State the main advantage of making a primary amine from a nitrile rather than from a halogenoalkane and ammonia.

The nitrile route gives only the primary amine, so there is no mixture of secondary, tertiary and quaternary products to separate.

Give the reagents for the two steps that convert bromoethane into propylamine.

Bromoethane is first refluxed with potassium cyanide in ethanol, and the propanenitrile formed is then reduced with lithium tetrahydridoaluminate(III) in dry ethoxyethane.

Explain why converting a halogenoalkane to a nitrile and then reducing it lengthens the carbon chain by one.

The cyanide ion brings its own carbon atom into the molecule when it substitutes for the halogen, and that carbon is retained when the nitrile group is reduced.

Eduqas A-Level Chemistry A410QS

Formulae and Equations

Topic overview Formulae of common ions Writing formulae for ionic compounds Oxidation numbers and the rules for assigning them Oxidation numbers in ions and less obvious cases Constructing and balancing chemical equations Ionic equations and state symbols

Basic Ideas About Atoms

Topic overview Radioactive decay and nuclear equations Behaviour of α, β and γ radiation Half-life and radioactive decay calculations Radiation hazards and the uses of radioisotopes Ionisation energy and its variation between elements Successive ionisation energies and electronic structure Orbitals and electron configurations of elements 1 to 36 Emission and absorption spectra The hydrogen spectrum, E = hf and the convergence limit

Chemical Calculations

Topic overview Relative atomic, isotopic, formula and molecular mass Principles of the mass spectrometer Mass spectra, isotopic abundance and relative atomic mass Empirical and molecular formulae The mole, the Avogadro constant and molar mass Moles, grams and numbers of particles Concentration and solubility Molar volume and gas volume corrections The ideal gas equation Stoichiometry and reacting quantities Acid-base titration calculations Atom economy, percentage yield and percentage error

Bonding

Topic overview Ionic bonding and the formation of ions Covalent bonding and the balance of forces Coordinate bonding Electronegativity and bond polarity The ionic–covalent continuum Intermolecular forces, permanent and temporary dipoles Hydrogen bonding VSEPR and the shapes of simple molecules and ions

Solid Structures

Topic overview Sodium chloride and caesium chloride structures Diamond and graphite Iodine and ice Metallic bonding and the electron sea model Structure, bonding and physical properties

The Periodic Table

Topic overview Arrangement of the elements and the s-, p- and d-blocks Oxidation and reduction as electron transfer Trends across periods and down groups Reactions of Group 2 elements with oxygen, water and steam Reactions of the aqueous cations Mg²⁺, Ca²⁺ and Ba²⁺Flame colours Reactivity of Group 1 and Group 2 metals Thermal stability of the Group 2 carbonates and hydroxides Solubility of the Group 2 hydroxides and sulfates Basic character of the Group 1 and Group 2 oxides and hydroxides Volatility of the halogens and their reactions with metals Oxidising power, displacement reactions and the silver nitrate test Water treatment, salt preparation and gravimetric analysis

Simple Equilibria and Acid-Base Reactions

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Thermochemistry

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Rates of Reaction

Topic overview Collision theory and the conditions that change rate Energy profiles and activation energy The Boltzmann distribution and the effect of temperature Catalysts and how they work Calculating rates from experimental data Methods of following the course of a reaction

The Wider Impact of Chemistry

Topic overview Social, economic and environmental impact of chemical synthesis The production of energy and the choices it forces Green chemistry and sustainability

Organic Compounds

Topic overview Representing organic compounds Naming organic compounds Boiling temperature and solubility of organic compounds Structural isomerism Bond fission, electrophiles, nucleophiles and radicals

Hydrocarbons

Topic overview Alkanes and the sigma-bonded framework Combustion of alkanes and the use of fossil fuels Free radical substitution and the photochlorination of alkanes Alkenes and the reactivity of the C=C bond E–Z isomerism Electrophilic addition of bromine to alkenes Tests for alkenes Markovnikov addition of hydrogen bromide and carbocation stability Catalytic hydrogenation of alkenes Addition polymerisation

Halogenoalkanes

Topic overview Nucleophilic substitution of primary halogenoalkanes Elimination reactions forming alkenes Bond polarity, bond enthalpy and the ease of substitution The silver nitrate test for halogenoalkanes Uses of halogenoalkanes and the regulation of their use CFCs and their effect in the upper atmosphere Heating under reflux

Alcohols and Carboxylic Acids

Topic overview Industrial preparation of ethanol from ethene Fermentation and the distillation of ethanol Biofuels and the issues they raise Classifying alcohols as primary, secondary and tertiary Dehydration of alcohols to alkenes Oxidation of primary alcohols to aldehydes and carboxylic acids Oxidation of secondary alcohols to ketones The dichromate(VI) test for alcohols Carboxylic acids and the sodium hydrogencarbonate test Reactions of carboxylic acids with bases, carbonates and hydrogencarbonates Esterification and separation by distillation

Instrumental Analysis

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Redox and Standard Electrode Potential

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Redox Reactions

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Chemistry of the P-Block

Topic overview Amphoteric behaviour of aluminium and lead The inert pair effect in Groups 3, 4 and 5 Electron-deficient compounds and expanded octets Al₂Cl₆ and donor-acceptor compounds Hexagonal and cubic boron nitride Stability of oxidation states II and IV in Group 4 Carbon dioxide and lead(II) oxide Bonding in the Group 4 chlorides Hydrolysis of the Group 4 chlorides Reactions of aqueous lead(II) ions Chlorine with cold and warm aqueous sodium hydroxide Bleaching and bactericidal action of chlorine and chlorate(I)Sodium halides with concentrated sulfuric acid

Chemistry of the D-Block Transition Metals

Topic overview Oxidation states of the d-block elements Important oxidation states and the colours of aqueous ions Bonding in tetrahedral and octahedral complexes The origin of colour and the splitting of d-orbitals Ligand exchange and change of coordination number Colours and formulae of copper and cobalt complex ions Heterogeneous and homogeneous catalysis Nickel in hydrogenation and iron in the Haber process Vanadium(V) oxide and manganese(IV) oxide as catalysts Reactions of Cr³⁺, Fe²⁺, Fe³⁺ and Cu²⁺ with excess aqueous hydroxide

Chemical Kinetics

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Enthalpy Changes for Solids and Solutions

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Entropy and Feasibility of Reactions

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Equilibrium Constants

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Acid-Base Equilibria

Topic overview The Lowry–Brønsted theory and conjugate pairs Strong and weak acids and the dissociation constant Ka The ionic product of water, Kw pH of strong acids and strong bases pH of weak acids from Ka and pKa Titration curves How buffer solutions work Buffer calculations Buffers in living systems and industry Salt hydrolysis and the choice of indicator

Stereoisomerism

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Aromaticity

Topic overview Structure and bonding in benzene Delocalisation and resistance to addition Electrophilic substitution: nitration and halogenation Friedel-Crafts alkylation and the ring's interaction with substituents

Alcohols and Phenols

Topic overview Forming alcohols from halogenoalkanes and carbonyl compounds Alcohols with hydrogen halides, ethanoyl chloride and carboxylic acids Acidity of phenol Reactions of phenol and the iron(III) chloride test

Aldehydes and Ketones

Topic overview Preparing aldehydes and ketones by oxidation of alcohols Distinguishing aldehydes and ketones with Tollens’ reagent and Fehling’s solution Reduction of aldehydes and ketones using NaBH₄ Nucleophilic addition of HCN to aldehydes and ketones Reaction with 2,4-dinitrophenylhydrazine The triiodomethane (iodoform) test

Carboxylic Acids and Their Derivatives

Topic overview Relative acidity of carboxylic acids, phenols, alcohols and water Preparing carboxylic acids by oxidation Reduction and decarboxylation of carboxylic acids Acid chlorides and their reactions Esters and their hydrolysis Amides and their hydrolysis Nitriles from carboxylic acids and halogenoalkanes Hydroxynitriles, hydrolysis and reduction of nitriles

Amines

Topic overview Amines from halogenoalkanes and ammonia Amines from the reduction of nitriles Aromatic amines from nitrobenzene Basicity of amines Ethanoylation of primary amines Reaction of primary amines with cold nitric(III) acid Azo coupling, azo dyes and the origin of colour

Amino Acids, Peptides and Proteins

Topic overview α-amino acids and their general formula Zwitterions and amphoteric behaviour Melting temperature, solubility and the isoelectric point Dipeptides, polypeptides and the peptide link Protein structure and the role of proteins

Organic Synthesis and Analysis

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Specified Practical Work

Topic overview Gravimetric analysis and qualitative analysis of unknown solutions Standard solutions, standardising an acid and preparing a soluble salt Back titration and double titration Determining enthalpy changes by calorimetry Following a rate by gas collection, the iodine clock and reaction order Electrochemical cells, redox titration and the estimation of copper Determining an equilibrium constant and following a titration with a pH probe Hydrolysis of 1-bromobutane and the preparation of an ester Organic synthesis, purification and identification

Practical Skills and Techniques

Topic overview Choosing apparatus and recording measurements Volumetric technique with pipette, burette and volumetric flask Titration procedure and the choice of indicator Heating, heating under reflux and distillation Filtration, purification and qualitative testing Melting temperature, chromatography and electrochemical cells Variables, errors and risk in evaluating a method

Mathematical Skills in Chemistry

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Amines

Amines from the reduction of nitriles

3 things to know
Component 2

Overview

Two reagents that reduce a nitrile to a primary amine, conditions used for the catalytic hydrogenation of a nitrile and amine obtained by reducing butanenitrile.

What you need to know

Answer each one before you reveal it.

Your recallNot started

Key term

Name two reagents that reduce a nitrile to a primary amine.

Key term

State the conditions used for the catalytic hydrogenation of a nitrile.

Key term

Write the equation, using [H], for the reduction of ethanenitrile.

Questions from this subtopic

Each one with the model answer underneath.

1
Name two reagents that reduce a nitrile to a primary amine.
Model answer
Lithium tetrahydridoaluminate(III) in dry ethoxyethane will do it, and so will hydrogen with a nickel catalyst.
2
State the conditions used for the catalytic hydrogenation of a nitrile.
Model answer
Hydrogen is passed over the nitrile with a nickel catalyst at high temperature and high pressure.
3
Write the equation, using [H], for the reduction of ethanenitrile.
Model answer
CH₃CN + 4[H] → CH₃CH₂NH₂.
4
State the main advantage of making a primary amine from a nitrile rather than from a halogenoalkane and ammonia.
Model answer
The nitrile route gives only the primary amine, so there is no mixture of secondary, tertiary and quaternary products to separate.
5
Give the reagents for the two steps that convert bromoethane into propylamine.
Model answer
Bromoethane is first refluxed with potassium cyanide in ethanol, and the propanenitrile formed is then reduced with lithium tetrahydridoaluminate(III) in dry ethoxyethane.
6
Explain why converting a halogenoalkane to a nitrile and then reducing it lengthens the carbon chain by one.
Model answer
The cyanide ion brings its own carbon atom into the molecule when it substitutes for the halogen, and that carbon is retained when the nitrile group is reduced.

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