A LevelChemistryCambridge (CIE)Exam Questions16. Hydroxy CompoundsAlcohols

Alcohols (Cambridge (CIE) A Level Chemistry): Exam Questions

Exam code: 9701

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Alcohols

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1
1 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

Choose your answer

2
1 mark

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

 

Primary

Secondary

Tertiary

A

3

3

2

B

4

2

2

C

4

3

1

D

5

2

1

    Choose your answer

    3
    1 mark

    Which reagents could be used in the laboratory to convert propan-1-ol into 1-bromopropane?

    • Concentrated sulfuric acid and bromine

    • Concentrated sulfuric acid and potassium bromide

    • Ethanolic sodium hydroxide and bromine

    • Ethanolic sodium hydroxide and potassium bromide

    Choose your answer

    4
    1 mark

    Which skeletal formula represents 4-chloropentan-2-ol?

    • Skeletal formula of 2-chlorohexan-4-ol
    • Skeletal formula of 2-chloropentan-3-ol
    • Skeletal formula of 3-chloropentan-2-ol
    • Skeletal formula of 4-chloropentan-2-ol

    Choose your answer

    5
    1 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

    Choose your answer

    6
    1 mark

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

    • Warming with acidified aqueous potassium manganate(VII)

    • Warming with acidified aqueous potassium dichromate(VI)

    • Dehydration, followed by reaction with Br2 (aq)

    • Oxidation, followed by reaction with Tollens' reagent or Fehling's solution

    Choose your answer

    7
    1 mark

    An alcohol with molecular formula CnH2n+1OH has a chiral centre but does not react with hot, acidified aqueous potassium dichromate(VI).

    What is the smallest possible value for n?

    • 5

    • 6

    • 7

    • 8

    Choose your answer

    8
    1 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.

    CH2CH2OH rightwards arrow with step space 1 on top CH3CHO rightwards arrow with step space 2 on top CH3CH(OH)CH2CHO rightwards arrow with step space 3 on top CH2=CHCH-CH2

    Which term could be used to describe step 1?

    • Condensation

    • Dehydration

    • Dehydrogenation

    • Hydrogenation

    Choose your answer

    9
    1 mark

    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

    Choose your answer

    1
    1 mark

    Which isomer of C4H10O forms three alkenes (including stereoisomers) on dehydration?

    • Butan-1-ol

    • Butan-2-ol

    • 2-methylpropan-1-ol

    • 2-methylpropan-2-ol

    Choose your answer

    2
    1 mark

    Acidified potassium dichromate(VI) and acidified potassium manganate(VII) can both oxidise primary alcohols. 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

    Green

    Orange

    Purple

    Colourless

    B

    Orange

    Green

    Colourless

    Purple

    C

    Orange

    Green

    Purple

    Colourless

    D

    Purple

    Colourless

    Orange

    Green

      Choose your answer

      3
      1 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 aqueous potassium dichromate(VI)

      • Ethanol

      • Sodium

      • Aqueous sodium hydroxide

      Choose your answer

      4
      1 mark

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

      • 2,4-dinitrophenylhydrazine

      • Aqueous potassium manganate(VII)

      • Bromine in carbon tetrachloride

      • Sodium

      Choose your answer

      5
      1 mark

      Which reagent reacts with both ethanol and ethanoic acid?

      • Acidified aqueous potassium dichromate(VI)

      • Aqueous sodium carbonate

      • Aqueous sodium hydroxide

      • Sodium

      Choose your answer

      6
      1 mark

      Which reagent reacts with prop-2-en-1-ol, CH2=CHCH2OH, to form a product that shows optical isomerism?

      • Bromine

      • Hydrogen with a nickel catalyst

      • Phosphorus pentachloride

      • Sodium

      Choose your answer

      7
      1 mark

      In its reaction with an excess of sodium, 1 mol of compound X produces 1 mol of H2 (g).

      Which compound could X be?

      • CH3CH2CH2CH2OH

      • (CH3)3COH

      • CH3CH2CH2CO2H

      • CH3CH(OH)CO2H

      Choose your answer

      8
      1 mark

      What volume of oxygen, measured at room conditions, is needed for the complete combustion of 0.100 mol of propan-1-ol?

      • 10.8 dm3

      • 12.0 dm3

      • 21.6 dm3

      • 24.0 dm3

      Choose your answer

      9
      1 mark

      A 2.30 g sample of ethanol is mixed with acidified aqueous potassium dichromate(VI) and the mixture is heated. The desired organic product is collected by immediate distillation. The yield of the product is 70.0%.

      What mass of organic product is collected?

      • 1.54 g

      • 1.61 g

      • 2.10 g

      • 2.20 g

      Choose your answer

      10
      1 mark

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

      • Butan-1-ol

      • Butan-2-ol

      • 2-methylpropan-1-ol

      • 2-methylpropan-2-ol

      Choose your answer

      11
      1 mark

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

      CH3CH2CH=CHCH2CH2OH

      leaf alcohol

      Which organic product is formed when 'leaf alcohol' is heated under reflux with an excess of acidified aqueous potassium dichromate(VI)?

      • CH3CH2CH(OH)CH(OH)CH2CO2H

      • CH3CH2COCOCH2CO2H

      • CH3CH2CH=CHCH2CO2H

      • CH3CH2CO2H and HO2CCH2CO2H

      Choose your answer

      12
      1 mark

      Which reagents and conditions convert propan-2-ol into propanone?

      • NaBH4 in aqueous methanol

      • K2Cr2O7, dilute H2SO4, heat under reflux

      • LiAlH4 in dry ether

      • Concentrated H2SO4 at 170 °C

      Choose your answer

      13
      1 mark

      Which reaction produces propanoic acid?

      • Heating propan-1-ol with acidified aqueous potassium dichromate(VI) under reflux

      • Heating propan-2-ol with acidified aqueous potassium dichromate(VI) under reflux

      • Reacting 1-bromopropane with aqueous sodium hydroxide

      • Reacting propan-1-ol with methanoic acid and concentrated sulfuric acid

      Choose your answer

      1
      1 mark

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

      J reacts with aqueous sodium hydroxide 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

      Choose your answer

      2
      1 mark

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

      CH3(CH2)2CHO rightwards arrow with HCN comma space NaCN on top X rightwards arrow with hot space dilute space straight H subscript 2 SO subscript 4 on top Y rightwards arrow from trace space of space conc. space straight H subscript 2 SO subscript 4 to CH subscript 3 CH subscript 2 OH comma space heat of Z

      What could Z be?

      • CH3(CH2)3COOCH2CH3

      • CH3(CH2)2CH(OH)COOCH2CH3

      • CH3CH2CH(OH)COOCH2CH3

      • CH3(CH2)2CH(OCH2CH3)COOH

      Choose your answer

      3
      1 mark

      Which reagent reacts differently with the two isomeric alcohols, (CH3)3CCH2OH and (CH3)2CHCH2CH2OH?

      • Sodium

      • Acidified aqueous potassium dichromate (VI)

      • Phosphorus pentachloride

      • Concentrated sulfuric acid

      Choose your answer

      4
      1 mark

      Compound Q has the molecular formula C10H14O and is unreactive towards hot acidified aqueous potassium dichromate(VI).

      Which structure could be formed by the dehydration of compound Q?

      • Skeletal formula of [(2E)-but-2-en-1-yl]benzene
      • Skeletal formula of (but-3-en-1-yl)benzene
      • Skeletal formula of [(2E)-but-2-en-2-yl]benzene
      • Skeletal formula of [(2E)-but-2-en-2-yl]benzene

      Choose your answer

      5
      1 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 \rightarrow CO2 + SO2 + 2H2O

      A sample of 15 cm3 of methanethiol vapour is exploded with 90 cm3 of oxygen.

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

      • 30 cm3

      • 45 cm3

      • 75 cm3

      • 105 cm3

      Choose your answer

      6
      1 mark

      1.50 g of butan-2-ol is mixed with excess acidified potassium dichromate(VI). The reaction mixture is heated under reflux and the organic product is collected by distillation. The yield of product is 80.0%.

      What mass of product is collected?

      • 0.91 g

      • 1.17 g

      • 1.43 g

      • 1.46 g

      Choose your answer

      7
      1 mark

      Alcohols are weaker acids than water. Which statement correctly explains this?

      • Alkyl groups have a negative inductive effect, withdrawing electron density from oxygen and destabilising the alkoxide ion

      • Alkyl groups have a negative inductive effect, withdrawing electron density from oxygen and stabilising the alkoxide ion

      • Alkyl groups have a positive inductive effect, donating electron density to oxygen and destabilising the alkoxide ion

      • Alkyl groups have a positive inductive effect, donating electron density to oxygen and stabilising the alkoxide ion

      Choose your answer