ST AUGUSTINE INTERNATIONAL SCHOOL
YEAR 12 ORGANIC CHEMISTRY
TEST 1 2024
Attempt all questions.
Time allowed: 1 Hour 30 minutes.
1. Alkenes undergo an addition reaction with a 1:1 mixture of CO and H2 to form aldehydes.
Fig. 3.1 shows the reaction of propene with a 1:1 mixture of CO and H2.
(a) (i) Define addition reaction.
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(ii) Aldehydes A and B are structural isomers.
State the type of structural isomerism shown by A and B.
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(iii) Name A.
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(iv) The complete reaction of propene with a 1:1 mixture of CO and H2 produces A and B
only. The product mixture contains 96% A and 4% B.
Calculate the mass of A produced in this reaction when 5.00 × 103 kg of propene is used.
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mass of A = ..................................................... kg [1]
(b) A and B show reactions typical of aliphatic aldehydes.
(i) A undergoes a nucleophilic addition reaction with a mixture of HCN and KCN, forming
compound C.
Complete the diagram to show the mechanism for this reaction.
Include charges, dipoles, lone pairs of electrons and curly arrows, as appropriate.
Draw the structure of the organic intermediate.
[4]
(ii) Table 3.1 shows information about three experiments involving B.
Complete Table 3.1.
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(iii) B, C4H8O, is oxidised by acidified potassium manganate(VII).
Complete the equation for this reaction. Use [O] to represent one atom of oxygen from
the oxidising agent.
C4H8O + ...................................................................................................................... [1]
(iv) C is a chiral molecule.
Circle any chiral centres in the structure of C shown in Fig. 3.2.
[1]
(c) When propene reacts with CO and an excess of H2, an alkane and a mixture of alcohols are
formed instead. The alcohols are isomers of each other.
Suggest the molecular formulae of the alkane and the alcohols that are formed under these
conditions.
molecular formula of alkane .....................................................................................................
molecular formula of alcohols ...................................................................................................[2]
[15]
2. Fig. 4.1 shows some reactions of compound D, 2‑bromobutane.
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(a) (i) State the reagent and conditions used to form E in reaction 1.
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(ii) Draw the structure of one repeat unit of the addition polymer that forms from E.
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(iii) E also forms when F is heated strongly in the presence of an Al 2O3 catalyst.
Write an equation for this reaction.
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(b) (i) Predict what is observed in reaction 2.
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(ii) Identify the yellow precipitate and the organic ion formed in reaction 3.
yellow precipitate ...............................................................................................................
organic ion .........................................................................................................................[2]
(c) (i) State the type of reaction that occurs in reaction 4.
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(ii) Reaction 5 is similar to the reaction of LiAl H4 with carboxylic acids to form alcohols.
Suggest the role of LiAl H4 in reaction 5.
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(d) (i) Fig. 4.2 shows the infrared spectrum of one of the compounds D, E, F, G or H.
Use information from Table 4.1 (on page 14) to identify which of the compounds D, E, F,
G or H produces the infrared spectrum in Fig. 4.2.
Explain your answer.
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(ii) In the mass spectrum of D, the relative abundance of the molecular ion peak is 3.4.
Predict the relative abundance of the M+2 peak for D.
Explain your answer.
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[Total: 11]
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