CAPE CHEMISTRY UNIT II

Assignment # 2
October 10, 2017
Total marks: 38

INSTRUCTIONS: Place your answers for the questions in the spaces provided. Submit the
completed worksheet by no later than Thursday October 19, 2017

I. A compound A, C3H8O, when refluxed with acidified potassium dichromate (vi)

produced a liquid B with a sharp smell, which effervesced with sodium carbonate
solution. Another compound C, containing two carbon atoms, when heated with
concentrated sulphuric acid at temperatures of about 160oC, produced a gas D
which decolorized aqueous bromine. C also produced yellow crystals when warmed
with sodium hydroxide and iodine. C when refluxed with B in the presence of
concentrated sulphuric acid produced a sweet-smelling compound E, which is used
in the perfumery industry.

Deduce the identities of compounds A – E, providing reasons for your answers.

Compound Name of compound Explanation

A Propan-1-ol Compound A, an alcohol is named based off
of its formula C3H8O (C3H7OH).
B Propanoic Acid This compound is formed when an alcohol is
refluxed with acidified potassium
dichromate. The dichromate oxidises 1-
propanol in two stages first to an aldehyde
and then to propanoic acid. This acid is
known to have a sharp smell and the
effervescence indicates the production of
carbon dioxide, generally produced when
acids are mixed with carbonates.
C Compound C is also an alcohol. It is an
Ethanol alcohol because it gave a positive result for
the iodoform test (produced yellow crystals
when warmed with sodium hydroxide and
iodine). It is the only primary alcohol that
gives a positive result for an iodoform test.
The name ethanol suggests that it contains
two carbon atoms.
D This is the gas produced from the
Ethene dehydration of ethanol. Ethene gas
 decolorizes bromine water.
E Compound E is an ester, which in this case is
Ethyl Propanoate a product of the reaction between ethanol
and propanoic acid in the presence of conc
sulphuric acid. Esters are generally sweet
smelling compounds.
(15mks)

II. Outline how you would prepare 1-butanol from the following. Indicate any special
conditions required:
a. 1-butenes
b. 1-chlorobutane

Starting Required Special conditions Type of reaction

material reagents which would take
place
1-butene Concentrated Addition of water to the Addition Reaction
Sulphuric Acid product and the mixture
is warmed
1-chlorobutane Ethanol The primary Nucleophillic
halogenoalkane is reacted Substitution
with water or OH- ions to
form primary alcohols
(6 mks)
III. Which alkyl halide (bromopropane or chloropropane) would you expect to undergo
nucleophilic substitution faster? Give an explanation for your answer.

As electronegativity increases, nucleophilicity decreases. As you go down a group on the

periodic table, electronegativity decreases as it is harder for an atom to lose its electrons.
Since the electronegativity decreases down a group, nucleophilicity increases. On the
periodic table, chlorine is found before bromine in group seven. This means that going
from chlorine to bromine electronegativity has decreased and nucleophilicity has
increased. Therefore bromopropane would undergo nucleophilic substitution faster since
the nucleophilicity increased.

(4 mks)
IV. A compound A with the molecular formula C9H18, reacts with hot acidic potassium
permanganate to give two compounds B and C. Both B and C form an orange
precipitate when they react with Brady’s reagent. Compound B gives a positive test
for Tollen’s reagent but compound C, a compound with a molecular formula of
C5H10O, does not. Compound C gives a positive result for the iodoform test but
compound B does not. Deduce the structures and hence the names of A, B and C.
Provide explanations for your answers.

Compound Name of compound Explanation

A
Non-1-ene Compound A obtained its name from
its formula C9H18. Alkenes have the
general formula CnH2n.
1mk

2 mks
B
An aldehyde, which is a product when
Butanal an alkene reacts with hot acidified
potassium permanganate. It has
1mk proven to be an aldehyde based on the
fact that it gives a positive result for
both Brady’s reagent and Tollen’s
reagent.

4mks
C Compound C is a ketone as it is a
product when an alkene reacts with
2- Pentanone hot acidified potassium permanganate.
It also gave a positive result for the
1mk iodoform test and when reacted with
Brady’s reagent which are
characteristics of a ketone. It is also
named based on its formula C5H10O

4 mks
(13 mks)