Cambridge International AS & A Level

4: Organic chemistry 1 – Topic questions

The questions in this document have been compiled from a number of past papers, as indicated in the table
below.

Use these questions to formatively assess your learners’ understanding of this topic.

Question Year Series Paper number

3 2017 March 22
4 2017 June 21
4 2017 June 22

The mark scheme for each question is provided at the end of the document.

You can find the complete question papers and the complete mark schemes (with additional notes where
available) on the School Support Hub at www.cambridgeinternational.org/support

4: Organic chemistry 1 - Topic questions UCLES © 2018 1

 3 (a) A series of reactions starting from 1-bromobutane is shown.

HCN and KCN reaction 1

1-bromobutane P CH3(CH2)3CO2H

OH–(aq) reaction 2

polymer
but-1-ene
Q
R

(i) Draw the displayed formula of compound P.

[1]

(ii) Identify the reagent(s) and conditions for reactions 1 and 2.

reaction 1 ............................................................................................................................

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

(iii) Draw the structure of the repeat unit of polymer Q.

[2]

4: Organic chemistry 1 - Topic questions UCLES © 2018 2

 (b) Complete the reaction scheme to show the mechanism of the reaction of 1-bromobutane with
OH–(aq) to produce R.

Include all necessary charges, dipoles, lone pairs and curly arrows and the structure of R.

CH3CH2CH2

H C Br

–
OH

[3]

(c) But-1-ene reacts with steam as shown to form a mixture of two structural isomers, S and T.

reflux
S U
Cr2O72– / H+
major product
but-1-ene + steam

minor product

S can be oxidised with acidified potassium dichromate(VI) to form compound U.

S and U both react with alkaline aqueous iodine.

(i) Identify the type of reaction that occurs when but-1-ene reacts with steam.

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

(ii) State what can be deduced about the structure of S from its reaction with alkaline aqueous
iodine.

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

4: Organic chemistry 1 - Topic questions UCLES © 2018 3

 (iii) Explain why S is the major product of the reaction of but-1-ene with steam.

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

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

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

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

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

(iv) Draw the skeletal formulae of S, T and U.

S T

U
[3]

(v) Write an equation to represent the oxidation of S to U by acidified potassium dichromate(VI).

You should use [O] to represent the oxidising agent.

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

4: Organic chemistry 1 - Topic questions UCLES © 2018 4

 (d) CH3(CH2)3CO2H is a colourless liquid with an unpleasant odour.

It reacts with methanol in the presence of an acid catalyst to produce an organic product V,
which has a pleasant fruity smell.

(i) Name V.

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

(ii) A student analysed CH3(CH2)3CO2H, methanol and V using infra-red spectroscopy. The
spectra were returned to the student without labels.

Identify which of the infra-red spectra, X, Y or Z, corresponds to V.

compound CH3(CH2)3CO2H methanol V

spectrum

Explain your answer with reference to relevant features of the three spectra in the region
above 1500 cm–1.

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

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

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

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

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

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

4: Organic chemistry 1 - Topic questions UCLES © 2018 5

 infra-red spectrum X
100

transmittance
50

0
4000 3000 2000 1500 1000 500
wavenumber / cm –1

infra-red spectrum Y
100

transmittance
50

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

infra-red spectrum Z
100

transmittance
50

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1
[Total: 21]

4: Organic chemistry 1 - Topic questions UCLES © 2018 6

 4 (a) The hydrocarbons A, C4H10, and B, C4H8, are both unbranched.

A does not decolourise bromine.

B decolourises bromine and shows geometrical isomerism.

(i) Draw the skeletal formula of A.

A
[1]

(ii) The hydrocarbon A, C4H10, has a branched isomer.

Suggest why unbranched A has a higher boiling point than its branched isomer.

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

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

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

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

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

(iii) Give the structural formula of B.

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

(iv) Explain why B shows geometrical isomerism.

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

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

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

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

4: Organic chemistry 1 - Topic questions UCLES © 2018 7

 (v) Draw the mechanism of the reaction of B with bromine, Br2.
Include all necessary charges, dipoles, lone pairs and curly arrows.

[4]

(vi) Explain the origin of the dipole on Br2 in this mechanism.

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

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

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

(b) The alcohols C and D are isomers of each other with molecular formula C4H10O. Both isomers
are branched.

When C is heated under reflux with acidifi d potassium dichromate(VI) no colour change is
observed.

When D is heated under reflux with acidified potassium dichromate(VI) the colour of the
mixture changes from orange to green and E, C4H8O2, is produced.

E reacts with aqueous sodium carbonate to form carbon dioxide gas.

(i) Identify C, D and E.

C D E
[3]

(ii) Write the equation for the reaction between E and aqueous sodium carbonate.

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

4: Organic chemistry 1 - Topic questions UCLES © 2018 8

 (c) The isomers F and G, C5H10O, both form an orange precipitate when reacted with 2,4-DNPH.

F is unbranched and reacts with alkaline aqueous iodine to produce a yellow precipitate.

G does not react with alkaline aqueous iodine. It contains a chiral centre and produces a silver
mirror when warmed with Tollens’ reagent.

(i) Name the yellow precipitate produced by the reaction between F and alkaline aqueous
iodine.

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

(ii) Give the structural formula of F and of G.

F .........................................................................................................................................

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

(iii) Explain the meaning of the term chiral centre.

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

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

4: Organic chemistry 1 - Topic questions UCLES © 2018 9

 (d)H and I are isomers with molecular formula C2H4O2. The infra-red spectra of isomers H and I
are shown.

H
100

percentage
transmittance
50

0
4000 3000 2000 1500 1000
wavenumber / cm–1

I
100

percentage
transmittance
50

0
4000 3000 2000 1500 1000
wavenumber / cm–1

(i) Identify the bonds responsible for the principal peaks above 1500 cm–1 in each spectrum.

spectrum of H ......................................................................................................................

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

spectrum of I .......................................................................................................................

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

(ii) Name H and I.

H .........................................................................................................................................

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

[Total: 23]
4: Organic chemistry 1 - Topic questions UCLES © 2018 10
 4 P, Q and R all have the molecular formula C3H6O. They are all structural isomers of each other.

P and Q each contain an oxygen atom bonded directly to a carbon atom that is sp2 hybridised.
R contains an oxygen atom bonded directly to a carbon atom that is sp3 hybridised.

(a) (i) Explain the meaning of the term structural isomers.

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

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

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

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

(ii) Explain how sp2 and sp3 hybridisation can occur in carbon atoms.

sp2 hybridisation .................................................................................................................

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

sp3 hybridisation .................................................................................................................

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

(iii) State the bond angles normally associated with each type of hybridisation in carbon atoms.

sp2 .......................................................................................................................................

sp3 .......................................................................................................................................
[2]

(b) R contains two different functional groups, one of which is an alkene group.
R reacts with cold, dilute, acidified manganate(VII) ions to form propane-1,2,3-triol.

H H H

HO C C C OH

H OH H

propane-1,2,3-triol

(i) Give the displayed formula of R.

[1]

4: Organic chemistry 1 - Topic questions UCLES © 2018 11

 (ii) State the type of reaction and what you would observe when R
reacts with bromine water.

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

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

(iii) Draw the structure of the product formed when R reacts with bromine water.

[1]

(iv) Identify the gaseous product formed when R reacts with hot, concentrated,
acidified manganate(VII) ions.

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

(c) P and Q (C3H6O) both form an orange precipitate when reacted with 2,4-DNPH. Only Q
produces a yellow precipitate when reacted with alkaline aqueous iodine.

(i) Name P and Q.

P .........................................................................................................................................

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

(ii) Identify the yellow precipitate formed by the reaction of Q with alkaline aqueous iodine.

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

(d) P and Q each react with hydrogen cyanide to form a single product.
The product formed from P exists as a pair of optical isomers.
The product formed from Q does not exhibit optical isomerism.

(i) Explain the meaning of the term optical isomers.

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

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

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

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

4: Organic chemistry 1 - Topic questions UCLES © 2018 12

 (ii) Ethanal, CH3CHO, also reacts with hydrogen cyanide. The product of this reaction is
CH3CH(OH)CN.

Draw the mechanism of this reaction.

Include all necessary charges, dipoles, lone pairs and curly arrows.

[3]

[Total: 19]

4: Organic chemistry 1 - Topic questions UCLES © 2018 13

 Question Answer Marks
3 (a) (i) 1

3 (a) (ii) reaction 1 = HCl (aq) 1

reaction 2 = (conc.) NaOH / KOH AND ethanol 1

3 (a) (iii)

C–C backbone with dangling bonds 1

rest of structure 1

3 (b)

lone pair on O AND curly arrow from O to C of C–Br 1

dipole on C–Br AND curly arrow from C–Br to Br 1

product (butan-1-ol) 1

3 (c) (i) (electrophilic) addition 1

3 (c) (ii) S has CH3CHOH OR methyl / CH3 group next to CHOH 1

3 (c) (iii) positive inductive effect of more alkyl groups / more alkyl groups donate 1
electron density
secondary carbocation / secondary intermediate is more stable (than 1
primary)
3 (c) (iv) 1
S=

1
T=

1
U=

3 (c) (v) CH3CHOHCH2CH3 + [O] → CH3COCH2CH3 + H2O 1

3 (d) (i) methyl pentanoate 1

3 (d) (ii) (compound V is) spectrum X 1

spectra X and Z show a C=O (stretch) at 1730 (cm–1) 1

spectra Y and Z show O–H (stretches) above 2500 (cm–1) 1

V has a C=O (bond) and no O–H (bond) 1

Total: 21
4: Organic chemistry 1 - Topic questions UCLES © 2018 14
 Question Answer Marks
4 (a) (i) (A = ) 1

4 (a) (ii) (A / straight chain) has strong(er) (temporary dipole-) induced dipole 1
(attractions) ora
(because A / straight chain has) bigger (surface) area / more (points of) 1
contact (in unbranched isomer) ora
OR
(so) more energy required to break the intermolecular forces ora

4 (a) (iii) CH3CHCHCH3 OR CH3CH=CHCH3 1

4 (a) (iv) No rotation / restricted / limited rotation of C=C / (carbon) double bond 1

One (of the two) methyl groups / one (of the two) H (atoms) is on each C 1
(of C=C)

4 (a) (v) 1

arrow from the C=C double bond drawn to the bromine

dipole on Br2 in correct orientation AND arrow from the Br-Br bond to the 1
Brδ–

correct carbocation / bromonium ion from the structure with C=C drawn 1
Br– with lone pair, negative charge AND arrow from lone pair to the 1
carbon atom of intermediate
OR
using both arrows shown (in alternative diagram)

4 (a) (vi) electrons in pi bond induce it (the dipole) OR 1

(high) electron density in pi bond / double bond / C=C repels electrons
(away from nearest Br)
OR
polarised by (high) electron density in pi bond / double bond / C=C

4 (b) (i) C = (2-)methylpropan-2-ol / (CH3)3COH / any unambiguous structure 1

D = (2-)methylpropan-1-ol / (CH3)2CHCH2OH / any unambiguous 1

structure

E = (2-)methylpropanoic acid /(CH3)2CHCO2H / any unambiguous 1

structure

4 (b) (i) 2C4H8O2 + Na2CO3 → 2C4H7O2Na + H2O + CO2 1

4 (c) (i) triiodomethane 1

4: Organic chemistry 1 - Topic questions UCLES © 2018 15
 Question Answer Marks
4 (c) (ii) F = CH3CH2CH2COCH3 1

G = C2H5CH(CH3)CHO 1

4 (c) (iii) a (tetrahedral) atom with four different groups / atoms / substituents 1
attached
OR
a carbon (atom) with four different groups / atoms / substituents attached

4 (d) (i) H C=O (group / bond) AND O–H (group / bond) 1

I C=O (group / bond) AND C–H (group / bond) 1

Total: 21

Question Answer Marks

4 (a) (i) (molecules / isomers with) the same molecular formula / same number 1
of atoms of each element

different structural / displayed formulae / arrangement of bonds 1

4 (a) (ii) sp2 overlap of (2)s with (2)p (atomic) orbitals 1

sp3 overlap of (2)s with all three (2)p (atomic) orbitals 1

4 (a) (iii) sp2 = 116° – 124° 1

sp3 = 106° – 112° 1

4 (b) (i) 1

4 (b) (ii) (electrophilic) addition 1

bromine decolourises / turns colourless / fades (from orange / brown) 1

4 (b) (iii) 1

HOCH2CHBrCH2Br OR

4 (b) (iv) CO2 / carbon dioxide 1

4 (c) (i) P = propanal 1

Q = propanone 1

4: Organic chemistry 1 - Topic questions UCLES © 2018 16

 Question Answer Marks
4 (c) (ii) 1

tr(i)iodomethane / CHI3

4 (d) (i) (molecules / isomers with) the same (molecular and) structural formula 1

Any two of: 1

• Chiral centre / C attached to four different groups / atoms
• Non-super(im)posable mirror images
• Different spatial / 3D arrangement of atoms (owtte)
• Different rotation of plane-polarised light

4 (d) (ii) 1

curly arrow from lone pair on :C≡N to C(δ+) 1

correct dipole on carbonyl δ+C=Oδ- AND curly arrow from bond to O(δ-) 1

correct intermediate, including C–O- AND curly arrow from lone pair to 1
H+

Total: 19
Notes about the mark scheme are available separately.

4: Organic chemistry 1 - Topic questions UCLES © 2018 17