QUESTION BANK

ALCOHOLS, PHENOLS AND ETHERS

Question 1

a) Write a note on following name reactions:

i) Reimer Tiemann reaction
ii) Kolbe’s reaction
iii) Cumene process (industrial method of preparation of phenol) did I teach this in class?
iv) Dow’s process
v) Williamson’s ether synthesis

b) How will you distinguish the following pair of compounds using chemical tests:
i) Ethanol and isopropyl alcohol
ii) Isopropyl alcohol and tertiary butyl alcohol
iii) Ethanol and phenol
iv) Methanol and ethanol
v) Ethanol and acetic acid
vi) Phenol and acetic acid.
vii) Phenol and picric acid
viii) Phenol and benzoic acid.
ix) Isopropyl alcohol and acetone.

Question 2

a) Effect the following conversions:

i) Ethyl chloride to sodium ethoxide
ii) Ethane to ethanol
iii) Methane to methanol
iv) Propene to propan-1-ol
v) Propene to propan-2-ol
vi) Methanol to ethanol
vii) Ethanol to isopropyl alcohol
viii) Isopropyl alcohol to tertiary butyl alcohol
ix) Propan-1-ol to propan-2-ol
x) Propan-2-ol to propan-1-ol
xi) Formaldehyde to methyl chloride
xii) Acetaldehyde to ethene
xiii) Acetone to isopropyl chloride
xiv) Acetic acid to 1,2-dibromoethane
xv) Ethyl acetate to isopropyl alcohol.
xvi) Methyl amine to ethane nitrile
 xvii) Ethyl amine to ethanoic acid
xviii) Ethene to diethyl ether
xix) Acetyl chloride to ethyl acetate
xx) Acetic anhydride to ethyl acetate
xxi) Ethyl amine to acetaldehyde
xxii) Isopropyl chloride to acetone
xxiii) Propene to propanal
xxiv) Propene to acetone
xxv) Aniline to phenol
xxvi) Benzene to phenol
xxvii) Benzene sulphonic acid to phenol
xxviii) Chlorobenzene to o-nitro phenol
xxix) Cumene to picric acid
xxx) Phenol to nitrobenzene
xxxi) Phenol to toluene
xxxii) Aniline to 2,4,6-tribromo phenol
xxxiii) Chlorobenzene to picric acid.
xxxiv) Benzene diazonium chloride to phenyl acetate
xxxv) Benzene diazonium chloride to salicyl aldehyde
xxxvi) Benzene sulphonic acid to salicylic acid
xxxvii) Phenol to benzaldehyde
xxxviii) Phenol to benzoic acid
xxxix) Ethanol to perchloro diethyl ether
xl) Methanol to methyl tert-butyl ether
xli) Benzene to anisole
xlii) Phenol to 4-bromoanisole
xliii) Chlorobenzene to p-methyl anisole
xliv) anisole to benzene
xlv) diethyl ether to acetaldehyde
xlvi) ethanol to dichloro diethyl ether

b) Give balanced chemical equations for the following:

i) Addition of water to propene in the presence of dil.acid
ii) Reaction between formaldehyde with sodium borohydride
iii) Reaction between acetaldehyde and lithium aluminium hydride
iv) Reaction between acetic acid and lithium aluminium hydride
v) Reaction between acetone with hydrogen in the presence of platinum.
vi) Reaction between ethylamine with nitrous acid.
vii) Reaction between ethanol and sodium metal
viii) Reaction between ethanol and phosphorous trichloride
ix) Reaction between ethanol and phosphorous pentachloride
 x) Reaction between ethanol and thionyl chloride
xi) Reaction between ethanol and acetyl chloride
xii) Reaction between ethanol and acetic anhydride
xiii) Reaction of ethanol with acidified potassium permanganate
xiv) Reaction of methanol with acidified potassium dichromate
xv) Reaction of ethanol with acidified potassium dichromate in controlled conditions
xvi) Reaction of isopropyl alcohol with conc.nitric acid
xvii) Reaction of isopropyl alcohol with pyrdinium chloro chromate
xviii) Reaction of ethanol with chromium oxide.
xix) Reaction of ethanol with conc. sulphuric acid at 443 K
xx) Reaction of ethanol with conc.sulphuric acid at 413 K.
xxi) Reaction of phenol with zinc
xxii) Reaction of phenol with sodium
xxiii) Reaction of phenol with chloroform and potassium hydroxide
xxiv) Reaction of sodium phenoxide and CO2 at 403K and 7 atm.
xxv) Reaction of phenol with nitration mixture
xxvi) Reaction of phenol with dil.nitric acid
xxvii) Reaction of phenol with bromine water
xxviii) Reaction of phenol with bromine in CS2
xxix) Reaction between ethyl chloride and sodium ethoxide
xxx) Reaction between tertiary butyl chloride and sodium methoxide
xxxi) Reaction between methyl chloride and sodium tertiary butoxide
xxxii) Reaction of diethyl ether with chlorine gas in dark.
xxxiii) Reaction of diethyl ether with chlorine gas in sunlight
xxxiv) Reaction of ethyl methyl ether with little HI (cold.dil.HI)
xxxv) Reaction of diethyl ether with excess HI (conc HI)
xxxvi) Reaction of methyl ter-butyl ether with little HI (cold.dil.HI)
xxxvii) Reaction of diethyl ether in the presence of atmospheric oxygen
xxxviii) Reaction of diethyl ether with phosphorous pentachloride
xxxix) Reaction of anisole with methyl chloride in the presence of anhydrous.AlCl 3
xl) Reaction of anisole with acetyl chloride in the presence of Anhydrous.AlCl 3
xli) Reaction between sodium phenoxide and methyl chloride.

Question 3

a) Give reasons for the following:

i) Alcohols are having higher boiling point compared to ethers having similar molecular
weight.
ii) Lower members of aliphatic alcohols are soluble in water.
iii) Phenol is acidic in nature.
 iv) Phenol is less acidic compared to acetic acid.
v) Only methyl halide or primary alkyl halide must be used in Williamson’s ether synthesis.
vi) Reaction between methyl tert-butyl ether with little HI gives tert-butyl iodide and
methanol as product. Whereas usually the iodide part will be added to smaller alkyl
group.
vii) Ethers should not be evaporated to dryness.
viii) On nitration of phenol using dil.nitric acid, two isomers are formed as products. How will
you separate the ortho and the para isomers of nitrophenol.

b) Arrange the following as directed.

i) Water, ethanol, phenol, acetic acid ( in the decreasing order of acid strength)
ii) Phenol, p-nitrophenol , p-methylphenol (increasing order of acid strength)
iii) Ethanol, isopropyl alcohol, tet-butyl alcohol (decreasing order of acid strength)
iv) Pentan-1-ol, butan-1-ol, butan-2-ol, ethanol, propan-1-ol, methanol ( increasing order of
boiling point)
v) Ethoxy ethane, n-butane, pentanal, pentan-1-ol ( increasing order of boiling point)

c) State the characteristics test for phenols.

d) Write a note on Luca’s test.