Write the equation for the reaction of bromoethane with excess ammonia.

The equation is CH₃CH₂Br + 2NH₃ → CH₃CH₂NH₂ + NH₄Br.

Why is a large excess of ammonia used in this reaction?

The amine formed is itself a nucleophile that can attack more halogenoalkane, so a large excess of ammonia makes it far more likely that a halogenoalkane molecule meets ammonia rather than the amine, which raises the yield of the primary amine.

CCEA A-Level Chemistry 1110

Formulae, Equations and Amounts of Substance

Topic overview Ionic charges and the formulae of compound ions Writing and balancing full and ionic equations The mole, molar mass and Avogadro's constant Reacting masses and reactants in excess Hydrated salts and water of crystallisation

Atomic Structure

Topic overview Protons, neutrons and electrons Atomic number, mass number and the composition of ions Isotopes and relative isotopic mass Relative atomic, molecular and formula mass Mass spectra and relative atomic mass calculations Mass spectra of diatomic elements Electronic configuration and the building up principle Orbitals, electron spin and orbital shapes The s-, p-, d- and f-blocks of the Periodic Table Ionisation energies and their equations Trends in ionisation energy as evidence for shells and subshells

Bonding

Topic overview Ionic bonding and electron transfer Dot and cross diagrams for ionic compounds Covalent bonding and the shared pair Lone pairs and co-ordinate bonding Dot and cross diagrams for covalent molecules and ions The octet rule and its limitations Electronegativity and bond polarity Metallic bonding

Intermolecular Forces and Structure

Topic overview Van der Waals' forces and permanent dipole-dipole attractions Hydrogen bonding, boiling points and solubility Giant ionic, metallic and giant covalent structures Molecular covalent structures and melting points across Period 3

Shapes of Molecules and Ions

Topic overview Electron pair repulsion and VSEPR theory Shapes and bond angles up to four electron pairs Shapes with five and six electron pairs Polar bonds and polar molecules

Redox

Topic overview Rules for assigning oxidation states Oxidation states in peroxides, hydrides and Roman numeral names Oxidation, reduction and electron transfer Oxidising agents, reducing agents and disproportionation Half-equations and combining them into redox equations

The Halogens

Topic overview Colours, physical states and solubility of the halogens Chlorine with water and the treatment of drinking water Disproportionation of the halogens with sodium hydroxide Oxidising ability and displacement reactions Solid halides with concentrated sulfuric and phosphoric acid

Acid-Base Titrations

Topic overview Strong and weak acids and bases Concentration, molarity and units Preparing a standard solution Titration technique, mean titres and uncertainty Indicators and the end point Titration calculations

Qualitative Tests

Topic overview Chemical tests for the gases Flame tests for metal cations Testing for the ammonium ion, sulfate and carbonate Distinguishing the halides, and the starch test for iodine

Formulae and Amounts of a Substance

Topic overview Empirical and molecular formulae Calculating formulae from composition data Molar gas volume and reacting gas volumes Percentage yield Atom economy

Nomenclature and Isomerism in Organic Chemistry

Topic overview Homologous series and functional groups IUPAC rules for naming organic compounds Structural, displayed and skeletal formulae Structural isomerism Geometrical isomerism and E–Z notation

Alkanes

Topic overview Alkanes as saturated hydrocarbons Boiling points of alkanes and van der Waals' forces Boiling points of branched isomers Complete and incomplete combustion of alkanes Pollutants from alkane fuels and the atmosphere Catalytic converters Radicals, homolytic fission and heterolytic fission Free radical substitution of alkanes

Alkenes

Topic overview Unsaturated hydrocarbons and the bromine water test Sigma and pi bonds in the carbon–carbon double bond Electron density at C=C, reactivity and catalytic hydrogenation Addition of chlorine and bromine to alkenes Addition of hydrogen chloride and hydrogen bromide Electrophiles, heterolytic fission and the addition mechanism Carbocation stability and Markovnikov addition Addition polymerisation of alkenes

Halogenoalkanes

Topic overview Classification and boiling points of halogenoalkanes Laboratory preparation of a halogenoalkane from an alcohol Nucleophiles and hydrolysis with aqueous alkali Reactions with ammonia and with potassium cyanide Relative rates of hydrolysis and carbon–halogen bond enthalpy Elimination using ethanolic potassium hydroxide CFCs and the ozone layer

Alcohols

Topic overview Hydrogen bonding, boiling point and solubility of alcohols Classifying alcohols and preparing them from halogenoalkanes Combustion of alcohols and their use as fuels Reactions with sodium, hydrogen bromide and phosphorus pentachloride Oxidation with acidified potassium dichromate(VI)

Infrared Spectroscopy

Topic overview Molecular vibrations and the absorption of infrared radiation Characteristic absorptions and the wavenumber scale Identifying functional groups from infrared spectra Distinguishing compounds and following reactions by infrared

Energetics

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Kinetics

Topic overview Reaction rate and the factors that change it Collision theory and activation energy The Maxwell–Boltzmann distribution of molecular energies Catalysts and the activation energy barrier

Equilibrium

Topic overview Reversible reactions and dynamic equilibrium Changing conditions and the position of equilibrium The equilibrium constant Kc and its units The magnitude of Kc and the extent of reaction Industrial processes and compromise conditions

Group II Elements and Their Compounds

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Lattice Enthalpy, Entropy and Free Energy

Topic overview Lattice enthalpy and the factors that control it Born–Haber cycles for Group I halides Born–Haber cycles for Group II halides and oxides Enthalpy of hydration and enthalpy of solution Calculations on dissolving ionic compounds Entropy and the limits of enthalpy change Standard entropy change calculations Free energy and the temperature of feasibility

Rates of Reaction

Topic overview Rate of reaction, order and the rate constant Deducing rate equations from initial rate data Concentration–time graphs and half-lives Rate–concentration graphs and orders Rate-determining steps, SN1 and SN2 Experimental methods and the effect of temperature on the rate constant

Equilibrium and Acid-Base Equilibria

Topic overview Equilibrium concentrations from initial amounts Kc expressions, values and units Brønsted–Lowry acids, bases and conjugate pairs Kw, pH and the pH of strong acids and bases Ka, pKa and the pH of weak acids Buffer solutions and how they resist pH change Calculating the pH of a buffer solution Titration curves, indicators and the pH of salt solutions

Isomerism

Topic overview Structural isomerism between different families Chiral centres and optical isomers Representing optical isomers in three dimensions Plane polarised light, optical activity and racemic mixtures Stereochemistry, drug action and receptor sites

Aldehydes and Ketones

Topic overview Structure and naming of aldehydes and ketones Boiling points and solubility of carbonyl compounds Preparation from primary and secondary alcohols Reaction with hydrogen cyanide and the nucleophilic addition mechanism Racemic mixtures from nucleophilic addition 2,4-dinitrophenylhydrazine and the identification of carbonyls Distinguishing aldehydes from ketones, and reduction with lithal

Carboxylic Acids

Topic overview Structure, naming and physical properties of carboxylic acids Preparation from primary alcohols and aldehydes Formation by hydrolysis of esters and nitriles Salt formation with carbonates, hydroxides and ammonia Reactions with alcohols, phosphorus pentachloride and lithal

Derivatives of Carboxylic Acids

Topic overview Esters and acyl chlorides: structure and naming Boiling points and solubility of monoesters Making esters from alcohols with carboxylic acids or acyl chlorides The laboratory preparation of a liquid ester Fats and oils as esters of glycerol Transesterification, biodiesel and margarine Reactions of acyl chlorides with water and alcohols

Aromatic Chemistry

Topic overview The structure of benzene and delocalised π electrons The stability of benzene compared with alkenes Electrophilic substitution: bromination and nitration of benzene Friedel–Crafts reactions and the nitration of methyl benzoate

Spectroscopy and Chromatography

Topic overview The mass spectrum: molecular ion and base peak Fragmentation and the formulae of fragment ions High resolution mass spectrometry Nuclear magnetic resonance and the TMS standard Chemically equivalent hydrogens and chemical shift Integration curves Spin–spin splitting and the n+1 rule Deducing a structure from an nmr spectrum Paper and thin-layer chromatography Gas–liquid chromatography

Volumetric Analysis

Topic overview Iodine–thiosulfate titrations Manganate(VII) titrations Deducing titration equations from half-equations Back titration

Transition Metals

Topic overview The characteristic properties of the transition metals Electronic configurations of the metals and their ions Complexes, ligands and coordination number Oxidation number, redox and disproportionation Monodentate, bidentate and polydentate ligands Ligand strength and the entropy of ligand replacement Ligand replacement in copper(II) complexes The colours of the aqueous transition metal ions Hydroxide precipitates with sodium hydroxide Precipitates with aqueous ammonia and their dissolution Vanadium and the interconversion of its oxidation states

Electrode Potentials

Topic overview Standard electrode potential Types of half-cell Cell representation and calculating emf Non-rechargeable, rechargeable and fuel cells The hydrogen–oxygen fuel cell Electrode potentials and reactivity

Amines

Topic overview Structure and classification of amines Physical properties of amines Preparing aliphatic and aromatic amines Amines as bases Reaction with ethanoyl chloride and identifying amines Diazonium salts and coupling Colour and delocalisation

Amides and Polymers

Topic overview The amide group and its preparation Reactions of amides The basicity of amides Condensation polymerisation Polyesters and polyamides in use Comparing addition and condensation polymers

Amino Acids and Proteins

Topic overview The structure of amino acids Optical activity Zwitterions and physical properties Reactions of amino acids Peptides and protein structure Enzymes as catalysts Temperature, pH and enzyme activity Enzymes in analysis and industry

Chemistry in Medicine

Topic overview Indigestion remedies Analysing an indigestion remedy by back titration Treating the skin Silver nitrate and cisplatin Aspirin: synthesis and analysis Chromatography in identifying drugs Haemoglobin, carbon monoxide and edta Drugs, testing and judgement

Halogenoalkanes

Reactions with ammonia and with potassium cyanide

3 things to know
Unit AS 2

Overview

Organic product formed when bromoethane reacts with excess ammonia, mechanism operates when ammonia reacts with a halogenoalkane and organic product formed when bromoethane reacts with potassium cyanide.

What you need to know

Answer each one before you reveal it.

Your recallNot started

Key term

Why is a large excess of ammonia used when it reacts with a halogenoalkane?

Key term

State the reagent and conditions for the reaction of a halogenoalkane with ammonia.

Key term

Why is the reaction with ammonia carried out in a sealed tube?

Questions from this subtopic

Each one with the model answer underneath.

1
State the reagent and conditions for the reaction of a halogenoalkane with ammonia.
Model answer
The halogenoalkane is heated with an excess of concentrated ammonia dissolved in ethanol, in a sealed tube.
2
Why is the reaction with ammonia carried out in a sealed tube?
Model answer
Ammonia is a gas that would escape from an open flask as soon as the mixture was heated, so the tube is sealed to hold it in the mixture under pressure.
3
Write the equation for the reaction of bromoethane with excess ammonia.
Model answer
The equation is CH₃CH₂Br + 2NH₃ → CH₃CH₂NH₂ + NH₄Br.
4
Name the organic product formed when bromoethane reacts with excess ammonia.
Model answer
The product is ethylamine, which is a primary amine.
5
What type of mechanism operates when ammonia reacts with a halogenoalkane?
Model answer
It is nucleophilic substitution, in which the lone pair on the nitrogen atom of the ammonia molecule attacks the δ+ carbon atom and displaces the halide ion.
6
Why is a large excess of ammonia used in this reaction?
Model answer
The amine formed is itself a nucleophile that can attack more halogenoalkane, so a large excess of ammonia makes it far more likely that a halogenoalkane molecule meets ammonia rather than the amine, which raises the yield of the primary amine.

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Reactions with ammonia and with potassium cyanide

Overview

What you need to know

Why is a large excess of ammonia used when it reacts with a halogenoalkane?

State the reagent and conditions for the reaction of a halogenoalkane with ammonia.

Why is the reaction with ammonia carried out in a sealed tube?

Questions from this subtopic

State the reagent and conditions for the reaction of a halogenoalkane with ammonia.

Why is the reaction with ammonia carried out in a sealed tube?

Write the equation for the reaction of bromoethane with excess ammonia.

Name the organic product formed when bromoethane reacts with excess ammonia.

What type of mechanism operates when ammonia reacts with a halogenoalkane?

Why is a large excess of ammonia used in this reaction?

Other ways to work this

What is inside Levo

The 3-step method, run for you

Cram a whole paper in one sitting

Blank Blitz makes facts automatic

Build It gets the exam shape right

Test It catches misconceptions

Brain Breaks between sessions

Every question in Halogenoalkanes, on a schedule.