Tutorial 1

1) Write equations to show the production of ethanol by

i)
fermentation of glucose
C6H12O6 2C2H5OH + 2CO2
35 55 oC, yeast, no oxygen
ii)
hydration of ethane
C2H4 + H2O C2H5OH
300 oC, 60 atm, conc. H3PO4
Give the conditions needed for each process and state the relative advantages and disadvantages of
each process.

Advantages of fermentation:
sugar cane is a renewable resource (ethene is non-renewable)
it is a low technology process (hydration is a high-technology process)
Advantages of hydration:
it is a continuous process (fermentation is a batch process)
it makes ethanol quickly (fermentation is slow)
it makes pure ethanol (fermentation does not make pure ethanol)
2) Identify the organic product or products formed by the dehydration of
a) ethanol
ethane
b) butan-1-ol

but-1-ene
c) butan-2-ol

but-1-ene and but-2-ene

d) dimethylpropan-1-ol

none (cannot be dehydrated)

3) Give the names and structures of all eight alcohols with the formula C 5H12O. State in each
case whether they are primary, secondary or tertiary alcohols.

a) Identify the three isomers which can give two different alkenes when dehydrated and identify the
possible alkene products in each case.
pentan-2-ol can give pent-1-ene and pent-2-ene
2-methylbutan-2-ol can give 2-methylbut-1-ene and 2-methylbut-2-ene

3-methylbutan-2-ol can give 3-methylbut-1-ene and 3-methylbut-2-ene

b) Identify the seven alcohols which can undergo mild oxidation and identify the oxidation products
in each case.
pentan-1-ol gives pentanal
pentan-2-ol gives pentan-2-one
pentan-3-ol gives pentan-3-one
2-methylbutan-1-ol gives 2-methylbutanal
3-methylbutan-2-ol gives methylbutanone
3-methylbutan-1-ol gives 3-methylbutanal
dimethylpropan-1-ol gives dimethylpropanal
c) Of these oxidation products, four can undergo further oxidation. Identify these four aldehydes and
identify the further oxidation product in each case.
pentanal gives pentanoic acid
2-methylbutanal gives 2-methylbutanoic acid
3-methylbutanal gives 3-methylbutanoic acid

dimethylpropanal gives dimethylpropanoic acid

4) Using structural formulae, write equations for the following processes:
a) mild oxidation of propan-1-ol

b) oxidation of butanal

c) oxidation of propan-2-ol

5) State two chemical tests you could carry out to distinguish between butanal and butanone.
State what you would do and what you would see in each case.

add Fehlings solution

add Tollens reagent

heat
brick-red precipitate will appear with butanal
no change with butanone

heat
silver mirror will appear with butanal
no change with butanone