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Cape Chemistry Unit 2: Module 1: The Chemistry of Carbon Compounds

This document discusses phenol and its reactions. Phenol is weakly acidic and can lose an H+ ion from its hydroxyl group. It reacts with alkalis to form a soluble sodium phenoxide salt. Phenol also reacts vigorously with sodium metal, producing hydrogen gas and sodium phenoxide. When reacted with acyl chlorides like ethanoyl chloride, phenol forms esters and releases hydrogen chloride gas. Bromine water readily reacts with phenol, decolorizing the orange solution and forming a white precipitate of 2,4,6-tribromophenol. Diazotization involves the reaction of phenylamine with nitrous acid below 10°C to form diazonium

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Malik Muhammad
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227 views

Cape Chemistry Unit 2: Module 1: The Chemistry of Carbon Compounds

This document discusses phenol and its reactions. Phenol is weakly acidic and can lose an H+ ion from its hydroxyl group. It reacts with alkalis to form a soluble sodium phenoxide salt. Phenol also reacts vigorously with sodium metal, producing hydrogen gas and sodium phenoxide. When reacted with acyl chlorides like ethanoyl chloride, phenol forms esters and releases hydrogen chloride gas. Bromine water readily reacts with phenol, decolorizing the orange solution and forming a white precipitate of 2,4,6-tribromophenol. Diazotization involves the reaction of phenylamine with nitrous acid below 10°C to form diazonium

Uploaded by

Malik Muhammad
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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CAPE CHEMISTRY UNIT 2: MODULE

THE CHEMISTRY OF CARBON


COMPOUNDS
SECTION 2

FUNCTIONAL GROUP ANALYSIS


REACTIONS & MECHANISMS
PHENOL AND DYES
PHENOLS
Ø Phenol, C6H5OH, is a crystalline solid that melts a
43 °C.

Ø It is used to manufacture a wide range of product

Ø Its structure is:


PHENOLS
Ø Phenol is weakly acidic, losing an H+ ion from its
group:
PHENOLS
Ø Phenol is weakly acidic, losing an H+ ion from its
group:

Ø However, phenol is still a stronger acid than wate


alcohol.
PHENOLS
Ø Phenol is weakly acidic, losing an H+ ion from its
group:

Ø However, phenol is still a stronger acid than wate


alcohol.
REACTIONS OF PHENOLS
REACTION WITH ALKALIS

Ø Although phenol is only slightly soluble in water,


dissolves well in an alkaline solution.
Ø As you have just learnt, phenol is a weak acid so i
react with an alkali to give a salt plus water:

Ø The salt formed, sodium phenoxide, is solu


water.
REACTIONS OF PHENOLS
REACTION WITH SODIUM

Ø Phenol also reacts vigorously with sodium metal,


off hydrogen gas and again forming sodium phenox
REACTIONS OF PHENOLS
REACTION WITH ACYL HALIDES

Ø Phenol reacts with ethanoyl chloride at room


temperature, although the reaction isn't as fast a
one between ethanoyl chloride and an alcohol.

Ø Phenyl ethanoate is formed together with hydrog


chloride gas.
REACTIONS OF PHENOLS
REACTION WITH ACYL HALIDES

CH3COCl + C6H5OH à CH3COOC6H5 + HC

Ethanoyl chloride phenol phenyl ethanoate hydroge


REACTIONS OF PHENOLS
REACTION WITH BROMINE (SUBSTITUTION)

Ø Compared with benzene, phenol reacts more rea


with electrophiles.

Ø It ‘activates’ the benzene ring, especially at positio


and 6
REACTIONS OF PHENOLS
REACTION WITH BROMINE (SUBSTITUTION)

Ø Bromine water reacts readily with phenol, decolo


the orange solution and forming a white precipita
2,4,6-tribromophenol

Ø No halogen carrier needed (like in benzene)


DIAZOTISATION AND COUPLING
DIAZOTISATION

Ø Reaction between phenylamine and nitrous acid

Ø Particularly its reaction at temperatures of less th


to produce diazonium salts.
DIAZOTISATION AND COUPLING
COUPLING REACTION

Ø Benzene diazonium chloride reacts with an alkalin


solution of phenol to form an orange dye (4-
hydroxyphenylazobenzene)

Ø Temperature kept below 10oC to prevent decomp


of the diazonium salt
DIAZOTISATION AND COUPLING
COUPLING REACTION

Ø The positive charge on the diazonium ion acts an


electrophile and substitutes into the 4-position of
of the phenol

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