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Kimia Organik

Andi Nina Asriana: Chapter 1


Ruang Lingkup Ilmu Kimia Organik
Sub : pokok bahasan
1. Definisi
2. Ruang lingkup bahan perkuliahan
3. Klasifikasi
4. Tata nama
KIMIA ORGANIK
• 1850 Kimia dari senyawa yang datang dari
benda hidup ………muncul istilah organik
• 1900 ahli kimia mensintesa senyawa kimia
baru di lab yang tidak ada hubunganya
dengan makhluk hidup

KIMIA KARBON
APAKAH KIMIA
ORGANIK ?
Ilmu yang mempelajari
senyawa-senyawa hidrokarbon
dan derivatnya

Perbandingan :
7 million senyawa organik
1.5 million senyawa anorganik
• Materi tanaman / hewan
• Makanan
• Bahan farmasi/ kosmetik
• Plastik
• Komponen minyak bumi
• Pakaian
Some organic chemicals

DNA Medicines
•Active Pharmaceutical Ingredients
•Excipients

Fuels

Materials Essential oils Pigments


KLASIFIKASI SENYAWA
ORGANIK
• Klasifikasi didasarkan pada GUGUS FUNGSI
• Tiga kelompok utama :
– Hidrokarbon
– Senyawa yang mengandung oksigen
– Senyawa yang mengandung nitrogen
HIDROKARBON
• Alkana: ikatan tunggal, karbon sp3
• Sikloalkana: rangkaian karbon membentuk
cincin
• Alkene: ikatang rangkap dua, karbon sp2
• Sikloalkena: ikatan rangkap dua di dalam cincin
• Alkyne/alkuna: ikatan rangkap tiga, karbon sp
• Aromatis: terdapat cincin/inti benzene
Senyawa yang
mengandung oksigen
• Alkohol: R-OH
• Eter: R-O-R' O
CH3CH2 C H O
• Aldehid: RCHO
CH3 C CH3
• Keton: RCOR
• Asam karboksilat dan turunannya
Asam karboksilat dan turunannya
O
• Asam karboksilat : RCOOH C OH

• Klorida asam : RCOCl O

• Ester : RCOOR' C Cl

• Amida : RCONH
O 2 O
C NH C
2 OCH3
Senyawa yang
mengandung nitrogen
• Amina : RNH2, RNHR', or R3N
• Amida : RCONH2, RCONHR, RCONR2
O

N CH3

CH3 C N
• Nitril : RCN
ALKANA
C4H10 mempunyai 2 bentuk, rumus molekul sama,
tetapi berbeda penataannya (berbeda
strukturnya) ISOMER (=ISOMER STRUKTUR)

H H H HH
H H
H C H C
C C H
C H C H
C C
H H H H H
H H H

boiling pt. 1oC -15oC


C5H12
CH3 CH3
CH3CH2CH2CH2CH3 CH3CHCH2CH3 CH3CCH3
CH3

the same
CH3
CH3CHCH2
CH3
• Atom-atom karbon di dalam alkana dan senyawa
organik yang lain diklasifikasikan berdasarkan
jumlah atom karbon lain yang langsung terikat
pada atom C tersebut
Klasifikasi atom C dan atom H
CH 1o (primary) methyl group
3
H C H
methine 3o (tertiary) H C CH
3
group H C H 2o(secondary) methylene
CH group
3
H’s on 1o C referred to as primary hydrogens
2o - secondary H
3o - tertiary H
CH3
CH3 C CH2 CH3
CH3

4o quaternary carbon
Alkana - CnH2n+2
metana CH 4 CH 4
etana C 2 H6 CH 3 CH 3
propana C 3 H8 CH 3 CH2 CH3
butana C4 H10 CH 3 (CH 2 ) 2 CH 3
pentana C5 H12 CH 3 (CH 2 ) 3 CH 3
heksana C6 H14 CH 3 (CH 2 ) 4 CH 3
heptana C7 H16 CH 3 (CH 2 ) 5 CH 3
oktana C8 H18 CH 3 (CH 2 ) 6 CH 3
nonana C9 H20 CH 3 (CH 2 ) 7 CH 3
dekana C10 H22 CH 3 (CH 2 ) 8 CH 3
dodekana C12 H26 CH 3 (CH 2 ) 10 CH 3
tetradekana C14 H30 CH 3 (CH 2 ) 12 CH 3
Gugus Alkil
metil -CH3
etil -CH2CH3
propil -CH2CH2CH3
isopropil -CH(CH3)2
butil -CH2CH2CH2CH3
isobutil -CH2CH(CH3)2

sec-butil -CH(CH3)CH2CH3
tert -butil -C(CH3)3
Nama IUPAC
• Tentukan rantai karbon terpanjang.
• Beri no setiap atom karbon, mulai dari atom C
yang terdekat dengan cabang pertama.
• Beri nama gugus cabang yang terikat pada
rantai utama dan beri no sesuai no atom C
yang mengikatnya.
• Semua substituen/cabang diurut berdasarkan
alfabetik.
• Gunakan di-, tri-, dst untuk substituen/cabang
yang sama.
Manfaat utama Alkana
• C1-C2: gas (gas alam)
• C3-C4: liquified petroleum (LPG)
• C5-C8: gasoline
• C9-C16: diesel, kerosene, jet fuel
• C17-up: lubricating oils, heating oil
• Origin: petroleum refining
Sikloalkana
Sikloalkana mempunyai rumus molekul CnH2n. Atom-atom
C membentuk cincin. Sikloalkana sederhana diberi nama
dengan menambah awalan siklo- pada nama alkana
asiklik dengan jumlah atom C yang sama.
ALKENA
Tata Nama :
• Rantai utama adalah rantai atom karbon
terpanjang yang mempunyai ikatan rangkap.
• Nama rantai utama sama dengan alkana,
akhiran - ana pada alkana diganti dengan -
ena untuk alkena dan - una untuk alkuna.
• Penomoran rantai utama dicari agar atom C
yang mengandung ikatan rangkap bernomor
kecil.
• Penamaan dan penomoran gugus cabang
sama dengan alkana
Isomer cis/trans
• Gugus yang sama berada pada sisi yang
sama pada ikatan rangkap : cis alkena
• Gugus yang sama berada pada sisi yang
berlawanan dari ikatan rangkap : trans
alkena.
• Sikloalkena berkonfigurasi cis.
• Trans-sikloalkena tidak stabil. Struktur
mulai stabil pada sikloalkana dengan
jumlah minimal 8 atom C
Name these:
H CH3 Br Br
C C C C
CH3CH2 H H H

trans-2-pentene cis-1,2-dibromoethene
trans-pent-2-ene
E-Z Nomenclature
• Gunakan aturan Cahn-Ingold-Prelog untuk
menentukan urutan prioritas gugus-gugus
yang terikat pada atom C ikatan rangkap.
• Jika gugus-gugus yang berprioritas lebih
tinggi berada pada sisi yang sama, diberi
nama Z (zusammen).
• Jika gugus-gugus yang berprioritas lebih
tinggi berada pada sisi yang berlawanan,
diberi nama E (entgegen).
Example, E-Z

1 2 Cl
1
H3C Cl H 1CH CH3
C C C C
H CH2 H
2 2 1 2
2Z 5E
3,7-dichloro-(2Z, 5E)-2,5-octadiene
3,7-dichloro-(2Z, 5E)-octa-2,5-diene
Ikatan dalam Alkana
1s
ikatan sigma 

sp3
sp3
C C
1s
sp3 1s

1s
• Ikatan rangkap pada etena terdiri
dari 1 ikatan  merupakan
hibridisasi sp2 dan 1 ikatan 
yang terbentuk dari overlaping (
tumpang suh ) antara orbital 2p
yang tak berhibridisasi.
ALKUNA
Reaksi Alkena
• Sifat alkena ini merupakan ciri dari senyawa
yang mempunyai ikatan rangkap adalah
Reaksi adisi

• Adisi terjadi melalui pemutusan ikatan 


( bersifat lebih lemah ) pada ikatan rangkap.

• Terbentuk ikatan sigma yang baru


• MACAM-MACAM DIENA
Other Polymers

=>
Chapter 7 34
SENYAWA AROMATIS
semua senyawa yang mempunyai sifat kimia
seperti benzena.
• Benzene adalah senyawa yang tidak
berwarna, m.p. 6o C dan b.p. 80o C, ditemukan
pada tahun 1825 oleh Michael Faraday.
• Memiliki cincin 6 anggota, rumus molekul
C6H6 yang menunjukkan adanya 3 ikatan
rangkap dalam cincin.
• Stuktur benzena masih merupakan tanda
tanya bagi ahli kimia pada abad ke 19. Rumus
molekulnya menunjukkan tingginya tingkat
ketidakjenuhan, tetapi tidak mengalami reaksi
adisi seperti halnya alkena pada umumnya
Struktur Benzena
• Struktur benzene pertama kali
diusulkan oleh August Kekulé
pada tahun 1865. Struktur
tersebut menggambarkan bahwa
struktur benzena tersusun 3
ikatan rangkap di dalam cincin 6
anggota.
• Ketiga ikatan rangkap tersebut
dapat bergeser dan kembali
dengan cepat sedemikian
sehingga 2 bentuk yang mungkin
tersebut tidak dapat dipisahkan.
Model Resonansi Benzene
Aturan Hückel
untuk menentukan kearomatisan adalah sebagai
berikut:
1. Senyawa harus berbentuk siklik.
2.Senyawa harus mempunyai satu orbital p di
tiap atom penyusun cincin.
3.Senyawa harus planar atau hampir planar
sehingga terdapat tumpang tindih dari semua
orbital p
4.Terdapat elektron  sejumlah (4n+2) di dalam
cincin.
TATANAMA DERIVAT BENZENA
1. menambahkan awalan gugus substituen diikuti nama
bensena, misal : klorobensena, bromobensena,
nitrobensena, dll Cl Br I NO 2

Klorobensena Bromobensena Iodobensena Nitrobensena

2. beberapa derivat bensena mempunyai nama


spesifik yang mungkin tidak menunjukkan nama dari
substituen yang terikat pada bensena, misal :
metilbensena dikenal sebagai toluene,
aminobensena sebagai aniline, dll
CH3 NH2 OH COOH SO3H

Toluena Anilin Fenol Asam Benzoat Asam Bensensulfonat


3. Apabila bensena mengikat lebih dari satu substituen, maka
nama substituen dan letak substituen harus dituliskan. Ada 3
(tiga) isomer yang mungkin untuk bensena yang tersubstitusi
oleh 2 gugus. Penamaan digunakan nama orto (1,2-); meta
(1,3-); para (1,4-)
Br Br Br
Br

Br
Br
o-Dibromobensena m-Dibromobensena p-Dibromobensena
orto meta para

4. Apabila 2 atau lebih substituen yang terikat pada bensena


berbeda, maka penamaannya diawali dengan nama substituen
berturut-turut dan diikuti dengan nama bensena atau diberi
nama khusus/spesifik.
CH3 Br OH NH2

1
Cl Br Br
NO 2
6 2
5 3
4
NO 2
NO 2 Br

o-Nitrotoluena m-bromonitrobensena 2-Kloro-4-nitrofenol 2,4,6-Tribromoanilin


Beberapa cincin benzena terfusi
Kimia Organik ?
• Benda hidup terbuat dari materi organik
• Rambut terbuat dari protein
• DNA, controls genetic
• Foods, medicines
• Examine structures below

44
Origins of Organic Chemistry
Foundations of organic chemistry from mid-1700’s.

Compounds obtained from plants, animals hard to isolate, and purify.

Compounds also decomposed more easily.

Torben Bergman (1770) first to make distinction between organic and


inorganic chemistry.

It was thought that organic compounds must contain some “vital force”
because they were from living sources.
45
Because of “Vital force”, it was thought that organic compounds could
not be synthesized in laboratory like inorganic compounds.

1816, Chervrut showed that not to be the case, he could prepare soap
from animal fat and an alkali

1828, Wholer showed that it was possible to convert inorganic salt


ammonium cyanate into organic substance “urea”

46
• Organic chemistry is study of carbon
compounds.
• Why is it so special?
- 90% of more than 30 million chemical
compounds contain carbon.
- Examination of carbon in periodic chart
answers some of these questions.
- Carbon is group 4A element, it can share 4
47 valence electrons and form 4 covalent
Why this chapter?
• Review ideas from general chemistry: atoms, bonds, molecular
geometry

48
1.1 Atomic Structure
• Structure of an atom
– Positively charged nucleus (very dense, protons and neutrons) and
small (10-15 m)

– Negatively charged electrons are in a cloud (10-10 m) around


nucleus

• Diameter is about 2  10-10 m (200 picometers (pm))

49
Atomic Number and Atomic Mass
• The atomic number (Z) is the number of protons in the atom's
nucleus
• The mass number (A) is the number of protons plus neutrons
• All the atoms of a given element have the same atomic number
• Isotopes are atoms of the same element that have different
numbers of neutrons and therefore different mass numbers

50
1.2 Atomic Structure: Orbitals
• Quantum mechanics: describes electron energies and locations
by a wave equation
– Wave function solution of wave equation
– Each wave function is an orbital,

• A plot of 2 describes where electron most likely to be

• Electron cloud has no specific boundary so we show most


probable area

51
Shapes of Atomic Orbitals for Electrons
• Four different kinds of orbitals for electrons based on those
derived for a hydrogen atom
• Denoted s, p, d, and f
• s and p orbitals most important in organic and biological
chemistry
• s orbitals: spherical, nucleus at center
• p orbitals: dumbbell-shaped, nucleus at middle
• d orbitals: elongated dumbbell-shaped, nucleus at center

52
Orbitals and Shells part 1
• Orbitals are grouped in shells of increasing size and energy
• Different shells contain different numbers and kinds of orbitals
• Each orbital can be occupied by two electrons

53
Orbitals and Shells part 2
• First shell contains one s orbital, denoted 1s, holds only two
electrons
• Second shell contains one s orbital (2s) and three p orbitals (2p),
eight electrons
• Third shell contains an s orbital (3s), three p orbitals (3p), and
five d orbitals (3d), 18 electrons

54
p-Orbitals
• In each shell there are three perpendicular p orbitals, px,
py, and pz, of equal energy

• Lobes of a p orbital are separated by region of zero


electron density, a node

55
1.3 Atomic Structure: Electron Configurations
• Ground-state electron configuration (lowest energy arrangement)
of an atom lists orbitals occupied by its electrons. Rules:
• 1. Lowest-energy orbitals fill first: 1s  2s  2p  3s  3p  4s
 3d (Aufbau (“build-up”) principle)
• 2. Electrons act as if they were spinning around an axis. Electron
spin can have only two orientations, up  and down . Only two
electrons can occupy an orbital, and they must be of opposite spin
(Pauli exclusion principle) to have unique wave equations
• 3. If two or more empty orbitals of equal energy are available,
electrons occupy each with spins parallel until all orbitals have one
electron (Hund's rule).

56
1.4 Development of Chemical Bonding
Theory
• Kekulé and Couper independently observed that carbon always
has four bonds

• van't Hoff and Le Bel proposed that the four bonds of carbon
have specific spatial directions

– Atoms surround carbon as corners of a tetrahedron

57
• Atoms form bonds because the compound that results is more
stable than the separate atoms
• Ionic bonds in salts form as a result of electron transfers
• Organic compounds have covalent bonds from sharing electrons
(G. N. Lewis, 1916)

58
• Lewis structures (electron dot) show valence electrons of an
atom as dots
– Hydrogen has one dot, representing its 1s electron
– Carbon has four dots (2s2 2p2)
• Kekule structures (line-bond structures) have a line drawn
between two atoms indicating a 2 electron covalent bond.
• Stable molecule results at completed shell, octet (eight dots) for
main-group atoms (two for hydrogen)

59
• Atoms with one, two, or three valence electrons form one, two, or
three bonds.

• Atoms with four or more valence electrons form as many bonds


as they need electrons to fill the s and p levels of their valence
shells to reach a stable octet.

• Carbon has four valence electrons (2s2 2p2), forming four bonds
(CH4).

60
• Nitrogen has five valence electrons (2s2 2p3) but forms only three
bonds (NH3).

• Oxygen has six valence electrons (2s2 2p4) but forms two bonds
(H2O)

61
62
Non-bonding electrons
• Valence electrons not used in bonding are called nonbonding
electrons, or lone-pair electrons
– Nitrogen atom in ammonia (NH3)
• Shares six valence electrons in three covalent bonds and
remaining two valence electrons are nonbonding lone pair

63
1.5 The Nature of Chemical Bonds:
• Covalent Valence
bond forms when twoBond Theory
atoms approach each
other closely so that a singly occupied orbital on one
atom overlaps a singly occupied orbital on the other
atom
• Two models to describe covalent bonding.

Valence bond theory, Molecular orbital theory

Valence Bond Theory:


• Electrons are paired in the overlapping orbitals and
are attracted to nuclei of both atoms
– H–H bond results from the overlap of two singly
occupied hydrogen 1s orbitals
– H-H bond is cylindrically symmetrical, sigma ()
bond

64
Bond Energy
• Reaction 2 H·  H2 releases 436 kJ/mol
• Product has 436 kJ/mol less energy than two atoms: H–H has
bond strength of 436 kJ/mol. (1 kJ = 0.2390 kcal; 1 kcal = 4.184
kJ)

65
Bond Length
• Distance between
nuclei that leads to
maximum stability
• If too close, they repel
because both are
positively charged
• If too far apart, bonding
is weak

66
1.6 sp3 Orbitals and the Structure of Methane
• Carbon has 4 valence electrons (2s2 2p2)
• In CH4, all C–H bonds are identical (tetrahedral)
• sp3 hybrid orbitals: s orbital and three p orbitals combine to
form four equivalent, unsymmetrical, tetrahedral orbitals (sppp =
sp3), Pauling (1931)

67
The Structure of Methane
• sp3 orbitals on C overlap with 1s orbitals on 4 H atoms to form
four identical C-H bonds
• Each C–H bond has a strength of 436 (438) kJ/mol and length of
109 pm
• Bond angle: each H–C–H is 109.5°, the tetrahedral angle.

68
1.7 sp3 Orbitals and the Structure of Ethane
• Two C’s bond to each other by  overlap of an sp3 orbital from
each
• Three sp3 orbitals on each C overlap with H 1s orbitals to form
six C–H bonds
• C–H bond strength in ethane 423 kJ/mol
• C–C bond is 154 pm long and strength is 376 kJ/mol
• All bond angles of ethane are tetrahedral

69
1.8 sp Orbitals
2 and the Structure of
Ethylene
• sp2 hybrid orbitals: 2s orbital combines with two 2p orbitals,
giving 3 orbitals (spp = sp2). This results in a double bond.
• sp2 orbitals are in a plane with120° angles
• Remaining p orbital is perpendicular to the plane

70
Bonds From sp2 Hybrid Orbitals
• Two sp2-hybridized orbitals overlap to form a  bond
• p orbitals overlap side-to-side to formation a pi () bond
• sp2–sp2  bond and 2p–2p  bond result in sharing four
electrons and formation of C-C double bond
• Electrons in the  bond are centered between nuclei
• Electrons in the  bond occupy regions are on either side of a
line between nuclei

71
Structure of Ethylene
• H atoms form  bonds with four sp2 orbitals
• H–C–H and H–C–C bond angles of about 120°
• C–C double bond in ethylene shorter and stronger than single
bond in ethane
• Ethylene C=C bond length 134 pm (C–C 154 pm)

72
1.9 sp Orbitals and the Structure of Acetylene
• C-C a triple bond sharing six electrons
• Carbon 2s orbital hybridizes with a single p orbital giving two sp
hybrids
– two p orbitals remain unchanged
• sp orbitals are linear, 180° apart on x-axis
• Two p orbitals are perpendicular on the y-axis and the z-axis

73
Orbitals of Acetylene
• Two sp hybrid orbitals from each C form sp–sp  bond
• pz orbitals from each C form a pz–pz  bond by sideways overlap
and py orbitals overlap similarly

74
Bonding in Acetylene
• Sharing of six electrons forms C C

• Two sp orbitals form  bonds with hydrogens

75
76
1.10 Hybridization of Nitrogen and Oxygen
• Elements other than C can have hybridized orbitals
• H–N–H bond angle in ammonia (NH3) 107.3°
• C-N-H bond angle is 110.3 °
• N’s orbitals (sppp) hybridize to form four sp3 orbitals
• One sp3 orbital is occupied by two nonbonding electrons, and
three sp3 orbitals have one electron each, forming bonds to H
and CH3.

77
1.11 Molecular Orbital Theory
• A molecular orbital (MO): where electrons are most likely to be found
(specific energy and general shape) in a molecule

• Additive combination (bonding) MO is lower in energy

• Subtractive combination (antibonding) MO is higher energy

78
Molecular Orbitals in Ethylene
• The  bonding MO is from combining p orbital lobes with the
same algebraic sign
• The  antibonding MO is from combining lobes with opposite
signs
• Only bonding MO is occupied

79
1.12 Drawing Structures
• Drawing every bond in organic molecule can
become tedious.
• Several shorthand methods have been
developed to write structures.
• Condensed structures don’t have C-H or C-C
single bonds shown. They are understood.
e.g.
80
3 General Rules:
1) Carbon atoms aren’t usually shown. Instead a carbon atom is
assumed to be at each intersection of two lines (bonds) and at
the end of each line.

2) Hydrogen atoms bonded to carbon aren’t shown.

3) Atoms other than carbon and hydrogen are shown (See table
1.3).

81
Summary
• Organic chemistry – chemistry of carbon compounds
• Atom: positively charged nucleus surrounded by negatively charged electrons
• Electronic structure of an atom described by wave equation
– Electrons occupy orbitals around the nucleus.
– Different orbitals have different energy levels and different shapes
• s orbitals are spherical, p orbitals are dumbbell-shaped
• Covalent bonds - electron pair is shared between atoms
• Valence bond theory - electron sharing occurs by overlap of two atomic orbitals
• Molecular orbital (MO) theory, - bonds result from combination of atomic orbitals
to give molecular orbitals, which belong to the entire molecule

82
Summary (cont’d)
• Sigma () bonds - Circular cross-section and are formed by head-on interaction
• Pi () bonds – “dumbbell” shape from sideways interaction of p orbitals
• Carbon uses hybrid orbitals to form bonds in organic molecules.
– In single bonds with tetrahedral geometry, carbon has four sp3 hybrid orbitals
– In double bonds with planar geometry, carbon uses three equivalent sp2
hybrid orbitals and one unhybridized p orbital
– Carbon uses two equivalent sp hybrid orbitals to form a triple bond with linear
geometry, with two unhybridized p orbitals
• Atoms such as nitrogen and oxygen hybridize to form strong, oriented bonds
– The nitrogen atom in ammonia and the oxygen atom in water are sp3-
hybridized

83
Alkanes: Saturated Hydrocarbons
• Hydrocarbons are molecules composed of carbon & hydrogen
– Each carbon atom forms 4 chemical bonds
– A saturated hydrocarbon is one where all C - C bonds are “single”
bonds & the molecule contains the maximum number of H-atoms
– Saturated hydrocarbons are called ALKANES
Normal vs Branched Alkanes
• NORMAL alkanes consist of
CH2 CH2 continuous chains of carbon
CH3 CH2 CH3 atoms
• Alkanes that are NOT
continuous chains of carbon
CH2 CH3 atoms contain branches
CH3 CH • The longest continuous chain
of carbons is called the
CH3
parent chain
Structural Isomerism
• Structural isomers are
molecules with the same
CH2 CH2
chemical formulas but different CH3 CH2 CH3
molecular structures - different
“connectivity”. n-pentane, C5H12

• They arise because of the many CH2 CH3


ways to create branched CH3 CH
hydrocarbons.
CH3
• a.k.a. “Constitutional Isomers”
2-methlbutane, C5H12
The First 10 “Normal” Alkanes
Name Formula M.P. B.P. # Structural Isomers
• Methane CH4 -183 -162 1
• Ethane C1 - C4 are Gases
C2H6 -172 -89 1
• Propane C3H8 -187 -42 1
• Butane
at Room Temperature
C4H10 -138 0 2
• Pentane C5H12 -130 36 3
• Hexane C6H14 -95 68 5
• HeptaneC5 - C16 are Liquids
C7H16 -91 98 9
• Octane C8H18 -57 126 18
• Nonane at Room Temperature
C9H20 -54 151 35
• Decane C10H22 -30 174 75
IUPAC Rules for
Naming Branched Alkanes
– Find and name the parent chain in the hydrocarbon - this
forms the root of the hydrocarbon name
– Number the carbon atoms in the parent chain starting at
the end closest to the branching
– Name alkane branches by dropping the “ane” from the
names and adding “yl”. A one-carbon branch is called
“methyl”, a two-carbon branch is “ethyl”, etc…
– When there are more than one type of branch (ethyl and
methyl, for example), they are named alphabetically
– Finally, use prefixes to indicate multiple branches
Example 1: 2,2-dimethylpentane
• The parent chain is indicated by 2 4
the ROOT of the name - 1 CH2 3 CH2 5
“pentane”. This means there are CH3 CH2 CH3
5 carbons in the parent chain.
• “dimethyl” tells us that there are TWO
CH3 methyl branches on the parent chain.
4
A methyl branch is made of a single
C CH2 carbon atom.
CH3 CH2 CH3
• “2,2-” tell us that BOTH methyl
1
3 5

CH3
branches are on the second carbon
atom in the parent chain.
Example 2: 3-ethyl-2,4-dimethylheptane
2 4
• The parent chain is indicated by CH2 3 CH2 5
1
the ROOT of the name - CH3 CH2 CH2
“heptane”. This means there are
7 carbons in the parent chain.
H2C 6 7
CH3 CH3 CH3
• “2,4-dimethyl” tells us there are
CH CH TWO methyl branches on the
CH3 CH CH2 parent chain, at carbons #2 and #4.
• “3-ethyl-” tell us there is an ethyl
CH2 CH2 branch (2-carbon branch) on
CH3 CH3 carbon #3 of the parent chain.
Example 3: 2,3,3-trimethyl-4-propyloctane
• The parent chain is indicated by 3 5
the ROOT of the name - “octane”. 4 6
2
This means there are 8 carbons
in the parent chain. 1
7
8
CH3
3 5 • “2,3,3-trimethyl” tells us there are
2 4 CH3THREECmethyl branches CH2 - one on
6
CH #2 andCH
carbon two on carbonCH2#3.
7 CH3
1
8
• “4-propyl-”
CH3 tellCH
us there
2 is CH
a propyl
2
CH2 on CH3
branch (3-carbon branch)
carbon #4 of the parent chain.
CH3
Example 4: Name the molecules shown!
CH3
• parent chain has 5 carbons -
“pentane” CH2 CH
• two methyl branches - start CH3 CH CH3
counting from the right - #2 and #3
• 2,3-dimethylpentane CH3
• parent chain has 8 carbons - “octane”
• two methyl branches - start counting
from the left - #3 and #4
3
4
5 • one ethyl branch - #5
• name branches alphabetically
5-ethyl- 3,4-dimethyl octane
HOMEWORK ASSIGNMENT
• Read Zumdahl section 22-1
– make notes on REACTIONS OF ALKANES and
on CYCLIC ALKANES
– Copy table 22.2 on page 1040
– Pay attention to sample exercises!
• Answer end-of-chapter problems:
• 15, 16, 17, 18
Alkanes Review - Cycloalkanes
• A cycloalkane is made of a hydrocarbon chain
that has been joined to make a “ring”.
109.5° bond angle H2
60° bond angle
CH2 C unstable!!

CH3 CH3
H2C CH2
n-propane cyclopropane
C3H8 C3H6
•Note that two hydrogen atoms were lost in forming the ring!
•What is the general formula for a cycloalkane?
Other Cycloalkanes
Angle (ring) Strain - results from compression of
cyclobutane
the
C4internal
H8 - ~90°bondbond
angles.angles
Cyclopropane has the
greatest angle strain (60° bond angles) while the
strain is eliminated in cyclohexane.
cylcopentane
C5H10 ~109.5° bond angles
Torsional Strain - a barrier to free rotation around
single bonds, due to the eclipsing of atoms in a
molecule. This results when atoms are brought
cyclohexane
too close together in a particular conformation of
aCmolecule.
6H12 = 109.5° bond angles
Cycloalkanes: Cis-Trans Isomerism
• Consider
The Trans-isomer
1,2-dimethylcycloalkane
is the molecule with - abranches
moleculeonthatOPPOSITE
illustrates
GEOMETRIC
sides of the ring
ISOMERISM - compounds with the same molecular
• formula and connectivity
The Cis-isomer but differ
is the molecule within branches
their geometries.
on the SAME SIDE
• of
Thethemolecule
ring. on the left shows the two methyl branches on
• OPPOSITE SIDES ofisthe
Cis-Trans isomerism ring.
one typeThe molecule on
of geometric the right shows
isomerism
the two methyl branches on the SAME SIDE of the ring.

Trans-1,2-dimethylcyclopentane Cis-1,2-dimethylcyclopentane
Cis-Trans Isomers - Examples
cis-1,3-dimethylcyclobutane

Cl
1-chloro-1-methylcyclohexane

cis-1,2-dichlorocyclohexane 2

CH2
6

H3C CH
3
CH1

CH2
5
CH3
4

Cl Cl trans-1-ethyl-2-methylcyclopropane
Cyclohexane - Boat & Chair Conformations
• Cyclohexane is NOT a planar molecule. To achieve its
109.5° bond angles and reduce angle strain, it adopts
several different conformations.
• The BOAT and CHAIR (99%) are two conformations
Alkenes & Alkynes
• Alkenes are • The suffix for the parent
hydrocarbons that chains are changed from
contain at least one “ane” to “ene” and “yne”
carbon-carbon double – e.g. ethene, propyne
bond • Where it is ambiguous,
• Alkynes are the BONDS are
hydrocarbons that numbered like branches
contain at least one so that the location of
carbon-carbon triple the multiple bond may
bond be indicated
Alkenes & Alkynes: Examples
H
CH H2C C
H2C CH2 HC CH3
ethene ethyne propene

propyne 1-butene 2-pentyne

H2
CH C CH3 H3C C C CH2
C 16

H3C H2C C CH3


H
Cis-Trans Isomerism…Again!
• Like rings, alkenes and alkynes show cis-2-butene
restricted rotation - this time about the
H H
multiple bonds C C
• Because of the 120° bond angles in
H3C CH3
alkenes, cis-trans isomerism is possible
– If one of the carbons in the double bond
have two of the same substituents, there is
NO cis-trans isomerism! trans-2-butene
– Remember that “trans” means opposite CH3
sides of the double bond and “cis” means H
C C
the same side of the bond! H
– Use molar mass to prioritize the substituents H3C
to decide cis-trans isomerism
Name those alkenes...
H H
C C
cis-4-methyl-2-pentene 2-methyl-2-hexene
HC
3
CH CH 3

H3C

H2 trans-2-bromo-3-methyl-
C Br 2-pentene
H2cyclopentene
C CH2

C C cis-3-heptene
H H
Homework Assignment
• READ sections 22.2 (Alkenes & Alkynes), 22.3
(Aromatic Hydrocarbons) and 22.4 (The
Petrochemical industry)
– Don’t get hung up on “ and  bonds”
– Copy figure 22.11 and 22.12
– Summarize the use of ortho, meta, para prefixes when
naming benzene derivatives
– Make notes on section 22.4 - the Petrochemical Industry
• Complete Questions 19 - 25, 27, 29, 31, 32, 54 - 56