Sir Arthur Lewis Community College

Organic Chemistry-CHM211

Answer All questions

1. A. Lithium reacts with alcohols in a similar way as sodium. A small piece of lithium
metal is dropped onto a watch glass containing propan-1-ol.
a) What would you observe? [1]
b) Name the product of the reaction [2]
c) What difference would you expect to see if you used sodium instead of lithium in
this reaction? [1]

B. Concentrated sulphuric acid or phosphoric acid can also be used to catalyse the
dehydration of an alcohol. The alcohol and concentrated acid are heated to about 1700C.
The concentrated acid does not change chemically during the reaction.

a) Write an equation showing the dehydration of ethanol using concentrated

sulphuric acid [2]
b) If propan-1-ol was used instead of ethanol, name te organic product formed. [1]

C. Propan-1-ol can be oxidized to propanal, CH3CH2CHO and then to propanoic

acid CH3CH2COOH.

a) What reagents and conditions should be used to oxidise propan-1-ol to

propanal?[2]
b) Write a balanced chemical equation for this oxidation. Oxygen from the oxidizing
agent should be shown as [O] [2]
c) What reagents and conditions should be used to oxidise propan-1-ol to propanoic
acid? [2]
d) Write a balanced equation for this oxidation. Again show oxygen from the
oxidizing agent as [O][2]

2. A.
a) What reagent would you add to an unknown compound to see if it contains a
carbonyl group?
b) What result would you get if the unknown compound does contain a carbonyl
group? [1]
c) Why would it be useful to find the melting point of the product of this test? [1]
d) Describe the results you would expect to see if pentan-3-one and pentanal are
separately treated with Tollen’s reagent. Where a reaction takes place, name the
organic product and name the type of reaction that takes place. [4]
e) Write a balanced equation for the reaction that take place when propanal is
warmed with a solution of sodium tetrahydridoborate, using the symbol [H] to
represent a hydrogen atom from the reducing agent. [2]
f) Name the product formed in the reduction reaction if pentan-3one is warmed with
a solution of sodium tetrahydridoborate. [1]
g) Name the organic product that would be formed in the nucleophilic addition of
HCN to:
i. ethanal
ii. propanone [2]

h) Use equation and curly arrows to describe the mechanism of the reaction in part
(g) i. [4]