Chemistry 9701 · AS & A Level · States of matter

States of matter — practice question

Organochlorine compounds are able to hydrolyse according to $\text{R-Cl} + \text{H}_2\text{O} \rightarrow \text{R-OH} + \text{HCl}$.
(a)[3]

State and explain the comparative hydrolysis rates of the compounds $\text{CH}_3\text{CH}_2\text{Cl}$, $\text{CH}_3\text{COCl}$ and $\text{C}_6\text{H}_5\text{Cl}$.

(b(i))[1]

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

(b(ii))[1]

Epibatidine has two nitrogen atoms, and either one can act as a base. It reacts with $\text{HCl(aq)}$. Complete the structure to show the product of this reaction.

(c(i))[1]

As the nylon-6 monomer is hydrolysed, bonds are broken and made. Using the two stages of the reaction mechanism, complete the table by adding one tick ($\checkmark$) in each row to show the bond types broken and formed during the mechanism.

(c(ii))[2]

Draw two repeat units of nylon-6, with the amide bond shown in full.

(d)[2]

An addition polymer that is made from two different alkene monomers is known as 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.

(c)

Polyamides, including nylon-6, may be produced from a monomer that has both an amine and an acyl chloride functional group. The nylon-6 monomer is $\text{H}_2\text{N}-(\text{CH}_2)_5-\text{C}(=\text{O})\text{Cl}$.

(e)[1]

Explain why polyamides usually biodegrade more readily than polyalkenes.

(f)

Phenylethene can be made from benzene in three steps, as shown.

(f(i))[1]

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

(f(ii))[3]

Suggest the reagent(s) and conditions for steps 1-3.

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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