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CAIE A-Level Chemistry 32.2 Phenol

Practise phenol preparation, acid–base reactions, azo coupling and activated-ring nitration or bromination.

Syllabus
2028–2030
Course
Chemistry 9701
Level
A2

Exam points

  • prepare phenol through low-temperature diazotisation of phenylamine followed by warming with water
  • write phenoxide-forming reactions with NaOH or sodium and azo coupling with a diazonium ion in alkali
  • explain easy 2,4,6 substitution through oxygen lone-pair delocalisation and increased ring electron density

Covered syllabus points

32.2.1—Preparation of phenol32.2.2—Reactions of phenol32.2.3—Acidity of phenol32.2.4—Acidities of water, phenol and ethanol32.2.5—Phenol nitration and bromination conditions32.2.6—Phenol directing effects32.2.7—Reactions of phenolic compounds

32.2 Phenol 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

32.2 Phenol 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 ]

32.2 Phenol 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 ]
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