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CAIE A-Level Chemistry 32.2.6 Directing Effect of the Hydroxyl Group

Practise using the phenolic OH group’s 2,4,6-directing effect to predict major substitution products.

Syllabus
2028–2030
Course
Chemistry 9701
Level
A2

Exam points

  • treat the phenolic hydroxyl group as directing incoming electrophiles to the 2-, 4- and 6-positions
  • draw 2-nitrophenol and 4-nitrophenol as the major mononitration products of phenol
  • retain existing substituents and choose only available activated positions in a substituted phenolic ring

32.2.6—Phenol directing effects question 1

[Maximum number: 2]

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

cumene

cumene

Fig. 5.4 shows two reactions of phenol.

Fig. 5.4

Fig. 5.4

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 32.2.6—Phenol directing effects question 1 — CAIE A-Level Chemistry A2

explanation

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