CHM258 | SEP18-JAN19
TUTORIAL 3
ALKENES AND CYCLOALKENES
QUESTION 1
i) O3
Compound D + Compound E
ii) (CH3)2S
Compound C
a) Determine the chemical structures of compound D and E
b) Predict the observation when compound C is tested with Baeyer’s test
QUESTION 2
Alkene can undergo various reactions. Identify the structure of Q, R, S and T.
Compound R
H2, Pt
O O
HCl O3, (CH3)2S
Compound S Compound Q +
H
HBr, H2O2
Compound T
QUESTION 3
Two bottles of propane and propene are left on the laboratory table without labels after being used
in experiment.
a) Give a simple chemical test to differentiate between propane and propene by stating the
reagent, conditions and the expected observation
b) Predict the type of reaction involve in (a)
QUESTION 4
Pentane and pentene is classified as the hydrocarbon compounds.
a) Define hydrocarbon compounds. Indicate the differences between pentane and pentene
b) Describe a chemical test to distinguish pentane from pentene
QUESTION 5
Draw the product formed when 3-methyl-2-hexene reacts with the following reagent
a) HCl, peroxide
b) Br2 in CCl4
CHM258 | SEP18-JAN19
QUESTION 6
Refer to the following figure
Compound X
a) Give the IUPAC name of compound X
b) Draw the structure of the product(s) formed when compound X reacts with excess Br2 in
CCl4
QUESTION 7
Determine the structural formula of the product(s) formed when but-2-ene reacts with the
following reagents
a) HBr /H2O2
b) O3 / Zinc dust
QUESTION 8
Write the equation for the following chemical reactions
a) Addition of HBr to 3-methyl-1-butene
b) Addition of H2O to 2-methyl-1-butene
QUESTION 9
An alkene P (C6H12) reacts with cold basic KMnO4 to produce Q (C6H14O2). Hydrogenation of P
produces R (C6H14). Ozonolysis of P produces propanone (CH3COCH3) and propanal
(CH3CH2CHO).
a) Draw the structure of P, Q, R.
b) State the reagent(s) and condition for ozonolysis reaction
QUESTION 10
Draw the structural formula and give the IUPAC names for the geometrical isomers of 1,2-
dibromopent-1-ene.
QUESTION 11
Alkene is unsaturated hydrocarbon with general formula of CnH2n.
a) Illustrate the structural formula for 1,3,5-heptatriene and 3-methyl-1-heptene.
b) Predict the compound with a higher boiling point; pentene or propene.
CHM258 | SEP18-JAN19
QUESTION 12
Determine the major product(s) of the following reactions
a) CH3CH=CH2 + HBr
b) CH3CH=CH2 + HBr + di-tert-butylperoxide
QUESTION 13
Determine the reagent(s) and condition (if any) for Step 1 and Step 2.
Step 1 Br
Step 2
QUESTION 14
Cyclopentane and cyclopentene undergo bromination under different conditions. Explain the
reaction using chemical equation including reagent(s) and condition(s) required for bromination
of each compound above.
QUESTION 15
Consider below reaction scheme.
Compound W
Br2, CCl4
H H
Br
Reagent Y Mg / Ether
Compound X
H H2O
H H
Reagent Z
a) Draw and give the IUPAC name for compound W
b) W is an optically active compound. Identify the chiral centers in compound W with an
asterisk (*).
c) Draw the structural formula for compound X
d) Identify the name for reagent Y and reagent Z
CHM258 | SEP18-JAN19
QUESTION 16
Suggest the complete chemical reaction for:
a) Bromination of 4 methyl-2-pentene
b) Hydrogenation of 4-methyl-2-pentene
QUESTION 17
a) Determine a simple chemical test to differentiate between butane and butene complete
with reagent(s), condition(s), and expected observation.
b) Reaction of 3-methylpent-2-ene with ozone in the presence of dimethylsulfide produces
two products. Predict the chemical structure of the two products obtained.
QUESTION 18
Consider below reaction scheme.
Cl2, CCl4 H2, Pt
Compound A Compound B
a) Identify the chemical structure for compound A and B.
b) State the IUPAC name for compound B.
QUESTION 19
Refer to the following reaction.
Br
KOH, ethanol Compound A + Compound B
(Major) (Minor)
a) Identify the compound A and B.
b) Determine the IUPAC name for compound A.
