CIE AS Chemistry

Topic Questions

ASChemistryCIETopic Questions3. Organic Chemistry3.4 Hydroxy Compounds

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First teaching 2020

Last exams 2024

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3.4 Hydroxy Compounds

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11 mark

Compound X produces a carboxylic acid when heated under reflux with acidified potassium dichromate (VI). Compound X has no reaction with sodium metal.

What could be the identity of compound X?

  • Propanal

  • Propanone

  • Propan-1-ol

  • Propan-2-ol

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21 mark

Considering only structural isomers, what is the number of alcohols of each type with the formula C5H12O?

 

Primary

Secondary

Tertiary

A

B

C

D

3

4

4

5

3

2

3

2

2

2

1

1

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31 mark

Which sequence of reagents may be used in the laboratory to convert propan-1-ol into 2-bromopropane?

  • Concentrated sulfuric acid, followed by bromine

  • Concentrated sulfuric acid, followed by potassium bromide

  • Ethanolic sodium hydroxide, followed by bromine

  • Ethanolic sodium hydroxide, followed by potassium bromide

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41 mark

Which diagram gives the skeletal formula of 4-chloropentan-2-ol?

  • 3-4-e-3a

  • 3-4-e-3b

  • 3-4-e-3c

  • 3-4-e-3d

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51 mark

What can be produced when an aqueous solution of butan-2-ol is oxidised under suitable conditions?

 

1

Butanone

 

2

Butanoic acid

 

3

Butanal

  • 1, 2 and 3

  • 1 and 2

  • 2 and 3

  • 1 only

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61 mark

Which structures show a primary alcohol that cannot be dehydrated to form an alkene?

 

1

CH3OH

 

2

CH3CH2OH

 

3

CH3CH(OH)CH3

  • 1, 2 and 3

  • 1 and 2

  • 2 and 3

  • 1 only

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71 mark

Which alcohol has a chiral centre and can be oxidised to a ketone?

  • Pentan-2-ol

  • Pentan-3-ol

  • 3-methylhexan-1-ol

  • 3-methylhexan-3-ol

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81 mark

Which reaction will distinguish between a primary and a secondary alcohol?

  • Warming with H+ / MnO4-

  • Warming with H+ / Cr2O72-

  • Dehydration, followed by reaction with Br2 (aq)

  • Oxidation, followed by reaction with Fehling’s (or Tollens’) reagent

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91 mark

An alcohol with molecular formula CnH2n+1OH has a chiral carbon atom but does not react with hot, acidified K2Cr2O7.

What is the smallest possible value for n?

  • 5

  • 6

  • 7

  • 8

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101 mark

Buta-1,3-diene is currently obtained from fossil fuel sources. In future it may be obtained from ethanol, which can be produced from non-food agricultural crops. The sequence of reactions is as follows.

3-4-e-10

Which term could be used to describe step 1?

  • Condensation

  • Dehydration

  • Dehydrogenation

  • Hydrogenation

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111 mark

The functional group in a primary alcohol is –CH2OH.

Which reagent reacts with a primary alcohol, under suitable conditions, to give an organic product with the same number of oxygen atoms as the alcohol?

  • Al2O3

  • CH3CO2H

  • HBr

  • Na

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11 mark

Which of the following alcohols would give a positive triiodomethane reaction?

3-4-cie-ial-chemistry-diagram-q1hard

  • 1, 2 and 7

  • 2, 4 and 7

  • 3, 4 and 5

  • 6, 7 and 8

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21 mark

An organic compound J reacts with sodium to produce an organic ion with a charge of –3. 

J reacts with NaOH (aq) to produce an organic ion with a charge of –1. 

What could be the structural formula of J?

  • HO2CCH(OH)CH2CO2H

  • HO2CCH(OH)CH2CHO

  • HOCH2CH(OH)CH2CO2H

  • HOCH2COCH2CHO

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31 mark

The apparatus below shows an organic synthesis reaction:

3-4-cie-ial-chemistry-diagram-q3hard

Which processes could be shown using the above apparatus?

 

1

Dehydration of ethanol (liquid Z) 

 

2

Oxidation of ethanol (liquid Z)

 

3

Cracking of paraffin (liquid Z)

  • 1, 2 and 3

  • 1 and 2

  • 1 and 3

  • 1 only

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41 mark

An organic compound Y with molecular formula C5H12O, is oxidised to compound Z with molecular formula C5H10O2.

What could be the structural formula of Y?

 

1

CH3(CH2)4OH 

 

2

CH3CH2CH(CH2OH)CH3

 

3

CH3C(CH3)2CH2OH

  • 1, 2 and 3

  • 1 and 3

  • 2 and 3

  • 3 only

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51 mark

A number of alcohols with the formula C4H10O are separately oxidised. Using 65 g of the alcohols a 55% yield of organic product is achieved.

What mass of product could be obtained?

 

1

42.6 g of butanoic acid

 

2

42.6 g of 2-methylpropanoic acid 

 

3

34.6 g of butanone 

  • 1, 2 and 3

  • 1 and 2

  • 2 and 3

  • 1 only

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61 mark

In a multi-step synthesis reaction, butanal is converted into a compound Z.

begin mathsize 16px style C H subscript bold 3 bold open parentheses C H subscript bold 2 bold close parentheses subscript bold 2 C H O space space rightwards arrow with H C N comma space Na C N on top space space italic X bold space space rightwards arrow with hot space dilute space H subscript 2 S O subscript 4 on top space space Y bold space space rightwards arrow with space trace space of space conc point space H subscript 2 S O subscript 4 below and C H subscript 3 C H subscript 2 O H comma space heat on top space space italic Z end style

What could Z be?

  • CH3(CH2)3COOCH2CH3

  • CH3(CH2)2CH(OH)COOCH2CH3

  • CH3(CH2)CH(OH)COCH2CH3

  • CH3(CH2)2CH(OCH2CH3)COOH

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71 mark

What will react differently with the two isomeric alcohols, (CH3)3CCH2OH and (CH3)2CHCH2CH2OH?

  • Sodium

  • Acidified aqueous potassium dichromate (VI)

  • Phosphorus pentachloride

  • Concentrated sulfuric acid

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81 mark

Compound Q has the molecular formula C10H14O and is unreactive towards mild oxidising agents.

Which structure formed by the dehydration  of compound Q?

  • 3-4-h-8a

  • 3-4-h-8b

  • 3-4-h-8c

  • 3-4-h-8d

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91 mark

The foul smell that skunks spray is due to a number of thiols, one of which is methanethiol, CH3SH, which burns as follows.

CH3SH + 3O2 rightwards arrow CO2 + SO2 + 2H2O

A sample of 15 cm3 of methanethiol was exploded with 90 cm3 of oxygen.

What would be the final volume of the resultant mixture of gases when cooled to room temperature?

  • 30 cm3

  • 45 cm3

  • 75 cm3

  • 105 cm3

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101 mark

Use of the Periodic Table is relevant to this question.

1.50 g of butan-2-ol were mixed with excess acidified potassium dichromate (VI). The reaction mixture was then boiled under reflux for fifteen minutes. The organic product was then collected by distillation. The yield of product was 80.0%.

What mass of product was collected?

  • 0.91 g

  • 1.17 g

  • 1.43 g

  • 1.46 g

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11 mark

Which isomer of C4H10O forms three alkenes on dehydration?

  • Butan-1-ol

  • Butan-2-ol

  • 2-methylpropan-1-ol

  • 2-methylpropan-2-ol

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21 mark

Primary alcohols can be oxidised to aldehydes using either acidified potassium dichromate (VI) or acidified potassium manganate (VII). Both these oxidising agents change colour as they are reduced.

What is the colour of each oxidising agent before and after it has reacted?

 

Acidified potassium dichromate (VI)

Acidified potassium manganate (VII)
 

Before

After

Before

After

A

B

C

D

Green

Orange

Orange

Purple

Orange

Green

Green

Colourless

Purple

Colourless

Purple

Orange

Colourless

Purple

Colourless

Green

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31 mark

Lactic acid, CH3CH(OH)CO2H, causes pain when it builds up in muscles.

Which reagent reacts with both of the –OH groups in lactic acid?

  • Acidified potassium dichromate (VI)

  • Ethanol

  • Sodium

  • Sodium hydroxide

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41 mark

Which reagent could detect the presence of alcohol in a petrol consisting mainly of a mixture of alkanes and alkenes?

  • Na

  • Br2 (in CCl4)

  • KMnO4 (aq)

  • 2,4-dinitrophenylhydrazine

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51 mark

Which reagent reacts with ethanol and also reacts with ethanoic acid?

  • Acidified potassium dichromate (VI)

  • Sodium

  • Sodium carbonate

  • Sodium hydroxide

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61 mark

Prop-2-en-1-ol, also known as allyl alcohol, reacts to form a product that can exist as optical isomers. 

Which reagent would produce optical isomers from allyl alcohol?

  • Phosphorus pentachloride

  • Sodium

  • Bromine

  • Hydrogen and nickel

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71 mark

In its reaction with sodium, 1 mol of a compound X gives 1 mol of H2 (g). 

Which compound might X be?

  • CH3CH2CH2CH2OH

  • (CH3)3COH

  • CH3CH2CH2CO2H

  • CH3CH(OH)CO2H

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81 mark

Use of the Data Booklet is relevant to this question

Which volume of oxygen measured at room temperature and pressure is needed for complete combustion of 0.1 mol of propan-1-ol?

  • 10.8 dm3

  • 12.0 dm3

  • 21.6 dm3

  • 24.0 dm3

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91 mark

Which statements about 2-methylbutan-1-ol are correct?

 

1

It can give HCl (g) on reaction with PCl5.

 

2

It can be oxidised to give an aldehyde.

 

3

It exists in two optically active forms.

  • 1, 2 and 3

  • 1 and 2

  • 2 and 3

  • 1 only

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101 mark

Use of the Data Booklet is relevant to this question

2.30 g of ethanol were mixed with aqueous acidified potassium dichromate (VI) and the desired organic product was collected by immediate distillation under gentle warming. The yield of product was 70.0%.

What mass of product was collected?

  • 1.54 g

  • 1.61 g

  • 2.10 g

  • 2.20 g

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111 mark

Which alcohol gives only one possible oxidation product when warmed with dilute acidified potassium dichromate (VI)?

  • Butan-1-ol

  • Butan-2-ol

  • 2-methylpropan-1-ol

  • 2-methylpropan-2-ol

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121 mark

The compound ‘leaf alcohol’ is partly responsible for the smell of new-mown grass.

                                               CH3CH2CH=CHCH2CH2OH

                                                            leaf alcohol

What will be formed when ‘leaf alcohol’ is oxidised using an excess of hot, acidified K2Cr2O7 (aq)?

  • CH3CH2CH(OH)CH(OH)CH2CO2H

  • CH3CH2COCOCH2CO2H

  • CH3CH2CH=CHCH2CO2H

  • CH3CH2CO2H and HO2CCH2CO2H

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