Draw the three-dimensional shape of each enantiomer of this isomer showing their spatial relationship to each other.

When one enantiomer undergoes substitution by alkaline hydrolysis approximately 75 % of the product molecules show inversion of configuration. Comment on the mechanisms that occur.

Suggest why the rate of alkaline hydrolysis of an enantiomer of iodopropane is greater than that of an enantiomer of bromopropane.

(i) Draw diagrams to show how sigma (σ) and pi (π) bonds are formed between atoms.

(ii) State the number of sigma (σ) and pi (π) bonds in propane and propene.

Construct the mechanism of the formation of 2-bromopropane from hydrogen bromide and propene using curly arrows to denote the movement of electrons.

Distinguish between a sigma and pi bond.

Identify the hybridization of carbon in ethane, ethene and ethyne.

State, giving a reason, if but-1-ene exhibits cis-trans isomerism.

State the type of reaction which occurs between but-1-ene and hydrogen iodide at room temperature.

Explain the mechanism of the reaction between but-1-ene with hydrogen iodide, using curly arrows to represent the movement of electron pairs.

State, giving a reason, if the product of this reaction exhibits stereoisomerism.

Deduce the rate expression for this reaction.

Deduce the units of the rate constant.

Determine the initial rate of reaction in experiment 4.

Deduce, with a reason, the mechanism of the reaction between 2-chloropentane and sodium hydroxide.

Discuss the reason benzene is more reactive with an electrophile than a nucleophile.

State the full electron configuration of the chlorine atom.

State, giving a reason, whether the chlorine atom or the chloride ion has a larger radius.

Outline why the chlorine atom has a smaller atomic radius than the sulfur atom.

The mass spectrum of chlorine is shown.

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Outline the reason for the two peaks at $m/z=35$ and $37$.

Explain the presence and relative abundance of the peak at $m/z=74$.

Calculate the amount, in $\mathrm{mol}$, of manganese(IV) oxide added.

Determine the limiting reactant, showing your calculations.

Determine the excess amount, in $\mathrm{mol}$, of the other reactant.

Calculate the volume of chlorine, in ${\mathrm{dm}}^3$, produced if the reaction is conducted at standard temperature and pressure (STP). Use section 2 of the data booklet.

State the oxidation state of manganese in ${\mathrm{MnO}}_2$ and ${\mathrm{MnCl}}_2$.

Deduce, referring to oxidation states, whether ${\mathrm{MnO}}_2$ is an oxidizing or reducing agent.

Hypochlorous acid is considered a weak acid. Outline what is meant by the term weak acid.

State the formula of the conjugate base of hypochlorous acid.

Calculate the concentration of ${\mathrm{H}}^{+} \left(\mathrm{aq}\right)$ in a $\mathrm{HClO} \left(\mathrm{aq}\right)$ solution with a $\mathrm{pH}=3.61$.

State the type of reaction occurring when ethane reacts with chlorine to produce chloroethane.

Predict, giving a reason, whether ethane or chloroethane is more reactive.

Explain the mechanism of the reaction between chloroethane and aqueous sodium hydroxide, $\mathrm{NaOH} \left(\mathrm{aq}\right)$, using curly arrows to represent the movement of electron pairs.

Ethoxyethane (diethyl ether) can be used as a solvent for this conversion.
Draw the structural formula of ethoxyethane

Deduce the number of signals and chemical shifts with splitting patterns in the ¹H NMR spectrum of ethoxyethane. Use section 27 of the data booklet.

Calculate the percentage by mass of chlorine in ${\mathrm{CCl}}_2{\mathrm{F}}_2$.

Comment on how international cooperation has contributed to the lowering of $\mathrm{CFC}$ emissions responsible for ozone depletion.

$\mathrm{CFC}$s produce chlorine radicals. Write two successive propagation steps to show how chlorine radicals catalyse the depletion of ozone.

Predict the electron domain and molecular geometries around the oxygen atom of molecule A using VSEPR

State the type of hybridization shown by the central carbon atom in molecule B.

State the number of sigma ($\mathrm{\sigma }$) and pi ($\mathrm{\pi }$) bonds around the central carbon atom in molecule B.

The IR spectrum of one of the compounds is shown:

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Deduce, giving a reason, the compound producing this spectrum.

Compound A and B are isomers. Draw two other structural isomers with the formula ${\mathrm{C}}_3{\mathrm{H}}_6\mathrm{O}$.

The equilibrium constant, $K_{\mathrm{c}}$, for the conversion of A to B is $1.0\times {10}^8$ in water at $298 \mathrm{K}$.

Deduce, giving a reason, which compound, A or B, is present in greater concentration when equilibrium is reached.

Calculate the standard Gibbs free energy change, $∆G^{⦵}$, in $\mathbf{kJ}\mathbf{ }{\mathbf{mol}}^{\mathbf{–}\mathbf{1}}$, for the reaction (A to B) at $298 \mathrm{K}$. Use sections 1 and 2 of the data booklet.

Propanone can be synthesized in two steps from propene. Suggest the synthetic route including all the necessary reactants and steps.

Propanone can be synthesized in two steps from propene.

Suggest why propanal is a minor product obtained from the synthetic route in (g)(i).

Discuss the physical evidence for the structure of benzene.

State the typical reactions that benzene and cyclohexene undergo with bromine.

State the reagents used to convert benzene to nitrobenzene and the formula of the electrophile formed.

Explain the mechanism for the nitration of benzene, using curly arrows to show the movement of electron pairs.

State the reagents used in the two-stage conversion of nitrobenzene to aniline.

Deduce, giving a reason, which of the two compounds can show optical activity.

Draw three-dimensional representations of the two enantiomers.

State the reagents used in the nitration of benzene.

State an equation for the formation of NO₂⁺.

Explain the mechanism of the reaction between 2-bromo-2-methylpropane, (CH₃)₃CBr, and aqueous sodium hydroxide, NaOH (aq), using curly arrows to represent the movement of electron pairs.

State the class of compound to which ethene belongs.

State the molecular formula of the next member of the homologous series to which ethene belongs.

Justify why ethene has only a single signal in its ¹H NMR spectrum.

Deduce the chemical shift of this signal. Use section 27 of the data booklet.

Suggest two possible products of the incomplete combustion of ethene that would not be formed by complete combustion.

A white solid was formed when ethene was subjected to high pressure.

Deduce the type of reaction that occurred.

Sketch the mechanism for the reaction of propene with hydrogen bromide using curly arrows.

Explain why the major organic product is 2-bromopropane and not 1-bromopropane.

Explain why the major organic product is 2-bromopropane and not 1-bromopropane.

2-bromopropane can be converted directly to propan-2-ol. Identify the reagent required.

Propan-2-ol can also be formed in one step from a compound containing a carbonyl group.

State the name of this compound and the type of reaction that occurs.

Deduce what information can be obtained from the ¹H NMR spectrum.

Identify the functional group that shows stretching at 1710 cm^–1 in the infrared spectrum of this compound using section 26 of the data booklet and the ¹H NMR.

Suggest the structural formula of this compound.

Bromine was added to hexane, hex-1-ene and benzene. Identify the compound(s) which will react with bromine in a well-lit laboratory.

Deduce the structural formula of the main organic product when hex-1-ene reacts with hydrogen bromide.

State the reagents and the name of the mechanism for the nitration of benzene.

Outline, in terms of the bonding present, why the reaction conditions of halogenation are different for alkanes and benzene.

Below are two isomers, A and B, with the molecular formula C₄H₉Br.

Explain the mechanism of the nucleophilic substitution reaction with NaOH(aq) for the isomer that reacts almost exclusively by an S_N2 mechanism using curly arrows to represent the movement of electron pairs.

Several compounds can be synthesized from but-2-ene. Draw the structure of the final product for each of the following chemical reactions.

Determine the change in enthalpy, ΔH, for the combustion of but-2-ene, using section 11 of the data booklet. 

CH₃CH=CHCH₃(g) + 6O₂ (g) → 4CO₂(g) + 4H₂O (g)

State the hybridization of the carbon I and II atoms in but-2-ene.

Draw diagrams to show how sigma (σ) and pi (π) bonds are formed between atoms.

Sketch the mechanism for the reaction of 2-methylbut-2-ene with hydrogen bromide using curly arrows.

Explain why the major organic product is 2-bromo-2-methylbutane and not 2-bromo-3-methylbutane.

Deduce two features of this molecule that can be obtained from the mass spectrum. Use section 28 of the data booklet.

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Identify the bond responsible for the absorption at A in the infrared spectrum. Use section 26 of the data booklet.

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Deduce the identity of the unknown compound using the previous information, the ¹H NMR spectrum and section 27 of the data booklet.

SDBS, National Institute of Advanced Industrial Science and Technology (AIST).

Draw the stereoisomers of butan-2-ol using wedge-dash type representations.

Outline how two enantiomers can be distinguished using a polarimeter.

Compare and contrast the mechanisms by which 1-chlorobutane, CH₃CH₂CH₂CH₂Cl, and 2-chloro-2-methylpropane, (CH₃)₃CCl, react with aqueous sodium hydroxide, giving two similarities and one difference.

Outline why the rate of reaction of the similar bromo-compounds is faster.

State the organic product of the reaction between 1-chlorobutane, CH₃CH₂CH₂CH₂Cl, and aqueous sodium hydroxide.

Suggest how this product could be synthesized in one step from butanoic acid.

Deduce the name of the class of compound formed when the product of (c)(i) reacts with butanoic acid.

State the name of Compound B, applying International Union of Pure and Applied Chemistry (IUPAC) rules.

Compound A and Compound B are both liquids at room temperature and pressure. Identify the strongest intermolecular force between molecules of Compound A.

State the number of $\text{σ}$ (sigma) and $\mathrm{\pi }$ (pi) bonds in Compound A.

Deduce the hybridization of the central carbon atom in Compound A.

Identify the isomer of Compound B that exists as optical isomers (enantiomers).

Draw the structural formula of the alkene required.

Explain why the reaction produces more (CH₃)₃COH than (CH₃)₂CHCH₂OH.

Deduce the structural formula of the repeating unit of the polymer formed from this alkene.

Deduce what would be observed when Compound B is warmed with acidified aqueous potassium dichromate (VI).

Identify the type of reaction.

Outline the requirements for a collision between reactants to yield products.

Explain the mechanism of the reaction using curly arrows to represent the movement of electron pairs.

The polarity of the carbon–halogen bond, C–X, facilitates attack by HO^–.

Outline, giving a reason, how the bond polarity changes going down group 17.

Draw arrows in the boxes to represent the electron configuration of a nitrogen atom.

Deduce a Lewis (electron dot) structure of the nitric acid molecule, HNO₃, that obeys the octet rule, showing any non-zero formal charges on the atoms.

Explain the relative lengths of the three bonds between N and O in nitric acid.

State a technique used to determine the length of the bonds between N and O in solid HNO₃.

Write an equation for the reaction between the acids to produce the electrophile, NO₂⁺.

Draw the structural formula of the carbocation intermediate produced when this electrophile attacks benzene.

Deduce the number of signals that you would expect in the ¹H NMR spectrum of nitrobenzene and the relative areas of these.

Identify the wavenumber of one peak in the IR spectrum of benzoic acid, using section 26 of the data booklet.

Identify the spectroscopic technique that is used to measure the bond lengths in solid benzoic acid.

Outline one piece of physical evidence for the structure of the benzene ring.

Draw the structure of the conjugate base of benzoic acid showing all the atoms and all the bonds.

Outline why both C to O bonds in the conjugate base are the same length and suggest a value for them. Use section 10 of the data booklet.

The pH of an aqueous solution of benzoic acid at 298 K is 2.95. Determine the concentration of hydroxide ions in the solution, using section 2 of the data booklet.

Formulate the equation for the complete combustion of benzoic acid in oxygen using only integer coefficients.

The combustion reaction in (f)(ii) can also be classed as redox. Identify the atom that is oxidized and the atom that is reduced.

Suggest how benzoic acid, M_r = 122.13, forms an apparent dimer, M_r = 244.26, when dissolved in a non-polar solvent such as hexane.

State the reagent used to convert benzoic acid to phenylmethanol (benzyl alcohol), C₆H₅CH₂OH.

Ethane, ${\text{C}}_{\text{2}}{\text{H}}_{\text{6}}$, reacts with chlorine in sunlight. State the type of this reaction and the name of the mechanism by which it occurs.

Formulate equations for the two propagation steps and one termination step in the formation of chloroethane from ethane.

Deduce the splitting patterns in the ¹H NMR spectrum of C₂H₅Cl.

Explain why tetramethylsilane (TMS) is often used as a reference standard in ¹H NMR.

One possible product, X, of the reaction of ethane with chlorine has the following composition by mass:

carbon: 24.27%, hydrogen: 4.08%, chlorine: 71.65%

Determine the empirical formula of the product.

The mass and ¹H NMR spectra of product X are shown below. Deduce, giving your reasons, its structural formula and hence the name of the compound.

When the product X is reacted with NaOH in a hot alcoholic solution, C₂H₃Cl is formed. State the role of the reactant NaOH other than as a nucleophile.

Chloroethene, ${\text{C}}_{\text{2}}{\text{H}}_{\text{3}}\text{Cl}$, can undergo polymerization. Draw a section of the polymer with three repeating units.

State the number of ¹H NMR signals for this isomer of xylene and the ratio in which they appear.

Draw the structure of one other isomer of xylene which retains the benzene ring.

Write the equation for the production of the active nitrating agent from concentrated sulfuric and nitric acids.

Explain the mechanism for the nitration of benzene, using curly arrows to indicate the movement of electron pairs.

Identify the initiation step of the reaction and its conditions.

1,4-dimethylbenzene reacts as a substituted alkane. Draw the structures of the two products of the overall reaction when one molecule of bromine reacts with one molecule of 1,4-dimethylbenzene.

The organic product is not optically active. Discuss whether or not the organic product is a racemic mixture.

Outline two differences between the bonding of carbon atoms in C₆₀ and diamond.

Explain why C₆₀ and diamond sublime at different temperatures and pressures.

State two features showing that propane and butane are members of the same homologous series.

Describe a test and the expected result to indicate the presence of carbon–carbon double bonds.

Draw the full structural formula of (Z)-but-2-ene.

Write the equation for the reaction between but-2-ene and hydrogen bromide.

State the type of reaction.

Suggest two differences in the ¹H NMR of but-2-ene and the organic product from (d)(ii).

Predict, giving a reason, the major product of reaction between but-1-ene and steam.

Explain the mechanism of the reaction between 1-bromopropane, CH₃CH₂CH₂Br, and aqueous sodium hydroxide, NaOH (aq), using curly arrows to represent the movement of electron pairs.

Deduce the splitting pattern in the ¹H NMR spectrum for 1-bromopropane.

Calculate the enthalpy change of the reaction, ΔH, using section 11 of the data booklet.

Draw and label an enthalpy level diagram for this reaction.

State a reason why most halogenoalkanes are more reactive than alkanes.

Classify 1-bromopropane as a primary, secondary or tertiary halogenoalkane, giving a reason.

Explain the mechanism of the reaction between 1-bromopropane with aqueous sodium hydroxide using curly arrows to represent the movement of electron pairs.

State, giving your reason, whether the hydroxide ion acts as a Lewis acid, a Lewis base, or neither in the nucleophilic substitution.

Suggest two advantages of understanding organic reaction mechanisms.

State the type of reaction.

State the IUPAC name of the major product.

Outline why it is the major product.

Write an equation for the reaction of the major product with aqueous sodium hydroxide to produce a C₃H₈O compound, showing structural formulas.

Determine the rate expression from the results, explaining your method.

Deduce the type of mechanism for the reaction of this isomer of C₃H₇Cl with aqueous sodium hydroxide.

Sketch the mechanism using curly arrows to represent the movement of electrons.

Write an equation for the complete combustion of the compound C₃H₈O formed in (a)(iv).

Determine the enthalpy of combustion of this compound, in kJ mol⁻¹, using data from section 11 of the data booklet.

State the reagents for the conversion of the compound C₃H₈O formed in (a)(iv) into C₃H₆O.

Explain why the compound C₃H₈O, produced in (a)(iv), has a higher boiling point than compound C₃H₆O, produced in d(i).

Explain why the ¹H NMR spectrum of C₃H₆O, produced in (d)(i), shows only one signal.

Propene is often polymerized. Draw a section of the resulting polymer, showing two repeating units.

Draw the repeating unit of polyphenylethene.

Phenylethene is manufactured from benzene and ethene in a two-stage process. The overall reaction can be represented as follows with ΔG^θ = +10.0 kJ mol⁻¹ at 298 K.

Calculate the equilibrium constant for the overall conversion at 298 K, using section 1 of the data booklet.

The benzene ring of phenylethene reacts with the nitronium ion, NO₂⁺, and the C=C double bond reacts with hydrogen bromide, HBr.

Compare and contrast these two reactions in terms of their reaction mechanisms.

Similarity: 

Difference:

Outline why the major product, C₆H₅–CHBr–CH₃, can exist in two forms and state the relationship between these forms.

Two forms: 

Relationship:

The minor product, C₆H₅–CH₂–CH₂Br, can exist in different conformational forms (isomers).

Outline what this means.

The minor product, C₆H₅–CH₂–CH₂Br, can be directly converted to an intermediate compound, X, which can then be directly converted to the acid C₆H₅–CH₂–COOH.

C₆H₅–CH₂–CH₂Br → X → C₆H₅–CH₂–COOH

Identify X.

Deduce the structural formulas of the two possible isomers.

Mass spectra A and B of the two isomers are given.

Explain which spectrum is produced by each compound using section 28 of the data booklet.

State the type of bond fission that takes place in a S_N1 reaction.

State the type of solvent most suitable for the reaction.

Draw the structure of the intermediate formed stating its shape.

Suggest, giving a reason, the percentage of each isomer from the S_N1 reaction.

Nitrobenzene, C₆H₅NO₂, can be converted to phenylamine via a two-stage reaction.

In the first stage, nitrobenzene is reduced with tin in an acidic solution to form an intermediate ion and tin(II) ions. In the second stage, the intermediate ion is converted to phenylamine in the presence of hydroxide ions.

Formulate the equation for each stage of the reaction.

State the equation for the reaction of each substance with water.

Draw a diagram showing the delocalization of electrons in the conjugate base of butanoic acid.

Deduce the average oxidation state of carbon in butanoic acid.

A 0.250 mol dm⁻³ aqueous solution of butanoic acid has a concentration of hydrogen ions, [H⁺], of 0.00192 mol dm⁻³. Calculate the concentration of hydroxide ions, [OH⁻], in the solution at 298 K.

Determine the pH of a 0.250 mol dm⁻³ aqueous solution of ethylamine at 298 K, using section 21 of the data booklet.

Sketch the pH curve for the titration of 25.0 cm³ of ethylamine aqueous solution with 50.0 cm³ of butanoic acid aqueous solution of equal concentration. No calculations are required.

Explain why butanoic acid is a liquid at room temperature while ethylamine is a gas at room temperature.

State a suitable reagent for the reduction of butanoic acid.

Deduce the product of the complete reduction reaction in (e)(i).

Suggest why the three-membered ring in methyloxirane is unstable.

Draw two structural isomers of methyloxirane.

State, giving a reason, whether methyloxirane can form cis-trans isomers.

Predict the chemical shift and splitting pattern of the signal produced by the hydrogen atoms labelled X in the ¹H NMR spectrum of the polymer. Use section 27 of the data booklet.