State the reactants and conditions for two different types of reactions that both produce diethylamine, CH3CH2NHCH2CH3. reaction one .......................................................................................................... reaction two ..........................................................................................................

1. (a)State the reactants and conditions for two different types of reactions that both produce diethylamine, CH3CH2NHCH2CH3. reaction one .......................................................................................................... reaction two ..........................................................................................................[4]
2. (b)Describe the relative basicities of diethylamine, phenylamine and ammonia in aqueous solution. Explain your answer in terms of structure. least basic .......................................................................................................... explanation .......................................................................................................... most basic .......................................................................................................... explanation ..........................................................................................................[3]
3. (c)Phenylamine reacts with HNO2(aq) at 4°C to form compound P. Compound P reacts with phenol under alkaline conditions at 4°C. The product of this reaction is acidified, forming azo compound Q. Draw the structure of compound Q. Circle the azo group on your structure. State one use of an azo compound such as Q. compound Q: [Figure for drawing box] An azo compound can be used ..........................................................................................................[2]
4. (d)(i)CH3CH2NHCH2CH3 reacts with ethanoyl chloride, CH3COCl, to give the amide N,N-diethylethanamide, CH3CON(C2H5)2· An incomplete description of the mechanism of this reaction is shown in Fig. 9.1. box one Cl H3C-C=O H-N-C2H5 C2H5 reactants box two Cl H3C-C-O H intermediate N-C2H5 C2H5 Fig. 9.1 box three O H3C-C-N-C2H5 C2H5 and products Complete the mechanism in Fig. 9.1. You should include: • all relevant dipoles (δ+ and δ-) and full electric charges (+ and -) on the species in box one and in box two • all relevant lone pairs on the species in box one and in box two • all relevant curly arrows to show the movement of electron pairs in box one and in box two • the formula of the second product in box three.[4]
5. (d)(ii)Name this mechanism.[1]

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