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Electrophilic addition
Hydrogenation, H2
1)
Halogenations, Cl2, Br2
2)
Hydrohalogenation, HCl, HBr
3)
Hydration, H2O
4)
b) oxidation
complete combustion
5)
present catalyst, Ag
6)
cold KMnO4, H+
7)
hot KMnO4, H+
8)
ozonolysis, O3
9)
c)
addition polymerization
QUESTIONS
ANSWERS
(1) Write down the structure of the products, if any, of the following reactions
(a)
(ethene)
(b)
(c)
(2) Write down the structure of the products, if any, of the following reactions.
(a)
(b)
(3) 10.8 g of an alkene required 9.6 dm3 of hydrogen gas for complete hydrogenation at room conditions.
Write down the possible structural formula of the alkene. [Molar mass of the alkene = 54.0 g mol -1; 1 mol of gas
occupies 24.0 dm3 at room conditions]
QUESTION
ANSWER
3
(1) Give the equations, the conditions and the names of the products when
(a) propene reacts with bromine
(2)
Would you expect a species which attacks
alkenes to be an electrophile or a nudeophile?
Give a reason for your answer.
(3)Name and draw structural formulae for the products of the following halogenation
(a)
(b)
1. An alkene reacts readily at room temperature with an aqueous solution of bromine (bromine water) to produce a
mixture of products, bromo alcohol and dibromoalkane.
2. The bromine water would be decolorised
1. Write a
Note: 2-B
unsymme
Water has lone pairs of electrons and can act as nucleophiles in competition with bromide ions, Br - .
2. Write a
(a) but-2-
(b) but-l-e
3. When ethene is bubbled into bromine water, the reddish-brown bromine water is rapidly decolorised
and a mixture of 2-bromoethanol and 1,2-dibromoethane is produced
4. If the bromine water is dilute, bromoalcohol would be the main product because there will be more
water molecules than bromide ions present.
(b) The addition of hydrogen halide to a carbon-carbon double bond in an unsymmetrical alkene follows the
MARKOVNIKOFF'S RULE, that is, the hydrogen atom of the hydrogen halide adds to the carbon atom of
the double bond with the greatest number of hydrogen atoms.
(c)An unsymmetrical carbon-carbon double bond is
one whose two carbon atoms hold unequal number
of hydrogen atoms.
EXAMPLES :
The carbon-carbon double bond is a site that can accept a proton from an acid and forms carbocation
STABILITY OF CARBOCATION
(a) In the reaction between propene and hydrogen bromide, the initial attack is by the acid catalyst
(b) When the hydrogen ion, H+, attacks the double bond in propene, two different carbocatino
can be formed.
(f)
The order of stability of the carbocations is as follows:
The tertiary carbocation is the most stable because it has three electron-donating alkyl groups which tend to cancel out
the positive charge more than the secondary or primary carbocation.
QUESTIONS
(a) When but-1-ene, CH3 - CH2 - CH = CH2, reacts
with hydrogen bromide, what are the
structures of the two possible intermediate
carbocations formed?
ANSWERS
QUESTIONS
ANSWERS
(1)Name and draw the structural formulae for the major products of these addition reactions of alkenes.
(a)
(b)
(c)
(2)
Suggest why when 2-methylpropene reacts with hydrogen iodide, the major product is 2 - iodo- 2 - methylpropane.
When 2-methylpropene reacts with hydrogen iodide, two different carbocations could be formed:
(4) Name and draw structural formulae for the major products of these addition reactions of alkenes
(a)
(b)
(c)
QUESTIONS
ANSWERS
2. Draw structural formulae for the major products of these acid-catalysed hydration reactions of alkenes.
(a)
(b)
(c)
(4)
1. When steam and ethene are passed over a catalyst, ethanol is produced. A temperature of 330C and a pressure of
60 atm are used in the presence of phosphoric acid catalyst.
Name and draw structural formulae for the major products of these addition reactions of alkenes
(a)
(b)
2. When ethene is added to dilute potassium manganate(VII) acidified with dilute sulphuric(VI) acid at room
10
temperature, the purple colour of the potassium manganate(VII) is decolorised and ethene is oxidised to
ethane- I,2-diol.
3. If the reaction involves cold dilute potassium manganate(VII) in alkaline conditions, the purple colour of the
potassium manganate(VII) is decolorised, producing ethane-l,2-diol and a brown precipitate of manganese(IV) oxide.
(2) Reaction With Hot, Concentrated Potassium Manganate (Vii)
Acidified With Dilute Sulphuric(Vi) Acid
1. If an alkene is added to hot, concentrated potassium manganate(VII) acidified with dilute sulphuric(VI)
acid, the carbon-carbon double bond is oxidatively cleaved, i.e. the double bond breaks and produces
ketones, aldehydes, carboxylic acid (from further oxidation of aldehydes formed), carbon dioxide or
mixtures of these.
3. When 2-methylbut-2-ene is added to hot, concentrated acidified potassium manganate(VII), it is oxidised with the
breaking of the carbon-carbon double bond to give ethanal (an aldehyde) and propanone (a ketone). The ethanal is further
oxidised to ethanoic acid. The purple colour of the potassium manganate(VII) is decolorised.
1. An unknown alkene X with the formula CSH16 was found on oxidation with hot, acidified potassium manganate(VII) to
11
2. Write structures for the product(s) that would form under the conditions shown:
(a)
(b)
(c)
(d)
(e)
QUESTIONS
ANSWERS
3.Write structures for the organic product(s) that would form under the conditions shown
(a)
(b)
(c)
12
(d)
(b)
POLYMERISATION
1. Alkenes containing carbon-carbon double
bonds can polymerise (addition
polymerization) joining together to form
long chain molecules. No atoms or
molecules are eliminated in this process.
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3. There are two types of poly(ethene), depending on the conditions used for preparation.
(a) (i) Low-density poly(ethene) is manufactured by
heating ethene at about 200C and a pressure of 1 200
atmosphere with traces of oxygen (initators).
(ii) Low-density poly(ethene) has chain branching
which makes it difficult to pack closely.
It has a low melting point, 105C, softens in boiling
water and deforms easily.
(iii) It is used for making plastic bags and wrappers.
Ethane-1,2-diol is prepared by
reacting ethene with oxygen in the
presence of a heated silver catalyst,
followed by addition of water.
Ethanol is manufactured by
hydration of ethene using
phosphoric acid catalyst on silica al
300C and 60 atmospheres.
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REACTIONS
1
TYPE OF
REACTION
Electrophilic
addition
Alkene alkane
Alkene dihaloalkane
Alkene haloalkane
4
5
Alkenedibromoalkane
+
bromoalcohol
Alkenealcohol
Alkenediol
Carboxylic
Alkene diol
(industrial method)
REAGENT(S)
CONDITION(S)
H2(g); Ni catalyst
150C; 5 atm
H2(g); Pt catalyst
Room temperature
Electrophilic
addition
Electrophilic
addition
Electrophilic
addition
Room temperature
Electrophilic
addition
Oxidation
Cold
Warm
Cold
Cold
Hot
Hot
O2(g); Ag catalyst
followed by water
180C
Room temperature
Oxidation and
cleavage
acid
Oxidation
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