Carbonyl Compounds Tutorial 2024 Semester 1

CATHOLIC JUNIOR COLLEGE

H2 CHEMISTRY (SYLLABUS 9729)
CARBONYL COMPOUNDS TUTORIAL
Level 1 (Self–check questions)
The following is the summary of the basic chemistry of carbonyl compounds that you have to
master before doing the rest of the questions in the different Levels 2 & 3. However, some short
questions will be set at this Level 1 based on the summary.

SUMMARY and QUESTIONS

1 (a) Give the organic products in the spaces provided (answers are already provided for
you.)
1 2 3

Fehling’s solution KMnO4(aq)/H2SO4(aq)

Tollens’ reagent heat heat under reflux
4 heat 5
CH3⎯C⎯H
I2(aq)/NaOH(aq) ║ LiAlH4 in dry ether
O
heat Ethanal HCN
trace of NaOH(aq)
2,4-DNPH 10 oC – 20 oC
heat
6 7
HCN
trace of NaOH(aq)

8 9
I2(aq)/NaOH(aq) CH3⎯C⎯CH3 LiAlH4 in dry ether
heat heat ║
O
Propanone
HCN
2,4-DNPH trace of NaOH(aq), 10 oC – 20 oC
10 heat
11

I2(aq)/NaOH(aq)
heat

Note: ● Ketones do not react with Tollens’ reagent or Fehling’s solution and
KMnO4/H2SO4 as they are not easily oxidised. Both Tollens’ reagent and Fehling’s
solution are mild oxidising agents.

T u t o r i a l q u e s t i o n s – P a g e | 15-28
Carbonyl Compounds Tutorial 2024 Semester 1

(b) Both aldehydes and ketones react with HCN. State the name of the mechanism of reaction
they undergo?

(c) Both aldehydes and ketones react with 2,4-DNPH to form the corresponding
phenylhydrazones. State the name of the reaction and what is the colour of the precipitate
formed?

(d) In the tri-iodomethane or iodoform reaction (oxidation) with ethanal and certain ketones,
what is the colour of the solid, CHI3 formed?

(e) In the reaction with aldehydes, Tollens’ Reagent or Fehling’s Solution, are reduced to silver
mirror or Cu2O respectively. What is the colour of the precipitate, Cu2O formed?

Level 2
[4.1.1 Nucleophilic Addition of Hydrogen Cyanide]

2 Carbonyl compounds react with hydrogen cyanide to form cyanohydrins. Outline the
mechanism of this reaction, indicating clearly why a trace of sodium hydroxide is needed
for the reaction to take place.

3 In the reaction between an aldehyde and HCN catalysed by NaOH, which of the following
statements about the reaction mechanism are true?

1 A new carbon-carbon bond is formed.

2 In the intermediate, the oxygen carries a negative charge.
3 The last stage involves the formation of a hydrogen-oxygen bond.

T u t o r i a l q u e s t i o n s – P a g e | 15-29
Carbonyl Compounds Tutorial 2024 Semester 1

4 The Benzoin condensation is a coupling reaction between two aldehydes that allows the
preparation of -hydroxyketones. The first methods were only suitable for the conversion of
aromatic aldehydes such as benzaldehyde. Some of the steps involved in the reaction are
shown below:

Which of the following correctly represents the type of reaction occurring in Step 1 and
Step 2?
Step 1 Step 2
A nucleophilic addition condensation
B nucleophilic addition nucleophilic addition
C nucleophilic addition electrophilic substitution
D nucleophilic substitution nucleophilic addition

[4.1.3 Reduction]

5 What is the structural formula of the compound formed when CH2CHCH2CHO reacts with
NaBH4? [2016 A Level/P1/Q29]

A CH2CHCH2CO2H B CH2CHCH2CH2OH

C CH3CH2CH2CHO D CH3CH2CH2CH2OH

[4.1.3, 4.2.2 Reduction; 4.3 Tri-iodomethane (Iodoform) Reaction]

6 A carbonyl compound X, which contains five carbon atoms, does not react with alkaline
aqueous iodine or with Tollens’ reagent. Compound X can be reduced by NaBH4.

What is the organic product when X is reduced? [2016 A Level/P1/Q29]

A (CH3)2C(OH)CH2CH3 B CH3CH2CH(OH)CH2CH3

C CH3CH(OH)CH(CH3)2 D HOCH2CH2CH(CH3)2

T u t o r i a l q u e s t i o n s – P a g e | 15-30
Carbonyl Compounds Tutorial 2024 Semester 1

7 One of the compounds responsible for the flavour of butter is butan-2,3-dione:

H3C C C CH3

O O

Give the structural formulae of the organic products formed when

butane-2,3-dione reacts completely with (i) H2/Ni, (ii) I2/OH–

8 Which of the following reagents will distinguish between benzaldehyde, C6H5CHO, and
phenylethanone, C6H5COCH3?

A aqueous bromine B 2, 4-dinitrophenylhydrazine

C ammonical silver nitrate D aqueous iron(III) chloride

Level 3 (Integrated)

9 The main component of cinnamon oil is cinnamaldehyde.

cinnamaldehyde
Give the structural formula of the organic products formed when cinnamaldehyde reacts
completely with the given reagents under the conditions stated:

(i) HCN with trace NaOH, 10-20oC

(ii) LiAlH4 in dry ether
(iii) K2Cr2O7/H2SO4, heat under reflux
(iv) KMnO4/H2SO4, heat under reflux

[2. Preparation of ketones]

10 Propose a reaction synthesis route for the following conversion:

In your answer, state all reagents and conditions used, and show all reaction intermediates.

T u t o r i a l q u e s t i o n s – P a g e | 15-31
Carbonyl Compounds Tutorial 2024 Semester 1

[4.1 Reactions common to Both Aldehydes and Ketones]

[4.2 Reactions of aldehydes Only]
11 Three compounds E, F and G all have the molecular formula C3H6O. E is an alcohol, F is
a ketone and G is an aldehyde.

(i) Draw possible structural formulae for E, F and G. (E has two functional groups that
do not fall on the same carbon.)

(ii) Describe tests (reagents, conditions and observations with each compound) that
would allow you to show that:

1. E is an alcohol, whereas F and G are not.

2. F and G are carbonyl compounds, whereas E is not.

3. G is an aldehyde, whereas E and F are not.

Write balanced equations for all reactions that occur.

12 Outline the steps of the following synthesis. Indicate the reagents and conditions used
clearly in each step.

13 A certain industrial cleaner and paint solvent was distilled to produce a single compound
D. When D reacted with 2,4-dinitrophenylhydrazine, an orange precipitate was produced.
With alkaline aqueous iodine, D gave a pale yellow precipitate. D did not react either with
warm acidified potassium dichromate (VI) or with aqueous bromine. Reduction of D with
hydrogen over a catalyst produced an equimolar mixture of two isomers, E and F, with the
molecular formula C4H10O.
Suggest structural formulae for D, E and F and explain the reactions involved.

T u t o r i a l q u e s t i o n s – P a g e | 15-32
Carbonyl Compounds Tutorial 2024 Semester 1

Assignment Questions

14 Propanal reacts with HCN in the presence of trace amounts of NaCN to give an equimolar
mixture of two isomers, X and Y.

(a) Describe the mechanism involved in the above reaction. [3]

(b) Explain why an equimolar mixture of X and Y is formed, and state the type of
isomerism they exhibit. [2]

(c) Propanal is added to 2,4-dinitrophenylhydrazine. State the expected observations

and draw the structure of the organic product formed. [2]

[Total: 7]

15 A compound X has molecular formula C4H6O2. X reacts with hydrogen cyanide, HCN, to
give Y, the molecular formula of which is C6H8O2N2. X also reacts with warm acidified
sodium dichromate (VI) to give Z, molecular formula C4H6O3.

2.50 g of Z were dissolved in water and the solution made up to 250 cm3. 25.0 cm3 of this
solution were neutralised by 24.5 cm3 of 0.10 mol dm−3 sodium hydroxide.
(a) (i) Use the molecular formula of Z to calculate its relative molecular mass. [1]
(ii) What mass of Z would be neutralised by 1 mol of sodium hydroxide? [1]
(iii) What information does this give about Z? [1]
(b) Deduce one possible full structural formula of X. [3]
(c) Give the structures of Y and Z. [2]
(d) In fact there are 2 isomers which satisfy all the information so far. Give the structural
formula of the second isomer of X. Label this W. [1]
(e) State one test by which X and W could be distinguished. State what reagents and
conditions would be used, and how X and W could each respond. [2]
[Total: 11]

T u t o r i a l q u e s t i o n s – P a g e | 15-33