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Alcohols and Phenols

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                                              Date Performed: February 24, 2017

Group 2                                                                

Experiment No. 12

Alcohols and Phenols

OBJECTIVES:

  1. To differentiate alcohols from phenols

PROCEDURE:

A.                

   Ethyl alcohol                        Isopropyl alcohol                        Tertiary butyl alcohol[pic 1][pic 2][pic 3][pic 4][pic 5]

Equal amounts of conc. HCl[pic 6]

Shake & let stand[pic 7]

Observe

B.                        

   Ethyl alcohol                        Isopropyl alcohol                        Tertiary butyl alcohol[pic 8][pic 9][pic 10]

[pic 11][pic 12]

5 drops K2Cr2O7& dilute H2SO4[pic 13]

Warm[pic 14]

Note odor & color[pic 15]

Compare

C.

Heat copper spiral[pic 16]

Plunge to small beaker w/ ½ ml methyl alcohol & 5ml water[pic 17]

Repeat 5 times[pic 18]

+ 0.5%resorcinol sol’n[pic 19]

Incline TT, ½ ml conc. H2SO4[pic 20]

Acid will form layer at bottom[pic 21]

Note color at the junction of the 2 layers

D                                                                

                    Phenol                                                        salicylic acid        [pic 22][pic 23][pic 24][pic 25]

+2ml 10% KOH w/ crushed iced[pic 26]

    + gradually ½ ml acetic anhydride[pic 27]

   Shake few min.[pic 28]

Compare

E.

Phenol                                                                 Pentamethyl phenol[pic 29][pic 30]

[pic 31][pic 32]

                                         +1ml water & drop of ferric chloride[pic 33]

                                                                     Note color development

E.

phthalic anhydride + phenol[pic 34]

+ 2 dops conc. H2SO4[pic 35]

Heat gently[pic 36]

Until melt becomes dark red[pic 37]

   Cool[pic 38]

+5ml water[pic 39]

+2 drops [pic 40]

[pic 41][pic 42][pic 43][pic 44]

2ml HCl                                                2ml diluted NaOH[pic 45][pic 46]

[pic 47][pic 48]

Observe

DATA AND RESULTS:

Table1.

Solute

Treatment

Observation

Ethyl alcohol

Concentrated HCl

Slow formation of HCl surface layer

Isopropyl alcohol

Rapid formation of HCl surface layer

Tertiary butyl alcohol

Moderate formation of HCl surface layer

Ethyl alcohol

5 drops K2Cr2O7& dilute H2SO4

Warm

Dark orange, strong odor

Isopropyl alcohol

Pale orange, no odor

Tertiary butyl alcohol

Orange, lighter odor

Methyl alcohol and water

∆copper wire

0.5% resorcinol sol’n

Conc. H2SO4

In the bottom of the beaker there was a white like kerosene and it change in color which turned to lighter yellow or pale yellow an there was a black residue in the beaker.

Test tube 1 (phenol)

Test tube 2 (salicylic acid)

10% KOH

Crushed ice

Acetic anhydride

In TT1 there was a formation of white precipitate while in TT2 pale pink precipitate was formed.

Test tube 1 (phenol)

Test tube 2 (pentamethyl phenol)

Water

Ferric chloride

Phenol changed its color to purple while pentamethyl phenol was color green and formed a pink precipitate, also  two layers in the solution was formed.

Phthalic anhydride and phenols

Conc. sulphuric acid

∆ gently (low flame)

Cool

Water

As HCl was added the solution is still colorless, but when NaOH was added the solution change in color which is dark pink.

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