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Phenol Understand the reaction of phenol with bromine water

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Presentation on theme: "Phenol Understand the reaction of phenol with bromine water"— Presentation transcript:

1 Phenol Understand the reaction of phenol with bromine water
Understand reasons for the relative ease of bromination of phenol compared with benzene

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4 What reagents and conditions are required for the bromination of benzene?
Catalyst (Halogen carrier) Heated Under reflux

5 Room Temperature Bromine Water
What reagents and conditions are required for the bromination of phenol? Room Temperature Bromine Water

6 What is the obvious difference about the bromination of benzene and the bromination of phenol?

7 Discuss the following question….
Why do you think the reaction between phenol and bromine happens more readily than with benzene?

8 Reasons why… Oxygen in the OH group has lone pairs of electrons  these e- can merge with the electrons in the delocalised pi (P) bond Electron density above and below the ring of atoms is increased  referred to as ‘activation’ because the molecule is now much more reactive towards electrophiles Bromine molecules, although usually non-polar, are polarised as they approach the benzene ring. Eventually, the Br-Br bond breaks and the Br+ electrophile attacks the benzene ring.

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10 What is this compound?

11 Phenolphthaelin

12 Phenolphthaelin Colourless Pink

13 Questions Suggest why phenol is a solid at room temperature and is slightly soluble in water Write an equation for the formation of TCP from phenol

14 Answers Due to permanent dipole-dipole attractions due to the electronegativity of the oxygen - but is mainly due to hydrogen bonding. Hydrogen bonds can form between a lone pair on an oxygen on one molecule and the hydrogen on the -OH group of one of its neighbours. Phenol is moderately soluble in water - about 8 g of phenol will dissolve in 100 g of water. If you try to dissolve more than this, you get two layers of liquid. The top layer is a solution of phenol in water, and the bottom one a solution of water in phenol. The solubility behaviour of phenol and water is complicated, and beyond UK A level. Phenol is somewhat soluble in water because of its ability to form hydrogen bonds with the water. C6H5OH + 3Cl2  C6H2Cl3OH + 3HCl

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