CAIE A-Level Chemistry A2 32 Hydroxy Compounds Questions

Practise alcohol acylation and phenol preparation, acidity, substitution reactions and ring activation, selecting reagents and explaining how hydroxy groups affect aromatic behaviour.

Syllabus
2028–2030
Course
Chemistry 9701
Level
A2

Question 1

[Maximum number: 2]

Compound T,C5H9O2Cl\mathbf{T}, \mathrm{C}_{5} \mathrm{H}_{9} \mathrm{O}_{2} \mathrm{Cl}, is a useful synthetic intermediate.

Fig. 8.1 shows some reactions of T.

Fig. 8.1

Fig. 8.1

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

Question 2

[Maximum number: 5]

Question (a)

(a)

State and explain the relative acidities of ethanol and phenol.

[ 2 ]

Question (b)

(b)

In the table below, give the reaction conditions for the formation of organic products D and E and draw their structures.

Figure for Question (b) — CAIE A-Level Chemistry A2
Table for Question (b) — CAIE A-Level Chemistry A2
[ 3 ]

Question 3

[Maximum number: 6]

Compounds F and J are shown in Fig. 4.1.

Fig. 4.1

Fig. 4.1

Question (a)

(a)

K can also be synthesised from phenol, C6H5OH\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}.

Fig. 4.4 shows several reactions of phenol.

Fig. 4.4

Fig. 4.4

[ 3 ]

Question (i)

(i)

Write an equation for the formation of M in reaction 1 .

[ 1 ]

Question (ii)

(ii)

Explain why phenol is a weaker acid than K.

[ 2 ]

Question (b)

(b)

Phenol and benzene both react with nitric acid, as shown in Fig. 4.5.

Fig. 4.5

Fig. 4.5

Explain why the reagents and conditions for these two reactions are different.

[ 3 ]

Question 4

[Maximum number: 7]

Cumene is an aromatic hydrocarbon used in the synthesis of other useful chemicals.

cumene

cumene

Question (a)

(a)

Fig. 5.4 shows two reactions of phenol.

Fig. 5.4

Fig. 5.4

[ 7 ]

Question (i)

(i)

State the conditions for the bromination of phenol in reaction 2 .

Explain why these conditions are different from those for the bromination of benzene. conditions
explanation

[ 4 ]

Question (ii)

(ii)

Draw the structure of organic compound Q in Fig. 5.4.

[ 1 ]

Question (iii)

(iii)

The reaction of phenol with HNO3\mathrm{HNO}_{3} produces a mixture of isomers with molecular formula C6H5NO3\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NO}_{3}.

Identify the two isomers that are produced in the largest quantities.
Explain your answer.
isomer 1

Figure for Question (iii) — CAIE A-Level Chemistry A2

explanation

[ 2 ]
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