Organic Chem

1.
Which of the following statements about alkenes is not correct?

A.
They have reactive double bonds.
B.
They can form addition polymers.
C.
They react mainly by substitution.
D.
They can react with water to form alcohols.

(Total 1 mark)
2.
What is the type of mechanism and an important feature of the reaction between C(CH3)3Br
and aqueous NaOH?
Mechanism
Feature
A.
SN1
a transition state
B.
SN1
an intermediate
C.
SN2
a transition state
D.
SN2
an intermediate
(Total 1 mark)
3.
Which of the following are isomers of pentane?

I.
2-methylpentane
II.
methylbutane
III.
dimethylpropane
A.
I and II only
B.
I and III only
C.
II and III only
D.
I, II and III
(Total 1 mark)
IB Questionbank Chemistry
4.
Which of the following pairs are members of the same homologous series?
A.
CH3CH2CH2OH and CH3CH2CHO
B.
CH3CH(OH)CH3 and CH3CH2CH(OH)CH3
C.
CH3COCH3 and CH3CH2COOH
D.
CH3COCH2CH3 and CH3CH2CHO

(Total 1 mark)
5.
Alkenes are important starting materials for a variety of products.

(a)
State and explain the trend of the boiling points of the first five members of the alkene
homologous series.
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(3)
(b)
Describe two features of a homologous series.

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(2)
(Total 5 marks)
6.
Below is a schematic diagram representing some reactions of ethene. The letters AD represent
the organic compounds formed from the reactants and catalysts shown.
Deduce the structural formulas of compounds A, B, C, and D and state the IUPAC name of
compound C.
A:
B:
C:
IUPAC name: ..............................................................................................................
D:
(Total 5 marks)
7.
Describe a chemical test that could be used to distinguish between pent-1-ene and pentane.
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(Total 2 marks)
8.
State and explain whether the following molecules are primary, secondary or tertiary
halogenoalkanes.
E:
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F:
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G:
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(Total 4 marks)
9.
Explain, using equations, the following steps in the free-radical mechanism of the reaction of
methane with chlorine.
Initiation
Propagation
Termination
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(Total 4 marks)
10.
Butan-2-ol cannot be directly converted to 1,2-dibromobutane. The conversion can be carried

out in two stages by first converting butan-2-ol into X, which is then reacted with bromine.
Br2
? X
butan-2-ol
1,2-dibromobutane
(a)
State the name and draw the structural formula of X.

Name: ..........................................................................................................................
Structure:
(2)
(b)
State an equation and the conditions needed for the conversion of butan-2-ol into X.
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(2)
(c)
Describe the mechanism of the second stage of the conversion, which occurs when
bromine is added to X, using curly arrows to show the movement of electron pairs.
(3)
(d)
Butan-1-ol could be used instead of butan-2-ol. Compare the yield of 1,2-dibromobutane

expected for butan-1-ol with that obtained for butan-2-ol. Explain your answer.
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(2)
(Total 9 marks)
11.
Compare the rates of hydrolysis of the compounds below and suggest two reasons for the
difference in reactivity.
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(Total 3 marks)
12.
State the formula of the product formed when 2-chloropropane reacts with magnesium to form
a Grignard reagent and state the conditions required for this reaction to occur.
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(Total 2 marks)
13.
Grignard reagents are often used to increase the length of the hydrocarbon chain in molecules.
An alternative way of doing this is to use cyanohydrins such as:
(i)
State the reagents that react to produce this compound.

......................................................................................................................................
(1)
(ii)
Draw the structural formula of the organic compound that is produced by the hydrolysis
of this cyanohydrin.
(1)
(Total 2 marks)
14.
(a)
State the class of compounds to which the substance below belongs and deduce a
balanced equation for its reaction with aqueous sodium hydroxide.
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(2)
(b)
Explain how the pH of an aqueous solution of the organic product from part (a) would
compare with the pH of aqueous ammonia of the same concentration.
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(2)
(Total 4 marks)
15.
Which molecule has a chiral centre?

A.
CH3CH=CHCHO
B.
(CH3)2C=CHCH2OH
C.
CH3OCH2CH3
D.
CH3CHOHCH2CH3
(Total 1 mark)
16.
The compounds H2NCH2CH2NH2 and HOOCCH2COOH react to form a polymer. What is the
structure of the repeating unit of the polymer?
A.
( HNCH2CONHCH2CH2NHCO )
B.
( HNCH2CH2NHCOCH2CO )
C.
( OCCH2CONHCH2NHCO )
D.
( HNCH2CH2NHCOCH2NH )
(Total 1 mark)
10
17.
Which two molecules are cis-trans isomers of each other?
A.
X and Z
B.
X and Y
C.
W and Y
D.
W and Z
(Total 1 mark)
18.
What is the correct order of reaction types in the following sequence?

I C H OH
II C H COOH
III
C3H7Br
C2H5COOC2H5
3 7
2 5
I
II
III
A.
substitution
oxidation
condensation
B.
addition
substitution
condensation
C.
oxidation
substitution
condensation
D.
substitution
oxidation
substitution
(Total 1 mark)
11
19.
Two compounds, A and D, each have the formula C4H9Cl.

Compound A is reacted with dilute aqueous sodium hydroxide to produce compound B with a
formula of C4H10O. Compound B is then oxidized with acidified potassium manganate(VII) to
produce compound C with a formula of C4H8O. Compound C resists further oxidation by
acidified potassium manganate(VII).
Compound D is reacted with dilute aqueous sodium hydroxide to produce compound E with a
formula of C4H10O. Compound E does not react with acidified potassium manganate(VII).
Deduce the structural formulas for compounds A, B, C, D and E.
A:
B:
C:
D:
E:
(Total 5 marks)
12
20.
Deduce an equation for the reaction between propanoic acid and methanol. Identify the catalyst
and state the name of the organic compound, X, formed.
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(Total 4 marks)
C:
D:
E:
(Total 5 marks)
13
21.
2-chloro-3-methylbutane reacts with sodium hydroxide via an SN2 mechanism.

Explain the mechanism by using curly arrows to represent the movement of electron pairs.
(Total 4 marks)
22.
1-chlorobutane can be converted to a pentylamine via a two stage process.

Deduce equations for each step of this conversion including any catalyst required and name the
organic product produced at each stage.
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(Total 5 marks)
14
23.
Describe the mechanism for the reaction of water with ethanoyl chloride.
(Total 4 marks)
24.
(a)
Describe the mechanism for the reaction of benzene with chlorine, using curly arrows to
show the movement of electron pairs, including the role of any other substance required
for the reaction to occur.
(4)
15
(b)
Methylbenzene and nitrobenzene also react with chlorine under similar conditions.
Explain the relative rates at which these two reactions occur.
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(2)
(Total 6 marks)
25.
Which organic molecule is not a structural isomer of pentan-1-ol?

A.
pentan-2-ol
B.
2-methylpentan-2-ol
C.
2-methylbutan-2-ol
D.
pentan-3-ol
(Total 1 mark)
26.
Which of the structures below is an aldehyde?

A.
CH3CH2CH2CH2OH
B.
CH3CH2COCH3
C.
CH3CH2COOCH3
D.
CH3CH2CH2CHO
(Total 1 mark)
16
27.
What product is formed when CH3CH(OH)CH3 is reacted with acidified potassium

dichromate(VI)?
A.
CH3COOCH3
B.
CH3CH2CHO
C.
CH3CH2COOH
D.
CH3COCH3
(Total 1 mark)
28.
Which type of reaction occurs when 2-iodo-2-methylpropane, C(CH3)3I, reacts with aqueous
sodium hydroxide, NaOH(aq)?
A.
Addition
B.
Free-radical substitution
C.
SN1
D.
SN2
(Total 1 mark)
29.
(i)
Describe a chemical test that could be used to distinguish between propane and propene.
In each case state the result of the test.
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(2)
17
(ii)
Under certain conditions propene can polymerize to form poly(propene). State the type of
polymerization taking place and draw a section of the polymer to represent the repeating
unit.
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(2)
(iii)
Other than polymerization, state one reaction of alkenes which is of economic

importance.
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(1)
(Total 5 marks)
30.
Propan-1-ol and propan-2-ol are two structural isomers of C3H8O.

(i)
State the equation for the complete combustion of C3H8O.

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......................................................................................................................................
(2)
(ii)
Both propan-1-ol and propan-2-ol can be oxidized in aqueous solution by potassium

dichromate(VI). State any necessary conditions for the oxidation to occur and describe
the colour change during the oxidation process.
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(3)
18
(iii)
State the name(s) and structure(s) of the organic product(s) that can be formed when each
of the alcohols is oxidized and suggest why one of the alcohols gives two organic
products and the other only gives one organic product.
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(5)
(Total 10 marks)
31.
Benzene, C6H6, is a planar compound which differs from the non-planar structure of
cyclohexane, C6H12. The structures of benzene and the most stable form of cyclohexane are
represented below.
19
(a)
With reference to the compounds benzene, cyclohexane and 1,3-cyclohexadiene, state

which compound would contain the shortest carbon-carbon bond length.
......................................................................................................................................
(1)
(b)
Explain why it is more common for benzene to undergo substitution reactions than
addition reactions.
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(1)
(Total 2 marks)
32.
Suggest why chloromethylbenzene, C6H5CH2Cl, reacts with warm aqueous sodium hydroxide,
NaOH, easily whereas for chlorobenzene, C6H5Cl, stronger conditions such as high temperature
(e.g. 350 C) are needed.
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(Total 2 marks)
33.
(a)
Draw the structural formulas of the major organic products formed in the following
reactions.
(i)
H3CCH=CH2 + ICl
(1)
20
(ii)
H3CCHO + HCN
(1)
(iii)
(1)
(iv)
1. H 3CCHO
CH3MgI
2. H O
2
(1)
21
(b)
Draw the structural formula of the other product of the reaction in part (a) (i).
(1)
(c)
Identify each of the types of reaction in (a) as elimination, nucleophilic addition,

electrophilic addition, acid-base, addition-elimination or Grignard.
Reaction
Type
(a) (i)
(a) (ii)
(a) (iii)
(a) (iv)
(4)
(Total 9 marks)
22
34.
Identify a suitable catalyst for the dehydration reaction of ethanol, CH3CH2OH, and describe
and explain the mechanism of the reaction using curly arrows to represent the movement of
electron pairs. State the name of the organic product formed.
Catalyst:
................................................................................................................................................
Mechanism:
Name of organic product:

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(Total 4 marks)
35.
Deduce a two-step reaction pathway which can be used to convert butan-1-ol, CH3(CH2)3OH,
into 1,2-dibromobutane, CH3CH2CHBrCH2Br. State the reagents used in each step and identify
the product formed in step 1.
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(Total 3 marks)
23
36.
Halogenoalkanes can undergo SN1 and SN2 reactions with aqueous sodium hydroxide.
Which halogenoalkane will react fastest with a 0.1 mol dm3 solution of aqueous sodium
hydroxide?
A.
2-chloro-2-methylpropane
B.
2-iodo-2-methylpropane
C.
1-chlorobutane
D.
1-iodobutane
(Total 1 mark)
37.
Propanitrile can be prepared by reacting bromoethane with potassium cyanide. Which statement
is not correct about the reaction between bromoethane and potassium cyanide?
A.
The reaction is bi-molecular.
B.
The reaction follows the SN2 mechanism.
C.
Homolytic fission occurs between the carbon-bromine bond in bromoethane.
D.
The cyanide ion, :CN, acts as a nucleophile.

(Total 1 mark)
24
38.
Which reactants could be used to form the compound below?
A.
Butanoic acid and ethanol
B.
Propanoic acid and ethanol
C.
Ethanoic acid and propan-1-ol
D.
Ethanoic acid and butan-1-ol

(Total 1 mark)
25
39.
Which compound is optically active?
(Total 1 mark)
40.
There are several structural isomers with the molecular formula C5H11Br.
(a)
Deduce the name of one of the isomers which can exist as enantiomers and draw
three-dimensional representations of its two enantiomers.
......................................................................................................................................
(3)
26
(b)
All the isomers react when warmed with a dilute aqueous solution of sodium hydroxide
according to the equation below.
C5H11Br + NaOH C5H11OH + NaBr
(i)
The reaction with 1-bromopentane proceeds by an SN2 mechanism. Describe this

mechanism using structural formulas and curly arrows to represent the movement
of electron pairs.
(3)
(ii)
The reaction with 2-bromo-2-methylbutane proceeds by an SN1 mechanism.

Describe this mechanism using structural formulas and curly arrows to represent
the movement of electron pairs.
(3)
27
(iii)
Explain why 1-bromopentane reacts by an SN2 mechanism whereas

2-bromo-2-methylbutane reacts by an SN1 mechanism.
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(3)
(iv)
Explain whether the boiling point of 1-bromopentane will be higher, lower or the
same as that of 2-bromo-2-methylbutane.
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(3)
(v)
The product C5H11OH formed from the reaction with 1-bromopentane is warmed
with ethanoic acid in the presence of a few drops of concentrated sulfuric acid.
State the name of the type of reaction taking place and the structural formula of the
organic product.
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...........................................................................................................................
(2)
28
(c)
If the conditions of the reaction in (b) are changed so that a hot solution of sodium
hydroxide in ethanol is used then a different reaction occurs. The reaction with
2-bromo-2-methylbutane gives two different organic products. State the type of reaction
taking place and suggest the identity (name or structure) of these two products.
Explain whether or not they can exist as geometrical isomers.
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(4)
(Total 21 marks)
41.
Dihalogenoalkanes can react with warm dilute potassium hydroxide solution to form diols.
These diols can react with dicarboxylic acids.
(i)
Deduce the equation for the reaction of benzene-1,4-dicarboxylic acid with the diol
formed from 1,5-dibromopentane.
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(3)
29
(ii)
Outline the economic importance of the reaction of diols with dicarboxylic acids.
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(1)
(Total 4 marks)
42.
(a)
Identify all the major products, AD, in the following reactions.

(i)
CH3COCl + CH3CH2NH2 A + B
A:
B:
(1)
(ii)
H SO 4
+ 2HNO3 2
C + D + 2H2O
C:
D:
(1)
30
(b)
C and D are isomers. Explain the mechanism of the reaction in (a) (ii), forming one of
these two isomers, using curly arrows to represent the movement of electron pairs.
(3)
(Total 5 marks)
43.
Benzene reacts with ethanoyl chloride, CH3COCl, in the presence of an aluminium chloride
catalyst, AlCl3, in an acylation reaction. Explain the mechanism of the reaction, using curly
arrows to represent the movement of electron pairs. Include the formation of the electrophile.
(Total 4 marks)
31
44.
Which is the best definition of structural isomers?

A.
Compounds which have atoms with the same atomic numbers but different mass numbers
B.
Compounds which have the same general formula but differ by a CH2 group
C.
Compounds which have the same empirical formula but different molecular formulas
D.
Compounds which have the same molecular formula but different arrangements of atoms
(Total 1 mark)
45.
Which is the correct classification of these alcohols?
2
1
3
3
A.
tertiary
secondary
primary
B.
tertiary
primary
secondary
C.
tertiary
tertiary
secondary
D.
secondary
primary
secondary
(Total 1 mark)
32
46.
Which substances are possible products of the incomplete combustion of octane?

A.
Carbon dioxide and hydrogen gas
B.
Carbon monoxide and water vapour
C.
Carbon monoxide and hydrogen gas
D.
Methane and hydrogen gas

(Total 1 mark)
47.
Which structure could represent a repeating unit of a polymer formed from propene?
A.
( CH2CH(CH3) )
B.
( CH2CH2CH2 )
C.
( CH(CH3)CH(CH3) )
D.
( CH2CH2 )
(Total 1 mark)
48.
Chloroethene, C2H3Cl, is an important organic compound used to manufacture the polymer

poly(chloroethene).
(i)
Draw the Lewis structure for chloroethene and predict the H C Cl bond angle.
......................................................................................................................................
(2)
(ii)
Draw a section of poly(chloroethene) containing six carbon atoms.
(1)
33
(iii)
Outline why the polymerization of alkenes is of economic importance and why the
disposal of plastics is a problem.
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(2)
(Total 5 marks)
49.
(i)
Chloroethene can be converted to ethanol in two steps. For each step deduce an overall
equation for the reaction taking place.
Step 1:
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Step 2:
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(2)
(ii)
State the reagents and conditions necessary to prepare ethanoic acid from ethanol in the
laboratory.
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(2)
34
(iii)
State an equation, including state symbols, for the reaction of ethanoic acid with water.
Identify a Brnsted-Lowry acid in the equation and its conjugate base.
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(3)
(Total 7 marks)
50.
Ethanol is part of the homologous series of alcohols. Describe two features of a homologous
series.
(Total 2 marks)
35
51.
(a)
(i)
Below are four structural isomers of alcohols with molecular formula C4H10O.
State the name of each of the isomers A, B, C and D.
(4)
(ii)
Determine the isomer that cannot be oxidized by acidified potassium

dichromate(VI), K2Cr2O7.
(1)
(iii)
Determine the isomer which can be oxidized to butanal.

(1)
(iv)
Determine the isomer which can be oxidized to butanone.

(1)
(v)
Suggest the structural formula of another isomer of C4H10O.

(1)
36
(b)
(i)
Isomer A is formed by reacting 1-bromobutane with aqueous sodium hydroxide.

State whether the reaction would proceed via an SN1 or SN2 mechanism.
(1)
(ii)
Explain the mechanism named in part (b) (i) using curly arrows to represent the
movement of electron pairs.
(3)
(Total 12 marks)
52.
When bromoethane reacts with magnesium in the presence of a non-polar solvent, a Grignard
reagent is formed.
(a)
Give the equation for the reaction of this Grignard reagent with water.
......................................................................................................................................
......................................................................................................................................
(2)
(b)
This Grignard reagent can also react with aldehydes and ketones to give an initial
product which can then be hydrolysed by water to form an alcohol. State the names and
formulas of the alcohols formed when the Grignard reagent reacts with
(i)
ethanal.
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(2)
37
(ii)
propanone.
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(2)
(Total 6 marks)
53.
Alcohols can undergo elimination reactions in the presence of hot concentrated phosphoric
acid.
(i)
Name the organic product formed when butan-1-ol undergoes an elimination reaction.
......................................................................................................................................
(1)
(ii)
Explain the mechanism for this elimination reaction using curly arrows to represent the
(3)
(Total 4 marks)
38
54.
Alkenes can undergo electrophilic addition reactions with bromine and with hydrogen bromide.
(a)
Explain how a bromine molecule is able to act as an electrophile.

......................................................................................................................................
......................................................................................................................................
(1)
(b)
Name the product formed when but-2-ene reacts with

(i)
bromine.
...........................................................................................................................
(1)
(ii)
hydrogen bromide.
...........................................................................................................................
(1)
(Total 3 marks)
39
55.
When but-1-ene reacts with hydrogen bromide, two possible organic products could be formed
but in practice only one organic product is obtained in high yield. Explain the mechanism for
this reaction using curly arrows to represent the movement of electron pairs and explain clearly
why only one organic product is formed.
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(Total 4 marks)
56.
Benzene is sometimes represented as containing three alternate double and single bonds (Fig.1)
and sometimes represented as a hexagon with a circle in the middle (Fig.2).
Fig.1
Fig.2
40
(a)
Describe two different types of physical evidence which show that benzene does not
contain three double bonds.
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......................................................................................................................................
......................................................................................................................................
(2)
(b)
Explain how the reaction of benzene with bromine provides chemical evidence that
benzene does not contain three double bonds.
......................................................................................................................................
......................................................................................................................................
(1)
(Total 3 marks)
57.
What is the IUPAC name of CH3CH2CONH2?
A.
Aminopropanal
B.
Ethanamide
C.
Propylamine
D.
Propanamide
(Total 1 mark)
41
58.
What is the main organic product formed from the reaction of CH3CH2OH with
CH3CH2CH2COOH in the presence of an acid catalyst?
A.
Ethyl butanoate
B.
Butyl ethanoate
C.
Ethyl propanoate
D.
Propyl ethanoate
(Total 1 mark)
59.
What are some uses of esters?

I.
Flavouring agents
II.
Perfumes
III.
Solvents
A.
I and II only
B.
I and III only
C.
II and III only
D.
I, II and III
(Total 1 mark)
60.
How many isomers can exist for a compound with the molecular formula C2H2Cl2?
A.
B.
C.
D.
4
(Total 1 mark)
42
61.
(a)
Below are four structural isomers with molecular formula C4H9Br. State the name of
each of the isomers A, B, C and D.
(4)
(b)
(i)
Identify the isomer(s) which will react with aqueous sodium hydroxide almost
exclusively by an SN1 mechanism. State the meaning of the symbols in the term
SN1 mechanism.
(2)
(ii)
Using the formula RBr to represent a bromoalkane, state an equation for the rate
determining step of this SN1 reaction.
(1)
(iii)
Identify one isomer that will react with aqueous sodium hydroxide almost
exclusively by an SN2 mechanism. Draw the mechanism for this reaction using
curly arrows to represent the movement of electron pairs. Include the structural
formulas of the transition state and the organic product.
(4)
43
(c)
State and explain how the rates of the reactions in parts (b) (i) and (b) (iii) are affected
when the concentration of the sodium hydroxide is doubled.
(2)
(d)
State and explain how the rate of reaction of 1-bromobutane with sodium hydroxide
compares with that of 1-chlorobutane with sodium hydroxide.
(2)
(e)
Identify the isomer of C4H9Br that can exist as stereoisomers. Outline how a polarimeter
will distinguish between the isomers, and how their physical and chemical properties
compare.
(5)
(f)
(i)
State the type of reaction that occurs when isomer B, CH3CHBrCH2CH3, reacts
with a hot alcoholic solution of sodium hydroxide.
(1)
(ii)
Explain how the reaction in part (f) (i) occurs by drawing the mechanism, using
curly arrows to represent the movement of electron pairs and identify the two
possible organic products.
(4)
(Total 25 marks)
62.
Outline the different mechanisms involved in the manufacture of low-density poly(ethene) and
high-density poly(ethene).
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 2 marks)
44
63.
Methylbenzene can be prepared from benzene and iodomethane.

State the catalyst used in this reaction and explain the mechanism of the reaction using curly
arrows to represent the movement of electron pairs.
Catalyst: ................................................................................................................................
(Total 4 marks)
64.
Methylbenzene reacts when heated with a mixture of concentrated sulfuric acid and
concentrated nitric acid.
(i)
Name the major organic products formed.

......................................................................................................................................
......................................................................................................................................
(1)
(ii)
Identify the electrophile in this reaction and explain how it is formed.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)
(Total 4 marks)
45
65.
What is the structural formula of 2,3-dibromo-3-methylhexane?

A.
CH3CHBrCHBrCH(CH3)CH2CH3
B.
CH3CHBrCBr(CH3)CH2CH2CH3
C.
CH3CH2CHBrCBr(CH2CH3)2
D.
CH3CHBrCHBrCH(CH2CH3)2
(Total 1 mark)
66.
What happens when a few drops of bromine water are added to excess hex-1-ene and the
mixture is shaken?
I.
The colour of the bromine water disappears.
II.
The organic product formed does not contain any carbon-carbon double bonds.
III.
2-bromohexane is formed.
A.
I and II only
B.
I and III only
C.
II and III only
D.
I, II and III
(Total 1 mark)
67.
What is the product of the following reaction?

2
Cr2 O 7 /H
CH3CH(OH)CH3
A.
CH3COOH
B.
CH3COCH3
C.
CH3CH2COOH
D.
CH3CH2CH3
(Total 1 mark)
46
68.
Alkenes are an economically and chemically important family of organic compounds.

(i)
The reaction of alkenes with bromine water provides a test for unsaturation in the
laboratory. Describe the colour change when bromine water is added to chloroethene.
(1)
(ii)
Deduce the Lewis structure of chloroethene and identify the formula of the repeating unit
of the polymer poly(chloroethene).
(2)
(iii)
Besides polymerization, state two commercial uses of the reactions of alkenes.

(2)
(Total 5 marks)
69.
But-2-ene can be converted to butan-2-one in two stages.

(i)
Draw the structural formulas of but-2-ene and butan-2-one.

(2)
(ii)
Deduce a reaction pathway for the two stages of the reaction. Your answer should
include the fully balanced equation for each stage of the reaction and the reagents and
conditions for the two stages.
(5)
(Total 7 marks)
70.
(i)
Deduce the structural formulas of the two alcohol isomers of molecular formula C3H8O.
Name each isomer and identify each as either a primary or a secondary alcohol.
(3)
(ii)
Oxidation of the alcohol isomers lead to the formation of different organic products.
Determine the structures of the organic products formed from the oxidation of each
alcohol isomer in (i) above and list the conditions required to obtain the different
products.
(5)
(Total 8 marks)
47
71.
Addition of hydrogen halides to unsymmetrical alkenes produces a mixture of halogenoalkanes.

The latter can be converted into Grignard reagents by reaction with magnesium metal and then
used for the preparation of various organic molecules with an increased number of carbon
atoms.
State in the boxes below, the formulas of the organic substances needed to complete the
following reaction pathways.
(Total 4 marks)
48
72.
Describe, using equations and curly arrows to represent the movement of electron pairs, the
mechanism of the reaction between propene and hydrogen bromide. Compare the relative
stabilities of the two intermediate carbocations which lead to the formation of the major and
minor products.
(Total 4 marks)
73.
Hydrolysis of aliphatic and aromatic halides occurs under different conditions.

State an equation, using structural formulas, to show the reaction of 1-chloro-2-(chloromethyl)
benzene with excess sodium hydroxide at room temperature.
(Total 2 marks)
49
74.
Deduce a two-step reaction pathway for the conversion of butan-1-ol into 1,2-dibromobutane.
State the appropriate equations, the reaction conditions and the reaction type for each step.
Step 1:
................................................................................................................................................
Reaction type for step 1:
................................................................................................................................................
Step 2:
................................................................................................................................................
Reaction type for step 2:
................................................................................................................................................
(Total 5 marks)
75.
The acidity of carboxylic acids depends on the carbon chain length and the nature of
substituents in their molecules. Table 15 of the Data Booklet provides some examples.
(a)
State and explain how the presence of halogen atoms in the hydrocarbon chain affects the
acidity of carboxylic acids.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)
(b)
State how the acidity of 3-chloropropanoic acid compares to that of propanoic acid and
chloroethanoic acid.
......................................................................................................................................
......................................................................................................................................
(1)
50
(c)
Suggest the pKa value for 3-chloropropanoic acid.

......................................................................................................................................
(1)
(Total 5 marks)
76.
What organic product is formed in the following reaction?

H 2SO 4
(CH3CH2)CH=CH(CH2CH3) + H2O
A.
CH3(CH2)2CH(OH)CH2CH3
B.
CH3(CH2)5CH3
C.
CH3(CH2)2CH(OSO3H)CH2CH3
D.
CH3(CH2)6OH
(Total 1 mark)
77.
What is the IUPAC name for the following compound?

CH3(CH2)2COOCH3
A.
Methyl butanoate
B.
Butyl ethanoate
C.
Butyl methanoate
D.
Methyl propanoate
(Total 1 mark)
51
78.
What is the product of the following reaction?

Ni
CH3CH2CH2CN + 2H2
A.
CH3CH2CH2NH2
B.
CH3CH2CH2CH2NH2
C.
CH3CH2NH2
D.
CH3CH2CH2CH3
(Total 1 mark)
79.
How many chiral carbon atoms are present in a molecule of 2,3-dibromobutane?

A.
B.
C.
D.
4
(Total 1 mark)
80.
Existence of isomers leads to diversity of organic compounds.

(a)
Describe what is meant by the term stereoisomers.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
52
(b)
1,3-dichlorocyclobutane exists as geometrical isomers, a form of stereoisomers.

(i)
Draw and name the two geometrical isomers of 1,3-dichlorocyclobutane.
...........................................................................................................................
(2)
(ii)
Identify the isomer with the higher boiling point and explain your reasoning.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(3)
(Total 7 marks)
81.
Halogenoalkanes undergo two major types of reaction leading to the formation of different
organic compounds.
(i)
1-bromopropane can be converted to 1-butylamine (butan-1-amine) in two stages.

Draw the structural formulas of 1-bromopropane and 1-butylamine (butan-1-amine).
(1)
53
(ii)
Deduce a reaction pathway for the two-stage conversion of 1-bromopropane to

1-butylamine (butan-1-amine). Your answer should include an equation for each stage of
the reaction and the reaction conditions for the second stage.
(4)
(Total 5 marks)
82.
(i)
Describe the elimination of HBr from bromoethane. Your answer should include the
reagents, conditions and equation for the reaction.
(3)
(ii)
Explain the mechanism for the elimination of HBr from bromoethane.

(5)
(Total 8 marks)
83.
Alkylation of benzene is a common industrial process that allows substituents to be introduced

into the aromatic ring.
(a)
State an equation to show the reaction of benzene with chloromethane in the presence of
a Lewis acid.
(1)
54
(b)
Describe, using equations and curly arrows to represent the movement of electron pairs,
the mechanism of the above reaction.
(4)
(Total 5 marks)
84.
When benzene undergoes alkylation, more than one substituent can be introduced into the
aromatic ring. In contrast, acylation of methylbenzene usually gives a single organic product.
(a)
State an equation, using structural formulas, to show the reaction of methylbenzene with
ethanoyl chloride in the presence of a Lewis acid.
(2)
55
(b)
Give two reasons why other organic products do not form in this reaction.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 4 marks)
85.
State the structural formulas of the two organic products formed in the reaction below and state
the reaction type.
Reaction type: ........................................................................................................................

(Total 3 marks)
56
86.
Which of the following substances are structural isomers of each other?

I.
CH3(CH2)3CH3
II.
(CH3)2CHCH3
III.
CH3CH(CH3)CH2CH3
A.
I and II only
B.
I and III only
C.
II and III only
D.
I, II and III
(Total 1 mark)
87.
Which order is correct when the following substances are arranged in order of increasing
boiling point?
A.
CH3CH3 < CH3CHO < CH3CH2OH
B.
CH3CHO < CH3CH2OH < CH3CH3
C.
CH3CH2OH < CH3CH3 < CH3CHO
D.
CH3CH3 < CH3CH2OH < CH3CHO

(Total 1 mark)
57
88.
Which monomer could be used to form a polymer with the following repeating unit?
A.
CH3CH2Cl
B.
CH2ClCH2Cl
C.
CH2CHCl
D.
CHClCHCl
(Total 1 mark)
89.
Which reaction pathway describes how ethanol can be formed?

A.
addition
eliminatio n
ethene
chloroethane
ethanol
B.
substituti on
nucleophil ic substituti on
ethane
chloroethane
ethanol
C.
substituti on
ethene
ethanol
D.
addition
ethane
ethanol
(Total 1 mark)
58
90.
The alkenes are an example of a homologous series.

(a)
State the name of the alkene shown.
......................................................................................................................................
(1)
(b)
Bromine water, Br2(aq), can be used to distinguish between the alkanes and the alkenes.
(i)
Describe the colour change observed when the alkene shown in part (a) is added to
bromine water.
...........................................................................................................................
...........................................................................................................................
(1)
(ii)
Draw the structural formula and state the name of the product formed.
...........................................................................................................................
(2)
(Total 4 marks)
59
91.
The polymerization of the alkenes is one of the most significant reactions of the twentieth
century.
(i)
Outline two reasons why the polymers of the alkenes are of economic importance.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(ii)
State the type of polymerization reaction shown by the alkene below.
......................................................................................................................................
......................................................................................................................................
(1)
(iii)
Deduce the structure of the resulting polymer showing three repeating units.
(1)
60
(iv)
Explain why monomers are often gases or volatile liquids, but polymers are solids.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 6 marks)
92.
State the name of the product and identify the type of reaction which occurs between ethene
and hydrogen chloride.
(Total 2 marks)
93.
Consider the following sequence of reactions.

reaction 1
reaction 2
reaction 3
RCH3
RCH2Br
RCH2OH
RCOOH
RCH3 is an unknown alkane in which R represents an alkyl group.
(a)
The alkane contains 81.7 % by mass of carbon. Determine its empirical formula, showing
your working.
(3)
(b)
Equal volumes of carbon dioxide and the unknown alkane are found to have the same
mass, measured to an accuracy of two significant figures, at the same temperature and
pressure. Deduce the molecular formula of the alkane.
(1)
(c)
(i)
State the reagent and conditions needed for reaction 1.

(2)
(ii)
State the reagent(s) and conditions needed for reaction 3.

(2)
61
(d)
Reaction 1 involves a free-radical mechanism. Describe the stepwise mechanism, by

giving equations to represent the initiation, propagation and termination steps.
(4)
(e)
The mechanism in reaction 2 is described as SN2.

(i)
State the meaning of each of the symbols in SN2.

(1)
(ii)
Explain the mechanism of this reaction using curly arrows to show the movement
of electron pairs, and draw the structure of the transition state.
(3)
(Total 16 marks)
94.
Propan-1-ol has two structural isomers.

(i)
Deduce the structural formula of each isomer.

(2)
(ii)
Identify the isomer from part (i) which has the higher boiling point and explain your
choice. Refer to both isomers in your explanation.
(2)
(Total 4 marks)
95.
(a)
Describe the structure of benzene, C6H6.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)
62
(b)
State two pieces of evidence that support this description.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 5 marks)
96.
Draw the structural formula of the major organic products, A and B, formed in the following
reactions.
(a)
CH3CH2CH=CH2 + HBr A
A:
(1)
(b)
B:
(1)
(Total 2 marks)
63
97.
Deduce a two-step reaction pathway which can be used to convert 1-bromopropane into
butanoic acid. Draw the structural formula of the organic product formed for each step and
identify the reagents involved.
(Total 4 marks)
98.
Deduce a two-step reaction pathway which can be used to convert propan-2-ol into
1,2-dibromopropane. Draw the structural formula of the organic product formed for each step
and identify the reagents involved.
(Total 4 marks)
99.
(a)
State and explain which of the two compounds, phenol or ethanol, is the stronger acid.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
64
(b)
State and explain which of the two compounds, ethanoic acid or chloroethanoic acid, is
the stronger acid.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)
(Total 5 marks)
100. By which reactants and type of reaction can ethylamine (aminoethane) be produced?
Reactants
Type of reaction
A.
CH3Br + NH3
Nucleophilic substitution
B.
CH3CH2Br + NH3
Reduction
C.
CH3CN + H2
Nucleophilic substitution
D.
CH3CN + H2
Reduction
(Total 1 mark)
101. Which compound is an amide?

A.
CH3COOCH3
B.
CH3CONH2
C.
CH3NH2
D.
CH2(NH2)COOH
(Total 1 mark)
65
102. Which process can produce a polyester?

A.
Addition polymerization of a dicarboxylic acid
B.
Condensation polymerization of a diol and a dicarboxylic acid
C.
Addition polymerization of a diol and dicarboxylic acid
D.
Condensation polymerization of a dicarboxylic acid

(Total 1 mark)
103. Which statement about stereoisomers is correct?

A.
1,2-dichloroethane has two geometrical isomers.
B.
1,2-dichloroethane has two optical isomers.
C.
1,2-dichloroethene has two geometrical isomers.
D.
1,2-dichloroethene has two optical isomers.

(Total 1 mark)
104. (a)
There are four structural isomers with the molecular formula C4H9Br. One of these
structural isomers exists as two optical isomers. Draw diagrams to represent the
three-dimensional structures of the two optical isomers.
(2)
(b)
All the isomers can by hydrolysed with aqueous sodium hydroxide solution. When the
reaction of one of these isomers, X, was investigated the following kinetic data were
obtained.
Experiment
Initial [X] /
mol dm3
Initial [OH] /
mol dm3
Initial rate of reaction /

mol dm3 min1
2.0 102
2.0 102
4.0 103
2.0 102
4.0 102
4.0 103
4.0 102
4.0 102
8.0 103
66
(i)
Deduce the rate expression for the reaction.

(3)
(ii)
Determine the value of the rate constant for the reaction and state its units.
(2)
(iii)
State the name of isomer X and explain your choice.

(2)
(iv)
State equations for the steps that take place in the mechanism of this reaction and
state which of the steps is slow and which is fast.
(2)
(Total 11 marks)
105. The equation for the conversion of benzene into chlorobenzene in the presence of aluminium
chloride is shown below.
AlCl 3
C6H5Cl + HCl
C6H6 + Cl2
Explain the mechanism of this reaction, using curly arrows to represent the movement of
electron pairs.
(Total 4 marks)
67
106. Deduce a two-step reaction pathway which can be used to convert methylbenzene into the
molecule BrCH2(C6H4)Br shown below.
Draw the structural formula of the organic product formed for the first step, identify the
reagents involved and state any specific reaction conditions or catalysts.
(Total 3 marks)
107. (a)
State the formulas of the products E and F formed in the following reaction.
CH3COCl + 2CH3CH2NH2 E + F
E: .................................................................................................................................
F: .................................................................................................................................
(2)
(b)
Identify the nucleophile in the reaction in part (a).

......................................................................................................................................
(1)
68
(c)
State the type of reaction occurring in part (a).

......................................................................................................................................
(1)
(Total 4 marks)
108. Which three compounds can be considered to be a homologous series?

A.
CH3OH,
B.
CH3CH2OH,
C.
CH3CH2CH(OH)CH3,
CH3CH2CH2CH2OH,
D.
CH3CH2CH2CH2OH,
CH3CH2OCH2CH3,
CH3CH2OH,
CH3CH2CH2OH
CH3CHO,
CH3COOH
(CH3)3COH
(CH3)2CH2CHO
(Total 1 mark)
109. What is the IUPAC name for CH3CH2CH(CH3)CH3?

A.
1,1-dimethylpropane
B.
2-ethylpropane
C.
2-methylbutane
D.
3-methylbutane
(Total 1 mark)
110. When bromine water is shaken with a liquid organic compound, it is rapidly decolorized. What
can be determined from this test?
A.
The compound is an alcohol.
B.
The compound is an alkane.
C.
The compound is an alkene.
D.
The compound is an iodoalkane.

(Total 1 mark)
69
111. Which conditions are required to obtain a good yield of a carboxylic acid when ethanol is
oxidized using potassium dichromate(VI), K2Cr2O7(aq)?
I.
Add sulfuric acid
II.
Heat the reaction mixture under reflux
III.
Distil the product as the oxidizing agent is added
A.
I and II only
B.
I and III only
C.
II and III only
D.
I, II and III
(Total 1 mark)
112. Three compounds with similar relative molecular masses are butane, propanal and propan-1-ol.
(i)
List the three compounds in order of increasing boiling point (lowest first) and explain
the differences in their boiling points.
(4)
(ii)
Predict, with an explanation, which of the three compounds is least soluble or miscible in
water.
(2)
(iii)
When propan-1-ol is oxidized using a warm acidified solution of potassium

dichromate(VI) two different organic products can be obtained. Deduce the name and
structural formula for each of these two products.
(3)
(iv)
Propan-2-ol is an isomer of propan-1-ol. Draw the structure of propan-2-ol.

(1)
(v)
Identify the class of alcohols that propan-2-ol belongs to and state the name of the
organic product formed when it is oxidized by an acidified solution of potassium
dichromate(VI).
(2)
(Total 12 marks)
70
113. Ethanol can be formed from ethene in a two step reaction:
(i)
State the name of the reagent used for step 1.

(1)
(ii)
State the name of the reagent and the conditions used for step 2.
(2)
(iii)
The mechanism involved in step 2 is SN2. Explain how the reaction proceeds using curly
arrows to represent the movement of electron pairs.
(3)
(iv)
Outline how ethanol is manufactured from ethene in industry and state one important
commercial use of ethanol.
(2)
(Total 8 marks)
71
114. (a)
Describe the structure of benzene.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(4)
(b)
Cyclohexene, C6H10, reacts with hydrogen to form cyclohexane, C6H12.

C6H10 + H2 C6H12
Ho = 120 kJ mol1
Calculate the enthalpy change of hydrogenation of benzene to cyclohexane, assuming it

has the 1,3,5-cyclohexatriene structure.
......................................................................................................................................
......................................................................................................................................
(1)
(Total 5 marks)
115. (i)
State the structure of the organic product for the following reaction and name the
mechanism for the reaction.
......................................................................................................................................
......................................................................................................................................
(2)
72
(ii)
Explain why bromobenzene, C6H5Br, does not react with OH.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 4 marks)
116. Magnesium is a very electropositive metal which can be used in the formation of Grignard
reagents.
(i)
State the product when bromomethane and magnesium react together in a non-polar
solvent.
......................................................................................................................................
......................................................................................................................................
(1)
(ii)
Draw the structural formulas of the organic products formed in the following reactions.
CH3CH2MgBr
CO
2
H 2O
(CH )2 CO
CH3CH2MgBr 3
H 2O
(2)
(Total 3 marks)
73
117. Draw the structural formulas of the organic products, AD, formed in the following reactions.
A:
B:
C:
D:
(Total 4 marks)
74
118. Elimination reactions are common for tertiary alcohols. State the organic product formed in this
acid-catalysed reaction and explain the mechanism using curly arrows to show the movement of
electron pairs.
(Total 4 marks)
119. Identify the functional group present in HCOCH2CH3.

A.
Ester
B.
Ketone
C.
Aldehyde
D.
Alcohol
(Total 1 mark)
120. What is the IUPAC name for HCOOCH2CH2CH3?

A.
Butanoic acid
B.
Butanal
C.
Methyl propanoate
D.
Propyl methanoate
(Total 1 mark)
75
121. Which statements about substitution reactions are correct?

I.
The reaction between sodium hydroxide and 1-chloropentane predominantly

follows an SN2 mechanism.
II.
The reaction between sodium hydroxide and 2-chloro-2-methylbutane

predominantly follows an SN2 mechanism.
III.
The reaction of sodium hydroxide with 1-chloropentane occurs at a slower rate

than with 1-bromopentane.
A.
I and II only
B.
I and III only
C.
II and III only
D.
I, II and III
(Total 1 mark)
122. What is the organic product of the reaction between methylamine and ethanoic acid?
A.
CH3COONH4
B.
CH3NHCOCH3
C.
CH3COCH2NH2
D.
CH3CH2CONH2
(Total 1 mark)
123. Which compound can exist as stereoisomers?

A.
CH3CH2CHO
B.
CH3CH2COCH3
C.
CH3CH(CH3)2
D.
CH3CH2CHOHCH3
(Total 1 mark)
76
124. (a)
But-1-ene and 1-aminobutane (1-butylamine) can both be prepared from 1-bromobutane.

(i)
State the equation (using structural formulas) and the necessary reagents and
conditions for the preparation of but-1-ene from 1-bromobutane.
(3)
(ii)
Identify the type of reaction and explain the mechanism for the preparation of
but-1-ene from 1-bromobutane using curly arrows to represent the movement of
electron pairs.
(3)
(iii)
State the equation (using structural formulas) for the preparation of 1-aminobutane
from 1-bromobutane. State the necessary reagents and conditions of the reaction.
(3)
(iv)
Explain the mechanism for the preparation of 1-aminobutane from 1-bromobutane

using curly arrows to represent the movement of electron pairs.
(4)
(b)
2-bromobutane and 2-bromo-2-methylpropane are two isomers of 1-bromobutane.

(i)
Draw the structures of the two mirror images of the isomer that can exhibit optical
isomerism.
(2)
(ii)
Describe how the two optical isomers can be distinguished practically using
plane-polarized light.
(2)
(iii)
Explain why the mechanism of the reaction will be different if 1-bromobutane is

replaced by 2-bromo-2-methylpropane to form 2-amino-2-methylpropane in the
reaction in part (a)(iv).
(3)
(Total 20 marks)
77
125. One form of nylon has the repeating unit:
(i)
Identify the circled functional group.

(1)
(ii)
Deduce the structures of the two monomers used to make this form of nylon.
(2)
(iii)
Nylon is a condensation polymer. Another condensation polymer can be formed by

reacting ethane-1,2-diol with benzene-1,4-dicarboxylic acid.
Deduce the equation for this reaction using n moles of each reactant.
(2)
(Total 5 marks)
126. Benzene, C6H6, undergoes electrophilic substitution reactions in order to synthesize other
compounds.
(i)
Describe, using an equation, the formation of the electrophile in the nitration of benzene.
......................................................................................................................................
......................................................................................................................................
(2)
78
(ii)
Describe the stepwise mechanism for the reaction of benzene with ethanoyl chloride,
CH3COCl in the presence of aluminium chloride, using curly arrows to show the
(3)
(Total 5 marks)
79
127. Chlorobenzene can be converted in two steps into the compound below.
State the reagents and conditions required for each step and state the structure of the compound
formed after the first step.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 3 marks)
128. (i)
Methylbenzene can be converted in two steps into the compound below.
State the reagents and conditions required for each step.

......................................................................................................................................
......................................................................................................................................
(2)
80
(ii)
Deduce the formula of the product when the compound above reacts with hydroxide ions.
Explain your answer.
......................................................................................................................................
......................................................................................................................................
(2)
(Total 4 marks)
129. What is the product of the oxidation of butan-2-ol?

A.
But-2-ene
B.
Butanoic acid
C.
Butanal
D.
Butanone
(Total 1 mark)
130. Which is a tertiary halogenoalkane?

A.
CH3CH2CH2Br
B.
CH3CH2CH(CH3)Cl
C.
C(CH3)3Br
D.
CH3CHClCH2CH3
(Total 1 mark)
81
131. What is the IUPAC name of the following compound?
A.
2-methylbutane
B.
Ethylpropane
C.
3-methylbutane
D.
Pentane
(Total 1 mark)
132. Which equations represent the incomplete combustion of methane?

I.
CH4(g) + 2O2(g) CO2(g) + 2H2O(g)
II.
CH4(g) + 1O2(g) CO(g) + 2H2O(g)
III.
CH4(g) + O2(g) C(s) + 2H2O(g)
A.
I and II only
B.
I and III only
C.
II and III only
D.
I, II and III
(Total 1 mark)
82
133. In some countries, ethanol is mixed with gasoline (petrol) to produce a fuel for cars called
gasohol.
(i)
Define the term average bond enthalpy.

(2)
(ii)
Use the information from Table 10 of the Data Booklet to determine the standard
enthalpy change for the complete combustion of ethanol.
CH3CH2OH(g) + 3O2(g) 2CO2(g) + 3H2O(g)
(3)
(iii)
The standard enthalpy change for the complete combustion of octane, C8H18, is
5471 kJ mol1. Calculate the amount of energy produced in kJ when 1 g of ethanol and
1 g of octane is burned completely in air.
(2)
(iv)
Ethanol can be oxidized using acidified potassium dichromate, K2Cr2O7, to form two
different organic products.
CH3CH2OH
State the structural formulas of the organic products A and B and describe the conditions
required to obtain a high yield of each of them.
(4)
(v)
Deduce and explain whether ethanol or A has the higher boiling point.
(2)
(vi)
Ethene can be converted into ethanol by direct hydration in the presence of a catalyst
according to the following equation.
C2H4(g) + H2O(g)
CH3CH2OH(g)
For this reaction identify the catalyst used and state one use of the ethanol formed other
than as a fuel.
(2)
(Total 15 marks)
83
134. (i)
State the name of one structural isomer of pentane.

(1)
(ii)
Sodium hydroxide reacts with 1-bromopentane via an SN2 mechanism.

Describe the mechanism of this reaction using curly arrows to represent the movement of
electron pairs.
(4)
(Total 5 marks)
135. Benzene is an important molecule containing delocalized electrons.

(a)
Explain the term delocalized electrons.

......................................................................................................................................
......................................................................................................................................
(1)
(b)
State and explain one piece of physical evidence and one piece of chemical evidence for
the presence of delocalized electrons in the structure of benzene.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(4)
(Total 5 marks)
84
136. Describe and explain the relative rates of the reactions of hydroxide ions with chlorobenzene,
C6H5Cl, and (chloromethyl)benzene, C6H5CH2Cl.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 3 marks)
137. Predict and explain the structures of the major and minor products when hydrogen bromide is
added to 2-methylbut-2-ene, (CH3)2CCHCH3.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 5 marks)
85
138. Draw the structural formulas of the two elimination products formed when butan-2-ol,
CH3CH2CH(OH)CH3 is heated with phosphoric acid.
(Total 2 marks)
139. (a)
Outline the formation of a Grignard reagent. Include any necessary conditions.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
86
(b)
2-methylbutan-2-ol is formed by the reaction of a ketone with a Grignard reagent.

Draw the structural formula of 2-methylbutan-2-ol and deduce the structural formulas of
the ketone and the Grignard reagent used for the reaction.
......................................................................................................................................
......................................................................................................................................
(3)
(Total 5 marks)
140. What structural feature must a molecule have in order to undergo addition polymerization?
A.
Two functional groups
B.
A carboncarbon double bond
C.
Carbon atoms singly bonded together
D.
A polar covalent bond

(Total 1 mark)
141. What is the organic product of the reaction between CH3CH2NH2 and CH3CH2COOH?
A.
CH3CH2NHCOCH2CH3
B.
CH3CH2CH2NHCOCH3
C.
CH3CH2NHCOCH3
D.
CH3NHCOCH3
(Total 1 mark)
87
142. What is the IUPAC name of the compound CH3CH2COOCH2CH3?

A.
Ethyl ethanoate
B.
Propyl ethanoate
C.
Ethyl propanoate
D.
Pentyl propanoate
(Total 1 mark)
143. Which statement is correct about the enantiomers of a chiral compound?

A.
Their physical properties are different.
B.
All their chemical reactions are identical.
C.
A racemic mixture will rotate the plane of polarized light.
D.
They will rotate the plane of polarized light in opposite directions.

(Total 1 mark)
144. Ethanol can be oxidized using acidified potassium dichromate, K2Cr2O7, to form two different
organic products.
CH3CH2OH
State the structural formulas of the organic products A and B and describe the conditions
required to obtain a high yield of each of them.
(Total 4 marks)
145. Ethene can be converted into ethanol by direct hydration in the presence of a catalyst according
to the following equation.
C2H4(g) + H2O(g)
CH3CH2OH(g)
For this reaction, identify the catalyst used and state one use of the ethanol formed other than as
a fuel.
(Total 2 marks)
88
146. Deduce a two-step synthesis for each of the following conversions. For each step, state the
structural formulas of all reactants and products and state the conditions used in the reactions.
(i)
Ethanol to ethyl ethanoate.

(2)
(ii)
Propene to propanone.
(2)
(Total 4 marks)
147. The reagents used in an elimination reaction are shown below.
Explain the mechanism of this reaction using curly arrows to represent the movement of
electron pairs.
(Total 3 marks)
148. (i)
Describe geometrical isomerism.

(1)
(ii)
Draw the geometrical isomers of but-2-ene.

(2)
(iii)
Draw the two enantiomers of butan-2-ol.

(2)
(Total 5 marks)
89
149. State the name of the product formed from the chlorination of nitrobenzene in which one
chlorine atom is introduced into the benzene ring. Describe and explain the effect of the nitro
group on the reaction. Your answer should include a comparison of the rate of chlorination of
benzene to that of nitrobenzene.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 5 marks)
150. State the equation for the reaction of ethanoyl chloride, CH3COCl, with sodium hydroxide.
Identify the mechanism for the reaction and explain it using curly arrows to show movement of
electron pairs.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 5 marks)
90
151. How many structural isomers exist with the formula C3H5Cl3?
A.
B.
C.
D.
6
(Total 1 mark)
152. Which substance is produced by the reaction of hydrogen with a vegetable oil?
A.
Margarine
B.
Nylon
C.
Polypropene
D.
Soap
(Total 1 mark)
153. Which substance is not produced during the combustion of alkanes?

A.
CO2
B.
CO
C.
D.
H2
(Total 1 mark)
91
154. Propene is converted to propanone in a two stage process.

Propene X Propanone
What is the formula of compound X?
A.
CH3CHBrCH3
B.
CH3CH2CH2Br
C.
CH3CHOHCH3
D.
CH3CH2CH2OH
(Total 1 mark)
155. (a)
The boiling points of the isomers of pentane, C5H12, shown are 10, 28 and 36 C, but not
necessarily in that order.
(i)
Identify the boiling points for each of the isomers A, B and C and state a reason
for your answer.
Isomer
Boiling point
...........................................................................................................................
...........................................................................................................................
(3)
92
(ii)
State the IUPAC names of isomers B and C.

B: .......................................................................................................................
C: .......................................................................................................................
(2)
(b)
Both C5H12 and C5H11OH can be used as fuels. Predict which compound would release a
greater amount of heat per gram when it undergoes complete combustion. Suggest two
reasons to support your prediction.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)
(Total 8 marks)
156. Halogenoalkanes can undergo substitution reactions with potassium hydroxide solution.
(i)
State an equation for the reaction of C4H9Cl with KOH.

(1)
(ii)
Substitution reactions may occur by either of two mechanisms namely SN1 or SN2.
Outline the meaning of the term SN1.
(2)
(iii)
Predict the mechanism (SN1 or SN2) expected for the reaction of the following
halogenoalkanes with aqueous KOH.
1-chlorobutane to form butan-1-ol
2-chloro-2-methylpropane to form 2 methylpropan-2-ol.
(2)
93
(iv)
Explain the mechanism of each reaction in part (iii) using curly arrows to represent the
(6)
(Total 11 marks)
157. (i)
Draw four structural isomers of molecular formula C4H10O which contain the OH
group.
(4)
(ii)
On reaction with acidified potassium dichromate(VII), two of the isomers are oxidized in
two steps to produce different products. Draw the structural formula of the two products
formed from one of the isomers.
(2)
(iii)
A third isomer is oxidized in one step. Draw the structural formula of the organic product
formed.
(1)
(iv)
State the colour change that takes place in these oxidation reactions.
(1)
(v)
Identify the isomer which resists oxidation by acidified potassium dichromate(VI).

(1)
(Total 9 marks)
158. Consider the two amines methylamine, CH3NH2, and dimethylamine, (CH3)2NH.
(a)
Using Table 15 of the Data Booklet, state which of the amines is the more basic.
......................................................................................................................................
(1)
94
(b)
Explain the relative basicities of the two amines.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 3 marks)
159. Explain why chloroethanoic acid is a stronger acid than ethanoic acid.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 2 marks)
160. Starting with chloromethane, outline one possible reaction pathway to synthesize ethanoic acid.
Your answer should include:
the reagents used
a relevant chemical equation for each step.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 2 marks)
95
161. The carbonyl chemistry of both aldehydes and ketones involves a number of different types of
reactions.
(a)
State the formulas of the products A and B, formed in the following reactions.
(i)
CH 3CH 2 MgBr
(CH3)2CO
A
H 2O
A: ......................................................................................................................
(1)
(ii)
B: ......................................................................................................................
(1)
(b)
State the type of reaction involved in the formation of B and H2O in (a)(ii).
......................................................................................................................................
(1)
(Total 3 marks)
96
162. Alkenes commonly react by electrophilic addition reactions. Describe the mechanism of the
following reaction, using curly arrows to show the movement of electron pairs, and suggest the
reason for the formation of the major organic product, C.
CH2=CH(CH2CH3) + HI C
......................................................................................................................................
......................................................................................................................................
(Total 5 marks)
163. Alcohols can undergo elimination reactions. Describe the mechanism of the following reaction,
using curly arrows to show the movement of electron pairs, and identify the organic product, D.
CH3CH2OH + H3PO4 D
(Total 5 marks)
97
164. Which reaction occurs via a free-radical mechanism?

A.
C2H6 + Br2 C2H5Br + HBr
B.
C2H4 + Br2 C2H4Br2
C.
C4H9I + OH C4H9OH + I
D.
(CH3)3CI + H2O (CH3)3COH + HI

(Total 1 mark)
165. Which compound could rotate the plane of polarization of polarized light?
A.
(CH3)2CHCH2Cl
B.
CH3CH2CH2CH2Cl
C.
CH3CH2CHClCH3
D.
(CH3)3CCl
(Total 1 mark)
166. What is the name of the ester formed when CH3CH2COOH and CH3OH react together?
A.
Ethyl methanoate
B.
Methyl ethanoate
C.
Propyl methanoate
D.
Methyl propanoate
(Total 1 mark)
98
167. Which formula represents a polyamide?

A.
( CH2CHCl ) n
B.
( NH(CH2)6NHCO(CH3)4CO ) n
C.
( CF2CF2 ) n
D.
( O(CH2)2OCO
CO ) n
(Total 1 mark)
168. The compound C4H7Cl can exhibit stereoisomerism.

(i)
Draw the structural formulas of the two geometrical isomers of 1-chloro-but-2-ene.

(2)
(ii)
Explain why 1-chloro-but-2-ene shows geometrical isomerism.

(1)
(iii)
Draw the structural formula of one isomer of C4H7Cl that shows optical isomerism and
identify the chiral carbon atom with an asterisk (*).
(2)
(Total 5 marks)
169. The compound but-2-ene-1,4-dioic acid forms two geometrical isomers which have different
physical and chemical properties.
(i)
Explain the difference in the melting points of the two isomers.

(3)
(ii)
Outline how the two isomers behave differently when gently heated.
(1)
(Total 4 marks)
99
170. The reaction between bromoethane, CH3CH2Br, and potassium cyanide is an example of a
nucleophilic substitution reaction.
(i)
State whether this reaction is SN1 or SN2.

(1)
(ii)
Explain the mechanism of the reaction using curly arrows to represent the movement of
electron pairs.
(4)
(iii)
The organic product obtained in part (ii) can be reduced to form an amine.
State an equation for the reaction, naming the catalyst involved.
(2)
(Total 7 marks)
171. Bromoethane reacts with potassium hydroxide to undergo mainly a substitution reaction or an
elimination reaction depending on the reaction conditions used.
(i)
State an equation and the reaction conditions used to control the products formed in each
case.
(4)
(ii)
Explain the mechanism of the elimination reaction using curly arrows to represent the
(4)
(iii)
Under certain conditions, the major product obtained in the elimination reaction can
undergo polymerization. Identify the type of polymerization this major product
undergoes.
(1)
(Total 9 marks)
100
172. Both benzene and methylbenzene undergo electrophilic substitution reactions.

State the formulas of the reagents, EG, including any catalysts used, in the following
conversions.
E: ...........................................................................................................................................
F: ...........................................................................................................................................
G: ...........................................................................................................................................
(Total 3 marks)
173. (i)
State whether OH can be described as an activating or deactivating group with respect

to aromatic electrophilic substitution reactions.
......................................................................................................................................
(1)
101
(ii)
Describe the directing effect of OH on a benzene ring in an aromatic electrophilic

substitution reaction.
......................................................................................................................................
(1)
(iii)
Explain the decreased reactivity due to the presence of the NO2 group in an aromatic
electrophilic substitution reaction.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 4 marks)
174. Which statement about successive members of all homologous series is correct?
A.
They have the same empirical formula.
B.
They differ by a CH2 group.
C.
They have the same physical properties.
D.
They differ in their degree of unsaturation.

(Total 1 mark)
102
175. The following is a three-dimensional representation of an organic molecule.
Which statement is correct?

A.
The correct IUPAC name of the molecule is 2-methylpentane.
B.
All the bond angles will be approximately 90.
C.
One isomer of this molecule is pentane.
D.
The boiling point of this compound would be higher than that of pentane.
(Total 1 mark)
103
176. Which compound forms when hydrogen bromide is added to but-2-ene?

A.
2-bromobutane
B.
2,3-dibromobutane
C.
1-bromobutane
D.
1,2-dibromobutane
(Total 1 mark)
177. Which products can be potentially obtained from crude oil and are economically important?
I.
II.
III.
Plastics
Margarine
Motor fuel
A.
I and II only
B.
I and III only
C.
II and III only
D.
I, II and III
(Total 1 mark)
178. Propane, C3H8, undergoes incomplete combustion in a limited amount of air. Which products
are most likely to be formed during this reaction?
A.
Carbon monoxide and water
B.
Carbon monoxide and hydrogen
C.
Carbon dioxide and hydrogen
D.
Carbon dioxide and water

(Total 1 mark)
104
179. (a)
List two characteristics of a homologous series.

.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(1)
(b)
Ethanol and ethanoic acid can be distinguished by their melting points. State and explain
which of the two compounds will have a higher melting point.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(2)
(c)
Draw the three isomers containing the alcohol functional group of formula C4H9OH.
(2)
(Total 5 marks)
105
180. The following is a computer-generated representation of the molecule, methyl

2-hydroxy benzoate, better known as oil of wintergreen.
(i)
Deduce the empirical formula of methyl 2-hydroxy benzoate and draw the full structural
formula, including any multiple bonds that may be present.
The computer-generated representation shown does not distinguish between single and
multiple bonds.
(2)
(ii)
In this representation, two of the carbon-oxygen bond lengths shown are 0.1424 nm and
0.1373 nm. Explain why these are different and predict the carbon-oxygen bond length in
carbon dioxide.
(2)
(iii)
Name all the functional groups present in the molecule.

(2)
(Total 6 marks)
106
181. (i)
State and explain the trend in the boiling points of the first six alkanes involving
straight-chains.
(2)
(ii)
Write an equation for the reaction between methane and chlorine to form chloromethane.
Explain this reaction in terms of a free-radical mechanism.
(5)
(Total 7 marks)
182. (i)
Identify the formulas of the organic products, AE, formed in the reactions, IIV:
+
I.
H
H
CH3(CH2)8OH + K2Cr2O7
A
B
II.
(CH3)3CBr + NaOH C
III.
H
(CH3)2CHOH + K2Cr2O7
D
IV.
H2C=CH2 + Br2 E
(5)
(ii)
H2C=CH2 can react to form a polymer. Name this type of polymer and draw the
structural formula of a section of this polymer consisting of three repeating units.
(2)
(Total 7 marks)
183. What is the product of the following reaction?

Ni
CH3CH2CH2CN + H2
A.
CH3CH2CH2NH2
B.
CH3CH2CH2CH3
C.
CH3CH2CH2CH2CH3
D.
CH3CH2CH2CH2NH2
(Total 1 mark)
107
184. What is the correct IUPAC name for the following compound?
CH 3 CHCH 2 CH 2 CN
CH 3
A.
4-methylbutanenitrile
B.
4-methylpentanenitrile
C.
2-methylbutanenitrile
D.
2-methylpentanenitrile
(Total 1 mark)
185. What is the organic product of the reaction between ethanol and ethanoic acid in the presence
of sulfuric acid?
A.
CH3CHO
B.
CH3COOCH3
C.
CH3CH2COOCH3
D.
CH3COOCH2CH3
(Total 1 mark)
186. Which compound can exist as optical isomers?

A.
H2NCH2COOH
B.
H3CCONH2
C.
H3CCHBrI
D.
HCOOCH3
(Total 1 mark)
108
187. The molecular formula, C3H4Cl2 represents several isomeric compounds. Some isomers are
cyclic and some are unsaturated.
(a)
Draw the structures of two cyclic compounds that are structural isomers and state the
names of both isomers.
(2)
(b)
Two of the non-cyclic compounds have geometrical isomers. Draw the structures of these
compounds and their geometrical isomers.
(2)
(Total 4 marks)
188. The compound, 2-bromobutane, CH3CHBrCH2CH3, can react with sodium hydroxide to form
compounds F, G and H.
Compound F, C4H10O, exists as a pair of optical isomers. Compounds G and H, C4H8, are
structural isomers, and compound H exists as a pair of geometrical isomers.
(i)
Draw the structures of the two optical isomers of F.

(2)
(ii)
Outline the use of a polarimeter in distinguishing between the optical isomers.

(2)
(iii)
Draw diagrams to show the shapes of the two geometrical isomers of H.

(2)
109
(iv)
Draw the mechanism, using curly arrows to represent the movement of electron pairs, to
show the formation of G.
(3)
(Total 9 marks)
189. A compound, J, has the molecular formula C2H4O2 and is obtained from a reaction between
methanoic acid and methanol. Write an equation for this reaction and state the name of
compound J.
(Total 3 marks)
190. When hydrogen cyanide reacts with an aldehyde or a ketone the product molecule has one more
carbon atom.
(a)
Write an equation to show the addition of hydrogen cyanide to propanone.

.....................................................................................................................................
(1)
(b)
Describe, using curly arrows, a mechanism for the reaction of hydrogen cyanide with
propanone.
(4)
110
(c)
Write an equation for the acid hydrolysis of this product. State the two functional groups
in the organic product.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(2)
(Total 7 marks)
191. The structure of benzene can be represented in two ways.
structure A
(a)
structure B
Use information from Table 9 of the Data Booklet to explain why structure B is used in
preference to structure A.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(2)
111
(b)
The enthalpy changes for the hydrogenation of cyclohexene and benzene are as follows.
(i)
C6H10 + H2 C6H12
UH = 120 kJ mol1
C6H6 + 3H2 C6H12
UH = 210 kJ mol1
Explain how this information can be used to support the statement that structure B
is more stable than structure A.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)
(ii)
State what the circle in structure B represents.

...........................................................................................................................
...........................................................................................................................
(1)
(Total 5 marks)
192. Cyclohexanone can react with 2,4-dinitrophenylhydrazine in aqueous solution.

(a)
State the type of reaction that takes place.

.....................................................................................................................................
(1)
(b)
Complete the equation for this reaction using structural formulas for the products.
H2 N
N
O
NO 2
NO 2
(2)
112
(c)
State why the product from this particular reaction can be used to confirm that the
reactant was cyclohexanone and not any other carbonyl compound.
.....................................................................................................................................
.....................................................................................................................................
(1)
(Total 4 marks)
193. Explain how the presence of the NO2 group on a benzene ring affects the rate of further
substitution.
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
(Total 4 marks)
113

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Which of the following statements about alkenes is not correct?

They have reactive double bonds.

They can form addition polymers.

They react mainly by substitution.

They can react with water to form alcohols.

Which of the following are isomers of pentane?

I and III only

II and III only

CH3CH2CH2OH and CH3CH2CHO

CH3CH(OH)CH3 and CH3CH2CH(OH)CH3

CH3COCH3 and CH3CH2COOH

CH3COCH2CH3 and CH3CH2CHO

Alkenes are important starting materials for a variety of products.

Describe two features of a homologous series.

IUPAC name: ..............................................................................................................

Butan-2-ol cannot be directly converted to 1,2-dibromobutane. The conversion can be carried

State the name and draw the structural formula of X.

Butan-1-ol could be used instead of butan-2-ol. Compare the yield of 1,2-dibromobutane

State the reagents that react to produce this compound.

Which molecule has a chiral centre?

Which two molecules are cis-trans isomers of each other?

What is the correct order of reaction types in the following sequence?

Two compounds, A and D, each have the formula C4H9Cl.

2-chloro-3-methylbutane reacts with sodium hydroxide via an SN2 mechanism.

1-chlorobutane can be converted to a pentylamine via a two stage process.

Which organic molecule is not a structural isomer of pentan-1-ol?

Which of the structures below is an aldehyde?

What product is formed when CH3CH(OH)CH3 is reacted with acidified potassium

Other than polymerization, state one reaction of alkenes which is of economic

Propan-1-ol and propan-2-ol are two structural isomers of C3H8O.

State the equation for the complete combustion of C3H8O.

Both propan-1-ol and propan-2-ol can be oxidized in aqueous solution by potassium

With reference to the compounds benzene, cyclohexane and 1,3-cyclohexadiene, state

Identify each of the types of reaction in (a) as elimination, nucleophilic addition,

Name of organic product:

The reaction is bi-molecular.

The reaction follows the SN2 mechanism.

Homolytic fission occurs between the carbon-bromine bond in bromoethane.

The cyanide ion, :CN, acts as a nucleophile.

Which reactants could be used to form the compound below?

Butanoic acid and ethanol

Propanoic acid and ethanol

Ethanoic acid and propan-1-ol

Ethanoic acid and butan-1-ol

Which compound is optically active?

The reaction with 1-bromopentane proceeds by an SN2 mechanism. Describe this

The reaction with 2-bromo-2-methylbutane proceeds by an SN1 mechanism.

Explain why 1-bromopentane reacts by an SN2 mechanism whereas

Identify all the major products, AD, in the following reactions.

Which is the best definition of structural isomers?

Which is the correct classification of these alcohols?

Which substances are possible products of the incomplete combustion of octane?

Carbon dioxide and hydrogen gas

Carbon monoxide and water vapour

Carbon monoxide and hydrogen gas

Methane and hydrogen gas

Chloroethene, C2H3Cl, is an important organic compound used to manufacture the polymer

Draw a section of poly(chloroethene) containing six carbon atoms.

Determine the isomer that cannot be oxidized by acidified potassium

Determine the isomer which can be oxidized to butanal.

Determine the isomer which can be oxidized to butanone.

Suggest the structural formula of another isomer of C4H10O.