Chemistry 9701 · AS & A Level · Halogen compounds

Halogen compounds — practice question

Organochlorine compounds may be hydrolysed like this: $\text{R-Cl} + \text{H}_2\text{O} \rightarrow \text{R-OH} + \text{HCl}$.
(a)[3]

State and explain how the hydrolysis rates compare for these compounds: $\text{CH}_3\text{CH}_2\text{Cl}$, $\text{CH}_3\text{COCl}$, $\text{C}_6\text{H}_5\text{Cl}$.

(b(i))[1]

Epitabidine is a weak base. State what the term weak base means.

(b(ii))[1]

A molecule of epibatidine has two nitrogen atoms, and either can behave as a base. Epibatidine reacts with $\text{HCl(aq)}$. Complete the structure to suggest the product formed in this reaction.

(c(i))[1]

Polyamides, such as nylon-6, may be made from a monomer containing both an amine and an acyl chloride functional group. When the nylon-6 monomer is hydrolysed, bonds are broken and formed. If you think about the two steps in the reaction mechanism, complete the table by putting one tick (✓) in each row to show the types of bonds broken and formed during the mechanism.

(c(ii))[2]

Draw two repeat units of nylon-6. The amide bond must be shown in full.

(d)[2]

An addition polymer formed from two different alkene monomers is called a co-polymer. A section of a polyalkene co-polymer is shown. Draw the structures of the two alkene monomers that form this co-polymer.

(e)[1]

Explain why polyamides usually biodegrade more readily than polyalkenes.

(f(i))[1]

Deduce what compound $\text{H}$ is and draw its structure in the box.

(f(ii))[3]

Suggest reagents and conditions for each of steps $1$-$3$ used to prepare phenylethene from benzene.

Worked solution & mark scheme

This 15-mark question has a full step-by-step worked solution and mark scheme. One marking point: Hydrolysis rate order: $CH_3COCl > CH_3CH_2Cl > C_6H_5Cl$

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