Documenti di Didattica
Documenti di Professioni
Documenti di Cultura
Introduction
Organic chemistry is the chemistry of the compounds of
carbon.
Inorganic Chemistry: the chemistry of the other ~100
elements.
Carbon can form more compounds due to its ability to form
not only single, double or triple C-C bonds, but also to link up
with each other in chains and ring structures.
Over 13 million synthetic and natural organic compounds are
known – significantly greater than so known inorganic
compounds
Organic chemicals, those from living organisms (animal,
vegetable) were complex and contained C, H, and often N
and/or O.
Inorganic chemicals (mineral) were simpler, could contain a
variety of elements, but only rarely carbon, except for
carbonates.
covalent bonding
- sharing electrons
- most common bonding in organic compounds
1
How to handle variety
2
Classes of organic compounds
Hydrocarbons
Aliphatic Aromatic
3
Resonance
Resonance structure
4
Resonance Rules
5
sp
sp2
sp3
Functional Groups
6
Polar Bonds to Carbon
Lewis structures
- all electrons shown
Kekule structures
- show bonds as lines
- lone pairs sometimes omitted
line structures
- omit lone pairs
- omit hydrogens on carbons
- omit carbons
(assumed to be at the end of every bond)
7
3-Dimensional Structures
dotted-line / wedge
ball-and-stick
space-filling
8
Metana, CH4
Alkanes (alkana)
general formula: Cn H2n+2 , n=1,2, …..
only single covalent bonds are present
also known as saturated hydrocarbons
because they contain the maximum number of
hydrogen atoms that can bond with the
number of carbon atoms present
Carbons are sp3 hybridized.
Bonds are σ-bonds. C-C bonds ~ 1.54Å; C-H
bonds ~ 1.10Å. Bond angles ~ 109o.
9
CH4, methane (metana)
the simplest alkane
natural product of the anaerobic
bacterial decomposition of vegetable
matter under water --- marsh gas
Termites are a natural source of
methane by digestively breaking down
cellulose (from wood) – estimated 170
million tons production annually
Sewage treatment processes also
produced methane
Commercially obtained from natural gas
10
isomers
Structural isomer: molecules that
have the same molecular formula but
different structures
in the alkane series, as the number of
C atoms increases, the number of
structural isomers increases rapidly
butane – 2 isomers; decane (C10H22)
– 75 isomers and C30H62 has over
than 4x108 isomers
11
Alkane nomenclature
based on recommendation of the International Union of Pure and
Applied Chemistry (IUPAC)
Metil - CH3
t-butil CH3
- C – CH3
CH3
12
Functional groups
Gugus fungsional Nama
- NH2 Amino
-F Fluoro
-Cl Kloro
-Br Bromo
-I Iodo
- NO2 Nitro
- CH = CH2 Vinil
CH3
13
Aliphatic hydrocarbon
• alkanes
• cycloalkanes
• alkenes
• alkynes
Struktur
proyeksi
Newman
proyeksi
Sawhorse
14
Reaksi kimia alkana
• Pembakaran
– sangat eksotermis CH 4( g ) + 2O2( g ) → CO2( g ) + 2 H 2 O(l ) ∆H = −890,4kJ
0
alkil halida
– substitusi 1 atau lebih CH 4 ( g ) + Cl 2 ( g ) → CH 3 Cl ( g ) + HCl ( g )
metil klorida
atom H oleh atom
halogen Jika tersedia gas klor berlebih:
• campuran gas metana CH 3Cl ( g ) + Cl 2( g ) → CH 2 Cl 2 (l ) + HCl ( g )
dan klor dipanaskan di metilen klorida
atas 100 oC atau diiradiasi
cahaya dengan λ tertentu CH 2 Cl 2(g) + Cl 2 ( g ) → CH Cl 3 ( l ) + HCl ( g )
kloroform
Apakah nama sistematik (sesuai aturan penamaan) untuk metil klorida, metilen klorida
dan kloroform?
Alkil halida
• Kloroform
– cairan volatil untuk anastesi
– toksik thd ginjal, hati dan jantung Æ dilarang
• Karbon tetraklorida
– cairan pembersih Æ noda minyak pada kain
– toksik
• Metilen klorida
– solven untuk de-kafeinasi kopi dan pembersih
cat
• Klorofluoro karbon
15
Sikloalkana
• Definisi: alkana yang rantai karbon dihubungkan
sebagai suatu cincin
• Rumus umum: CnH2n, n= 3,4,…..
• Yang paling sederhana adalah siklopropana
• Merupakan kandungan kimia senyawa
kolesterol, testosteron, dan progesteron
• Mempunyai 2 geometri berbeda
– chair
– boat
cortisone (a steroid)
chrysanthemic acid
penarik serangga
C5
C6 C8
16
Penamaan sikloalkana
17
Penamaan sikloalkana
NOT
alkena
• disebut juga olefin
• mempunyai sekurang-kurangnya 1 ikatan
rangkap C=C
• Rumus umum Cn H2n n=2,3,4,……
• Alkena paling sederhana : C2H4 (etilen
atau etena)
• Ada di alam cukup banyak
18
alkena di alam
• etilen Æ gas yang berperan dalam proses
kematangan buah
• α-pinena Æ komponen utama terpentin
• β-karoten Æ pigmen oranye pemberi
warna wortel, sumber vit A dan memberi
perlindungan terhadap penyakit kanker
α-pinena
β-karoten
etilen
Tata nama
•
•
alkena
nama senyawa menunjukkan posisi ikatan rangkap
nama senyawa induk/utama berakhiran dengan –ena
C=C
1,4-sikloheksadiena
CH3 H 1,5-dimetil-siklopentena
CH3
CH3 C-CH2-CH3 C=C
C=C H C-CH2-CH3
H H
CH3
19
Beberapa penamaan karena faktor sejarah, namun diterima oleh IUPAC:
• etena Æ etilen
• lihat tabel
Preparasi alkena
• via termal cracking gas alam (alkana C1-
C4) dan gasolin rantai lurus (C4-C8)
20
Halogenasi dan hidrogenasi
• HALOGENASI Æ aturan Markovnikov
C2H4 + HX Æ CH3CH2X etilena + Br2 Æ 1,2 dibromo etana
hidrogenasi
21
TINGKAT STABILITAS:
tetrasubstituted > tri-substituted > di- substituted > mono-substituted
NO
22
stabilitas isomer geometri
alkena
Cl Cl
µ= 1,89 D
C=C
• cis diklor etilen H H BP = 60,3 oC
Cl H
µ= 0 D
C=C
H Cl BP = 47,5 oC
• trans-diklor etilen
I. Aliphatic hydrocarbon –
alkynes
23
Alkynes = Alkuna
• Hydrocarbons that contain a C-C triple bond
Bonding
24
Reactions of alkynes
• Reduction to an alkene
– Geometrical isomerism possible for product, except
when alkyne is terminal (has triple bond at end).
Each of these
reactions is
stereoselective in
that each yields
predominantly
one stereoisomer
of two or more
possible ones.
• Reduction to an alkane
• Addition of Halogens
25
• Additions of Hydrogen Halides
Hydration of alkynes -
tautomerism
• Usually the equilibrium favors the ketone (or CH3 - CHO, when
the alkyne is acetylene) Æan acid - base equilibrium; -OH is a
stronger acid than -CH3.
• Structural isomers which exist in equilibrium with each other are
called tautomers.
• The particular type of tautomerism shown above is keto - enol
tautomerism.
26
Acidity of Alkynes – Alkynes in Synthesis —
• In general, it is possible to convert a terminal
alkyne to an anion by removing the terminal
hydrogen Æusually accomplished by using a base
which is stronger than an acetylide anion:
• Example problem 1 –
• Synthesize 2-hexyne from starting materials
which do not contain more than 3 carbons.
27
Tatanama
• mengikuti aturan seperti pada alkana dan
alkena, akhiran –una
• posisi ikatan rangkap tiga dinyatakan oleh atom
C pertama di dekat ikatan
• penomeran atom C rantai utama sedemikian
rupa sehingga nomer C ikatan rangkap sekecil
mungkin
6-metil-3-oktuna
Tatanama
• Jika ada lebih dari 1 ikatan rangkap 3 Æ diuna,
triuna, dst.
• Senyawa dengan 2 macam ikatan rangkap Æ
enuna
– penomeran C dimulai dari ujung C plg dekat
sembarang ikatan rangkap; double bonds
nomernya lebih rendah drpd triple bonds
4-metil-7-nonen-1-una
1-hepten-6-una
28
Ring structures Æ aromatic rings
• when carbons are arranged at the corners of a
hexagon with a hydrogen bonded to each carbon
and alternating double bonds between carbons
• the most basic ring structure is benzene (C6H6)
• H- substituted by functional groups Æ variety
different molecules
• hydrocarbons based on the benzene ring Æ arenes
– eg. benzene, toluene, naphtalene
benzin
29
• Many trees exude resinous materials called balsams when
cuts are made in their bark Æ some are fragrant – exotic oil
• Gum benzoin is a balsam obtained from a tree that grows in
Java and Sumatra.
• “Benzoin” is a word derived from the French equivalent,
benjoin, which in turn comes from the Arabic luban jawi,
meaning “incense from Java.”
• Benzoic acid is itself odorless but can easily be isolated from
gum benzoin.
• Compounds related to benzene were obtained from similar
plant extracts.
– tolu tree Æ tolu balsam; 1840 found that distillation of tolu
balsam Æ methyl derivative of benzene called toluene
Benzene
• Benzene is very unreactive
– • It gives substitution and not addition products
WHY ????
30
• 3 premises of August Kekulé (1866)
1. Benzene is C6H6.
2. All the hydrogens of benzene are
equivalent.
3. The structural theory requires that there be
four bonds to each carbon.
• Kekulé advanced: Four bonds to each carbon could be
accommodated by a system of alternating single & double
bonds with one hydrogen on each carbon.
31
• Both Kekulé structures of benzene are of equal
energy, and one of the principles of resonance
theory is that stabilization is greatest when the
contributing structures are of similar energy.
• Cyclic conjugation in benzene, then, leads to a
greater stabilization than is observed in noncyclic
conjugated trienes.
• How much greater that stabilization is can be
estimated from heats of hydrogenation.
1,3 sikloheksadiena
sikloheksena
32
Properties of Aromatic
Compounds —
• Cyclic and each atom in the
ring is a π-center (uses a p
atomic orbital to form π -type
bonds), ie, sp2 or sp.
• Unusually stable.
aromatic heterocycles
1997
1938
1887
sulfapiridin – antibiotik
antipirin –
mengurangi
demam 1970s
obat anti-ulcer
33
• p409 Carey
34