Chemistry 9701 · AS & A Level · Halogen compounds

Halogen compounds — practice question

Fig. 5.1 illustrates three reactions involving 2-bromopropane, $\text{CH}_3\text{CH(Br)CH}_3$.
(a)[6]

Fill in Table 5.1 for every reaction by giving the reagent, the conditions, and the reaction type that takes place.

(b)[2]

A sample of 2-iodopropane, $\text{CH}_3\text{CH(I)CH}_3$, reacts under the same conditions as reaction 1 to make $\text{CH}_3\text{CH(OH)CH}_3$. Explain why 2-iodopropane reacts faster than 2-bromopropane.

(c(i))[2]

In step 1, 1-bromopropane reacts with $\text{CN}^-$ to form butanenitrile. Complete Fig. 5.3 to show the mechanism for step 1. Include charges, dipoles, lone pairs of electrons and curly arrows where needed.

(c(ii))[1]

In step 2, butanenitrile is heated with $\text{HCl(aq)}$. A hydrolysis reaction takes place. Construct an equation for step 2.

(c(iii))[1]

Step 3 is a reduction reaction. Construct an equation for the reduction reaction in step 3. Use $[\text{H}]$ to represent one atom of hydrogen from the reducing agent.

(c(iv))[1]

State the identity of a suitable reducing agent for step 3.

Worked solution & mark scheme

This 13-mark question has a full step-by-step worked solution and mark scheme. One marking point: Reaction 1 reagent used: NaOH(aq)

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