Chemical properties of Ethanol & Phenol

Precaution
           1.> The filter paper, which have been soaked with paraffin oil on sodium metal, should be thrown properly since the unreacted sodium remains on
                  the paper may cause a fire.
           2.> Ensure that all sodium is reacted in test-tube before disposing the liquid.
           3.> Avoid adding too large sodium to ethanol or phenol since the reaction may be to vigorous.
           4.> Avoid contact with the crystal of phenol. If you contact with it accidentally, wash your hands with glycerol  or plenty of water, or your hands
                 may have white strain due to phenol's corrosive property.

Discussion
           1.> The smell of phenol is close to that in hospital.
           2.> Both pH test (acidic in phenol, neutral in ethanol), iodoform test (+ve in ethanol), solubility test (miscible between ethanol & water), reaction with
                 NaHCO3 (phenol is insoluble), reaction with Br2 water (phenol decolourize Br2) and reaction with neutral FeCl3 (Fe3+ and phenol forms a
                 violet complex) can distinguish between ethanol & phenol.
           3.> Phenol is much more soluble in NaOH than in water because the reaction between phenol and water to form H3O+ & phenoxide is reversible
                 (since phenol is a weak acid, most H+ formed will combine with phenoxide to form phenol again) whereas that between phenol and NaOH is not
                 and the formation of phenoxide ion is promoted:
                       
                      
                 Na+ & phenoxide ions are then dispersed by water molecules, thus phenol is highly soluble in NaOH.
           4.> Compare their reactions with Na, H2 evolves faster in phenol than in ethanol due to the acidic nature of phenol. The acidity of an acid is depends
                 on the relative stabilities of the acid (HA) & its conjugate base (A-). The more stable the conjugate base A-, the stronger is the acid. In case of
                 phenol, the phenoxide ion is stabilized by delocalization of p-electrons (the charge on O is more disperse & lower its charge density):
                        
                 The equilibrium of  shifts to right and thus phenol is acidic.
                 However, in case of ethanol, alkyl group is electron-donating group, which makes ethoxide ion unstable (C2H5→O-), thus it's neutral.
           5.> In the reaction with NaOH, the further addition of conc. HCl makes phenol becomes insoluble again which shows that phenol is a weaker acid
                 than mineral acids.
           6.> Phenol has an electron-rich centre (benzene ring) to attract electrophiles to attack and electron-donating hydroxyl group further increase its
                 nucleopilicity. This makes phenol has a much higher reactivity than benzene and react with Br2 readily even in the absence of catalyst & light.
                 On the other hand, ethanol is saturated and has no electron-rich centre, thus no reaction between ethanol and Br2.
           7.> Some of the reactions in this experiment is useful and is usually used for daily life. For example,
                 (a) Iodoform reaction is used to prepare a compound that is one carbon less than previous one and iodoform itself can be used as pesticide.
                 (b) Phenol and it's derivatives can be used as antiseptics so it's quite common to smell their smell in hospital.
                 (c) Esterification can be used to synthesize esters in perfumes.
                 (d) Phenol can be purified by adding NaOH to phenol and organic compound mixtures, sodium phenoxide can then be crystallized and
                       separated, phenol is regenerated by adding H+.
                 (e) FeCl3, Br2 and NaOH are used to test the presence of phenol if all these three tests show positive result.

Conclusion
           Both ethanol and phenol are widely used compounds, especially in disinfectant. To distinguish them, several tests are needed, since other compounds may also be positive on these tests. If all of these test shows positive result, then the uncertain organic compound may be either one of them.