Deduce the following information from the structure of estradiol, a phenol contain compound.
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1 A2 Chemistry: F324 Rings, Polymers and Analysis The Chemistry of Phenol Learning Outcomes: All (E) State the uses of phenols Most (C) Describe the reactions of phenol with aqueous alkalis and with sodium Describe the observation and write a balanced equation for the bromination of phenol Some (A) Explain the relative ease of bromination of phenol compared with benzene Further reading: Activity 1: Molecular Formula. Deduce the following information from the structure of estradiol, a phenol contain compound. 1. Molecular formula = 2. Empirical Formula= 3. Molecular Mass = 4. Name the different functional groups present in estradiol and circle them on the structure. Estradiol Bromination of Phenol. Phenol undergoes halogenation more readily than benzene as phenol has a greater electron density than benzene. One of the lone pairs of electrons on the oxygen of the OH overlaps with the delocalised ring system within the benzene ring. There is now 8 electrons distributed over 7 atoms causing a higher electron density, which causes greater polarisation of a halogen molecule (e.g. Br 2) therefore a greater attraction for the electrophile. The increase in the electron density of phenols extended ring, increases its reactivity towards electrophiles compared to benzene. One lone pair of electrons of the oxygen p-orbital becomes drawn into the delocalised ring of
2 The electron density is greatest at positions 2,4, and 6 so substitution takes place at these locations. Activity 2: Reactions of Phenol to Form Salts. a. Reactions with sodium hydroxide Phenol is a weak acid so can be neutralised with aqueous sodium hydroxide. The product formed is called sodium phenoxide. C 6H 5OH + NaOH C 6H 5O - Na + + H 2O b. Reactions with sodium. When sodium reacts with metals such as sodium hydrogen gas is produced so effervescence is visible. 2C 6H 5OH + 2Na 2C 6H 5O - Na + + H 2
3 Halogenation of Phenol Give the reaction for bromine water reacting with aqueous phenol. Complete the sentence below: When bromine water (aqueous bromine) is added to an aqueous solution of phenol the bromine water turns, indicating the presence of. Phenol Comprehension. Phenol is described as an aromatic alcohol; a benzene ring attached to an alcohol (-OH) group. Examples of compounds that contain a phenol group are: Paracetamol 2,4,6-trichlorophenol (TCP) 4-chloro-3,5-dimethylphenol (Dettol) At room temperature phenol is a white crystalline solid, frequently phenol is quoted as being a pink, in this case phenol has been delocalised due to impurities and moisture. Phenol is used in the production of plastics, for antiseptics, disinfectants, resins for paints, and the preparation of pharmaceutical drugs such as aspirin. Phenol is a weak acid (stronger than aliphatic alcohols), in water phenol is moderately soluble in water as it has the ability to form hydrogen bonds with water. C 6H 5OH + (aq) C 6H 5O - + H +
4 Questions: 1. Explain why benzene is less reactive than phenol towards chlorine. 2. Name and draw the structure of the product formed when phenol reacts with bromine. 3. State three uses for phenol or compounds containing phenol. 4. What would you observe if bromine was added to: a. Benzene?... b. Cyclohexene?... c. Phenol? Write an equation for the reaction of phenol with lithium hydroxide. 6. Explain the observations that would be seen if aqueous phenol was added to potassium. Write an equation for this reaction...
5 Past Exam Question. The diagram below shows some reactions of phenol. On the diagram identify the reagents that could be used to carry out reactions, I, II and III. (June 2009, 3 marks). State a use for the compound formed in reaction IV. (1 mark) Feedback: Activity 6: Tell me two things. that you have done well today that you know now that you didn t know at the start of the lesson
6 that you could have done better next lesson that you would like to know more about Notes.
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