Past paper questions for Organic Chemistry 1

TOPIC 14-1 Organic Chemistry I

1 (Nov. 2005, P3, Q4)
The alcohols form a homologous series. The first member is methanol and the fourth is butanol.

(a) (i) Give two general characteristics of a homologous series.

………………………………………………………………………………………………

………………………………………………………………………………………………

………………………………………………………………………………………………[2]
(ii) Calculate the mass of one mole of the C8 alcohol.

………………………………………………………………………………………………

………………………………………………………………………………………………[2]
(b) Give the name and structural formula of the third member of this series.

Name…………………………………………………
structural formula

[1]
(c) The structural formula of the fifth member, pentan-1-ol, is drawn below.

(i) Draw the structural formula of an isomer of this alcohol.

(ii) Predict the names of the product(s) formed when pentan-1-ol

• reacts with an excess of oxygen,

……………………………………and……………………………………… [1]
• is dehydrated to form an alkene,

………………………………………………………………………………. [1]
• is oxidised by acidified potassium dichromate(VI).

………………………………………………………………………………. [1]
2 (June 2005, P3, Q3)
A South Korean chemist has discovered a cure for smelly socks. Small particles of silver are
attached to a polymer, poly(propene), and this is woven into the socks.
(a) (i) Give the structural formula of the monomer.

[1]
(ii) Draw the structural formula of the polymer. [2]
2 Past paper questions for Organic Chemistry

(iii) Suggest which one, monomer or polymer, will react with aqueous bromine and why?
…………………………………………………………………………………………………
………………………………………………………………………..................................... [2]
(b) To show that the polymer contains silver the following test was carried out.
The polymer fibres were chopped into small pieces and warmed with nitric acid. The silver
atoms were oxidised to silver(I) ions. The mixture was filtered. Aqueous sodium chloride was
added to the filtrate and a white precipitate formed.
(i) Why was the mixture filtered?

………………………………………………………………….........................................[1]
(ii) Explain why the change of silver atoms to silver ions is oxidation.

………………………………………………………………….........................................[1]
(iii) Give the name of the white precipitate.

………………………………………………………………….........................................[1]
(c) The unpleasant smell is caused by carboxylic acids. Bacteria cause the fats on the skin to be
hydrolysed to these acids. Silver kills the bacteria and prevents the hydrolysis of the fats.
(i) Fats are esters. Give the name and structural formula of an ester.
Name…………………………………………………………………………….[1]
structural formula

[1]
(ii) Complete the word equation.
Ester + water  carboxylic acid + …………………….. [1]
(d) Propanoic acid is a weak acid.
(i) The following equation represents its reaction with ammonia.

Explain why propanoic acid behaves as an acid and ammonia as a base.

…………………………………………………………………………………………..

………………………………………………………………………………………….. [3]
(ii) Explain the expression weak acid.

………………………………………………………………………………………….. [1]
 Past paper questions for Organic Chemistry 3

3 (Nov. 2004, P6, Q3)

A liquid alkane was passed over heated aluminium oxide to make ethene.

(a) What is the purpose of the mineral wool?

………………………………………………………………………………………..[1]
(b) What is this type of chemical reaction called?

………………………………………………………………………………………..[1]
(c) Give a test for ethene.
Test………………………………………………………………………………..
Result…………………………………………………………………………….. [2]
(d) What precaution should be taken in the experiment when the heat is removed? Explain.

……………………………………………………………………………………………….

4 (Nov. 2005, P6, Q6)

The diagram shows how ethene can be made by cracking liquid alkanes.

(a) Indicate with arrows on the diagram where heat is applied. [2]

(b) Give a chemical test to show the presence of ethene.

test……………………………………………………………………………………..
4 Past paper questions for Organic Chemistry

result……………………………………………………………………………………[2]
(c) Why must the delivery tube be removed from the water before the heat is turned off?
……………………………………………………………………………………..….
……………………………………………………………………………………..….[2]

5 (Nov. 2004, P3, Q8)

The alkenes are a homologous series of unsaturated hydrocarbons.
(a) The table below gives the names, formulae and boiling points of the first
members of the series.
name formula boiling point / oC
ethene C2H4 -102
propene C3H6 -48
butene C4H8 -7
pentene C5H10 30
hexene
(i) Complete the table by giving the formula of hexene and by predicting its boiling point.

[2]
(ii) Deduce the formula of the alkene which has a relative molecular mass of 168. Show your
working.

[2]
(b) Describe a test that will distinguish between the two isomers, but-2-ene and cyclobutane.
Test……………………………………………………………………………………………….
result with but-2-ene……………………………………………………………………………
result with cyclobutane ……………………………………………………………………… [3]

6 (June 2003, paper 3. Q3)

Alkenes are unsaturated hydrocarbons. They undergo addition reactions.
(a) Two of the methods of making alkenes are cracking and the thermal decomposition of
chloroalkanes.
(i) Complete an equation for the cracking of the alkane, decane.

C10H22 → ............................ + ...................................

decane
(ii) Propene can be made by the thermal decomposition of chloropropane.
Describe how chloropropane can be made from propane.

reagents propane and ..............................

conditions ................................................... [4]
(b) The following alkenes are isomers.
CH3–CH2–CH=CH2

(i) Explain why they are isomers.

 Past paper questions for Organic Chemistry 5

............................................................................................. .....................................
............................................................................................. .....................................
(ii) Give the name and structural formula of another hydrocarbon that is isomeric with the
above.
name ......................................................

structural formula ......................................................

7 (Nov 2001, paper 3. Q1)

(c) Pure nickel is used to catalyse the reduction of unsaturated oils to saturated fats.

(i) What is meant by the terms saturated and unsaturated?

............................................................................................. .....................................
............................................................................................. .................................[2]
(ii) Name the functional group in fats.
............................................................................................. .................................[1]
(iii) How can a soap be made from a fat?

............................................................................................. .................................[2]

TOPIC 14-2 Organic Chemistry II (synthetic and natural macromolecules)

1 (June 2003, paper 3. Q3)
(c) Give the name of the product when but-1-ene reacts with each of the following.

steam .........................................................

hydrogen ....................................................

bromine ...................................................... [3]

(d) Alkenes can polymerise.
(i) Deduce the name and structural formula of the monomer from the structure of the
polymer.

name of monomer .......................................................

structural formula
6 Past paper questions for Organic Chemistry

(ii) Draw the structure of the polymer formed from the following monomer.

(iii) Describe the pollution problems caused by the disposal of polymers in landfill sites and
by burning.
landfill sites ...........................................................................................................[2]

burning ..................................................................................................................[1]

2 (Nov 2003, paper 3. Q4)

Esters occur naturally in plants and animals. They are manufactured from petroleum. Ethyl
ethanoate and butyl ethanoate are industrially important as solvents.
(a) (i) Explain the term solvent.

............................................................................................. ................................ [1]

(ii) Give the formula of ethyl ethanoate.

............................................................................................. .................................[1]
(iii) Ethyl ethanoate can be made from ethanol and ethanoic acid. Describe how these
chemicals can be made.
ethanol from ethene

............................................................................................. .....................................

...................................................................................... ........................................[2]
ethanoic acid from ethanol

............................................................................................. .....................................

............................................................................................. ................................ [2]

(iv) Name two chemicals from which butyl ethanoate can be made.

............................................................................................. .................................[1]
(b) The following equation represents the alkaline hydrolysis of a naturally occurring ester.

(i) Which substance in the equation is an alcohol? Underline the substance in the equation
above.

............................................................................................. .................................[1]
(ii) What is the major use for compounds of the type C17H35COONa?

............................................................................................. .................................[1]
(c) A polymer has the structure shown below.
 Past paper questions for Organic Chemistry 7

(i) What type of polymer is this?

............................................................................................. .................................[1]
(ii) Complete the following to give the structures of the two monomers from which the above
polymer could be made.

[2]

(d) Esters are frequently used as solvents in chromatography. A natural macromolecule was
hydrolysed to give a mixture of amino acids. These could be identified by chromatography.
(i) What type of macromolecule was hydrolysed?

............................................................................................. .................................[1]
(ii) What type of linkage was broken by hydrolysis?

............................................................................................. .................................[1]
(iii) Explain why the chromatogram must be sprayed with a locating agent before the
amino acids can be identified.

............................................................................................. .................................[1]
(iv) Explain how it is possible to identify the amino acids from the chromatogram.

............................................................................................. .................................[2]

3 (June 2003, paper 3. Q3)

A major food retailer in the UK is going to distribute sandwiches using hydrogen-powered
vehicles.
(a) A sandwich contains three of the main constituents of food.

These constituents of food can all be hydrolysed by boiling with acid or alkali.
Constituent of food linkage product of hydrolysis
protein
fat
complex ×
carbohydrate
(i) Complete the table. [5]
8 Past paper questions for Organic Chemistry

(ii) What type of synthetic polymer contains the same linkage as

proteins, .................................................................................................................
fats? ......................................................................................................................[2]
(iii) Fats can be unsaturated or saturated. A small amount of a fat was dissolved in an
organic solvent. Describe how you could find out if this fat was saturated or unsaturated.

reagent ......................................................................................................................

result if saturated ......................................................................................................

result if unsaturated ...............................................................................................[3]

4 (Nov 2002, paper 3. Q5)

Alkenes are unsaturated hydrocarbons. They show structural isomerism. Alkenes take part in
addition reactions and form polymers.
(a) Structural isomers have the same molecular formula but different structural formulae. Give an
example of structural isomerism.

molecular formula .........................................................................................................

two structural formulae

[3]
(b) Ethene reacts with each of the following. Give the name and structural formula of each
product.
(i) steam
name of product ..........................................................
structure of product

[2]
(ii) hydrogen
name of product ...........................................................
structure of product

[2]
(c) Alkenes polymerise by addition.
(i) Explain the term polymerise.

.........................................................................................................................................[2]
(ii) What is the difference between addition polymerisation and condensation
polymerisation?

………............................................................................................ .................................

………............................................................................................ .................................[2]
(iii) Poly(dichloroethene) is used extensively to package food. Draw its structure. The
structural formula of dichloroethene is drawn below.
 Past paper questions for Organic Chemistry 9

[2]

(d) Steel may be coated with another metal, eg zinc or chromium, or with a polymer, eg
poly(chloroethene), to prevent rusting.
(i) Suggest a property of poly(chloroethene) that makes it suitable for this purpose.

............................................................................................. .................................[1]
(ii) Explain why the steel will rust when the protective coating of chromium or polymer is
broken.

............................................................................................. .................................[1]
(iii) When the protective layer of zinc is broken, the steel still does not rust. Suggest an
explanation.

............................................................................................. .....................................

............................................................................................. .....................................

............................................................................................. .................................[2]

5 (June 2001, paper 3. Q4)

(a) (i) One of the isomeric butenes is but-1-ene which has the formula CH3-CH2-CH=CH2. Give
the name and structural formula of another butene.
name ............................................................................................................................
formula .........................................................................................................................
(ii) But-1-ene can be oxidised to two acids whose formulae are given below. Name these
acids.

CH3-CH2-CO2H ............................................................................................................

HCO2H ................................................................................................................. .....[4]

(b) But-1-ene can behave as a monomer and undergo addition polymerisation.
(i) Give the name and the structural formula of the polymer formed from but-1-ene.

name .........................................................................................................................
structure

(ii) Suggest a use for this type of polymer.

formula ......................................................................................................................[3]

(c) The equation, given below, represents the formation of one mole of butane from butene.

(i) What is the mass of one mole of butane molecules?

10 Past paper questions for Organic Chemistry

............................................................................................. .....................................
(ii) Complete the table that shows the bonds broken and formed in this reaction.

(iii) Use the data in the table to determine if the reaction is exothermic or endothermic.
Give a reason for your choice.

............................................................................................. .....................................

............................................................................................. .................................[6]
(d) The gases butene and ethene could be separated by liquefaction followed by fractional
distillation because they have different boiling points.

(i) Using the data in the table suggest another technique that would separate these gases.

............................................................................................. .....................................
(ii) Explain why the technique you have given in (i) would separate the gases.

............................................................................................. ................................ [3]

6 (June 2001,paper 3. Q5)

(c) Starch is a complex carbohydrate. Its formula is shown below. Starch reacts with iodine to
form a deep blue colour.

In the experiment illustrated below, samples are removed at intervals and tested with iodine.
 Past paper questions for Organic Chemistry 11

Typical results of this experiment are given in the table.

By referring to the chemistry involved, explain these results.

............................................................................................. .....................................

............................................................................................. .....................................

............................................................................................. ................................ [ 4]

7 (June 2004, P3, Q6)

In 2002, Swedish scientists found high levels of acrylamide in starchy foods that had been
cooked above 120oC. Acrylamide, which is thought to be a risk to human health, has the
following structure.

(a) (i) It readily polymerises to polyacrylamide. Draw the structure of this polymer.

[2]
(ii) Starch is formed by polymerisation. It has a structure of the type shown below.
Name the monomer.

............................................................................................. .................................[ 1]
(iii) What are the differences between these two polymerisation reactions, one forming
polyacrylamide and the other starch?

............................................................................................. .....................................

.............................................................................................. ................................[2]
(b) Acrylamide hydrolyses to form acrylic acid and ammonium ions.
(i) Describe the test for the ammonium ion.
Test …………………………………………………………………………………

............................................................................................. ..........................

result ……………………………………………………….…………………[2]
(ii) Given an aqueous solution, concentration 0.1 mol / dm3, how could you show that acrylic
acid is a weak acid.

............................................................................................. .....................................
12 Past paper questions for Organic Chemistry

.............................................................................................. ................................[2]
(c) The structural formula of acrylic acid is shown below. It forms compounds called acrylates.

(i) Acrylic acid reacts with ethanol to form the following compound.

Deduce the name of this compound. What type of organic compound is it?

name.................................................................................. .....................................

type of compound……………………………………………………………….. [2]

(ii) Acrylic acid is an unsaturated compound. It will react with bromine. Describe the colour
change and draw the structural formula of the product of this addition reaction.

colour change…………………………………………………………………………
structural formula of product

………………………………………………………………………………………….

8 (June 2005, paper 3. Q3)

A South Korean chemist has discovered a cure for smelly socks. Small particles of
silver are attached to a polymer, poly(propene), and this is woven into the socks.
(a) (i) Give the structural formula of the monomer.

[1]
(ii) Draw the structural formula of the polymer.

[2]
(iii) Suggest which one, monomer or polymer, will react with aqueous bromine
and why?
…………………………………………………………………………………………..
…………………………………………………………………………………………. [2]
(b) To show that the polymer contains silver the following test was carried out.
The polymer fibres were chopped into small pieces and warmed with nitric acid.
The silver atoms were oxidised to silver(I) ions. The mixture was filtered.
Aqueous sodium chloride was added to the filtrate and a white precipitate
formed.
(i) Why was the mixture filtered?

…………………………………………………………………………………………[1]
(ii) Explain why the change of silver atoms to silver ions is oxidation.

…………………………………………………………………………………………[1]
 Past paper questions for Organic Chemistry 13

(iii) Give the name of the white precipitate.

…………………………………………………………………………………………[1]
(c) The unpleasant smell is caused by carboxylic acids. Bacteria cause the fats on
the skin to be hydrolysed to these acids. Silver kills the bacteria and prevents
the hydrolysis of the fats.
(i) Fats are esters. Give the name and structural formula of an ester.

name………………………………………………………………………………. [1]
structural formula

[1]
(ii) Complete the word equation.
Ester + water carboxylic acid + ……………… [1]
(d) Propanoic acid is a weak acid.
(i) The following equation represents its reaction with ammonia.
CH3–CH2–COOH + NH3 CH3–CH2–COO- + NH4+
Explain why propanoic acid behaves as an acid and ammonia as a base.

………………………………………………………………………………………..

………………………………………………………………………………………..[3]
(ii) Explain the expression weak acid.

………………………………………………………………………………………..[1]

9 (June 2005, p3, Q5)

Enzymes are biological catalysts. They are used both in research laboratories and in
industry.
(b) Enzymes called carbohydrases can hydrolyse complex carbohydrates to simple
sugars which can be represented as . Draw the structure of a

complex carbohydrate.

[2]

(c) Fermentation can be carried out in the apparatus drawn below. After a few days
the reaction stops. It has produced a 12% aqueous solution of ethanol.
14 Past paper questions for Organic Chemistry

(i) Complete the equation.

C6H12O6 ……………. + ……………………..
glucose ethanol carbon dioxide [2]
(ii) Zymase catalyses the anaerobic respiration of glucose. Define the term
respiration.
……………………………………………………………………………………………
…………………………………………………………………………………………[2]
(iii) Suggest a reason why the reaction stops after a few days.

…………………………………………………………………………………………[1]
(iv) Why is it essential that there is no oxygen in the flask?

…………………………………………………………………………………………[1]
(v) What technique is used to concentrate the aqueous ethanol?

…………………………………………………………………………………………[1]

10 (June 2003, paper 3. Q5) (有机综合题)

The first three elements in Period 6 of the Periodic Table of the Elements are caesium, barium
and lanthanum.
(a) How many more protons, electrons and neutrons are there in one atom of lanthanum than in
one atom of caesium. Use your copy of the Periodic Table of the Elements to help you.
number of protons ................................................
number of electrons ................................................
number of neutrons ................................................ [3]
(b) All three metals can be obtained by the electrolysis of a molten halide. The electrolysis of the
aqueous halides does not produce the metal.
(i) Complete the equation for the reduction of lanthanum ions at the negative electrode
(cathode).
La3+ + ................ → ................
(ii) Name the three products formed by the electrolysis of aqueous caesium bromide.

........................................................ ................. ..................................................... [4]

(c) All three metals react with cold water. Complete the word equation for these reactions.

metal + water → ................................. + ............................. [2]

(d) Barium chloride is an ionic compound. Draw a diagram that shows the formula of the
compound, the charges on the ions and gives the arrangement of the valency electrons
 Past paper questions for Organic Chemistry 15

around the negative ion.

The electron distribution of a barium atom is 2.8.18.18.8.2
Use x to represent an electron from a barium atom.
Use o to represent an electron from a chlorine atom.

[2]
(f) The reactions of these metals with oxygen are exothermic.
2Ba(s) + O2(g) 2BaO(s)
(i) Give an example of bond forming in this reaction.

........................................................ ................. ..........................................................

(ii) Explain using the idea of bond breaking and forming why this reaction is exothermic.

........................................................ ................. ...................................................... [3] 