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Name……………………………………………………… Date…………………..

Ahmad Bin Majid International School

Department of Chemistry
AY – 2023-24

A2 CHEMISTRY: Aldehydes and Ketones

1. Which of the following reacts with hydrogen cyanide, HCN, to make a racemic
mixture?

A Methanal, HCHO

B Ethanal, CH3CHO

C Propanone, CH3COCH3

D Pentan-3-one, C2H5COC2H5

2. Which of the following is a redox reaction?

A Ethanal reacting with Tollens’ reagent.

B Ethanoyl chloride reacting with ammonia.

C Ethanoic acid reacting with ethanol.

D Ethanoic acid reacting with sodium hydroxide.

3. The following methods can be used to distinguish between pairs of organic

compounds without further tests.

A Warm each compound with Fehling’s or Benedict’s solution.

B Add solid sodium carbonate to each compound.

C Add 2,4-dinitrophenylhydrazine (Brady’s reagent) to each compound.

D Add water, drop by drop, to each compound.

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(a) Which test would distinguish propanone from propan-1-ol? (1)

(b) Which test would distinguish between aqueous solutions of ethanoic acid and
ethanol? (1)

A C

B D

(c) Which test would distinguish ethanoyl chloride from ethanol? (1)

4. When propanone reacts with iodine in the presence of sodium hydroxide, the
crystalline solid product has the formula (1)

A CH3I

B CHI3

C CH3COCH2I

D CH3COCI3

5. Hydrogen cyanide, HCN, reacts with propanal, CH3CH2CHO, in the presence of

potassium cyanide, KCN.

(a) The mechanism for this reaction is (1)

A nucleophilic addition.

B nucleophilic substitution.

C electrophilic addition.

D electrophilic substitution.

(b) The first stage of the mechanism of this reaction is (1)

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A the lone pair of electrons on carbon in CN– attacking C♪+ of propanal.

B the lone pair of electrons on nitrogen in CN– attacking C♪+ of propanal.

C the lone pair of electrons on oxygen in propanal attacking C♪+ of HCN.

D the lone pair of electrons on oxygen in propanal attacking H♪+ in HCN.

(c) The product of the reaction is (1)

A 1-hydroxypropanenitrile.

B 2-hydroxypropanenitrile.

C 1-hydroxybutanenitrile.

D 2-hydroxybutanenitrile.

6. Which of the following does not have hydrogen bonding in a pure sample, but
forms hydrogen bonds with water when it dissolves?

A Propane

B Propanal

C Propanol

D Propanoic acid

7. Which of the following has both optical and E-Z isomers?

A ClCH2CHClCH=CH2

B CH2=CClCH2CH2Cl

C ClCH2CH=CHCH2Cl

D CHCl=CHCHClCH3

8. One optically active isomer of 2-chlorobutane reacts with hydroxide ions to form

butan-2-ol.

C2H5CHClCH3 + OH– → C2H5CH(OH)CH3 + Cl–

The organic product is a mixture of enantiomers because

A butan-2-ol contains a chiral carbon atom.

B the reaction is a nucleophilic substitution.

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C 2-chlorobutane forms a carbocation intermediate.

D 2-chlorobutane forms a five-bonded transition state.

9.Ketones react with hydrogen cyanide, HCN, in the presence of cyanide ions, CN -.

(a) Which of these ketones does not form a racemic mixture in this reaction? (1)

A CH3CH2CH2COCH3

B CH3CH2COCH2CH3

C CH3CH2CH2CH2COCH3

D CH3CH2CH2COCH2CH3

(b) This type of reaction is classified as (1)

A nucleophilic substitution.

B nucleophilic addition.

C electrophilic addition.

D electrophilic substitution.

(Total for Question 9= 2 marks)

10. This question is about the four organic substances shown below.

A CH3CH2CH2CH2CHO

B CH3CH2CH2CH2COOH

C CH3COCH2CH2CH3

D CH3CH2CH2CH2COCl

Which substance will

(a) give a positive result with both Brady’s and Tollens’ reagents? (1)

A B

C D

(b) be formed by the oxidation of a secondary alcohol? (1)

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11. An organic compound reacts with both acidified potassium dichromate(VI) and

lithium tetrahydridoaluminate (lithium aluminium hydride). The organic compound

could be

A a primary alcohol.

B an aldehyde.

C a ketone.

D a carboxylic acid

12. Ketones react with

A both 2,4-dinitrophenylhydrazine solution and Tollens’ reagent.

B 2,4-dinitrophenylhydrazine solution but not with Tollens’ reagent.

C Tollens’ reagent but not with 2,4-dinitrophenylhydrazine solution.

D neither Tollens’ reagent nor 2,4-dinitrophenylhydrazine solution.

13. A solution of 2,4-dinitrophenylhydrazine (Brady’s reagent) is used as a test for

organic functional groups.

(a) The positive result of the test is the formation of (1)

A a yellow solution.

B an orange precipitate.

C a red solution.

D a green precipitate.

(b) Which of the following gives a positive result with a solution of 2,4-
dinitrophenylhydrazine? (1)
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A Only aldehydes

B Only ketones

C Only aldehydes and ketones

D Any compound containing the C= O group

(c) The initial attack by 2,4-dinitrophenylhydrazine, when it reacts, is by (1)

A a free radical.

B an electrophile.

C a nucleophile.

D a negative ion.

(d) The product of a positive test, a 2,4-dinitrophenylhydrazone, contains which of

the following bonds? (1)

AN=N

BC=N

CC=C

DC=O

14. This question is about the following isomeric compounds with the molecular
formula C4H8O and molar mass 72 g mol–1.

A CH3CH2CH2CHO

B (CH3)2CHCHO

C CH3CH2COCH3

D CH3CH= CHCH2OH

(a) Which compound would you expect to give a peak at m/e = 41 in its mass

spectrum? (1)

C
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(b) Which compound would NOT react with an acidified solution of potassium

dichromate(VI)? (1)

A C

B D

(c) Which compound would give a pale yellow precipitate when reacted with iodine

in alkaline solution? (1)

(d) Which compound can be reduced to give a chiral product? (1)

A C

B D

(e) Which compound would NOT react with hydrogen cyanide under suitable

conditions to form a hydroxynitrile? (1)

15. A sequence of reactions for the production of lactic acid is shown below.
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(a) (i) Name the type and mechanism of the reaction in step 2. (2)

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(ii) Which two substances need to be added to ethanal to carry out the reaction in

step 2? (2)

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(iii) Give the mechanism for the reaction in step 2, using curly arrows to show

movements of electron pairs. (3)

*(iv) The product of step 2 is not optically active even though it has a chiral carbon

atom in its formula. Explain, by reference to the mechanism, the reason for the

lack of optical activity. (2)

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16. Two organic compounds, X and Y, both with the molecular formula C4H8O,
contain a carbonyl group.

(a) Describe what you would see when 2,4-dinitrophenylhydrazine is added to either
of these compounds. (1)

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(b) It is suspected that X is a ketone and Y is an aldehyde. Outline a chemical test

you could carry out to confirm this, describing the results in each case. (3)

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(c) (i) Give the structural formulae of the two possible isomers of Y which are

aldehydes. (1)

(ii) Name the technique you would use to purify the product of the test with

2,4-dinitrophenylhydrazine. (1)

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(iii) Other than by spectroscopic techniques, how would you use the purified product

to identify compound Y? [Practical details are not required.] (2)

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17. The molecule

smells similar to watermelon.

(a) Give the systematic name for melonal. (2)

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(b) (i) Melonal can be prepared by the oxidation of a compound, X. Suggest the

formula of compound X and the names or formulae of the reagents needed to

oxidize X. (3)

Compound X ………………………………………………………………………………….

Reagents needed for oxidation ....................................................................................

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(ii) Briefly suggest a practical measure to maximise the yield of melonal in (b)(i).

Justify your answer (2)

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18. 2-hydroxypropanoic acid may also be prepared from ethanal in the following

sequence:

(i) Name the mechanism and type of reaction occurring in Reaction 1. (2)

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(ii) Identify the attacking species in Reaction 1. (1)

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(iii) Give the first step of the mechanism of Reaction 1, showing the formation of

the intermediate. (2)

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(iv) Explain, by referring to the mechanism in (c)(iii), why the 2-hydroxypropanoic

acid formed from ethanal shows no optical activity. (3)

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19. A flow chart for making 2-hydroxy-2-methylpropanoic acid from propan-2-ol is

shown below
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20. The following three carbonyl compounds are structural isomers of C5H10O2.

(a) Describe chemical tests that you could carry out in test-tubes to distinguish
between compounds C, D and E.

Include appropriate reagents and any relevant observations. Also include equations
showing structures for the organic compounds involved.

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(d) ‘Ozonolysis’ is a technique used in organic chemistry to break open a C=C

double bond.

During ozonolysis, an alkene reacts with ozone, O3. The products are carbonyl
compounds, as shown below.

(i) Draw the structures of the products you would expect from the complete
ozonolysis of the following alkenes.

• pent-2-ene

• hexa-2,4-diene

[3]

(ii) In another ozonolysis reaction, organic compound G reacted to form only

hexane-1,6-dial.

Compound G has six carbon atoms.

Draw the structure of compound G. [1]

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21 A naturally occurring ketone, compound A, contributes to the smell and flavour of

some blue cheeses.

Compound A

(a) Give the systematic name of A.

(1)

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(b) Compound B is an isomer of A with the same functional group.

Compound B

Describe a simple chemical test which would distinguish A from B.

State the result of the test for each of the compounds.

(2)

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(c) Give two chemical tests for B which, when used together, would confirm that B

contains a carbonyl group and is not an aldehyde. For each test, state the result

and what is deduced.

(4)

Test 1

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Test 2

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(d) Give the displayed or structural formula of the compound which forms when A

is reduced. State the name or formula of a suitable reducing agent. (2)

Formula

Reducing agent ............................................................................................................

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(e) (i) Hydrogen cyanide reacts with A in the presence of CN— ions.

Write a mechanism for this reaction, using the skeletal formula of A below.

(3)

*(ii) By considering the reaction mechanism, explain why the solution produced in

this reaction does not rotate the plane of plane-polarized light.

(3)

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