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Organic Chemistry
10.1 Introduction
20.1 Introduction (AHL)
10.2 Alkanes
10.3 Alkenes
10
10.4 Alcohols
10.5 Halogenoalkanes
10.6 Reaction pathways
20.5 Reaction pathways (AHL)
20.2 Nucleophilic substitution reactions (AHL)
20.3 Elimination reactions (AHL)
20.4 Condensation reactions (AHL)
20.6 Stereoisomerism (AHL)
10.1 introduction
10.1.1 Describe the features of a homologous
series.
10.1.2 Predict and explain the trends in boiling
points of members of a homologous
series.
10.1.13 Discuss the volatility and solubility
in water of compounds containing the
functional groups listed in AS 10.1.9.
IBO 2007
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Chapter 10
changes that occur in the strength of van der Waals forces
with increasing molar mass and in some cases a change in
molecular polarity. The simplest illustration of the effect
of chain length on physical properties is the variation of
the boiling point of the alkanes with the number of carbon
atoms in the chain, as illustrated in Figure 1002.
hydrocarbon skeleton
CORE
functional groups
FIGURE 1001 Diagrammatic representation of an organic
molecule
Boiling point / C
100
10
100
200
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Organic Chemistry
b.p. = 89C
O
H
H
H
Mr = 32
OH
CORE
CH3CH2CH2COOH or CH3(CH2)2COOH
condensed structural formula
As noted previously, the molecular formula gives the
actual number of each type of atom in the molecule and
the empirical formula the simplest whole number ratio of
these. For butanoic acid these are:
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Chapter 10
Isomers
CORE
Structural Isomers
Different bonding
Positional
Isomers
Hydrocarbon
Chain Isomers
Stereoisomers
Different shapes
Functional
Group Isomers
and
CH3 CH2 OH
Ethanol
CH3
CH3
Methoxymethane
CH3
Methylpropane
CH3 CH CH3
H5C2
C2H5
H
H2C
H2C
Hex-3-ene
H3C
CH2 C
Propanal
CH2
CH2
CH2
CH2
Cyclohexane
H
O
O
H3C
CH3
Propanone
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Organic Chemistry
Carboxylic acid and Ester
H3C
OH
Ethanoic Acid
H3C
O
H
Methyl methanoate
CORE
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Chapter 10
CORE
but
Butyl
pent
Pentyl
hex
Hexyl
Benzene ring
benz
Phenyl
H
H3C
CH
CH2
CH2
CH3
IBO 2007
No. of C atoms
Stem
Side chain
meth
Methyl
eth
Ethyl
prop
Propyl
CH3
H3C
CH2
CH
CH
CH2
Propane
Cyclopentane
CH3
H3C
CH2
CH
CH3
Methylbutane
Figure 1009
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Organic Chemistry
Name
Functional group
Prefix/suffix
Example
Alkane
None
-ane
CH4; methane
Alkene
C=C
-ene
CH2=CH2; ethene
Alcohol
OH or OH
CH3CH2OH; ethanol
Aldehyde
O
C
or
-anal
CH3CHO; ethanal
-anone
CH3COCH3; propanone
AHL
IBO 2007
CHO
O
C
Ketone
or CO
Carboxylic acid
C O H or COOH
Halogenoalkane
(chloro, bromo, or X (i.e. Cl, Br, I)
iodoalkane)
Amine
Ester
Nitrile
N H or NH2
(or amino-)
C N
O
R
Halogeno-
H
O
Amide
-anoic acid
H
H or CONH2
-anamide
CN
-anenitrile
or-CN
(or cyano-)
CH3COOH;
ethanoic acid
CH3CH2Cl; chloroethane
CH3CH2NH2; ethylamine
CH3CONH2; ethanamide
CH3COOCH3
Methyl ethanoate
CH3CN
Ethanenitrile
(cyanomethane)
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Chapter 10
this latter way, brackets are used to denote side chains, for
example methylbutane would be CH3CH(CH3)CH2CH3.
AHL
e.g.
HOCH2CH(CH3)CHO
is
3hydroxy-2-methylpropanal (h comes before m;
note CHO must be a terminal group and the COOH
group is the same)
is
C
C
X
C
H
Secondary
H
Primary
C
C
C
C
Tertiary
e.g.
(CH3)3CCl
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Organic Chemistry
1.
6.
20.1
A
B
C
D
2.
Hydrogen
2
1
1
2
Oxygen
2
2
3
3
B
C
D
H3C
H3C
CH2
H3C
H3C
8.
CH2
CH2
C
CH3 CH2 C
A
B
C
D
9.
CH2 CH2
D
Br
CH3
Ketone
Alcohol
Carboxylic acid
Aldehyde
CH3
CH2
2
3
4
8
CH2 CH3
A
CH2
B
CH2
7.
C3H8
CH3CH=CH2
CH3(CH2)3CH3
C4H10
AHL
Exercise
CH3CH2CH2CH2CH2NH2
CH3CH2CH2CH2NH2
CH3CH2CH2CONH2
CH3CH2CH2CH2CONH2
NH2
2-chlorobutanal
4-chlorobutanal
2-chloropentanal
4-chloropentanal
3.
4.
5.
a)
b)
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Chapter 10
c)
d)
e)
AHL
a)
b)
c)
d)
e)
formulae
of
the
following
Pentane
3ethylhexane
Bromoethane
2methylbut1ene
3.3dichloro2methylbutanoic acid
No. of Molecular
C atoms Formula
1
CH4
Structural
formula
Name
Methane
H
H
C2H6
Ethane
C3H8
Propane
positional isomerism
b)
c)
CH3OCH2CH2CH2CH3
C4H10
C5H12
C6H14
Butane
Pentane
Hexane
b)
CH3 C
CH2
CH3
CH3 CH2 CH
Cl
CH2 CH3
c)
CH3CHICH2CH2OH
d)
HOC(CH3)2CH2CH2COOH
264
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Organic Chemistry
H H
Butane
H
H
H
H
H H H
Methylpropane
C 5H12
H
H
H
H
H
Methylbutane
H
H
CO2 + H2O
C8H18 + O2
Pentane
CORE
C 4 H10
H
H
H
H
H
H
H
H
H
Dimethylpropane
10.2 Alkanes
10.2.1 Explain the low reactivity of alkanes
in terms of bond enthalpies and bond
polarity.
10.2.2 Describe, using equations, the complete
and incomplete combustion of alkanes.
IBO 2007
C8H18 + 12 O2
8 CO2 + 9 H2O
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Chapter 10
CORE
Cl
Cl
Cl
Cl
+ H
CH3
CH3 + Cl
Cl
Cl
Cl
H +
CH3
Cl + Cl
CH3
Cl
Cl
+ Cl
+
CH3
CH3 + CH3
Cl
Cl
CH3
CH3
Cl
CH3
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10.3 Alkenes
10.1.7 Deduce structural formulas for the
isomers of the straight-chain alkenes up
to C6.
CORE
Organic Chemistry
No. of C atoms
Molecular formula
Name
Structural formula
H
C2H4
Ethene
C3H6
Propene
C4H8
C5H10
C6H12
Pent-1-ene
Hex-1-ene
C
H
H
C
H
H
But-1-ene
H
H
H
H H H
H H H
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Chapter 10
10.3.1 Describe, using equations, the reactions of
alkenes with hydrogen and halogens.
CORE
+ Br 2
Br Br
+ HCl
H Cl
C + H2
Nickel
Catalyst
H H
+ H2O
OH
H
H
H
H
Ethene monomers
H H H H H H
C
H H H H H H
Polyethene polymer
268
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Organic Chemistry
n CH2=CH2
[CH2CH2]n
n CH2=CHCl
H
H
[CH2CHCl]n
Cl
Cl
Exercise
1.
B
C
D
2.
H Cl H Cl H Cl
C
H H H H H H
Poly(chloroethene) [PVC] polymer
Figure 1022 Polymerisation of chloroethene to form
poly(chloroethene)
3.
n CH2=CHCH3
H
H
CH3
CH3
CH3
H
Propene monomers
4.
BrCH2CH=CH2
CH3CH2CHBr2
CH3CHBrCH2Br
BrCH2CBr=CH2
[CH2CHCH3]n
10.3
Cl
Chloroethene monomers
CORE
C3H6
C6H14
C8H18
C12H26
Moles of water
8
8
4
4
Polypropene polymer
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Chapter 10
5.
CORE
A
B
C
D
6.
Nitrogen
Hydrogen
Water vapour
Carbon monoxide
7.
8.
b)
c)
d)
e)
f)
b)
c)
is very reactive.
results from the breaking of a covalent
bond.
is formed by the action of UV light on a
molecule.
contains unpaired electrons.
a)
a)
9.
CH3CH=CH2
CH3CH2CH3
d)
e)
f)
g)
b)
c)
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Organic Chemistry
C6H12O6 (aq)
O H
H
Primary
(One C atom
on OH carbon)
H
C
O H
C
Secondary
C2H5OH (g)
catalyst
C2H5OH (l)
CORE
10.4 Alcohols
(Two C atoms
on OH carbon)
C
C
O H
C
Tertiary
(Three C atoms
on OH carbon)
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Chapter 10
Tertiary
Alcohol
C
C
CORE
Secondary
H
Alcohol
C C
Primary
Alcohol
C
Ketone
C C O
No further oxidation
Aldehyde
Carboxylic acid
CH3CH2OH + 2 [O]
Cr2O72/H+
ethanol
Intermediate stage
CH3COOH + H2O
ethanoic acid
(a) Distillation
Water out
Alcohol
Water out
Water in
Water in
Aldehyde
Reaction mixture
Reaction mixture
Heat
Heat
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Organic Chemistry
O
O
R
H
(aq)
H+
(aq)
(aq)
FIgure 1027
Exercise
1.
2.
3.
10.4
4
5
9
10
10.5
Halogenoalkanes
10.5.1 Describe, using equations, the
substitution reactions of halogenoalkanes
with sodium hydroxide.
10.5.2 Explain the substitution reactions of
halogenoalkanes with sodium hydroxide
in terms of SN1 and SN2 mechanisms.
CORE
IBO2007
RX (l) + OH (aq)
C+
X-
(slow)
OH
(fast)
Carbocation
intermediate
C+
OH
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Chapter 10
Experimentally, the rate expression for this reaction is
found to be:
CORE
rate = k [RX]
that is it is first order with respect to halogenoalkane and
independent of (zero order in) the concentration of the
hydroxide ion.
The second mechanism is known as SN2. In this
mechanism, the bimolecular (hence the 2) attack of the
hydroxide ion on the halogenoalkane molecule is rate
determining. The reaction passes through a transition
state (or activated complex) in which the bond to the
hydroxide ion is starting to form at the same time as the
bond to the halogen breaks, hence the substitution occurs
in one concerted step:
OH
With
primary
halogenoalkanes
(for
example
CH3CH2CH2CH2Cl) reaction with nucleophiles, such as
the hydroxide ion, usually occurs by the SN2 mechanism,
whereas with tertiary halogenoalkanes (for example
(CH3)3CCl) it usually occurs by the SN1 mechanism. With
secondary halogenoalkanes (such as CH3CH2CHClCH3)
both mechanisms can occur.
Exercise
1.
2.
HO
3.
HO
rate = k[R-X]1[OH]1
Like alcohols, halogenoalkanes can be divided into
primary, secondary and tertiary according to the number
of groups bonded to the same carbon as the halogen:
H
C
H
X
Primary
Secondary
Tertiary
CH3CH2CHBrCH2CH3
CH3CH2CH2CH2CH2Br
CH3C(CH3)BrCH2CH3
CH3CH2CH2CHBrCH3
CH3COCH3
CH3CH2CH2I
CH3CH2CH2OH
CH3CH(OH)CH3
Transition state
10.5
C
D
4.
5.
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Organic Chemistry
CH3CH2CH2I + OH
CH3CH2CH2OH + I
CH3CH2CH2OH + [O]
CH3CH2CHO + H2O
alkane
CORE
10.6 Reaction
pathways
Cr2O72-/H+
dihalogenoalkane
trihalogenoalkane
tetrahalogenoalkane
halogenoalkane
alkene
poly(alkene)
aldehyde
carboxylic acid
alcohol
M = mechanism required
ketone
Figure 1031 Standard Level Reaction Pathways
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Chapter 10
M
alkene
halogenoalkane
nitrile
amine
alcohol
carboxylic acid
ester
amide
AHL
M = mechanism required
Figure 1032 Higher Level Reaction Pathways
HIGHER LEVEL
20.5 Reaction
pathways (AHL)
Exercise
1.
2.
3.
CH3Cl
CH2Cl2
CHCl3
CCl4
CH3CH2Br (g)
(* indicates HL question)
A
B
C
D
IBO2007
10.5
an aldehyde.
an alcohol.
a halogenoalkane.
an alkane.
An aldehyde.
A ketone.
A carboxylic acid.
An alkane.
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Organic Chemistry
4*. Which one two compounds can react to form an
amide?
An alcohol and a carboxylic acid.
An amine and an alcohol.
A halogenoalkane and an amine.
An amine and a carboxylic acid.
Energy
20.2 Nucleophilic
substitution
reactions (AHL)
AHL
A
B
C
D
HIGHER LEVEL
Intermediate
R3C+
Reactants
R3C-X
Products
R3C-X---Nu
Extent of reaction
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Chapter 10
In the SN2 mechanism the breaking of the carbon-halogen
bond occurs simultaneously with the formation of the new
bond to the nucleophile. The point at which both are half
completed is known as the transition state and it occurs at
a potential energy maximum on the energy level diagram
in Figure 1034.
Transition state
Energy
Ea
C -- X: broken
C -- Nu: made
CH3CH2X
CH3CH2Nu
AHL
Progress of reaction
Figure 1034 Energy profile of a SN2 reaction
The rate at which these reactions occur depends on the
nature of both the nucleophile and the halogenoalkanes.
For example some species are described as being stronger
nucleophiles because they more readily attack a carbon with
a partial positive charge. The hydroxide ion, for example,
is a stronger nucleophile than the water molecule because
it is negatively charged and hence attracted to the partial
positive charge on the carbon attached to the halogen. As
a result SN2 hydrolysis reactions occur far more rapidly in
aqueous alkali than in neutral solution.
The nature of the halogen also affects the rate of reaction.
There are two factors. Firstly, as the halogen changes from
chlorine to iodine, the polarity of the carbonhalogen
bond decreases and this would be expected to decrease
the rate of reaction going from chlorine to iodine because
the partial positive charge on the carbon would become
smaller. Secondly, the strength of the carbonhalogen bond
decreases going from chlorine to iodine and it would be
expected to have the opposite effect. In practice it is found
that the rate of hydrolysis is greater for iodoalkanes than it
is for chloroalkanes, implying that the bond strength is the
dominant factor: see Figure 1035.
CCl
CBr
CI
278
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Organic Chemistry
NC
NC
H3N
Transition state
Transition state
H+ + H2N
1.
Note that the product above is the cation formed from the
amine and it must lose a hydrogen ion to form the amine
itself. Similarly the reaction of a primary halogenoalkane
with the cyanide ion to form a nitrile will occur by an SN2
mechanism as shown in Figure 1037.
RX (l) + CN (aq)
2.
20.2
a nitrile
an amine
a carboxylic acid
an amide
3.
RCH2NH2 (l)
Exercise
H3N
NC
AHL
CH3CH(CH3)CH2Br
(CH3)3CBr
CH3CH2CH2CH2Br
CH3CHBrCH2CH3
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Chapter 10
A
B
C
D
4.
a)
b)
c)
d)
AHL
5.
Ammonia
Water
Bromide
Hydroxide
a)
b)
c)
20.3 Elimination
reactions (AHL)
20.3.1 Describe, using equations, the
elimination of HBr from bromoalkanes.
20.3.2 Describe and explain the mechanism
for the elimination of HBr from
bromoalkanes.
C2H5OH + OH
C2H5O + H2O
C2H5O
C2H5O
Br
Br -
IBO2007
C2H5OH + Br-
C2H5Br
(substitution)
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Organic Chemistry
1.
2.
Concentration
Temperature
Ethanol
5 mol dm-3
70C
Ethanol
40C
Water
5 mol dm-3
40C
Water
70C
3.
20.3
a nucleophile.
an oxidising agent.
a reducing agent.
a base.
pent-1-ene only.
pent-2-ene only.
a mixture of pent-1-ene and pent-2-ene.
a mixture of pent-1-ene and pentan-3ol.
4.
5.
b)
c)
d)
20.4 Condensation
reactions (AHL)
20.4.1 Describe, using equations, the reactions
of alcohols with carboxylic acids to form
esters, and state the uses of esters.
IBO2007
CH3 CO
OH + CH3 CH2 OH
ethanoic acid
AHL
Exercise
ethanol
H2 SO 4
catalyst
CH3 CO
ethyl ethanoate
In these reactions, known as esterification reactions, the
small amount of sulfuric acid has two functions. Firstly,
and most importantly, the hydrogen ions act as a catalyst to
increase the rate of the reaction and secondly it reacts with
the water formed to shift the position of the equilibrium
to the right hand side (Le Chateliers principle) ensuring
a good yield of product. Note that unlike the acid and
alcohol, an ester does not contain an OH group and so is
much more limited in its ability to hydrogen bond to water
molecules, hence esters tend to be insoluble in water.
It can be seen that the naming of esters is rather different
from that of other organic compounds. They are named as
if they were salts of the alcohol and the acid; the alcohol
provides the first half of the name (alkyl) and the organic
acid provides the second half of the name (alkanoate). In
naming an ester it is important to remember that the CO
group is part of the carboxylic acid. The molecule below
is therefore methyl propanoate (not propyl methanoate),
because it can be considered as being formed from
methanol and propanoic acid.
This bond is part
This bond is part
of the acid
of the alcohol
CH 3
CO CH2 CH3
methanol/propanoic acid
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Chapter 10
polymers, two different functional groups are required
and for each new bond between the monomer units
(shown coloured below), a small molecule (often water) is
produced. Each monomer must also have two functional
groups. This can involve two different functional groups on
the same monomer or more frequently, as in the examples
below, two different monomers which have two identical
groups on them. One group of condensation polymers are
the polyesters, so called because the bonding depends on
the reaction of an alcohol with a carboxylic acid to form an
ester. The best known example of this polymer is Terylene,
formed by the reaction of benzene1.4dicarboxylic acid
with ethane1.2diol. as shown in Figure 1042(a)
Ethanoic acid
methylammonium ethanoate
[OCH2CH2OCO
AHL
Methylamine
N-methylethanamide
[HN(CH2)6NHCO(CH2)4CO].
...
HO
CH2CH2 OH
HOOC
COOH
HO
CH2CH2 OH
ethane1.2diol
...
CO].
COOH
HOOC
...
benzene1.4dicarboxylic acid
OCH2CH2O
CO
CO
OCH2CH2O
CO
CO
...
+ 3 H2O
Terylene
hexane1.6diamine
hexanedioic acid
HN(CH2)6NHCO(CH2)4COHN(CH2)6NHCO(CH2)4CO
+ H2O
+ H2O
+ H2O
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Organic Chemistry
1.
2.
3.
20.4
prop-1-yl methanoate.
prop-1-yl ethanoate.
ethyl propanoate.
methyl butanoate.
HOCOCH2CH2CH2COOH
HO
C
D
HOCOCH2CH2CH2NH2
CH3CH2CH2CONH2
COOH
4.
5.
a)
b)
c)
d)
20.6
Stereoisomerism
(AHL)
20.6.1 Describe stereoisomers as compounds
with the same structural formula but with
different arrangements of atoms in space.
20.6.2 Describe and explain geometrical
isomerism in non-cyclic alkenes.
20.6.3 Describe and explain geometrical
isomerism in C3 and C4 cycloalkanes.
20.6.4 Explain the difference in the physical
and chemical properties of geometrical
isomers.
IBO2007
AHL
Exercise
Geometric Isomerism
Cl
Cl
C
Cl
H
C
cis1.2dichloroethene
C
Cl
trans1.2dichloroethene
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Chapter 10
These isomers are known as geometric isomers and the
forms of 1.2dichloroethene (ClCH=CHCl) is a typical
example. The isomer in which the groups or substituents
are on the same side of the double bond is known as the
cisisomer, the one with them on opposite sides is the
transisomer.
AHL
CO
OH
CO
OH
cis1.2 dichlorocyclopropane
Cl
C
H
Cl
trans1.2 dichlorocyclopropane
Cl
C
Cl
Optical isomerism
20.6.5 Describe and explain optical isomerism in
simple organic molecules.
20.6.6 Outline the use of a polarimeter in
distinguishing between optical isomers.
20.6.7 Compare the physical and chemical
properties of enantiomers.
IBO2007
CO
CO
H2O
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Organic Chemistry
OH
OH
*C
CH3
C5H5
Rotate by 180
*C
C5H5
OH
CH3
*C
CH3
H
C5H5
Mirror images
Figure 1046 Optical isomerism
Optically inactive
Incident
normal
light
Vertical
polarising
filter
Second
polarising
filter
Light
passing
through
Vertical
maximum
Horizontal
none
AHL
Optically active
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AHL
Chapter 10
Plane polarised light can be considered to be light in which
the oscillation of the wave is restricted to one plane, say the
vertical. This can be achieved by passing the light through a
polarising filter. If the light is now passed through a second
polarising filter orientated in the same direction (vertical)
then there is virtually 100% transmission (see Figure 1045).
If the second polarising filter has its axis at right angles to
the first (horizontal) then no light will pass. A pure optical
isomer placed between the two filters will rotate the plane
of polarisation in one direction (say clockwise) so that
maximum transmission is no longer when the second
filter is aligned with the first one. The second optical
isomer will rotate the plane of polarisation by exactly the
same amount (assuming equal concentration), but in the
opposite direction (anticlockwise). Substances that affect
polarised light in this way are said to be optically active.
An instrument containing two polarising filters that can be
rotated relative to each other, separated by a compartment
in which the plane polarise light passes through a liquid,
allowing the angle through which the plane of polarisation
is rotated is called a polarimeter. See Figure 1047.
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Reflux with
acidified
Cr2O72-
R/H-CH2 -CO-H
Distil with
acidified
Cr2O72-
High T &
conc. alc.
alkali
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R/H-CHX-CH2 X
R/H-C 2 H3 X2
isomers
X 2 at
room
T&P
R/H-CH2 -CO-OH
Heat with
trace of
c. H2SO 4
R/H-CH=CH 2
HX at
room
T&P
R/H-CHX-CH3
R/H-CH2 -CH2 -X
R/H-C 2 H4 X
isomers
R/H-CO-CH3
Heat with
acidified
Cr2O72-
R/H-CH(OH)-CH3
H2 & Ni
catalyst
R/H-CH2 -CH3
Polyhalogenated
isomers
Organic Chemistry
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Chapter 10
Exercise
1.
20.6
CH3CH=CH2
CH3CCl=CH2
CH3CH=CHCl
CH3CH=CCl2
2.
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A
B
C
D
3.
b)
The first
The second
The third
The fourth
CH3CH2CH2CH2OH
(CH3)2CHCH2OH
CH3CH2CH(OH)CH3
(CH3)3COH
5.
a)
4.
6.
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