbonetos
derivados do benzeno
✓C6H5Br = bromobenzeno
✓C6H5NO2 = nitrobenzeno
✓C6H5CH2CH2CH3 = n-propilbenzeno
![Page 32: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/32.jpg)
McMurry Organic Chemistry 6th edition Ch 15 (c) 2003
32
The Phenyl Group
• When a benzene ring is a substituent, the term phenyl is used (for C6H5 )
– You may also see “Ph” or “f” in place of “C6H5”
• “Benzyl” refers to “C6H5CH2”
![Page 33: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/33.jpg)
McMurry Organic Chemistry 6th edition Ch 15 (c) 2003
33
Disubstituted Benzenes
• Relative positions on a benzene ring
– ortho- (o) on adjacent carbons (1,2)
– meta- (m) separated by one carbon (1,3)
– para- (p) separated by two carbons (1,4)
• Describes reaction patterns (“occurs at the para position”)
![Page 34: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/34.jpg)
McMurry Organic Chemistry 6th edition Ch 15 (c) 2003
34
![Page 35: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/35.jpg)
McMurry Organic Chemistry 6th edition Ch 15 (c) 2003
35
Naming Benzenes With More Than Two Substituents
• Choose numbers to get lowest possible values
• List substituents alphabetically with hyphenated numbers
• Common names, such as “toluene” can serve as root name (as in TNT)
![Page 36: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/36.jpg)
McMurry Organic Chemistry 6th edition Ch 15 (c) 2003
36
![Page 37: Funções e nomenclatura - Moodle USP: e-Disciplinas](https://reader030.vdocument.in/reader030/viewer/2022012622/61a2549fdf48c91bf76e8050/html5/thumbnails/37.jpg)
Michael Faraday (1791-1867)
•Mais conhecido por suas descobertas sobre fenômenoselétricos. Contudo, iniciou sua carreira com estudos naárea da química.
• Isolou o benzeno do resíduo oleoso encontrado na postesde iluminação a gás das ruas de Londres e determinou quea razão C:H era de 1:1.
•O nome do grupamento fenila, usado quando uma unidade de benzeno encontra-se como um substituinte, deriva de sua origem, pois a palavra grega pheno significa“Eu tenho a luz”.
•O benzeno foi sintetizado, em 1834, por Eilhard Mitscherlich, o qual determinousua fórmula molecular como C6H6.
•Outros compostos com uma baixa razão C:H apresentavam um aroma agradável,desta maneira foram classificados como aromáticos.