Section 1.1 Section 1.2 Section 1.3 - The Student Room

SECTION 14
Section 13.10
1 a
+
–
NH 3 HSO 4
b
+
–
N N HSO 4
c
N N OH
(strictly the sodium salt)
2 a
HO
+
N N Cl –
b
i
+
HO N N Cl – + OH HO N N OH + HCl
ii
HO
+
HO N N Cl – + HO N N
+ HCl
HO
iii
+
HO N N Cl – + NH 2 HO N N NH 2 + HCl
3
HOO 2 S
+
N N X –
and
N
CH 3
CH 3
O 2 N
+
N N X –
and
OH
NH 2
and
X – N
+ N
N + N X –
4 The diazonium salt is a relatively weak electrophile and will only
react with particularly electron-rich activated benzene rings.
SO 2 OH
204
Section 14.1
1 a 73.9%
b 73.1%
2 Route I (Route I 40%; Route II 30%)
3 16.2 g
4 a (Selection of starting materials); reaction; extraction of
product from reaction mixture; purification of product.
Section 14.2
1 a A solution of hydrogen bromide (HBr) in a polar
solvent at room temperature.
b Reflux with dilute aqueous sodium hydroxide solution
b A small amount of product is never recovered from the
reaction mixture. This is due to factors such as wetting
of the walls of the reaction vessel, incomplete
crystallisation of the product, loss on filter papers, loss
by evaporation, etc.
c Reflux with an acidified solution of potassium
dichromate(VI)
d Treat with hydrogen cyanide solution with a small
amount of alkali.