c



  
  
 
Ethanol is two-thirds alkyl chain and one-third water itself, so it is close enough to be
completely soluble at any ratio with water by forming hydrogen bond with water
molecule. However, phenol is only around one-seventh "water" with the rest of it
trapped in a carbon ring. This prevents water being able to bond at all with most of the
molecule, and is thus only slightly soluble.

Phenol is more soluble in NaOH than in water is because phenol is slightly acidic.
The Ka for phenol in water is 1e-10 which is not very strong. But by mixing with
NaOH, it causes the phenol to release the H+ to form sodium phenoxide. The one
negative charge on this compound can move to different locations in the phenol to
form different resonances and create very stable compound. Furthermore, the reaction
between NaOH and phenol is exothermic, and the equilibrium lies far to the right
making the sodium phenoxide extra stable. 

   

Alcohols and phenol contain an -OH group attached to a hydrocarbon which is a very
weak acid. A hydrogen ion can break away from the -OH group and transfer to a base
to form a Hydronium ion (H30).

The phenol molecule has weak tendencies to lose the H+ ion to from the hydroxyl
group, resulting in the highly water-soluble phenolate anion C6H5 Oí, called
phenoxide anion. Compared to aliphatic alcohols, phenol shows much higher acidity.
The increased acidity of phenol over alcohols is cause by the resonance
stabilization of the phenoxide anion by the aromatic ring, the negative charge on
oxygen is shared by the ortho and para carbon atoms.

  

Phenol reacts with sodium hydroxide solution to give a colourless solution containing
sodium phenoxide.
]n this reaction, the hydrogen ion has been removed by the strongly basic hydroxide
ion in the sodium hydroxide solution. Therefore the test did not give a positive result
but changed to colourless.

 


Acids react with the more reactive metals to give out hydrogen gas. The reaction of
phenol with sodium is a slower reaction because phenol is a weak acid.

Metallic sodium is added to phenol and then form in a water bath to speed up the
reaction. The gases gives a pop sound when tested with burning splinter indicate the
gas is hydrogen gas.


  
 


Alcohol is reacted with carboxylic acids to produce esterbut it doesn't work with
phenols. Phenol is a compounds where the -OH group is attached directly to a
benzene ring, therefore Phenols react with carboxylic acids so slowly that the reaction
is unusable for preparation purposes.

Esters are produced when carboxylic acids are heated with alcohols in the presence of
an acid catalyst (concentrated sulphuric acid.). The esterification reaction is slow and
reversible. The equation for the reaction between an acid RCOOH and an alcohol
R'OH (where R and R' can be the same or different) is:

So, for example, if you were making ethyl ethanoate from ethanoic acid and ethanol,
the equation would be:

c
 
 

]f bromine water is added to a solution of phenol in water, the bromine water is

decolourised and a white precipitate is formed which smells of antiseptic.
The precipitate is 2,4,6-tribromophenol.

Phenol is more reactive due to the presence of an electron donating hydroxyl group
and reacts with bromine by a substitution reaction forming hydrogen bromide
gas. The reaction between phenol and bromine is the reaction of an activated benzene
ring - which is highly unsaturated - and the bromine reacts by electrophilic
substitution. Ethanol is saturated, and never reacts by electrophilic substitution.

ë 

During Triiodomethane reaction ethanol will give a positive result which form yellow
precipitate but phenol will give a negative result which is the brown colour
decolourises. The colour of ethanol remain unchanged when reaction with halogen
indicate that no chemical reaction occur but phenol decolourises when react with
halogen. These two tests can be used to distinguish between ethanol and phenol.