Chemistry 9701 · AS & A Level · Nitrogen compounds

Nitrogen compounds — practice question

The displayed diagram shows the structure of butamben.
(a(i))[1]

Butamben is able to behave as a base. Complete the equation for the reaction in which butamben behaves as a base.

(a(ii))[1]

Predict whether butamben is a stronger base or a weaker base than ammonia. Give a reason for your response.

(b)[3]

Complete the reaction scheme below so that it shows the structural formulae of the products obtained when butamben is treated separately with the reagent stated.

(c(i))[1]

State how many peaks in the proton NMR spectrum of butamben in $\text{CDCl}_3$ exhibit a triplet splitting pattern.

(c(ii))[1]

On the butamben diagram below, circle the protons that produce the peak or peaks you identified in (c)(i).

(c(iii))[2]

Describe and explain how the proton NMR spectrum of butamben in $\text{D}_2\text{O}$ would be different from that of butamben in $\text{CDCl}_3$.

(d)[1]

The mass spectrum of butamben has peaks at $m/e = 92$ and $57$. Identify the fragments responsible for these peaks.\n\n$m/e = 92 = \\ldots$\n\n$m/e = 57 = \\ldots$

Worked solution & mark scheme

This 10-mark question has a full step-by-step worked solution and mark scheme. One marking point: Either $\text{RNH}_2 + \text{H}^+ \rightarrow \text{RNH}_3^+$ or $\text{RNH}_2 + \text{HCl} \rightarrow \text{RNH}_3\text{Cl}$

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