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Tutorial 2 PDF

This document contains 14 questions about alkanes and cycloalkanes. The questions cover topics such as drawing structural formulas, predicting products of reactions like halogenation and combustion, naming compounds using IUPAC nomenclature, describing reaction mechanisms and explaining concepts like Baeyer strain theory. Students are asked to identify and illustrate reaction intermediates and products, write balanced chemical equations, compare reactivity and stability of cyclic compounds, and describe synthetic routes involving reactions like hydrolysis and reduction of alkyl halides.

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Alees Rahaizan
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419 views

Tutorial 2 PDF

This document contains 14 questions about alkanes and cycloalkanes. The questions cover topics such as drawing structural formulas, predicting products of reactions like halogenation and combustion, naming compounds using IUPAC nomenclature, describing reaction mechanisms and explaining concepts like Baeyer strain theory. Students are asked to identify and illustrate reaction intermediates and products, write balanced chemical equations, compare reactivity and stability of cyclic compounds, and describe synthetic routes involving reactions like hydrolysis and reduction of alkyl halides.

Uploaded by

Alees Rahaizan
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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CHM258 | SEP19-JAN20

TUTORIAL 2

ALKANES AND CYCLOALKANES

QUESTION 1

Compound B
a) Give two possible isomers of compound B.
b) Predict the balance chemical equation for complete combustion of compound B.
c) Identify and indicate the major and minor product(s) formed if compound B undergo
chlorination reaction.
d) Suggest how to synthesize compound B using suitable Grignard reagent.

QUESTION 2
2-bromobutane can be prepared in the lab by using organic chemicals and bromine in inert solvent.
a) Give the initiation step, the two propagation steps and one possible termination step that
are involve in the production of 2-bromopropane with the presence of uv light.
b) Predict the name of the mechanism in (a).

QUESTION 3
State a balance equation for the complete combustion reaction of the following compounds:
a) 2-methylpentane
b) 2,2,3 - trimethylpentane

QUESTION 4
1,1-dichloroethane is the product of free radical substitution reaction of ethane. Show the overall
mechanism including initiation, propagation and termination steps.

QUESTION 5
a) Cyclopropane exhibit Baeyer’s strain. Explain this statement.
b) Compare the reactivity of ring opening reactivity between cyclopropane and cyclobutane
based on the Baeyer’s Strain theory.
c) Organized the following cycloalkane in correct order of decreasing stability based on
Baeyer strain theory.
Cyclopropane, cyclobutane, cyclopentane

QUESTION 6
Draw the structural formula for each of the following compounds:
a) 3-ethyl-2,4,5-trimethyloctane
b) 4-tert-butyl-2-chloro-3,5-dimethylnonane
CHM258 | SEP19-JAN20

QUESTION 7
Compound X with the molecular formula of C4H10 produces two structural isomers, isomer A and
isomer B. Isomer A is known to possess higher boiling point compared to isomer B. Isomer A is
then reacted with Cl2 with the presence of light to produce 2-chlorobutane.
a) Illustrate and indicate the IUPAC name of isomer A and isomer B respectively.
b) Suggest the complete chemical equation for reaction of 2-chlorobutane with zinc in
hydrogen chloride

QUESTION 8
a) Predict the products of the following reaction.

H2O, H2SO4
Cyclopropane

H2, Pt

b) Identify reagent X and reagent Y required for the following reaction.

Reagent X Reagent Y
Cl Cl

QUESTION 9
Consider the following reaction scheme.

CH3

CH3CHCH2CCH3

CH3 CH3
Compound Q

a) Give the IUPAC name for compound Q.


b) Indicate the balanced chemical equation for complete combustion of compound Q.
c) Illustrate the step-wise mechanism (initiation, propagation and termination) of the
chlorination of compound Q to produce its major product.

QUESTION 10
a) Describe briefly which compound (hexane or 2,3-dimethylbutane) possess lower boiling
point.
b) Identify the major and minor product(s) for the chlorination of hexane
CHM258 | SEP19-JAN20

QUESTION 11
Suggest a balanced chemical equation for the following reactions:
a) Reaction of C6H14 with bromine, Br2 in the presence of light.
b) Reduction of 2-bromohexane

QUESTION 12
Show the preparation of propane from 2-chloropropane by each of the following methods using
suitable reagent(s) and condition(s), if required.
a) Hydrolysis of Grignard reagent.
b) Reduction of alkyl halide.

QUESTION 13
Bromination of 2-methylbutane with the present of uv light will produce major and minor
product(s).
a) Illustrate the structural formula for all possible major and minor product(s) formed.
b) Predict the IUPAC name for the major product(s) formed in (a).

QUESTION 14
Express the condensed structural formula for the following compounds:
a)

b) 2-methyloctane

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