Chemistry 9701 · AS & A Level · An introduction to A Level organic chemistry

An introduction to A Level organic chemistry — practice question

Chlorobenzene forms when benzene reacts with chlorine gas. This can be viewed as benzene molecules reacting with $\text{Cl}^+$ ions. A suitable catalyst added to the chlorine gas produces the $\text{Cl}^+$ ions.
(a)[1]

State the name or formula of a catalyst that may be used for this reaction.

(b(i))[2]

In diagram 1, the movement of a pair of electrons is shown by $x$. State where this pair of electrons is located before step 1 takes place. State where this pair of electrons is located after step 1 has taken place.

(b(ii))[2]

In diagram 2, the movement of a different pair of electrons is represented by $y$. State where this pair of electrons is before step 2 takes place. State where this pair of electrons is after step 2 has taken place.

(c)[1]

Diagram 2 contains six carbon atoms. State how many of these carbon atoms are $sp$ hybridised, how many are $sp^2$ hybridised, and how many are $sp^3$ hybridised.

(d)[1]

Complete the equation for the reaction between benzene and chlorine. $\text{C}_6\text{H}_6 + \ldots \rightarrow \ldots + \ldots$

(e)[1]

The mechanism for this reaction is electrophilic substitution. Complete the sentence below. Write formulae in the spaces provided. During this reaction, the electrophile is \ldots and a \ldots atom in benzene is substituted by a \ldots atom.

(f(i))[1]

Name the mechanism of the reaction chloroethane undergoes with $\text{NaOH(aq)}$, and identify the major organic product formed.

(f(ii))[2]

Explain why chloroethane and chlorobenzene show different reactivities when they are treated with $\text{NaOH(aq)}$.

Worked solution & mark scheme

This 11-mark question has a full step-by-step worked solution and mark scheme. One marking point: $\text{AlCl}_3$ or aluminium chloride

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