Name: ________________________

Elimination reactions
and ozone depletion Class: ________________________

Date: ________________________

Time: 64 minutes

Marks: 58 marks

Comments:

Page 1 of 18
 The diagram shows some compounds made from a halogenoalkane.
1.

(a) Draw the displayed formula of compound J.

(1)

(b) Name the mechanism for Reaction 2 and give an essential condition used to ensure that
CH3CH2CH2NH2 is the major product.

Name of mechanism __________________________________________________

Condition ___________________________________________________________
(2)

(c) Calculate the mass, in grams, of CH3CH2CH2NH2 produced from 25.2 g of CH3CH2CH2Br
in Reaction 2 assuming a 75.0% yield.

Give your answer to the appropriate number of significant figures.

Mass ____________________ g
(3)

Page 2 of 18
(d) When Reaction 2 is carried out under different conditions, a compound with molecular
formula C9H21N is produced.

Draw the skeletal formula of the compound.

Identify the functional group in the compound including its classification.

Skeletal formula

Functional group including classification ____________________

(2)

(e) Identify the reagent and conditions used in Reaction 3.

___________________________________________________________________
(1)

(f) Name and outline a mechanism for Reaction 3.

Name of mechanism __________________________________________________

Mechanism

(4)
(Total 13 marks)

Page 3 of 18
 2-bromo-2-methylpentane is heated with potassium hydroxide dissolved in ethanol. Two
2. structural isomers are formed.

(a) State the meaning of the term structural isomers.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

(b) Name and draw the mechanism for the formation of one of the isomers.

Name of mechanism __________________________________________________

Mechanism

(5)
(Total 6 marks)

Page 4 of 18
 Consider the following scheme of reactions.
3.

(a) Give the IUPAC name for compound P and that for compound Q.

P _________________________________________________________________

Q _________________________________________________________________
(2)

(b) The conversion of P into Q in Reaction 1 uses HCl

Name and outline a mechanism for this reaction.

___________________________________________________________________
(5)

(c) The conversion of Q into R in Reaction 2 uses NH3

Name and outline a mechanism for this reaction.

___________________________________________________________________
(5)

Page 5 of 18
 (d) State the type of reaction shown by Reaction 3.

Identify a reagent for this reaction.

Give one condition necessary for a high yield of product when Q is converted into P.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

(e) Hydrogen bromide (HBr) could be used in the overall conversion of P into R, instead of
using HCl
Hydrogen bromide is made by the reaction of NaBr with concentrated phosphoric acid.
Concentrated sulfuric acid is not used to make HBr from NaBr

Write an equation for the reaction of NaBr with H3PO4 to produce HBr and Na3PO4 only.

Identify two toxic gases that are formed, together with HBr, when NaBr reacts with
concentrated H2SO4

State the role of H2SO4 in the formation of these two toxic gases.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(4)
(Total 19 marks)

CFCs were used as refrigerants and in aerosols.

4.
The scientists Rowland and Molina published research in 1974 to show that CFCs are
responsible for the destruction of ozone molecules in the upper atmosphere.

A few years later, other scientists discovered that the concentration of ozone in the upper
atmosphere was decreasing.

In 1987 there was an agreement by many countries to restrict the use of CFCs.

Page 6 of 18
(a)  The molecule CFC-11 was commonly used as a refrigerant.

Use IUPAC rules to name CFC-11

___________________________________________________________________
(1)

(b)  A molecule of CFC-11 breaks down in the upper atmosphere to form a chlorine free radical.

Give the equation for this reaction.

___________________________________________________________________
(1)

(c)  A typical refrigerator contained 0.50 kg of CFC-11 (Mr = 137.5).

One molecule of CFC-11 causes the destruction of approximately 100 000 molecules of
ozone.

Use these data to estimate the number of molecules of ozone that can be destroyed by
0.50 kg of CFC-11
Give your answer in standard form.

The Avogadro constant, L = 6.022 × 1023 mol–1

Number of molecules of ozone ____________________

(2)

Page 7 of 18
 (d)  State the benefit to life on Earth of ozone in the upper atmosphere.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

(e)  Suggest one reason why the use of CFCs was not restricted until several years after
Rowland and Molina published their research.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

(f)  CFC-11 is a greenhouse gas that can contribute to global warming.

State and explain how CFC-11 is able to contribute to global warming.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)
(Total 8 marks)

This question is about the ozone layer in the upper atmosphere.

5.
(a)  State why the ozone layer is beneficial for living organisms.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

Page 8 of 18
 (b)  State how chlorofluorocarbons (CFCs) form chlorine atoms in the upper atmosphere.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

(c)  Give equations to show how chlorine atoms catalyse the decomposition of ozone.

___________________________________________________________________

___________________________________________________________________
(2)

(d)  Hydrochlorofluorocarbons (HCFCs) have been used in place of CFCs.

In the mechanism to make an HCFC from a fluoroalkane, two incomplete steps are shown.

Complete each step in the mechanism.

Give the name of the type of step shown by both these equations.

____________________ → ● CHF2 + HCl

● CHF2 + Cl2 → ____________________

Type of step ________________________________________________________

(3)
(Total 7 marks)

Which statement is not correct about ozone?

6.
A It absorbs harmful ultraviolet radiation in the upper atmosphere.

B Its decomposition is catalysed by chlorine molecules.

C It decomposes to form oxygen.

D Ozone holes are regions of the upper atmosphere where there is a

reduced concentration of ozone.

(Total 1 mark)

Page 9 of 18
 Which compound is not formed by reacting 3-bromo-3-methylhexane with warm, ethanolic
7. potassium hydroxide?

A 2-ethylpent-1-ene

B 3-methylhex-1-ene

C 3-methylhex-2-ene

D 3-methylhex-3-ene

(Total 1 mark)

Which of the following mechanisms does not occur in reactions of bromoethane?

8.

A Electrophilic addition

B Elimination

C Nucleophilic substitution

D Radical substitution

(Total 1 mark)

Which compound could not be produced by reacting 2-bromo-3-methylbutane with sodium

9. hydroxide?

A 2-methylbut-1-ene

B 3-methylbut-1-ene

C 2-methylbut-2-ene

D 3-methylbutan-2-ol

(Total 1 mark)

How many different alkenes are formed when 2-bromo-2-methylbutane reacts with ethanolic
10. potassium hydroxide?

A 2

B 3

C 4

D 5
(Total 1 mark)
Page 10 of 18
Mark schemes
(a)
1.

Must be displayed
1

(b) Nucleophilic substitution

1

Excess NH3
Ignore aqueous, alcoholic, conc, dil, temp, heat, pressure
1

(c) Amount of CH3CH2CH2Br   25.2/122.9 (=0.205) (mol)

M1

Amount of CH3CH2CH2NH2  M1 × 0.75 (= 0.154) (mol)

M2

Mass CH3CH2CH2NH2     M2 × 59.0 = 9.07g  Must be 3sf

M3
If either Mr incorrect or used incorrectly then only award 1 mark for
75% yield calculation
(ignore rounding to 123 for CH3CH2CH2Br)

OR
Max mass amine = M1 × 59.0 (= 12.1) (g)
Actual mass = M2 × 0.75 = 9.07g Must be 3sf

Allow 9.09 but if 9.08 check for AE

18.9 scores 1 for 75%

(d)

Must be skeletal
Ignore lone pair
1

tertiary amine or 3° amine (only award if a tertiary amine shown)

1

Page 11 of 18
 (e) NaOH/ ethanol or KOH / ethanol (both required)
NOT aqueous
Ignore heat, temp, conc., dil,
Accept alcoholic for ethanol
1

(f) (Basic) Elimination

Also credit E1 mechanism

M1 arrow from lone pair on O of hydroxide to correct H (or to space mid way between
hydroxide O and H)

M2 arrow from C-H bond to C-C bond following attack by OH− on the correct H

M3 arrow from C-Br bond to Br

If nucleophilic substitution shown then allow M3 only in mechanism

If wrong haloalkane used then Max 2 for mechanism

M3 curly arrow for loss of Br− & structure of carbocation
M1 arrow from lone pair on O of hydroxide to H (or to space mid
way between hydroxide O and H) (same as E2)
M2 arrow from C-H bond to C-C bond (same as E2)
3
[13]

(a) (Compounds with the) same molecular formula but different structural / displayed / skeletal
2. formula
1

(b) (basic) elimination

1

Page 12 of 18
 Mechanism points:

Correct arrow from lone pair on :OH– to H on C adjacent to C–Br

1

Correct arrow from C–H bond to C–C

1

Correct arrow from C–Br bond to Br

1

Structure of chosen product

1

OR

[6]

(a) P 3,3−dimethylbut−1−ene
3. OR
accept 3,3−dimethylbutene
Ignore absence of commas, hyphens and gaps
Require correct spelling

Q 3−chloro−2,2−dimethylbutane
OR
accept 2−chloro−3,3−dimethylbutane
In Q, “chloro” must come before “dimethyl”
2

Page 13 of 18
(b) M1 Electrophilic addition

M2 must show an arrow from the double bond towards the H atom of HCl
M3 must show the breaking of the H−Cl bond
M4 is for the structure of the carbocation
M5 must show an arrow from the lone pair of electrons on the negatively charged
chloride ion towards the positively charged carbon atom on their carbocation.

NB The arrows here are double−headed

M1 both words required
For the mechanism
M3 Penalise incorrect partial charge on H−Cl bond and penalise
formal charges
Ignore partial negative charge on the double bond.
Maximum 3 of 4 marks for a correct mechanism using HBr or
the wrong organic reactant or wrong organic product (if shown) or a
primary carbocation
Penalise once only in any part of the mechanism for a line and two
dots to show a bond
Credit the correct use of “sticks”
For M5, credit attack on a partially positively charged carbocation
structure, but penalise M4
5

Page 14 of 18
(c) M1 Nucleophilic substitution
For M1, both words required.
Accept phonetic spelling

M2 must show an arrow from the lone pair of electrons on the nitrogen atom of an
ammonia molecule to the correct C atom
M3 must show the movement of a pair of electrons from the C− Cl bond to the Cl
atom. Mark M3 independently provided it is from their original molecule
M4 is for the structure of the alkylammonium ion, which could be a condensed
formula. A positive charge must be shown on, or close to, the N atom.
M5 is for an arrow from the N−H bond to the N atom
Award full marks for an SN1 mechanism in which M2 is the attack of the ammonia on the
intermediate carbocation

NB These are double-headed arrows

For the mechanism
Penalise M2 if NH3 is negatively charged.
Penalise M3 for formal charge on C of the C−Cl or incorrect partial
charges on C−Cl
Penalise M3 for an additional arrow from the Cl to something else
The second mole of ammonia is not essential for M5; therefore
ignore any species here
Penalise once only for a line and two dots to show a bond
Maximum 3 of 4 marks for the mechanism for wrong organic
reactant OR wrong organic product if shown
Accept the correct use of “sticks”
5

Page 15 of 18
 (d) M1 (base) elimination
M1 Dehydrohalogenation

M2 KOH OR NaOH
M3 Must be consequential on a correct reagent in M2, but if incomplete or
inaccurate attempt at reagent (e.g. hydroxide ion), penalise M2 only and mark on

Any one from

• high temperature OR hot OR heat / boil under reflux
• concentrated
• alcohol / ethanol (as a solvent) / (ethanolic conditions)
M3 not “reflux” alone
M3 if a temperature is stated it must be in the range 78°C to 200 °C
Ignore “pressure”
3

(e) M1
3NaBr + H3PO4 3HBr + Na3PO4
M1 Credit correct ionic species in the equation

M2 and M3
SO2 and Br2 identified
M4
Concentrated sulfuric acid
• is an oxidising agent
• oxidises the bromide (ion) or Br− or NaBr or HBr
• is an electron acceptor
In M2 and M3 the two gases need to be identified. If equations are
used using sulfuric acid and the toxic gases are not identified
clearly, allow one mark for the formulas of SO2 and Br2
• apply the list principle as appropriate but ignore
any reference to HBr
• the marks are for identifying the two gases either
by name or formula
4
[19]

(a) trichlorofluoromethane
4. 1

(b)

CCl3F → •CCl2F + •Cl

radical dot anywhere on each radical
1

Page 16 of 18
 (c) M1 amount of CFC-11 = ( = 3.64) mol
Allow ECF from M1 to M2
1

M2 molecules of O3 = 3.64 x 100,000 x 6.022 x 1023 = 2.19 x 1029

Allow answers in range 2 x 1029 to 2.20 x 1029 (1sf is acceptable as
this is an estimate)
1

(d) Absorbs (harmful) ultraviolet / uv (light / radiation)

Protects us from (harmful) uv
Ignore other wavelengths / types of light
1

(e) One of these reasons:

•   lack of evidence that ozone was being depleted

•   lack of alternatives to CFCs
•   commercial interest to continue to use CFCs
•   hard to obtain international agreement
1

(f) M1 absorbs infrared radiation

M1 idea of IR being taken in
1

M2 molecule has polar bonds

M2 accept polar molecule
1
[8]

(a) Absorbs/prevents harmful uv

5.
Allow reduced risk of skin cancer from uv
1

(b) C-Cl bonds broken (homolytically)

Could show in an equation showing the bond
1

(c) Cl● + O3 → ClO● + O2

M1

ClO● + O3 → Cl● + 2O2

M2

Page 17 of 18
 (d) Cl● + CH2F2 →
Penalise missing dot once only
M1

→ CHClF2 + Cl●
M2

Propagation
M3
[7]

C
6.
Its decomposition is catalysed by chlorine molecules
[1]

B
7.
3-methylhex-1-ene
[1]

A
8.
[1]

A
9.
2-methylbut-1-ene
[1]

A
10.
[1]

Page 18 of 18