OCR AS Chemistry

Topic Questions

ASChemistryOCRTopic Questions4. Core Organic Chemistry4.4 Alcohols

4.4 Alcohols

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11 mark

What is the correct name and classification of alcohol for the following compound?

q2-3-5-easy-mcq-alcohols

 

IUPAC name

Classification

A

2-chloropentan-3-ol

Tertiary

B

2-chloropentan-3-ol

Secondary

C

3-chloropentan-2-ol

Tertiary

D

3-chloropentan-2-ol

Secondary

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21 mark

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

  • Butanone

  • Butanal

  • Butanoic acid

  • Butyl butanoate 

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31 mark

Which structure shows a primary alcohol that cannot be dehydrated to form an alkene?

  • CH3OH

  • CH3CH2OH

  • CH3CH(OH)CH3

  • CH3CH3CH2OH

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41 mark

Which alcohol can be oxidised to form a carboxylic acid?

  • Butan-2-ol

  • Pentan-3-ol

  • 3-methylhexan-1-ol

  • 3-methylhexan-3-ol

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51 mark

What is the correct equation for the complete combustion of butanol?

  • C4H9OH + 3O2 → 2CO2 + H2O

  • C4H9OH + 9.5O2 → 4CO + 5H2O

  • C4H9OH + 6O2 → 4CO2 + 5H2O

  • C4H9OH + 8O2 → 4CO + 5H2O

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61 mark

Which of the following equations for the oxidation of an alcohol is correct?

  • CH3CH(OH)CH3 + [O] → CH3CH2COOH + H2O

  • CH3CH(OH)CH3 + [O] → CH3COCH3 + H2O

  • CH3CH(OH)CH3 + [O] → CH3CH2CHO + H2O

  • CH3CH(CH3)(OH)CH3 + H+ → CH3C(CH3)CH2 + H2O

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71 mark

Some alcohols react with concentrated sulfuric acid to form alkenes. 

What is the type of this reaction?

  • Oxidation

  • Addition

  • Elimination

  • Substitution

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81 mark

What is the general formula of alcohols?

  • CnH2n+2OH

  • CnH2n+1OH

  • CnH2n+3O

  • CnH2nOH

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91 mark

Which of the following statements about ethanol is not true?

  • The strongest type of intermolecular force in ethanol is hydrogen bonding 

  • Ethanol is less soluble than pentan-2-ol 

  • Ethanol is produced during fermentation 

  • Ethanol is a primary alcohol

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101 mark

Chloroethane is formed from ethanol in the presence of NaCl and H2SO4.

What type of reaction is this?

  • Elimination

  • Addition

  • Oxidation

  • Substitution

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11 mark

Which alcohol reacts with an acid catalyst to form E and Z stereoisomers?

  • Pentan-3-ol

  • Pentan-1-ol

  • 2-methylbutan-2-ol

  • 2,2-dimethylpropan-1-ol

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21 mark

There are four alcohols with a molecular formula of C4H10O.

  • W is the major product formed from the hydration of but-1-ene.
  • X is the minor product formed from the hydration of but-1-ene.
  • Y does not react with acidified potassium dichromate.
  • Z has a lower boiling point than W and X.

What are the identities of W, X, Y and Z respectively?

  • 2-methylpropan-2-ol, 2-methylpropan-1-ol, butan-2-ol, butan-1-ol

  • butan-2-ol, butan-1-ol, 2-methylpropan-2-ol, 2-methylpropan-1-ol

  • 2-methylpropan-1-ol, butan-2-ol, 2-methylpropan-2-ol, butan-1-ol

  • butan-2-ol, butan-1-ol, 2-methylpropan-1-ol, 2-methylpropan-2-ol

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31 mark

Propan-1-ol is oxidised under reflux.

Which of the following statements is correct?

  • A bung must be used at the top of the condenser to ensure that no product is lost.

  • Water must flow in at the top of the condenser and out at the bottom of the condenser.

  • There must be small glass beads in the round-bottomed flask to allow the reaction mixture to boil more vigorously

  • Adding sodium hydrogencarbonate will allow the product to be distinguished from the reactants.

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41 mark

Which of the following statements is/are correct regarding the molecules pentan-2-ol, pent-1-ene and butan-2-ol?

  1. In complete combustion, per mole of fuel, two molecules will require the same number of moles of oxygen and two molecules produce the same moles of a substance that turns limewater cloudy.
  2. The order of increasing boiling point is pent-1-ene, butan-2-ol, pentan-2-ol.
  3. The order of increasing solubility in water is pentan-2-ol, butan-2-ol, pent-1-ene.

  • 1, 2 and 3

  • Only 1 and 2

  • Only 2 and 3

  • Only 1

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51 mark

Which statements about the reactions of pent-3-en-1-ol is/are correct?

  1. In an elimination reaction with concentrated sulfuric acid, penta-1,3-diene is produced.
  2. In an elimination reaction with concentrated sulfuric acid, the product shows E/Z isomerism in two places.
  3. In a substitution reaction with hydrogen bromide, 1-bromopent-3-ene is produced.

  • 1, 2 and 3

  • Only 1 and 2

  • Only 2 and 3

  • Only 1

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11 mark

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

  • Pentan-2-ol

  • Pentan-1-ol

  • 2-methylbutan-1-ol

  • 2-methylbutan-2-ol 

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21 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=CHCH2COH

  • CH3CH2CH=CHCH2CO2H

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31 mark

Hydroxyethanal has the structural formula HOCH2CHO. 

In an experiment hydroxyethanal is heated under reflux with an excess of acidified potassium dichromate(VI) until no further oxidation takes place.

Which functional group will be formed in the product? 

  • Ketone

  • Alcohol

  • Carboxylic acid 

  • Aldehyde 

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41 mark

Pentan-1-ol is a primary alcohol which can undergo oxidation. Which of the following compounds cannot be produced by the oxidation of pentan-1-ol?

  • Pentan-2-one

  • Pentanal

  • Pentanoic acid

  • Carbon dioxide

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51 mark

How many isomers of C5H12O are primary alcohols?

  • 2

  • 3

  • 4

  • 5

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61 mark

Which of the following is a possible catalyst used to form compound A from 2-methylbutan-2-ol via dehydration? 

ocr-as-4-4m-q6-compound-a

  • Al2O3 

  • Concentrated HCl 

  • Dilute H3PO4

  • Aqueous NaOH

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71 mark

Which alcohol reacts with an acid catalyst to form a mixture of stereoisomers?

  • 2-methylpropan-2-ol

  • Butan-1-ol

  • 2,2-dimethylpropan-1-ol

  • Butan-2-ol 

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81 mark

What are the correct reagents for the conversion below?

CH3CH2CH2CH2OH → CH3CH2CH2CH2Cl

  • PCl3 with heating 

  • Cl2 and H2SO4

  • KCl and NaOH

  • Cl2

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91 mark

Which synthetic route will cause the following transformation?

converting-propan-1-ol-into-2-bromopropane

  • Heat / H2SO4 followed by Br2 / UV light

  • Heat / H2SO4 followed by HBr

  • Br2  / UV light

  • NaBr / H2SO4

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