Chemistry 9701 · AS & A Level · Halogen compounds

Halogen compounds — practice question

(a)[2]

Describe how chloroethane and chlorobenzene differ in reactivity with $\text{OH}^-(\text{aq})$. Explain your answer.

(b)

Compound $T$, $\text{C}_5\text{H}_9\text{O}_2\text{Cl}$, is a useful synthetic intermediate. Fig. 8.1 presents several reactions of $T$.

(b(i))[1]

Give the systematic name of $T$.

(b(ii))[4]

Draw the structures of $W$, $X$, $Y$ and $Z$ shown in Fig. 8.1.

(b(iii))[2]

State the reagents and conditions for steps 1 and 2 in Fig. 8.1.

(i)[1]

Give the systematic name of $T$.

(ii)[4]

Draw the structures of W, X, Y and Z shown in Fig. 8.1.

(iii)[2]

State the reagents and conditions for steps 1 and 2 in Fig. 8.1. step 1: step 2:

(c)

Fig. 8.2 shows the proton ($^{1}\text{H}$) NMR spectrum of compound T, $\text{C}_5\text{H}_9\text{O}_2\text{Cl}$, in CDCl$_3$.

(c(i))[1]

Suggest why CDCl$_3$ is chosen as the solvent rather than CHCl$_3$ for the proton ($^{1}\text{H}$) NMR spectrum.

(c(ii))[4]

Complete Table 8.2 using the proton ($^{1}\text{H}$) NMR spectrum of T.

(c(iii))[1]

Explain the splitting pattern shown by the peak at $\delta = 3.9\,\text{ppm}$.

Worked solution & mark scheme

This 22-mark question has a full step-by-step worked solution and mark scheme. One marking point: Chlorobenzene is less reactive because of delocalisation / partial double C-Cl bond

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