Phenol
Cambridge A-Level Chemistry (9701) · Unit 32: Carbonyl compounds (A Level) · 10 flashcards
Phenol is topic 32.2 in the Cambridge A-Level Chemistry (9701) syllabus , positioned in Unit 32 — Carbonyl compounds (A Level) , alongside Alcohols.
Marked as A2 Level: examined at A Level in Paper 4 (A Level Structured Questions) and Paper 5 (Planning, Analysis and Evaluation). It is not tested on the AS-only papers (Papers 1, 2 and 3).
The deck below contains 10 flashcards — 10 key concepts — covering the precise wording mark schemes reward.
What the Cambridge 9701 syllabus says
Official 2025-2027 spec · A2 LevelThese are the exact learning outcomes Cambridge sets for this topic. The candidate is expected to be able to do each of these on the relevant paper.
- recall the reactions (reagents and conditions) by which phenol can be produced: (a) reaction of phenylamine with HNO₂ or NaNO₂ and dilute acid below 10 °C to produce the diazonium salt; further warming of the diazonium salt with H₂O to give phenol
- recall the chemistry of phenol, as exemplified by the following reactions: (a) with bases, for example NaOH(aq) to produce sodium phenoxide (b) with Na(s) to produce sodium phenoxide and H2(g) (c) in NaOH(aq) with diazonium salts, to give azo compounds (d) nitration of the aromatic ring with dilute HNO₃(aq) at room temperature to give a mixture of 2-nitrophenol and 4-nitrophenol (e) bromination of the aromatic ring with Br₂(aq) to form 2,4,6-tribromophenol
- explain the acidity of phenol
- describe and explain the relative acidities of water, phenol and ethanol
- explain why the reagents and conditions for the nitration and bromination of phenol are different from those for benzene
- recall that the hydroxyl group of a phenol directs to the 2-, 4- and 6-positions
- apply knowledge of the reactions of phenol to those of other phenolic compounds, e.g. naphthol
Cambridge syllabus keywords to use in your answers
These are the official Cambridge 9701 terms tagged to this section. Mark schemes credit responses that use the exact term — weave them into your answers verbatim rather than paraphrasing.
Tips to avoid common mistakes in Phenol
- › Construct balanced half-equations to determine electron transfer; remember one mole of dichromate(VI) ions gains six moles of electrons.
- › Always check for chiral centers in isomerism questions; for instance, 2-methylbutanal has two optical isomers.
- › Ensure the molecule contains the -CH(OH)CH3 or -COCH3 group at both ends to produce a dicarboxylic acid via the iodoform reaction.
Outline the reagents and conditions required to produce phenol from phenylamine.
First, react phenylamine with HNO₂ or NaNO₂ and dilute acid below 10 °C to form a diazonium salt. Then, warm the diazonium salt with H₂O to produce phenol.
Describe the reaction of phenol with NaOH(aq), including the product.
Phenol reacts with NaOH(aq) to produce sodium phenoxide. This demonstrates phenol's acidic character as it donates a proton to the base.
What products are formed when phenol reacts with Na(s)?
Phenol reacts with sodium metal (Na(s)) to form sodium phenoxide and hydrogen gas (H₂).
Outline the reagents and conditions for the reaction of phenol with diazonium salts in NaOH(aq). What type of product is formed?
Phenol reacts with diazonium salts in NaOH(aq) to give azo compounds. These reactions are important in the synthesis of dyes.
Describe the nitration of phenol, including reagents, conditions, and the products formed.
Phenol reacts with dilute HNO₃(aq) at room temperature to undergo nitration. This produces a mixture of 2-nitrophenol and 4-nitrophenol.
Describe the bromination of phenol, including reagents, conditions, and the product formed.
Phenol reacts rapidly with Br₂(aq) to form 2,4,6-tribromophenol. No halogen carrier is required, unlike the bromination of benzene.
Explain why phenol is more acidic than both water and ethanol.
Phenol's conjugate base, the phenoxide ion, is stabilized by delocalization of the negative charge into the benzene ring. This stabilization makes phenol more willing to donate a proton, increasing its acidity compared to water and ethanol, where the negative charge on the conjugate base cannot be delocalized to the same extent.
Explain why the nitration and bromination of phenol occur under milder conditions than the nitration and bromination of benzene.
The lone pair of electrons on the oxygen of the phenol's -OH group is partially delocalized into the benzene ring. This increases the electron density of the ring, making it more susceptible to electrophilic attack, and thus requiring milder reaction conditions compared to benzene.
Describe the directing effect of the hydroxyl group in phenol.
The hydroxyl group (-OH) in phenol is an activating and 2,4-directing group. This means that electrophilic substitution reactions, like nitration and bromination, will preferentially occur at the 2-, 4-, and 6-positions of the benzene ring.
Apply your knowledge of phenol reactions to predict the products of the reaction of 1-naphthol with aqueous bromine.
Similar to phenol, 1-naphthol will react rapidly with aqueous bromine. Expect to see substitution at the positions ortho and para to the hydroxyl group on the naphthalene ring, likely resulting in a polybrominated product analogous to 2,4,6-tribromophenol.
More Chemistry flashcards
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All Chemistry FlashcardsMore topics in Unit 32 — Carbonyl compounds (A Level)
Phenol sits alongside these A-Level Chemistry decks in the same syllabus unit. Each uses the same spaced-repetition system, so progress in one informs the next.
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