F324 Amines HW (MS)
1.	(a)	(i)	Diamino
two/2 amine groups (1)
	1,4
their position on the ring / numbering of carbons
around ring (or shown on a diagram) (1)	2
 (b)	(i)	reduction / redox (1)	1
(ii)	tin and HCl (1)
conc acid under reflux (1)	2
or H2 gas + Ni/Pd catalyst
(iii)

H2O as product (1)
and the equation balanced (1)	2
 (c)	(i)	accepts H+ using the lone pair (on N) (1)
which is donated/forms a (dative) covalent bond (1)	2
either mark can be obtained with a good diagram
(ii)

correct structure with charges shown (1)(1)
one mark for either:	just one neutralised,
	both neutralised, but without Cl–,
	both neutralised, but no charges shown	2
(iii)	hexane-1,6-diamine is a stronger base because:
	electrons move towards the N (due to the inductive effect)
(in hexane-1,6-diamine) (1)
	the lone pair from N is (partially) delocalised around the ring
(in diaminobenzene) (1)
	so the electron pair is more easily donated /
H+ more easily accepted (in hexane-1,6 diamine) ora (1)	3
[14]

2.	(a)	(i)

	H2O as product (1) balancing (1)	2
(ii)	reducing agent (1)	1
 (b)

(or as the ionic equation without Na+ or Cl–)
	C6H5NH2 (1) balanced (1)	2

(c)	moles C6H5NO2 used = 0.0300 (mol) (1)
	theoretical yield of C6H5NH2 = 2.79(3) (g) (1) or ecf
	actual 72.1% yield = 2.014 (g) / (calculator value 2.013753) (1) or ecf
	to three sig figs = 2.01 (g) (1) or ecf	4
[9]

 3.	(i)

		3
(ii)	dye / colouring / indicator (1)	1
(iii)	phenylamine (1)
NaNO2 / HNO2 (1) + HCl (1)
< 10°C (1)
add to alkaline phenol (1)	5
[9]

 4.	sodium nitrite + HCl / nitrous acid (1)
	<10°C (1)
	 (1)
	phenol/named example (added to the products from above) AW (1)
alkaline conditions / OH– (1)
	example of an azo dye that could be formed from phenylamine,
eg  (1)	6
[6]

5.	(i)	nitrous acid / HNO2	1
(ii)
 (1)	1
(iii)	diazonium (ion /salt) (1)	1
(iv)	to prevent decomposition / it reacting (diazonium ion) is unstable AW	1
(v)	structure showing the amine coupled to the phenol or its salt – e.g.

–N=N– (1) rest of structure (joined by two nitrogens) (1)	2
[6]

6.	(a)	1st stage
aromatic amine / named aromatic amine / structure (1)
sodium nitrite / nitrous acid (1)
HCl/H2SO4 (but not conc) /H+ (1)
at <10°C (1)
	which forms a diazonium salt / ion (1)
if more than four are given, mark any wrong reagents, conditions first
	2nd stage
the product from the first stage mixed with the phenol AW (1)
(in excess) hydroxide / alkali (1)	7
allow correct formulae for the reagents
(b)	(i)
 (1)	1
allow any benzene rings as well as N=N circled, as long as no other groups are
(ii)	…16… carbon and ……10….. hydrogen atoms
	(1)	(1)	2
 (c)	Na / NaOH / OH– etc (1)	1

(d)

	(1)	(1)	2
allow 1 mark if they are both correct, but in the wrong boxes
only penalise a slip with SO3– Na+ once
[13]

 7.	(i)	CH3CH2CH2NH2 (1)	1
(ii)

diazo link (1); rest of structure (1)	2
[3]