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+ Br
C
2
H
5
+ HBr propagation
C
2
H
5
+ Br
2
C
2
H
5
Br + Br
propagation
Br
+ Br
Br
2
termination
16. What may be used as an initiator in free-radical halogenation reactions?
An initiator would be the molecular form of the halogen that undergoes homolytic fission upon the absorption of
ultraviolet light to form free radicals.
17. Label the following equations as initiation, propagation and termination:
a) CH
2
CH
+ Cl
2
CH
2
CHCl + Cl
propagation
b) X
+ Y
XY
termination
c) CH
3
+ H
CH
4
termination
d)
Cl
2
2Cl
UV
initiation
e) X
+ RY RX + Y
propagation
20
18. CH
3
Cl in the troposphere is far more stable than CH
3
I. CH
3
Cl will last for about a year in the
troposphere and this gives it sufficient time to enter the stratosphere, where it can destroy ozone.
However, CH
3
I has about a week in the troposphere before being destroyed by light.
a) What is the name given to a light initiated reaction?
A photochemical reaction.
b) Explain why CH
3
Cl is more stable than CH
3
I.
The bond enthalpy of the CCl bond is 338 kJ mol
-1
and the bond enthalpy of the CI bond is 238 kJ mol
-1
. This
means, that more energy is required to break the CCl bond than the CI bond. The reason for this is that CCl
covalent bond is much shorter and hence stronger than the CI covalent bond. Thus, the compound CH
3
Cl is
more stable.
c) Write an equation to show the decomposition of CH
3
I by light energy.
CH
3
I
UV
CH
3
+
+ I
-
10.3 Exercises
1. Define the following terms
a) addition reaction
The addition of a molecule across the double or triple bond in an unsaturated compound.
b) substitution reaction
Where a functional group or a H atom in a molecule is replaced with another functional group or atom.
c) hydrogenation
The addition of hydrogen across the double bond of an alkene or a triple bond in an alkyne.
d) hydrohalogenation
The reaction of alkenes with hydrogen halides to form an addition product where hydrogen and the halide have
added across the double bond. Also applicable to the alkynes.
e) hydration
The addition of water to form another compound. The addition of water across a double bond to give an alcohol
is an example.
f) addition polymerisation
The reaction of alkenes with themselves to form a polymer.
g) polymer
A molecule comprised of repeating units, monomers, connected by covalent bonds.
h) monomer
A small molecule that may bond chemically with other monomers to form a polymer.
i) repeating unit
The shortest sequence that can be found repeatedly in the polymer.
21
2. Why do alkanes typically undergo substitution reactions while alkenes typically undergo addition
reactions?
Alkanes are saturated, alkenes are not. Alkenes typically undergo addition reactions due to the presence of the
double bond, which the reactant may add across. Alkanes do not have this double bond for the reactant to add
across and thus undergo substitution reactions.
3. Hydrogenation is a type of addition reaction.
a) What is the catalyst used in hydrogenation?
A metal catalyst is used, often Ni, Pt or Pd
b) Write a balanced equation to show the reaction for the addition of hydrogen to ethene.
C
2
H
4
+ H
2
C
2
H
6
c) The reaction in (b) is exothermic. Suggest four ways of shifting the equilibrium to the right.
Remove the hydrogenated product as it is produced
Cool down the system
Add excess hydrogen
Add excess ethene
d) How could you check if the reaction in b) was complete?
Add bromine water to the product of the reaction. If the orange colour remains, the reaction has gone to
completion. If the colour disappears, the bromine is adding across a double bond, so starting material must still
be present.
4. The product of the following reaction: CH
3
CH
2
CHCHCH
2
CH
3
+ HCl ? is,
Answer: B This is addition across the double bond.
5. Using structural formula, write the equation for the reaction between 2-butene and
a) H
2
CH
3
CH CH CH
3
+ H
2
CH
3
CH CH CH
3
H H
b) Br
2
CH
3
CH CH CH
3
+ Br
2
CH
3
CH CH CH
3
Br Br
c) HBr
CH
3
CH CH CH
3
+ HBr CH
3
CH CH CH
3
H Br
d) H
2
O (with H
2
SO
4
catalyst)
CH
3
CH CH CH
3
+ H
2
O CH
3
CH CH CH
3
H OH
H
2
SO
4
22
6. When a trace of a strong acid, eg sulfuric acid, is added to a mixture of an alkene and water an
addition reaction occurs.
a) Give an equation for the addition reaction
C
2
H
4
+ H
2
O C
2
H
5
OH
b) What is the role of the sulfuric acid?
The sulphuric acid acts as a catalyst.
7. Which of the following compounds will discolour bromine water?
Answer: D - I and III These are the only unsaturated compounds listed.
8. Give a structural equation and conditions for ethene reacting with:
a) water with H
2
SO
4
catalyst
CH
2
CH
2
+ H
2
O CH
2
CH
2
H OH
H
2
SO
4
b) hydrogen
CH
2
CH
2
+ H
2
CH
2
CH
2
H H
c) bromine
CH
2
CH
2
+ Br
2
CH
2
CH
2
Br Br
d) hydrogen bromide
CH
2
CH
2
+ HBr CH
2
CH
2
H Br
e) with itself in a polymerization reaction
CH
2
CH
2
CH
3
CH
2
CH
2
CH
2
+ CH
2
CH
3
9. Polythene and polyvinylchloride (PVC) are two common plastics.
a) give an equation to show the formation of polythene.
CH
2
CH
2
n
CH
2
CH
2
n
b) give an equation to show the formation of polyvinylchloride.
C C n
C C
n
Cl
H
H
H
H
H
Cl
H
23
c) draw the repeating unit in PVC.
C C
H
H
Cl
H
10. Propene is the monomer used to make polypropene, which may be used in carpets and clothes.
Using structural formulas, give the equation for this polymerization.
C C
CH
3
H
H
H
C C
H
H
CH
3
H
n
n
11. Complete this equation:
a) CH
2
CH=CHCH
2
CH
3
+ Br
2
(aq)
CH
2
CH=CHCH
2
CH
3
+ Br
2
(aq) CH
2
CH
2
CH
2
CH
2
CH
3
b) Describe the colour change seen during the reaction
The orange solution will change to a colourless one.
12. Write an equation to show how you could prepare 1,2-dichlorobutane from an alkene.
CH
2
CH CH
2
CH
3
+ Cl
2
CH
2
CH CH
2
CH
3
Cl Cl
13. What is the main difference between fats and oils?
Fats have higher melting points whereas oils have lower melting points. This is due to the presence of double
bonds which change the shape of the molecule, resulting in kinks in the hydrocarbon chains of fats. These
kinks make the molecules less able to pack together so the van der Waals forces between the molecules are
decreased. This means that these fats have higher melting points.
14. The polyunsaturated oil, linoleic acid and the saturated fat, stearic acid have the same number of
carbon atoms and yet have very different melting points. Explain, with reference to their structures.
C H
2
C
CH
2
H
2
C
CH
2
H
2
C
CH
2
H
2
C
CH HC
CH
2
HC
HC
CH
2
H
2
C
CH
2
H
2
C
CH
3
O
OH
linoleic acid, C
18
H
32
O
2
(mp -5C)
24
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
C
OH
O
CH
2
CH
2
H
3
C
stearic acid, C
18
H
36
O
2
(mp 69C)
Linoleic acid contains alkene groups in the hydrocarbon chain, whereas stearic acid does not. These carbon to
carbon double bonds cause kinks in the chain. These "kinks" do not allow the linoleic acid molecules to align
close together. This is unlike stearic acid, where regular straight chain of carbon atoms allow the molecules to
pack closely together resulting in increased van der Waals, forces. The increased van der Waals forces
between stearic acid molecules are responsible for its higher boiling point over linoleic acid.
15. Indicate which of the following statements are TRUE for the industrial scale production of ethanol:
a) Ethene is used as the starting material
true
b) The product would discolour bromine water
false
c) An acid catalyst is used
true
d) Water is added across a double bond
true
16. The reactions of alkenes have economic importance. For the three key manufacturing processes
that you have learnt about in this topic:
a) Give the name of each reaction
Hydrogenation, hydration and addition polymerisation
b) Illustrate the chemistry behind each reaction by providing a reaction equation for each process
using ethene as the starting material
Hydrogenation: C
2
H
4
+ H
2
C
2
H
6
Hydration: C
2
H
4
+ H
2
O C
2
H
5
O
Addition polymerisation:
C C
H
H
H
H
C C
H
H
H
H
n
n
c) Give the desired product of each manufacturing process
Hydrogenation: to manufacture margarine
Hydration: to produce ethanol from ethene
Addition polymerisation: to manufacture plastics
25
d) Explain the need or importance of the processes by indicating uses of the products.
The hydrogenation of liquid oils to make solid margarine provides a more appropriate melting point substance
for use in the food industry, to manufacture other food products or in the home as a polyunsaturated substitute
for butter.
Ethanol is widely used as a solvent and a precursor in the manufacturing of so many other chemicals.
Polymers for use as plastics are vital in our everyday lives. Polymers may be used as synthetic fibres in
clothing, packaging and technology. Plastics are highly versatile!
10.4 Exercises
1. Write equations for the complete combustion of propanol and butanol.
C
3
H
7
OH
(l)
+ 5O
2
3CO
2(g)
+ 4H
2
O
(l)
C
4
H
9
OH
(l)
+ 6O
2
4CO
2(g)
+ 5H
2
O
(l)
2. Using your IB Chemistry data booklet, compare the standard enthalpies of combustion of ethanol
and octane (major constituent of petrol).
a) Comment on the relative energy densities of ethanol and octane, and propose a reason for the
difference.
The standard enthalpy of combustion of octane is H
o
C
= -5512 kJ mol
-1
.
The standard enthalpy of combustion of ethanol is H
o
C
= -1371 kJ mol
-1
.
So, upon combustion, octane releases much more energy than ethanol per mole. The reason being that ethanol
is already partially oxidised (it contains O) and octane is a larger molecule (4 x more C).
Energy density- energy per gram of fuel:
Octane C
8
H
16
M
r
= 114.26
Number of moles in 1 g =
n = 1g/114.26 g mol
-1
= 8.75 x 10
-3
moles
Energy content per gram =
8.75 x 10
-3
moles x 5512 kJmol
-1
= -48.24 kJ
Ethanol C
2
H
5
OH M
r
= 46.08
Number of moles in 1g
n = 1g/46 g mol
-1
= 0.0217 moles
Energy content per gram =
0.0217 moles x 1371 kJmol
-1
= -29.75 kJ
Octane has the higher energy density.
In deciding what fuel is best to use the chemist considers, among other factors, the
energy density of the fuel. The energy density is the heat energy given out per g or per
kg of fuel. Fuels are purchased by the L or kg, not by the mol. Hence energy density
will give a better comparison of the heat energy available from fuels.
26
b) Considering your answer to (a) why is ethanol being used as a fuel?
As well as the energy content per gram of fuel the other factors that should be taken into account when sourcing
fuel include how much energy is needed to extract or mine the substance, how much energy is required to
transport the fuel, what are the by-products of combustion and how efficient is the fuel (i.e. a fuel may have a
high energy content but may be very inefficient, very little of the fuel may be converted to useful energy). The
main advantage of ethanol is that it is renewable (extracted from corn or sugar cane) while octane is sourced
from oil which is non-renewable and carbon intensive.
c) What are the likely impacts of production of biofuels such as ethanol from biomass?
In the case of ethanol, which is often extracted from cornfields, we must also consider the cost of farming the
land for fuel, as in this case of many countries in South America; the growing of crops for ethanol may come at
the great price of deforestation. Forests are "carbon sinks", they absorb CO
2
from the atmosphere by
photosynthesis. Deforestation may therefore increase CO
2
levels in the atmosphere, contributing to global
warming. The carbon offset obtained from using biofuels such as ethanol may not be significant!
3. Oxidation of primary alcohols can involve two steps.
a) Write equations to illustrate the two step oxidation process of propan-1-ol.
CH
2
CH
2
CH
3
OH
CH CH
2
CH
3
O
C CH
2
CH
3
O
HO
H
+
/Cr
2
O
7
2-
[O]
H
+
/Cr
2
O
7
2-
[O]
b) How could the product of the first oxidation step be isolated in good yield from the reaction?
Refer to intramolecular forces in your answer.
Add the oxidant mixture drop wise into the propanol at the same rate as the propanal (bp 48
O
C) distils over.
The boiling points of propan-1-ol, propanal and propanoic acid are different. Propan-1-ol and propanoic acid are
both capable of hydrogen bonding whilst propanal is not. Only weaker dipole-dipole forces are able to operate
between propanal molecules. As a result, propanol and propanoic acid have much higher boiling points than
propanal. Watch the temperature as you distil. If it exceeds 48
O
C then stop. Collect only the lower bp fraction.
Restricting the amount of oxidant also prevents further oxidation.
c) Outline the reaction conditions required in order to produce a good yield of propanoic acid.
To ensure that all the propan-1-ol is oxidised to propanoic acid, the reaction should be carried out by heating
under reflux with excess oxidant. This will not allow the propanal to escape, as it will condense back in to the
reaction mixture where it can be further oxidised to propanoic acid.
4. Write an equation to show the conversion of butanol to the corresponding aldehyde.
CH
2
CH
2
CH
3
OH
CH CH
2
CH
3
O
H
+
/Cr
2
O
7
2-
[O]
CH
3
CH
3
27
5. Write half equations to show the oxidation of ethanol to ethanal by potassium permanganate in acid
solution. (Hint: you may need to refer back to Topic 9 if you have forgotten how to write half
equations!)
8H
+
+ 5e
-
+ MnO
4
-
Mn
2+
+ 4H
2
O
C
2
H
5
OH C
2
H
4
O + 2H
+
+ 2e
-
6. Determine the products, if any of the following reactions:
a)
C H
3
C C
CH
3
CH
3
OH
H
+
/Cr
2
O
7
2-
[O]
H
H
No reaction the reactant is a tertiary alcohol
b)
CH
2
H
3
C CH
CH
3
OH
[O]
H+/Cr
2
O
7
2-
CH
2
H
3
C C
CH
3
O
but-2-one
c)
H
+
/Cr
2
O
7
2-
[O]
CH
3
(CH
2
)
3
OH
CH
3
(CH
2
)
2
COOH
heated at reflux
2 hrs
butanoic acid
d)
CH
2
CH CH
2
CH
3
CH
2
C
H
+
/Cr
2
O
7
2-
[O]
CH
3
CH
2
CH
3
OH
CH
3
O
pent-3-one
e)
CH
2
OH
H
+
/Cr
2
O
7
2-
[O]
Distill lower boiling
product from mixture
C H
O
aldehyde (benzaldehyde)
28
7. Suggest what alcohol and reaction conditions you might use to obtain the following products after
oxidation:
a) CH
3
CH
2
CHO
Reactant: propan-1-ol
Reaction conditions: Distillation of low boiling point material from reaction mixture. Limit addition of oxidant.
b)
O
Reactant: cyclohexanol
OH
Reaction conditions: Heat under reflux with oxidant. This ketone can not be further oxidised sos there is no need
for a distillation.
c)
H
3
C CH
2
C
O
OH
Reactant: propan-1-ol
Reaction conditions: Heat under reflux. Excess oxidant.
d)
H
3
C
CH
2
CH
CH
2
H
3
C
C
O
OH
Reactant: 2-ethylbutan-1-ol
H
3
C
CH
2
CH
CH
2
H
3
C
CH
2
OH
Reaction conditions: Heat under reflux. Excess oxidant.
e)
H
3
C
CH C
O
OH H
3
C
Precursor: 2-methylpropan-1-ol. Reaction conditions: Heat under reflux. Excess oxidant.
29
f) CH
3
(CH
2
)
3
CHO
Reactant: pentan-1-ol
Reaction conditions: Distillation of low boiling point material from reaction mixture. Limit oxidant.
10.5 Exercises
1. Define, with an example, the following terms:
a) Electrophile
An ion or molecule that is electron deficient and can accept electrons. They may do this by reacting with (or
"attacking") parts of molecules that are rich in electrons in order to gain electrons. An example is a carbon atom
attached to an electronegative group, i.e. the C+ end of a polar covalent bond. H
+
is another.
b) Nucleophile
An ion or molecule that can donate electrons. They are either negative ions (eg OH
-
) or molecules that have
electron pairs (lone pairs or double bonds) eg NH
3
. They are electron rich and in reactions tend to attack
positively charged parts of a molecule.
Electrophiles are electron loving; they seek out electrons.
Nucleophiles seek out the positive; they are nucleus loving.
2. What do curly arrows indicate when used in a reaction mechanism?
Curly arrows are used to show the movement of pairs of electrons in the reaction mechanism. The arrow begins
on the electron pair and the head of the arrow shows where the electrons have moved to.
3. What do
+
and
-
indicate?
Partial positive charge and partial negative charge. These symbols indicate the polarity of a bond moment or
dipole moment. The
-
end of the polar bond is the atom which has the greatest share of the electron pair in the
bond (the more electronegative atom) whilst the
+
end is the atom which does not have the greatest share of
the electron pair in the bond (less electronegative).
4. Consider the following halogenoalkanes: C
2
H
5
I, C
2
H
5
Br, C
2
H
5
Cl and C
2
H
5
F. Which is the least
reactive? Which is the most reactive? Give reasons for your answer.
C
2
H
5
F is the least reactive; C
2
H
5
Br is the most reactive. The CF covalent bond is the strongest because the
small F atom is closest to the C atom. Because the two atoms are closer together, increased orbit overlap
results in a stronger bond. In this case the distance factor overrules the electronegativity factor (ie
electronegativity decreases down the group, and lower electronegativity differences would normally result in a
stronger bond). As a result of the increasing bond strength, the order of these compounds in decreasing
reactivity is: C
2
H
5
I, C
2
H
5
Br, C
2
H
5
Cl and C
2
H
5
F.
30
5. Explain the difference between homolytic and heterolytic bond cleavage. What is the difference
between fission and fusion?
Homolytic bond cleavage is the breaking of a chemical bond into two free radicals, with each radical taking one
electron from the broken chemical bond. Heterolytic cleavage is the breaking of a compound where the two
fragments are oppositely charged ions, with one fragment taking both electrons from the bond.
Fission means splitting, e.g. in nuclear fission the atom is split.
Fusion means joining, e.g. in nuclear fusion H atoms join to make He atoms.
6. Formal charge
a) How many valence electrons does the carbon atom of a carbocation have?
The carbon of a carbocation has three valence electrons. A C atom has 4 outer shell electrons: to become a C+
it must lose one electron, leaving three valence electrons.
Carbocations have a positive C atom, C+, they are intermediates of some organic
reactions.
b) Draw the Lewis structure for the hydroxide ion.
O H
c) What is the formal charge on the carbon atom of a carbocation and the oxygen of the hydroxide
ion?
+1 and -1
7. Number the following carbocations in order of increasing stability.
H
3
C CH
2
C H
3
C
CH
3
CH
3
C H
3
C
H
CH
3
C H
3
C
CH
3
4 1 3 2
The order of stability for carbocations is tertiary > secondary > primary. The more
groups other than hydrogen attached to the C+ the more stabilised the positive
charge.
31
8. Would the following halogenoalkanes undergo S
N
1 or S
N
2 reactions, or both?
Compound 1 , 2 or 3 halogenalkane mechanism
A H
3
C-Cl primary S
N
2
B
C H
3
C
CH
3
Br
tertiary
S
N
1
C CH
3
CH
2
F primary S
N
2
D CH
3
CH(Cl)CH
3
secondary S
N
1 or S
N
2
Tertiary halogenoalkanes favour S
N
1 mechanism.
9. For S
N
1 and S
N
2 reactions, which molecular entities do the terms unimolecular and bimolecular refer
to?
The terms unimolecular and bimolecular refer to the number of molecules involved in the rate determining step
of the reaction. For the S
N
1 reaction, there is only one molecule involved in the rate determining step, whereas
for the S
N
2 reaction, there are two.
10. 1-bromobutane reacts with sodium hydroxide in a nucleophilic substitution reaction.
a) Write an equation for the reaction.
C
4
H
9
Br + NaOH C
4
H
9
OH + NaBr
b) Classify the halogenoalkane as primary, secondary or tertiary.
Primary
c) Explain whether the reaction will proceed by a S
N
1 or S
N
2, mechanism, give reasons for your
answer.
As a primary alkane is undergoing this substitution reaction, it will proceed via the S
N
2 mechanism. This is
because, a primary carbocation intermediate would form if this reaction proceeded by the S
N
1 mechanism. This
is very unstable.
d) Use curly arrows showing electron movement to illustrate the mechanism of the reaction, and
label the electrophile and nucleophile.
C CH
2
CH
2
CH
3
Br
H
H
electrophile
OH
nucleophile
C CH
2
CH
2
CH
3
OH
H
H
+ Br
11. 2-chloro, 2-methylpropane reacts with sodium hydroxide in a nucleophilic substitution reaction.
a) Write an equation for the reaction.
CH
3
(Cl)C(CH
3
)CH
3
+ NaOH CH
3
(OH)C(CH
3
)CH
3
+ NaCl
32
b) Classify the halogenoalkane as primary, secondary or tertiary.
tertiary
c) Explain whether the reaction will proceed by a S
N
1 or S
N
2, mechanism, give reasons for your
answer.
The reaction will proceed by an S
N
1 mechanism. The halogenalkane is tertiary, so when the C-Cl bond is
broken, a tertiary carbocation will be formed readily, as the three R groups are able to stabilise the positive
charge (inductive effects). In terms of steric effects: the tertiary carbocation is sterically hindered so the
nucleophile will not be able to attack the electrophilic carbon atom of the halogenoalkane, until the leaving
group, Cl leaves, ie an S
N
1 mechanism must occur.
d) Use curly arrows showing electron movement to illustrate the mechanism of the reaction, and
label the electrophile and nucleophile
C CH
3
CH
3
H
3
C
electrophile
OH
nucleophile
C CH
3
OH
CH
3
H
3
C
C CH
3
Cl
CH
3
H
3
C
C CH
3
CH
3
H
3
C
12. Suggest products for the following reactions and indicate whether the reaction is S
N
1 or S
N
2:
a)
CH
3
C
CH
3
CH
3
CH
2
Cl
NaOH
CH
3
C
CH
3
CH
3
CH
2
OH
+ NaCl
S
N
2 reaction mechanism
(primary halogenoalkane)
b)
CH
3
CH
2
Br
NaOH
CH
3
CH
2
OH + NaCl
S
N
2 reaction mechanism
(primary halogenoalkane)
10.6 Exercises
1. Complete the reaction pathways scheme on page 335.
Answers shown at end of this section.
33
2. Suggest starting materials and reaction conditions given the following products:
a)
CH
3
CH
2
C
OH
O
H
+
/Cr
2
O
7
2-
[O]
CH
3
CH
2
CH
2
OH
heat at reflux, excess oxidant
b)
CH
3
CH
2
C CH
3
O
H
+
/Cr
2
O
7
2-
[O]
CH
3
CH
2
CH CH
3
OH
heat at reflux (this material can not be oxidised further)
c)
H
3
C
CH
2
C
CH
3
CH
3
OH
CH
3
CH
2
C
CH
3
Cl
CH
3
+ NaOH
dilute NaOH(aq), S
N
1 as tertiary halogenoalkane
d)
H
3
C C C
H
H
Cl
CH
3
CH
3
C C
H
CH
3
CH
3
CH
3
+ HCl
gaseous HCl may be used
e)
HC C C
Br
H
CH
3
CH
3
CH
3
Br
CH
3
HC C C CH
3
CH
3
CH
3
H CH
3
+ Br
2
add Br
2
drop by drop, with shaking
3. Deduce reagents and reaction conditions for the conversions A-G. What are the structures of
products 1 and 2? Provide a mechanism for reactions involving reagents and conditions F and G.
H
2
, nickel
catalyst
B A
C
C
CH
3
H
H
C
C
CH
3
Br
OH
H
H
C
CH
3
H
3
C
OH
C
C
H
3
C
H
H
Br
Br
C E
C
CH
3
CH
3
Br
D
H
C
CH
3
CH
3
NaOH, S
N
1
G
HBr
H2O,
conc.
H
2
SO
4
Br
2
(aq)
Br
2
F
Br
2
2 1
34
4. Deduce reaction pathways given the following reactants and products. No more than two steps
should be used. Include equations, reagents and reaction conditions.
a) acetone from propene
CH
3
CH CH
2
+ H
2
O
CH
3
CH CH
2
OH H
H
+
/Cr
2
O
7
2-
[O]
CH
3
C CH
2
O H
b) acetic acid from ethanol
CH
3
CH
2
OH
H
+
/Cr
2
O
7
2-
[O]
CH
3
C OH
O
heat at reflux
c) carbontetrachloride from chloromethane
C H H
Cl
H
Cl
2
C Cl Cl
Cl
Cl
(heat and a catalyst)
d) formaldehyde from chloromethane
C H H
Cl
H
+ NaOH
C H H
OH
H
H
+
/Cr
2
O
7
2-
[O]
C
O
H H
(warm, dilute NaOH(aq) limited oxidant, methanal, bp 21
O
C, collected by distillation
35
Draw structural formulas for compounds 1-7 and provide reactants and conditions for steps A-J.
C C
H
H
H
H
Cl
2
HCl
H
2
O, conc.
H
2
SO
4
H
2
, Nickel
catalyst
H
+
/Cr
2
O
7
2-
[O]
C C
H
H
H
H
C C H
H
H
H
Cl Cl
C C H
H
H
H
H H
C C H
H
H
H
H Cl
C C
O
H
H
H
H
C C H
H
H
H
H OH
Cl
2
, UV
NaOH,
S
N
2
C C
O
OH
H
H
H
H
+
/Cr
2
O
7
2-
[O]
H
2
C CH
2
C C Cl
H
H
H
Cl Cl
Cl
2
, UV
Cl
2
, UV
A
F
J
I
H
E
C
B
G
D
n
alkene
poly(alkene)
carboxylic acid aldehyde alcohol
halogenalkane
alkane dihalogenoalkane
trihalogenoalkane
(or tetrahalogenalkane)
1 2 3
4
7 6 5
3
6