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KIMIA DASAR I

APAKAH KIMIA ORGANIK ?


Ilmu yang mempelajari senyawa-senyawa hidrokarbon dan derivatnya
Perbandingan : 7 million senyawa organik 1.5 million senyawa anorganik

H I D R O K A R B O N Senyawa yang terdiri dari


karbon dan hidrogen
Berdasarkan ikatannya
Hidrokarbon jenuh Hidrokarbon tak jenuh

alkana, alkena, alkuna, benzena

SENYAWA ORGANIK
Materi

tanaman / hewan Makanan, minuman Bahan farmasi/ kosmetik Plastik, pipa PVC Komponen minyak bumi Pakaian

Carbon (C)
Unsur kehidupan di atas bumi adalah

MENGAPA ???
memiliki 4 buah elektron bonding yang dapat membentuk ikatan kovalen yang kuat, dapat berupa ikatan tunggal dan rangkap (2 atau 3)

Molekul organik paling sederhana:


Carbon has 4 valence electrons Susunan OKTET yang stabil

H H C H methane metana H H H

H C H C H Ne Neon

Stable Octet required

Covalent Bonding Atoms Share Electrons

ALKANA

Bentuk dasar

C(6) - 1s2, 2s2, 2px1, 2py1, 2pz0


Hibridisasi

Bentuk tereksitasi

C(6) - 1s , 2s ,

1 2px ,

1 2py ,

1 2pz

4 sp3
+ 2s 2py + 2px + 2pz 4 X sp3

Struktur tetrahedral pada metana


109.5
0

H C H H H

Carbon yang menunjukkan hibridisasi sp3 4 buah ikatan C-H yang ekivalen (ikatan s) Semua ikatan tunggal dinamakan ikatan s

consist of only carbon and hydrogen bonded by single covalent bonds single

Alkana
H H H C C H H H ethane CH3CH3

CnH2n+2
H H H H H C C C C H H H H H butane CH3CH2CH2CH3 H H H H H H C C C C C H H H H H H pentane CH3CH2CH2CH2CH3

H H C H H methane CH3

H H H H C C C H H H H propane CH3CH2CH3

Skeletal structure of only carbon atoms


propane butane pentane

Contoh :
CH4
4 1 3 2 2 3 1 4

CH3

CH2

CH2

CH3

2-metilbutana

1 6 CH3

2 CH 5 CH3

3 CH 4 2

4 5 CH CH2 3 2 CH2 CH3

6 CH3 1

3-etil-5-metilheksana
4-etil-2-metilheksana

3+5=8
4+2=6

SIFAT FISIK

Senyawa non polar, densitas <1, dengan air membentuk dua lapisan Larut dalam pelarut organik non polar Alkana C 4, berbentuk gas, Alkana Mr >, berbentuk cair, Alkana Mr >>>, berbentuk padat Semakin besar jumlah atom C, Mr molekul semakin >, gaya dispersi tiap molekul >, titik didih semakin tinggi Alkana bercabang td < alkana rantai lurus padanannya Ada pengaruh gaya van der Waals antar molekul Ikatan tunggal mampu berotasi bebas

Melting (blue) and boiling (pink) points of the first 14 nalkanes in C.

Isomers the have the same molecular formula, but a different structures Structural Isomers same molecular formula, but atoms are bonded in different orders.
H H3C C CH3
C4H10 has two isomers, n-butane and isobutane (2-methylpropane)

CH3

Isobutane
H3 C CH CH3 CH2 CH3

Has the same molecular formula as n-pentane, C5H12

Isopentane (2-methylbutane)
CH3 H3C C CH3

CH3

Neopentane

Has different Physical Properties : m.p, b.p. density (2,2-dimethylpropane)

CYCLOALKANES

CnH2n

H2C CH2 C H2

C C H Cyclopropane Bond angles H 60 C H H


Cyclobutane Bond angles 88

H2C CH2 H2C CH2

Cyclopentane

Bond angles 108

Cyclohexane

Bond angles 109.5

CH3
metilsikloheksana

CH3
C

CH3

tert-butilsiklopentana

CH3
CH3
1,2-dimetilsikloheksana

CH3

How to draw Cyclohexane ?


H H
put in axial Hs

put in equitorial Hs

H H
H H H H

H H H H H

H H H

H
H H H

H H H H H

REACTIONS OF ALKANES
CH4

+ 2O

Combustion

CO2

+ 2 H O + energy
2

Dehydrogenation
RCH2 High Temp. catalyst CH2R RHC CHR alkene

Halogenation radical substitution reactions

light or heat + Br2

Br + HBr

Halogenation
H H C H H C H H

Heat or Light or hv
Br2 H

H C H

H C H Br

HBr

Ethane
H H C H

Bromoethane

Heat or Light or hv

H H C H chloromethane Cl

Cl2

HCl

H Methane

CH2Cl2 and CHCl3 may be observed

Substitution Reaction a reaction in which part


of a small reacting molecule replaces an atom or a group of atoms on the organic molecule

Alkyl Halides or Haloalkanes

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Naming them
Cl Cl C Cl Cl

Tend to be Heavier than water More Toxic than Alkanes


CH3 CH Cl CH CH3 CH3 CH3 CH Br CH2 CH2 Cl

Tetrachloromethane or carbon tetrachloride

2-Chloro-3-methylbutane

3-Bromo-1-chlorobutane

CH2CH3 Br F Cl

1-Bromobutane
F

1-Ethyl-2-fluorocyclohexane
Cl Cl C Cl F Cl

2-Chloropropane or Isopropyl chloride


F F C H H

C Cl

C F

Trichlorofluoromethane (Freon-11)

Dichlorodifluoromethane 1,1,1, 2-Tetrafluoroethane (Freon-12)

Chlorofluorocarbons (CFCs) Refrigerant Gases, Ozone Depletion, More Hs more degradable

X dd+ C

X = F, Cl, Br
X is readily displaced by nucleophiles

Nu Electronegativity is defined as the ability of atoms to attract shared electrons in a covalennt bond ------------ leads to nucleophilic substitution in alkyl halides

Cl Cl C Cl Cl

Symmetrical molecules have no dipole moment or have equal distribution of electrons within covalent bonds Therefore, they are unreactive!

STEREOCHEMISTRY

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Isomers are different compounds that have the same molecular formula
Structural isomers are isomers that differ because their atoms are connected in a different order

CH3OCH3 ---- dimethyl ether and CH3CH2OH ---- ethanol

Stereoisomers differ only in the arrangement of their atoms in space


Geometric Isomers

Cl Cl

H H

Cl H

C2H2Cl2
Cl cis-1,2-Dichloroethene trans-1,2-Dichloroethene

Enantiomers are stereoisomers whose molecules are nonsuperimposable mirror images of one another Objects that are superimposable on their mirror images are said to be achiral
Involves a tetrahedral sp3 atom

H CH3 C OH CH2 CH3

Chiral Centre
CH3 HO H C CH2 CH3

2-Butanol

CH3 Interchanging any two groups at a chiral H OH C


centre (stereocentre) that bears four into another

CH2 CH3

different groups converts one enantiomer

One structure can be superimposed on another

CH3 H C OH CH3

CH3 HO C H CH3 2-Propanol

If any of the groups attached to the tetrahedral atom are the same, the centre is achiral.

The ultimate way to test for molecular chirality is to construct models of the molecule and its mirror image and then determine whether they are superimposable

Screwdriver is achiral Socks are achiral Golf club is chiral Gloves are chiral

A molecule will not be chiral if it possess a centre or plane of Symmetry

What is a chiral object?

What is an achiral object?

Properties of Enantiomers
Enantiomers have identical melting points and boiling points Enantiomers have identical solubilities in solvents Enantiomers have identical spectra and refractive index Enantiomers interact, and react with achiral molecules in the same manner

Enantiomers interact and react with other chiral molecules at different rates Enantiomers rotate plane-polarised light by equal amounts but in opposite directions
Chiral molecules are optically active

Plane-polarised light

Oscillation of electrical field of ordinary light occurs in all possible directions

Polarimeter is a devise used to measure the effect of planepolarised light on an optically active compound

No Correlation between the direction of rotation of plane polarised light and the absolute configuration of a molecule Clockwise Rotation (+) dextrorotatory Anti-Clockwise Rotation (-) levorotatory

Same Configuration
CH3 H2C C H HO CH2CH3
(R)-(+)-2-Methyl-1-butanol

CH3 H2C C H Cl CH2CH3


(R)-(-)-1-Chloro-2-methylbutanol

An equimolar mixture of two enantiomers is called a Racemic Mixture It is Optically Inactive


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S-(+)-Carvone

R-(-)-Carvone

Principle component of Caraway seed oil and responsible for the characteristic odour

Principle component of Spearmint oil and responsible for the characteristic odour

Receptor Sites in the Nose are Chiral


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