Raffles Institution (Junior College)

H2 Chemistry 2008/9
Tutorial Hydroxy and Phenol Compounds
Prepared by: Mr Chen Yongchang, Joseph

Question 1
(a)

Draw the full structural formulae for all the alcohols with the molecular formula
C4H10O and classify each as a primary, secondary or tertiary.

(b)

Compare and contrast the behaviour of these alcohols with oxidising agents such as
acidified, aqueous potassium dichromate (VI).

(c)

One of these alcohols is found to have the following properties.

It exists as a pair of optical isomers.

On warming with iodine and aq NaOH a pale yellow precipitate is obtained.

On heating with an excess of concentrated sulphuric acid at 180oC a mixture

of three alkenes is obtained.
Identify the alcohol, explaining your reasoning. Also, give the full structural formulae
of the three alkenes.

Question 2
How, and under what conditions would you expect a compound with the formula given below
to react, if at all, with the following reagents. Draw the structural formula of the organic
product(s) formed (if any) for reagents from (a) to (j).
(a)
(b)
(c)
(d)
(e)
(f)
(g)
(h)
(i)
(j)

sodium
sodium hydroxide
sodium carbonate
phosphorus(V) chloride
hydrogen bromide
ethanoic acid
ethanoyl chloride
aqueous bromine
bromine in CCl4
potassium manganate(VII)

OH

CH CHCH2OH

Question 3
Alcohol B, with the molecular formula of C5H12O, forms esters which are responsible for the
flavours of various fruits. Reaction of B with acidified potassium dichromate(VI) produces a
compound C, C5H10O2. Heating B over Al2O3 produces D, C5H10. Vigorous oxidation of D
forms 2-methylpropanoic acid as one of the products.
Suggest structures for B, C and D and explain the reactions involved.
J94/I/10

Question 4
Arrange the following in order of increasing acidity:
phenol, 2-nitrophenol, ethanol, methylpropan-2-ol, water, methanol, 2-methylphenol.
Explain your answer.

Question 5
CH3CH(OH)CH2CH3
A

(CH3)3COH
B

Alcohols A and B are isomers.

(a)
Draw the structural formula of one other alcohol isomeric with A and B.
[1]
(b)
What reagent would you use to dehydrate A and B to alkenes? Draw the structural
formulae of the three alkenes that are obtained by dehydrating A.
[3]
(c)
Describe a reaction (reagent and observation) by which A could be distinguished
from B.
[2]
(d)
Name the class of compound formed when A reacts with ethanoyl chloride, and draw
its structural formula.
[2]
(e)
Draw diagrams to illustrate how A gives rise to optical isomerism.
[2]
N92/I/9