Paper 2: Advanced Organic and Physical Chemistry

What is the IUPAC name of CH₃CH₂CH(CH₃)CH₂OH?

Explain why but-2-ene has E/Z isomers but but-1-ene does not.

Outline the mechanism for the reaction of but-1-ene with bromine, and explain how the product would differ if the reaction were done in aqueous sodium chloride.

Describe how you would compare the rates of hydrolysis of 1-chlorobutane, 1-bromobutane and 1-iodobutane using aqueous silver nitrate in ethanol.

Give the reagents and conditions to convert butan-1-ol to butanal.

Compound Y has a molecular ion peak at m/z 72 and a strong IR absorption at 1720 cm⁻¹. It gives no reaction with Tollens' reagent. Its mass spectrum has a large peak at m/z 43. Identify Y, explaining each piece of evidence.

Figure 1 shows how [A] changes with time in a reaction. Use the graph to show that the reaction is first order with respect to A and calculate the rate constant.

Describe how a graph can be used to determine the activation energy of a reaction from rate constants at different temperatures.

The hydrolysis of 2-bromo-2-methylpropane has rate = k[C₄H₉Br]. Explain what this tells you about the mechanism.

Describe the mechanism of the reaction of propanone with HCN and explain why the product from propanal is optically inactive.

Give three different reactions of ethanoic acid that show it behaves as an acid or as a carbonyl compound, with reagents.

Write an equation for the reaction of ethanoyl chloride with ethanol and give two advantages of using ethanoyl chloride rather than ethanoic acid.

Explain why benzene undergoes substitution rather than addition with bromine.

Outline the mechanism for the reaction of benzene with ethanoyl chloride, including formation of the electrophile.

Explain why phenol reacts with bromine water at room temperature but benzene does not.

Draw the dipeptide formed from glycine (H₂NCH₂COOH) and alanine (H₂NCH(CH₃)COOH), and describe how the amino acids can be identified after hydrolysis.

Explain the difference between addition and condensation polymerisation, with an example of each.

Compound Z, C₃H₆O₂, is an ester. Its ¹H NMR spectrum has a singlet at δ 8.0 (1H), a quartet at δ 4.2 (2H) and a triplet at δ 1.3 (3H). Its ¹³C NMR spectrum has three peaks. Identify Z and explain each feature of the spectra.

Explain how high-performance liquid chromatography (HPLC) separates components of a mixture and how they are identified.

Devise a synthesis of N-phenylethanamide from benzene. Give the reagents and conditions for each step, and name the type of reaction.

Explain, using collision theory, why increasing the concentration and increasing the temperature both increase the rate of reaction, but only temperature changes the rate constant.

For 2SO₂(g) + O₂(g) ⇌ 2SO₃(g), ΔH = −197 kJ mol⁻¹. Explain the effect on the equilibrium yield and on Kp of (a) increasing the pressure and (b) increasing the temperature.

Describe how methylmagnesium bromide is prepared and how it can be used to make 2-methylpropan-2-ol from propanone. Give equations and conditions.

Describe a chemical test to distinguish propanal from propanone, giving the result for each.

2-hydroxypropanoic acid, CH₃CH(OH)COOH, is chiral. Explain what this means and how its two optical isomers can be distinguished.