Paper 2: Synthesis and analytical techniques

Which functional group is in CH₃COCH₃?

How many structural isomers have the formula C₅H₁₂?

What is the general formula of a non-cyclic alkene with one C=C?

Methane reacts with chlorine in UV light. The type of reaction is:

Which alcohol is tertiary?

Which is hydrolysed fastest by water?

A compound shows a broad absorption at 2500–3300 cm⁻¹ and a sharp one at 1710 cm⁻¹. It is most likely:

Which species catalyses the breakdown of ozone in the upper atmosphere?

Which reagent reduces propanal to propan-1-ol?

Which compound gives an orange precipitate with 2,4-dinitrophenylhydrazine?

Which is a primary amine?

How many peaks are in the ¹³C NMR spectrum of propan-2-ol?

What is the electrophile in the nitration of benzene?

Which forms a polyamide with hexane-1,6-diamine?

Which reagent increases the length of a carbon chain by one carbon atom?

Explain why the boiling points of the alkanes increase with chain length, and why branched isomers have lower boiling points.

Outline the mechanism for the reaction of methane with bromine in UV light.

Propene reacts with HBr. Outline the mechanism and explain why 2-bromopropane is the major product.

Propan-1-ol is heated with acidified potassium dichromate(VI). Explain how the apparatus determines which organic product is formed.

Outline the mechanism for the reaction of 1-bromopropane with aqueous hydroxide ions.

Explain how CFCs deplete the ozone layer. Include equations.

Cyclohexene can be made by heating cyclohexanol with concentrated phosphoric acid. Describe how to prepare and purify a sample of cyclohexene.

Compound P contains 62.1% C, 10.3% H and 27.6% O by mass. Its mass spectrum has M⁺ at m/z 58. Its IR spectrum has a strong absorption at 1715 cm⁻¹. It gives an orange precipitate with 2,4-DNP but no reaction with Tollens' reagent. Identify P.

Compound R, C₄H₈O₂, is an ester. Its ¹H NMR spectrum has a singlet at δ 2.0 (3H), a quartet at δ 4.1 (2H) and a triplet at δ 1.2 (3H). Its ¹³C NMR spectrum has four peaks. Identify R, explaining how the spectra support your answer.

Give three pieces of evidence that benzene does not have the Kekulé structure, and explain each.

Outline the mechanism for the nitration of benzene, including how the electrophile is formed.

Predict the main product when nitrobenzene is brominated and when phenylamine reacts with bromine water. Explain the difference in reactivity.

Outline the mechanism for the reduction of propanal by NaBH₄.

Compare the hydrolysis of ethyl ethanoate using dilute acid and using aqueous sodium hydroxide.

Give the organic products of ethanoyl chloride with water, with ammonia and with phenol.

Give the reagents and conditions to make ethylamine from bromoethane, and phenylamine from nitrobenzene.

Draw the structures of alanine, H₂NCH(CH₃)COOH, at low pH and at high pH, and explain why alanine shows optical isomerism.

Ethane-1,2-diol and benzene-1,4-dicarboxylic acid form a polyester. Draw the repeat unit and explain why polyesters can be broken down but poly(alkenes) cannot be hydrolysed.

Bromoethane is converted to propanenitrile, then to propanoic acid. Give reagents and conditions for both steps and explain why this route is useful.

Plan a three-step synthesis of 2-hydroxypropanoic acid from ethanol. Give reagents, conditions and intermediates, and comment on the stereochemistry of the product.

Explain how gas chromatography separates a mixture of three esters and how the proportions of each can be found.

Describe tests to show that a compound contains a C=C, an aldehyde group and a carboxylic acid group.