Syllabus Edition

First teaching 2023

First exams 2025

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Nitriles & Hydroxynitriles (CIE A Level Chemistry)

Topic Questions

11 mark

Hydrolysis of CH3CH2CN with dilute HCl produces which compound?

  • CH3COOH

  • CH3CH2CH2NH3

  • CH3CH2COOH

  • CH3CH2COH

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21 mark

The equation shows a chemical reaction

CH3CH2CHClCH3  +  CN  rightwards arrow  CH3CH2CH(CH3)CN  +  Cl

What is the name for this type of reaction?

  • Nucleophilic substitution

  • Electrophilic substitution

  • Free radical substitution

  • Nucleophilic addition

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31 mark

What are the reagents needed in the reaction of 1-bromopropane to butanenitrile?

  • KCN

  • Ethanol and heat

  • KCN, ethanol and heat

  • KCN and ethanol

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41 mark

What are the products in the reaction of ethanenitrile and hydrochloric acid?

  • Propanoic acid and ammonia

  • Propanoic acid and ammonium chloride

  • Ethanoic acid and ammonia

  • Ethanoic acid and ammonium chloride

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51 mark

What are the products in the reaction of ethanenitrile and sodium hydroxide?

  • Sodium propanoate and ammonia

  • Sodium propanoate ammonium chloride

  • Sodium ethanoate and ammonia

  • Sodium ethanoate and ammonium chloride

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61 mark

Which one of the following reactants would not produce a nitrile in a one-step reaction?

  • Amides

  • Aldehydes

  • Halogenoalkanes

  • Alkanes

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11 mark

What is the correct two-step synthesis to produce 2-hydroxybutanenitrile from propan-1-ol?

  • 1) NaCl / H2SO4
    2) NaCN / Ethanol

  • 1) NaCN / Ethanol
    2) NaCl / H2SO4

  • 1) NaCN (aq) / H+ (aq)
    2) K2Cr2O7 / H2SO4 under distillation

  • 1) K2Cr2O7 / H2SO4 under distillation;
    2) NaCN (aq) / H+ (aq)

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21 mark

Butanone can undergo addition when mixed with NaCN (aq) / H+ (aq), forming product Z. Product Z can then undergo hydrolysis when heated with dilute HCl, forming product Y.

Which compound is product Y?

  • 2-hydroxypentanoic acid

  • 2-hydroxybutylamine

  • 2-methyl-2-hydroxybutanoic acid

  • 2-ethyl-2-hydroxypropylamine

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31 mark

A student wanted to produce a hydroxynitrile. Which types of reactions, reactants and reagents are shown in the table would correctly describe this reaction?

 

Type of reaction

Reactants

Reagents

A

Addition

Aldehyde

HCN

B

Hydrolysis

Halogenoalkane

Ethanolic NH3

C

Substitution

Ketone

HCN

D

Addition

Halogenoalkane

KCN, ethanol

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41 mark

What would X, Y and Z be in the following reaction sequence?

CH subscript 3 CH subscript 2 CH subscript 2 Br space rightwards arrow with KCN space plus space ethanol space plus space heat on top space bold X space plus space KBr space rightwards arrow with NaOH space plus space straight H subscript 2 straight O space plus space heat on top space bold Y space plus space NH subscript 3 space rightwards arrow with dil space HCl on top space bold Z

 

X

Y

Z

A

CH3CH2CH2K

CH3CH2CH2COONa

CH3CH2CH2COOH

B

CH3CH2CH2CN

CH3CH2CH2COONa

CH3CH2CH2COOH

C

CH3CH2CH2K

CH3CH2CH2COOH

CH3CH2CH2COONa

D

CH3CH2CH2CN

CH3CH2CH2COOH

CH3CH2CH2COONa

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11 mark

Which of the following reactions would produce 2-hydroxy-2-methylpropanenitrile?

  • Ethanal + Sulphuric acid

  • Propanone + Hydrogen cyanide

  • Ethanal + Ammonia

  • Propanone + Ammonia

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21 mark

Reactions were carried out to produce nitriles. Which combination of reactants and reagents is not correct?

 

Reactant

Reagent

A

Halogenoalkane

Potassium cyanide and ethanol

B

Amide

Phosphorus (V) oxide

C

Aldehyde

Hydrogen cyanide

D

Ketone

Ammonia

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31 mark

The following equations show reactions with nitrogen compounds. Which one correctly shows the hydrolysis of nitriles with dilute acid?

  • CH3CN + HCl + 2H2rightwards arrow  CH3COOH + NH3Cl

  • CH3CN + HCl + 2H2rightwards arrow  CH3COOH + NH4Cl

  • CH3CN + HCl + H2O    rightwards arrow  CH3COOH + NH4Cl

  • CH3CN + HCl + 2H2rightwards arrow  CH3COOHCl + NH3

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41 mark

The following equations show reactions with nitrogen compounds. Which one correctly shows the hydrolysis of nitriles with dilute sodium hydroxide?

  • CH3CN +  NaOH +  H2O   rightwards arrow CH3COONa +  NH3

  • CH3CN +  NaOH +  2H2O rightwards arrow CH3COONa +  NH3

  • CH3CN +  NaOH +  H2O   rightwards arrow CH3COONa +  NH4

  • CH3CN +  NaOH +  2H2rightwards arrow CH3COONa +  NH4

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