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ORGANIC CHEMISTRY
CHAPTER 1 :
CARBON COMPOUND
1.1
The Chemistry of Carbon
Organic Chemistry ~ branch of chemistry concerning
compound of carbon (except CO, CO2, CO32-)
Aliphatic
compounds
Open chain
organic
compounds.
Do not have
special stability
like benzene.
Compound may
be unbranched
or branched
Alkane, alkene,
alkyne,
haloalkane
Alicyclic
compounds
Closed ring of
organic
compounds.
Rings may
contain single or
double bonds
Compound may
be branched or
unbranched
Cyclohexane,
cyclobutene
Aromatic
compounds
Contain at least
one benzene
ring (those with
in it)
Heterocyclic
compounds
Closed ring
contain element
other than
carbon in it (like
N, S, O)
Phenol,
naphthalene,
toluene
Pyridine
1.
Hybridisation of alkane, alkene and alkyne
14element. It has the electronic
Carbon is a Group ___
configuration of ______________
1s2 2s2 2p2
The orbital diagram
Ground state of C : _____
_____ _____ _____
2s
2p
Methane, CH4
Type of hybridisation :
Hybridised state :
sp3
Ethene, C2H4
Type of hybridisation :
Hybridised state :
sp2
Molecular shape
Trigonal planar
sp2
_____
pz
Ethyne, C2H2
Type of hybridisation :
Hybridised state :
_____ _____
sp
Molecular shape
Linear
sp
_____ _____
py
pz
Hybridisation in benzene
Benzene (C6H6) is a flat and symmetrical molecule. All the
atom (6 C atom and 6 H atom) in a benzene molecule lie in the
same plane. The Carbon atoms are arranged in the form of
hexagon as shown in diagram at the left.
The formation of benzene can be deduced using hybridisation
theory
_____
pz
hybrid
The structure of benzene is a .....
of 2 forms
The resonance hybrid of benzene can be expressed as
Unlike ethene, the double bond in benzene has a larger volume
(space) to delocalise electron. Hence the more space provided,
the lower the energy in benzene. This makes benzene posses
an extra stability.
1.2
The
the
(a)
(b)
(c)
(d)
Mass
85.63
14.37
Mol
85.63
12
= 7.14 mol
14.37
1
=14.37 mol
Ratio
7.14/7.14
=1
14.37/7.14
=2
Mass
0.8187
0.1822
0.3661
Mol
0.8187
12
=0.0682
0.1822
1
=0.1822
0.3661
16
=0.0229
Ratio
0.0682/0
.0229
=3
0.1822/0
.0229
=8
0.0229/
0.0229
=1
Mass
0.474
0.079
0.947
Mol
0.474
12
=0.0395
0.079
1
=0.079
0.947
16
=0.0592
Ratio
0.0395/0
.0395
=1
0.079/
0.0395
=2
0.0592/
0.0395
= 1.5
b) Displayed formula
a) Shorthand
CH3CH2CH2CH3
c) 3-D @
stereochemical
d) Skeletal formula
c) 3-D @
stereochemical
d) Skeletal formula
e) Simplified notation
CH3(CH2)2CH3
Example
: 2-methylhexane
a) Shorthand
CH(CH3)2CH2CH2CH2CH3
b) Displayed formula
Example :
4,4-dimethylpent-2-ene
a) Shorthand
C(CH3)3CH=CHCH3
b) Displayed formula
c) 3-D @
stereochemical
d) Skeletal formula
Example :
3-ethyl-2,4-dimethylhexane
a) Shorthand
CH(CH3)2CH(CH2CH3)CH(CH3)CH2CH3
c) 3-D @
stereochemical
d) Skeletal formula
b) Displayed formula
Example :
2,2,5-trimethylhex-3-yne
a) Shorthand
C(CH3)3CCCH(CH3)2
b) Displayed formula
c) 3-D @
stereochemical
d) Skeletal formula
1.3
Homologous
series
Alkanes
RH
Examples +
Structural formula
General
formula
pentane
CnH2n+2
Cycloalkane
CH3CH2CH2CH2CH3
heptane
CH3CH2CH2CH2CH2CH2CH3
cyclobutane
Cyclohexane
hex-1-ene
but-2-ene
CnH2n
Alkenes
RCH=CHR
CnH2n
CH2=CHCH2CH2CH2CH3
cyclohexene
Cycloalkene
CnH2n2
CH3CH=CHCH3
cyclobutene
Alkynes
RCCH
propan-1-ol
pentan-3-ol
Butanal
hexanal
Propanone
heptan-3-one
CnH2nO
Ketone
RCOR
2-bromopentane
CnH2n+1OH /
CnH2n+2O
Aldehyde
RCOH
1-chlorobutane
CnH2n+1X
(X = Cl, Br, I)
Alcohol
ROH
pent-1-yne
CnH2n2
Haloalkane
RX
Propyne
CnH2nO
Carboxylic
acid
RCOOH
propyl butanoate
ethylamine
butylamine
propylamide ;
pentylamide
CnH2n+1NH2
Amide
RCONH2
ethyl ethanoate ;
CnH2n+1COO
CmH2m+1 /
CnH2nO2
Primary
amine
RNH2
pentanoic acid
CnH2n+1COOH
CnH2nO2
Ester
RCOOR
butanoic acid ;
CnH2n+1CONH2
1.4
Alkyl and Type of Alkyl groups
Alkyl group ~ obtained by removing a hydrogen atom from an
alkane.
Symbol of alkyl is R, where R has the general formula of
CnH2n+1.
Alkane
Alkyl
Alkane
Alkyl
Methane
Methyl
CH3
Ethane
Ethyl
C2H5
Propane
Propyl
C3H7
Butane
Butyl
C4H9
C5H11
Hexane
Hexyl
C6H13
Pentane
Pentyl
Example
Comment
Primary
Secondary
Tertiary
1.5
Isomerism in Organic Compound
Isomers ~ substances which have the same molecular formula
but different molecular structure
Isomerism
Structural
isomerism
Chain
isomerism
Position
isomerism
Stereoisomerism
Functional
isomerism
Geometrical
isomerism
Optical
isomerism
Butan-1-ol (C4H9OH)
CH3CH2CH2CH2CH3
CH3CH2CH2CH2OH
C(CH3)4
CH(CH3)2CH2OH
CH3CH2CH(CH3)2
1-chloropentane (C5H11Cl)
Hexanal (C6H12O)
CH(CH3)2CH2CH2CHO
CH3CH2CH2CH2CH2CHO
CH3CH2CH2CH2Cl
CH3CH2CH(CH3)CH2Cl
C(CH3)3OH
C(CH3)3CH2CHO
C(CH3)3CH2Cl
CH(CH2CH3)2CHO
Bromohexane (C6H13Br)
CH3CHBrCH2CH2CH2CH3
CH2=CHCH2CH2CH2CH3 CH3CH=CHCH2CH2CH3
CH3CH2CH=CHCH2CH3
Pentanol (C5H11OH)
CH3CH2CH2CH2CH2OH
CH3CH2CH2CH(OH)CH3
CH3CH2CH(OH)CH2CH3
CH2BrCH2CH2CH2CH2CH3
CH3CH2CHBrCH2CH2CH3
Dichlorobenzene (C6H4Cl2)
3.
Functional isomerism ~ isomers which has the same
molecular formula but different molecule with different
functioning group.
Alkene and cycloalkane C5H10
1.5.2 Stereoisomerism
Geometrical Isomerism ~ same structural formula but different
spatial arrangement.
~ also known as cis-trans isomer
~The essential requirement for the existence of geometrical
isomerism in organic compound must contains a carbon carbon
double bond (C=C)
~ A ring structure which hinders the rotation of a CC single
bond in a ring.
However, cis-trans isomers cannot occur if one of the carbon
atoms in the double bond has 2 identical atoms / groups.
1,2-dichloroethene
1,1-dichloroethene
pent-2-ene
1,2-dimethylcyclobutene
But-2-ene-1,4-dioic acid
1,4-dichlorocyclohexane
(2)
Optical isomerism
Optical activity is the ability of certain crystal or solution of
certain substances to rotate the plane of plane-polarised light.
Such substances are said to be optically active (sometimes
are known as chiral molecule)
Optical isomers are optically active substances which possess
the same molecular structure but different in their effect
on plane polarised light.
For an optically active isomer, the object and mirrored image
cannot be superimposable to one and another. Example, in 1bromo-1-chloro-1fluoromethane (CHClBrF), it shows optical
active when brought to plane-polarised light.
CH3CH2CH(Cl)CH3
C(CH3)2(Br)(OH)
CH3CBr=CH2
HOCH2CH(NH2)COOH
CH3CH2CH(OH)CH3
Aluminium trichloride
react with chloride ion
to form
tetrachloroaluminate
ion
Water molecule
attached to cobalt ion
to form
hexaaquacobalt (III)
ion.
Definition
Examples
Electrophile
:OH
RO:
:Cl
H+ (H3O+)
NO2+
Cl2 ; Cl+
:Br
:I
CN:
Br2 ; Br+
I2 ; I+
carbonium
:C
carbanion
ROH
C=C
RN2+
R3C+
BF3
:NH2
RNH2
H2O
AlCl3
FeBr3
ZnCl2
1.7
Inductive Effect and Mesomeric Effect
Inductive effect is defines as the shift in electron density from one
atom to another to form a polar bond.
For example, in the bonding of CCl. In the presentation of inductive
effect, the arrow shows that carbon atom repel electrons
+
Cl ; Br
;I
NO2
CN
COOH
COOR
C=O
SO3H
C6H5
1.8
Type of Organic
Reaction
Substitution
Addition
Elimination
Definition : one or
more atom / group is
substitute by another
atom / group of atoms
Definition : a small
Definition : 2 reactants atom / group is
react together and
removed (eliminated)
form 1 product
from the molecule
involve
Example :
CH3CH2Cl + OH
CH3CH2OH + Cl
Example :
CH2=CH2 + Br2
CH2(Br) CH2(Br)
Example
CH3CH2OH
CH2=CH2 + H2O
Heterolytic fission
o Shared electron in the covalent bond
only goes to one of the atom. The pair
of electron usually goes to the atom
with higher electronegative
o Eventually, one will become negatively
charged (as a result of receiving extra
electron) while the other become
positively charged (lose electron to the
other party)
o Example :
Cl Cl :Cl + Cl
(CH3)3CBr :Br + (CH3)3C
Practice
1.Base on the molecular structure, draw the hybridisation diagram
of the following molecules, state the type of hybridisation and its
shape, and state the angle of each hybridised structure
a) CH3CH=CHOH
b) CHCCH2NH2
H
Displayed formula
CH(CH3)2C(CH3)2CH2CH2CH3
C(CH3)3CH(CH2CH3)2
CH(CH3)2CH(CH3)CH=C(CH3)2
CH(CH3)2CH(OH)CH(CH2CH3)2
Skeletal formula
CH2(NH2)CH(C6H5)CONH2
COHCH(Br)C(CH3)2CH2COOH
COHC(CH3)2CH(OH)CCCH3
COOHCH(CH3)CH2C(CH3)(CH2CH3)CH2CH(OH)(CH3)
CH2ClCOCH2CHNH2CH2CH2CONH2
Haloalkane,
Ketone ;
Amine ,
Amide
Aldehyde ;
Alcohol ;
Alkyne
Carboxylic acid
Molecules
Type of
isomerism
geometrical
geometrical
Optical
Diagram of isomers
CH2ClCH=C(CH3)CH2COOH
geometrical
geometrical
optical
optical
Particles
Particles
Particles
Br2
electrophile
Br+
electrophile
Br-
nucleophile
NH3
nucleophile
CH3NH2
nucleophile
NH2+
electrophile
CH3-
nucleophile
CH3COH
electrophile
CH3+
electrophile
nucleophile
nucleophile
electrophile