kimia organik biologi 1
TRANSCRIPT
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2012FKIP UNIB
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MetanaMetanaMetanaMetana
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KekuleKekule
C2H6O
Cair Cair GasGas
Agust Kekulé melalui menerangkan fakta tersebut Agust Kekulé melalui menerangkan fakta tersebut dengan menggunakan suatu model atom. Model dengan menggunakan suatu model atom. Model atom untuk penyusun diusulkan sebagai berikut:atom untuk penyusun diusulkan sebagai berikut:
Keterangan : Garis dalam hal ini disebut garis valensi
Atom Model atom
H
O
C
Hidrogen
Oksigen
Karbon
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IsomerIsomer
CH3 O CH3CH3 C
H2
OH
H
H
H
O H
H
H
H
H
H
O H
H
H
C C C C
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KekuléKekulé
4 H + C C H
H
H
H
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Teori ini mengembangkan konsep yang Teori ini mengembangkan konsep yang dikemukakan oleh Bhor. Bhor berpendapat bahwa dikemukakan oleh Bhor. Bhor berpendapat bahwa atom terdiri dari inti atom dan elektron, elektron atom terdiri dari inti atom dan elektron, elektron mengelilingi inti sesuai dengan kulitnya. mengelilingi inti sesuai dengan kulitnya.
+
Atom C dengan no atom 6
kulit 1 = 2 e
kulit 2 = 4 e (belum penuh)
+
Atom Ne dengan no atom 10
kulit 1 = 2 e
kulit 2 = 8 e (penuh)
LewisLewis
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Luwis mengusulkan konsep yang disebut bulir. 6 C, 2 elektron Luwis mengusulkan konsep yang disebut bulir. 6 C, 2 elektron di kulit K dan 4 elektron di kulit L, C dinotasikan oleh Lewis di kulit K dan 4 elektron di kulit L, C dinotasikan oleh Lewis mempunyai 4 titik. mempunyai 4 titik.
C
°°°
°
Menurut Kekulé C mempunyai garis valensi 4 buah Menurut Kekulé C mempunyai garis valensi 4 buah dan menurut Bhor atom karbon mempunyai dan menurut Bhor atom karbon mempunyai elektron valensi 4 buahelektron valensi 4 buah
Konsep BulirKonsep Bulir
+ 4 H °C C
H
H
HH
°°
°
°°°
°°°°
°°
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memanfaatkan persamaan gelombang Erwin memanfaatkan persamaan gelombang Erwin Schrodinger. Elektron mempunyai sifat dualistik yaitu Schrodinger. Elektron mempunyai sifat dualistik yaitu sebagai partikel dan sebagai gelombang. sebagai partikel dan sebagai gelombang.
2_
82
m
= Ek
H
X
_= ( E E p )( ) ( )
Penyelesaian dari persamaan di atas akan diperoleh harga-harga E danPenyelesaian dari persamaan di atas akan diperoleh harga-harga E dan ,
daridari akan diperolehakan diperoleh
adalah orbital. Orbital didifinisikan sebagai daerah disekitar inti yang adalah orbital. Orbital didifinisikan sebagai daerah disekitar inti yang keboleh jadiannya menemukankeboleh jadiannya menemukan elektron paling besarelektron paling besar.
2
2
Linus PaulingLinus Pauling
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Harga E bergantung pada harga-harga n dan l, Harga E bergantung pada harga-harga n dan l,
n adalah bilangan kuantum utama, n = 1, 2, 3, ……. dst, n adalah bilangan kuantum utama, n = 1, 2, 3, ……. dst,
l adalah bilangan kuantum azimut l = 0, 1, 2, 3, …… (n-1)l adalah bilangan kuantum azimut l = 0, 1, 2, 3, …… (n-1)
Harga-harga E dan 2
Untuk n = 1, maka l = 0. Untuk n = 1, maka l = 0. Jadi untuk n = 1 diperoleh 1 tingkat energi dengan harga yaitu Jadi untuk n = 1 diperoleh 1 tingkat energi dengan harga yaitu n = 1 dan l = 0 .n = 1 dan l = 0 .
Untuk n = 2, maka l = 0 dan l = 1. Untuk n = 2, maka l = 0 dan l = 1. Jadi untuk n = 2 diperoleh 2 tingkat energi dengan harga yaituJadi untuk n = 2 diperoleh 2 tingkat energi dengan harga yaitu n = 2 dan l = 0, serta n = 2 dan l = 1. n = 2 dan l = 0, serta n = 2 dan l = 1.
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E
n = 1
n = 2
n = 3
Bentuk diagram energinya sbb :Bentuk diagram energinya sbb :
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Harga bergantung pada n, l dan m,
n bilangan kuantum utama n = 1, 2, 3, ……. dst,
l bilangan kuantum azimut l = 0, 1, 2, 3, …… (n-1)
m bilangan kuantum magnetik m = -l, 0, + l
Untuk n = 1 maka l = 0 dan m = 0
Jadi untuk n =1 akan terdapat satu orbital dengan harga l = 0 dan m = 0 yang orbitalnya disebut orbital 1s.
2
x
y
z
orbital 1 s
OrbitalOrbital
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Untuk n = 2, diperoleh dua harga l yaitu l = 0 dan l = 1. Jadi :
n = 2, harga l = 0 dan m = 0 terdapat satu orbital adalah orbital 2s.
n = 2 harga l = 1 dan harga m = -1, m = 0 dan m = +1.
terdapat tiga orbital adalah orbital 2p.
Untuk :
n = 2, l = 1, dan m = -1 orbitalnya 2px,
n = 2, l = 1, dan m = 0 orbitalnya 2py
n = 2, l = 1, dan m = +1 orbitalnya 2pz
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x
y
z
orbital 2 px
x
y
z
orbital 2 pzorbital 2 py
x
y
z
Gambar masing-masing orbital 2 s dn 2p adalah sbb :
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Pengisian OrbitalPengisian Orbital
E
n = 1
n = 2
1s
2s
2p
1.1. Aufbau Aufbau : pengisian é dalam orbital ikatan dimulai dari : pengisian é dalam orbital ikatan dimulai dari orbital yang mepunyai energi terendah kemudian dilanjutkan orbital yang mepunyai energi terendah kemudian dilanjutkan pada orbital yang mempunyai energi lebih tinggi.pada orbital yang mempunyai energi lebih tinggi.
2. 2. Hund Hund : pengisian é berpasangan dalam orbital ikatan tidak : pengisian é berpasangan dalam orbital ikatan tidak akan terjadi sebelum orbital yang mempunyai E sama terisi 1 é.akan terjadi sebelum orbital yang mempunyai E sama terisi 1 é.
3. 3. PauliPauli : pengisiaan é dalam orbital ikatan hanya bisa terjadi : pengisiaan é dalam orbital ikatan hanya bisa terjadi bila mempunyai spin yang berlawanan.bila mempunyai spin yang berlawanan.
Ada 3 aturan
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Orbital Atom COrbital Atom C
E
n = 1
n = 2
1s
2s
2p
y
x
z
orbital 2s, 2 px, 2py, 2pz suatu atom C
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CH4 : atom C membentuk 4 ikatan kovalen dengan 4 CH4 : atom C membentuk 4 ikatan kovalen dengan 4 atom H, keempat ikatan kovalen, panjang ikatan (C-atom H, keempat ikatan kovalen, panjang ikatan (C-H =1,09 A°) dan energi disosiasi sama (104 H =1,09 A°) dan energi disosiasi sama (104 kkal/mol). kkal/mol).
grand state
E
2s
2p
exaited state: 1 é dipromosikan ke orbital kosong
E
2s
2p
E
1 orbital 2s dan 3 orbital 2p bergabung membentuk hibridisasi sp3
2s 2p
Hibridisasi sp3Hibridisasi sp3
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bentuk orbital atom H (orbital 1 s)
109,5 °
bentuk orbital atom C sp3
109,5 °109,5 °
C H
H
H
H
(sp3 - 1s)
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grand state
E
2s
2p
exaited state: 1 é dipromosikan ke orbital kosong
E
2s
2p
E
1 orbital 2s dan 2 orbital 2p bergabung membentuk hibridisasi sp2
2s 2p
2p
Di dalam senyawa etena [ CDi dalam senyawa etena [ C22HH4 4 atau atau HH22C = CHC = CH22] terdapat 1 ikatan rangkap] terdapat 1 ikatan rangkap
Hibridisasi sp2Hibridisasi sp2
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masing-masing orbital 2p saling overlap antar sisi membentuk ikatan pi
120°120°C C
(2p-2p)
(sp2-sp2)HH
H H
(sp2-1s)
120°
orbital C sp2
120°
orbital C sp2 dan orbital 2p yangtidak terhibridisasi
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Di dalam CDi dalam C22HH22 terdapat 1 ikatan rangkap tiga terdapat 1 ikatan rangkap tiga
dan 2 ikatan tunggal. dan 2 ikatan tunggal.
grand state
E
2s
2p
exaited state: 1 é dipromosikan ke orbital kosong
E
2s
2p
E
1 orbital 2s dan 1 orbital 2p bergabung membentuk hibridisasi sp
2s 2p
2p
Hibridisasi spHibridisasi sp
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Orbital atom C sp ini akan terjadi apabila atom karbon dalam Orbital atom C sp ini akan terjadi apabila atom karbon dalam molekul terikat oleh ikatan rangkap tiga. Bentuk orbital C sp adalah molekul terikat oleh ikatan rangkap tiga. Bentuk orbital C sp adalah linier, gambar orbitalnya sbb:linier, gambar orbitalnya sbb:
180°
orbital C sp
orbital C sp dan 2 orbital 2p yang tidak terhibridisasi
Dalam molekul CDalam molekul C22HH2 2 , 2 orbital sp pada atom C (1 dan 2) masing-, 2 orbital sp pada atom C (1 dan 2) masing-
masing akan overlap dengan 1 orbital 1s dari atom H dan 1 orbital sp masing akan overlap dengan 1 orbital 1s dari atom H dan 1 orbital sp dari atom C yang lain. Overlaping dari masing-masing orbital adalah dari atom C yang lain. Overlaping dari masing-masing orbital adalah sebagai berikutsebagai berikut
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masing-masing orbital 2p saling overlap antar sisi membentuk ikatan pi
C C2 (2p-2p)
(sp-sp)
HH
(sp-1s)
Ketiga teori struktur dari Ketiga teori struktur dari Kekulé, Lewis dan Linus PaulingKekulé, Lewis dan Linus Pauling sering sering dikenal dengan teori dikenal dengan teori Ikatan ValensiIkatan Valensi
Dua orbital 2p yang lain yatiu orbital yang tidak terhibridisasi dari Dua orbital 2p yang lain yatiu orbital yang tidak terhibridisasi dari masing-masing atom C (1 dan 2) dapat saling overlaping membentuk masing-masing atom C (1 dan 2) dapat saling overlaping membentuk 2 ikatan phi.2 ikatan phi.
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CH3-C CHC
H
H
H HC C
C
H
H
H C
H
H
O H CH3-CH2-OH atau CH3CH2OH
Ikatan yang biasa tidak ditulis adalah ikatan tunggalIkatan yang biasa tidak ditulis adalah ikatan tunggal
Seorang Chemist menulis struktur senyawa organik dengan struktur Seorang Chemist menulis struktur senyawa organik dengan struktur termampatkan akan tetapi di dalam pemikirannya harus sudah termampatkan akan tetapi di dalam pemikirannya harus sudah tergambar bahwa struktur yang ditulis tersebut adalah struktur Luwis tergambar bahwa struktur yang ditulis tersebut adalah struktur Luwis dan Pauling. dan Pauling.
Struktur termampatkanStruktur termampatkan
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contain not only C-C bonds but also contain not only C-C bonds but also C-H bonds.C-H bonds.
C-C and C-H bonds tend to be non-C-C and C-H bonds tend to be non-polarpolar because there is a small because there is a small difference in electronegativitesdifference in electronegativites
Most (but not all) organic compounds Most (but not all) organic compounds are relatively non-polarare relatively non-polar
generally not very soluble in watergenerally not very soluble in water
Organic compoundOrganic compound
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Organic CompoundsOrganic CompoundsOrganic CompoundsOrganic Compounds
Functional GroupsFunctional GroupsFunctional GroupsFunctional GroupsHydrocarbonsHydrocarbonsHydrocarbonsHydrocarbons
Classes of organic compoundClasses of organic compound
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The simplest organic compounds are the hydrocarbons:◦organic compounds that contain only carbon
and hydrogen
◦four general types: alkanes alkenes alkynes aromatic hydrocarbons
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HydrocarbonsHydrocarbonsHydrocarbonsHydrocarbons
AromaticAromaticAliphaticAliphaticAliphaticAliphatic
AlkanesAlkanes AlkynesAlkynesAlkenesAlkenes CycloAlkanesCycloAlkanes
HH
HH
HH
HH
HH
HH
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Only carbon and hydrogen
All single bondsCC H
H
HH
H
H
AlkanesAlkanes
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Only carbon and hydrogen
A carbon to carbon double bond
C C
H H
HH(Double bond: 4 electrons)
AlkenesAlkenes
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(Triple bond: 6 electrons)
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C C HHOnly carbon and
hydrogen
A carbon to carbon triple bond
AlkynesAlkynes
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Cycloalkanes are represented by polygons. Cycloalkanes are represented by polygons. A triangle represents cyclopropane, a A triangle represents cyclopropane, a square represents cyclobutane, a pentagon square represents cyclobutane, a pentagon represents cyclopentane, and so on.represents cyclopentane, and so on.
CycloalkanesCycloalkanes
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Aromatic compounds contain benzene.Benzene, C6H6 , is represented as a six carbon ring
with 3 double bonds.Two possible resonance structures can be drawn toshow benzene in this form.
H
H
H
H
H
H
HH
H
H
H
H
Aromatic compounds and benzeneAromatic compounds and benzene
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Functional GroupsFunctional Groups
Most organic chemistry involves substituents, which Most organic chemistry involves substituents, which are groups attached to hydrocarbon chains.are groups attached to hydrocarbon chains.
The substituents of organic molecules The substituents of organic molecules often contain O, N, S and Poften contain O, N, S and Palso are called functional groups also are called functional groups
They are the chemically functional parts of the molecules.They are the chemically functional parts of the molecules.
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Organic compounds can be classified according to theirOrganic compounds can be classified according to theirfunctional groups. functional groups.
They symbol R represents any carbon chains or rings They symbol R represents any carbon chains or rings attached to the functional group. attached to the functional group.
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Elements in Groups VII F, Cl, Br, IElements in Groups VII F, Cl, Br, I
CH2CH2CH2CH3 I
CH3CCH3
CH3
F
R-I
R-F
HalogenHalogenHalogenHalogen
CH3-Br
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Has 1 oxygen
No O-H or C=O group
The oxygen is sandwiched between two carbon atoms
C C
H
H O
H
C H
H
H
H
H
EtherEther
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Only one oxygenHas an O-H
functional group
Can classify as 1º/2º/3º according to position of O-H group on carbon skeleton
CC
H H
H
HH
HO
AlcoholsAlcohols
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Only one oxygen
Has an O-H group
The O-H group is directly attached to a benzene ring
HO
PhenolsPhenols
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Only one oxygen
Has a C=O group
C=O group is at the end of carbon chain, so is next door to a hydrogen atom
C C
H
H
O
HH
AldehydesAldehydes
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Only one oxygen
Has a C=O group
C=O group is not at the end of carbon chain, so is next door to 2 carbons
C C
H
H
O
H
H
C
H
H
Acetone
KetonesKetones
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Has 2 oxygens
Has O-H and C=O groups on the same carbon atom
This -COOH group has to be at the end of a carbon chain
C C
H
H
O
OH
H
Acetic acid
Carboxylic acidsCarboxylic acids
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Has 2 oxygens
One oxygen is part of a C=O bond, the other is next door, sandwiched between two carbons
C C
H
H
O
OH
C H
H
H
Methyl acetate
EstersEsters
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Functional Groups withFunctional Groups with Three Oxygens Three Oxygens
RCOCR'RCOCR'
OO OO
CHCH33CCOOCCHCCH33
OO OO
CC66HH55CCOOC(CHC(CH22))55CHCH33
OO OO
Acid Anhydride
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In amines, the functional group is a nitrogen atom. H HC —N – H or C —N —C
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Methyl amine
Dimethyl amine
AminesAmines
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In amides, the hydroxyl group of a carboxylic acid is replaced by a nitrogen group (-NH2).
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acetamide
AmidesAmides
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RCRC NN NNCC
CHCH33CHCHCHCH33Nitrile
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Thiols are carbon compounds
that contain a –SH group.
are named in the IUPAC system by adding thiol to the alkane name of the longest carbon chain.
Copyright © 2005 by Pearson Education, Inc.Publishing as Benjamin Cummings
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ThiolsThiols
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ThiolsThiols
Thiols often have
strong odors.
are used to detect gas leaks.
are found in onions, oysters, and garlic.
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Alkanes are often called saturated hydrocarbons ◦they contain the largest possible number of hydrogen atoms per carbon atom.
HydrocarbonsHydrocarbons
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AlkanesAlkanesOrganic compounds can be represented in
many different ways:
◦molecular formula: C4H10 (butane)
◦Kekule structure:
◦Condensed structural formula
CH3CH2CH2CH3
◦Line angle drawings
H
H C C C C H
H
H H H H
H H H
C C C C H
H H H H
HHHH
H
H C C C C H
H
H H H H
H H H
C C C C H
H H H H
HHHH
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AlkanesAlkanes
Some of the simplest alkanes:
CondensedFormula Name
CH4 methane
CH3CH3 ethane
CH3CH2CH3 propane
CH3CH2CH2CH3 butane
CH3CH2CH2CH2CH3 pentane
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Some of the simplest alkanes:
CondensedFormula Name
CH3CH2CH2CH2CH2CH3 hexane
CH3CH2CH2CH2CH2CH2CH3 heptane
CH3CH2CH2CH2CH2CH2CH2CH3 octane
CH3CH2CH2CH2CH2CH2CH2CH2CH3 nonane
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 decane
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AlkanesAlkanes
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AlkanesAlkanes
The previous alkanes are also called straight-chain hydrocarbons:◦all of the carbon atoms are joined in a
continuous chain
Alkanes containing 4 or more carbons can also form branched-chain hydrocarbons (branched hydrocarbons)◦some of the carbon atoms form a “branch” or
side-chain off of the main chain
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AlkanesAlkanesAn example of a straight chain hydrocarbon:
◦C5H12 CH3CH2CH2CH2CH3 pentane
Examples of a branched hydrocarbon:
◦C5H12 CH3CHCH2CH3 CH3
CH3 CH3CCH3
CH3
2-methylbutane
2,2-dimethylpropane
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AlkanesAlkanes
The three structures shown previously for C5H12 are structural isomers:◦compounds with the same molecular formula
but different bonding arrangements
Structural isomers generally have different properties:◦different melting points◦different boiling points◦often different chemical reactivity
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AlkanesAlkanes
Organic compounds can be named either using common names or IUPAC names.
IUPAC : The international Union of pure and Applied Chemistry
You must be able to name alkanes, alkenes, alkynes, and alcohols with 10 or fewer carbons in the main chain using the IUPAC naming system.
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AlkanesAlkanesAlkane Nomenclature:
◦Find the longest continuous chain of carbon atoms and use the name of the chain for the base name of the compound: longest chain may not always be written in a straight line
CH3 - CH - CH3
CH2 - CH2 - CH2 - CH3
1 2
3
4 5 6
Base name:Base name: hexanehexane
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AlkanesAlkanesAlkane Nomenclature:
◦Number the carbon atoms in the longest chain beginning with the end of the chain closest to a substituent groups attached to the main chain that have
taken the place of a hydrogen atom on the main chain
A substituentA substituent
CH3 - CH - CH3
CH2 - CH2 - CH2 - CH3
1 2
3
4 5 6
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AlkanesAlkanes
Alkane Nomenclature:◦Name and give the location of each substituent
group A substituent group that is formed by removing an
H atom from an alkane is called an alkyl group:
◦Name alkyl groups by dropping the “ane” ending of the parent alkane and adding “yl”
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AlkanesAlkanes
Alkane Nomenclature:◦Common alkyl groups (substituents):
CH3 methyl
CH3CH2 ethyl
CH3CH2CH2 propyl
CH3CH2CH2CH2 butyl
2-methylhexane2-methylhexane
CH3 - CH - CH3
CH2 - CH2 - CH2 - CH3
1 2
3
4 5 6
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alcohol
amine
carboxylic acid ester
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CHCH33CHCH22OHOH CHCH33OCHOCH33
Bagaimana menjelaskan senyawa berikut menurut teori Bagaimana menjelaskan senyawa berikut menurut teori ikatan valensiikatan valensi
Learning CheckLearning Check
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Classify each of the following as: alcohol, ether, aldehyde, ketone, carboxylic acid, ester, amine or amide.
1) CH3─CH2─CH2─OH
2) CH3─O─CH2─CH3
3) CH3─CH2─NH2
O O ║ ║
4) CH3─C─OH 5) CH3─C─O─CH3
alcohol
ether
amine
carboxylic acid ester
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Name the following compounds:
CH3CH2CHCH3
CH2CH2Br
CH2CH2CH3
CH3CHCHCH3
Cl
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Write the condensed structure for the following compounds:
3, 3-dimethylpentane
3-ethyl-2-methylhexane
2-methyl-4-propyloctane
1, 2-dichloro-3-methylheptane
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SUKSES