The University of Zambia

School of Natural Sciences

Chemistry Department
2020/21 ACADEMIC YEAR TERM

CHE1000 - INTRODUCTORY CHEMISTRY

TUTORIAL SHEET 13: September 2021

TOPIC: Organic Chemistry
TUTORIAL SHEET 2 : For the week beginning Monday, 20th September, 2021
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1. Give the molecular formula for a 5-carbon hydrocarbon with one π-bond and one ring.

2. Draw line structures of the following alkanes:

(i) 2,5-dimethylhexane
(ii) 4-isopropyl-2,5-dimethylheptane
(iii) 2,2-dimethyl-4-propyloctane
(iv) 2-ethyl-1,4-dimethylcyclohexane

3. Give the IUPAC names for each of the following:

(i) CH3CH2C(CH2CH3)2CH2CH2CH3

(ii)

(iii)

(iv)

(v)

(vi)

(vii)

3. Which of the following is an isomer of 2,2‑dimethylpentan‑1‑ol?

A CH3CH2CH2CH(CH3)CH2OH
B (CH3)3CCH(CH3)CH2OH
C CH3CH2CH2CH2CH2CH2CH2CH2OH
D (CH3)2CHC(CH3)2CH2CH2OH
4. Here are some exercises in sigma bond breaking. Supply the arrows which result in the products
shown.

5. Here are some examples of simultaneous sigma bond making and breaking. Where arrows are
supplied, indicate the resulting products. Where the products are given, supply the appropriate
arrows.
6. Here are some examples of simultaneous sigma bond making and π bond breaking. Where arrows
are supplied, indicate the resulting products. Where the products are given, supply the appropriate
arrows.

7. Here are some examples of simultaneous π bond making and sigma bond breaking. Where arrows
are supplied, indicate the resulting products. Where the products are given, supply the appropriate
arrows.

8. State whether each of the following (the ion, molecule or the indicated atom in the molecule)
could act as a nucleophile or an electrophile in a reaction.
9. One component of petrol is decane, C10H22.
(a) Decane reacts with chlorine in the presence of ultraviolet light to form a mixture of products.
(i) Complete the equation for the initiation step, including appropriate curly arrows.

(ii) Write equations, using molecular formulae, for two propagation steps.
(iii) Write equations, using molecular formulae, for two termination steps, other than the one in
which chlorine forms.
(b) The structure of decane can be changed by the process called reforming. Name the compound
shown, which can be produced in this process.

(c) Write an equation, using molecular formulae, for the incomplete combustion reaction in which
decane reacts to form carbon monoxide and one other product. State symbols are not required.

10. The halogenoalkane 1-chlorobutane reacts under suitable conditions with potassium hydroxide to
form the alcohol butan-1-ol.
(i) Name a suitable solvent for the potassium hydroxide in this reaction.
(ii) State the type and mechanism of this reaction.
(iii) Draw the mechanism for this reaction. Use curly arrows, and show relevant dipoles and
lone pairs.