ASSINGMENT

FUNDAMENTAL ORGANIC CHEMISTRY CHM457

March-August 2021

Details of the student 1:

Name: IRFAN NURHADI BIN AZAHAR
Matrix no: 2020819572
Group: AS2222A1
Submission date: 11 JUNE 2021

Details of the student 2:

Name: FARISHA HUSNA BINTI AZMAN
Matrix no: 2020897392
Group: AS2222A1
Submission date: 11 JUNE 2021

Details of the student 3:

Name: NADIATULMAISARAH ALI
Matrix no: 2020853166
Group: AS2222A1
Submission date: 11 JUNE 2021

Evaluation criteria:
Total marks: 60
Marks given:………..
Weightage:……. /20

CHM457_OCTOBER 2020_ASSINGMENT
QUESTION 1

a) Give IUPAC name for the following compounds. Use cis/trans or E/Z notation where
necessary.

i) H3C CH3
H H

ii) H CH(CH3)2
C C
H3C CH2OH

H3C H
iii C C
CH2CH2Cl
H
)

(3 marks)

b) When sighting along the C3-C4 bond in 3-methylhexane, different staggered and eclipsed
conformations revealed. Draw Newman projections for the most stable staggered and
eclipsed conformations.
(2 marks)

CHM457_OCTOBER 2020_ASSINGMENT
c) Although the axial and equatorial methylcyclohexane interconvert rapidly, there aren’t
equally stable. Draw the less stable conformation, show and name the steric interaction that
occurs in this conformation.
(2 marks)

QUESTION 2

Consider the sequence of reactions given below:

H2O, NaOH
Y KMnO4 + methylcyclohexene + HCl P X
hot
H2O, NaOH
cold H2O, H2SO4

Z + H2O
T

a) Write the structural formula of methyl cyclohexene, the intermediate P and the product x.

(3 marks)

CHM457_OCTOBER 2020_ASSINGMENT
b) Give the products Y and Z.

(2 marks)
c) Write the reaction mechanism for the acid catalyzed hydration of methylcyclohexene to
produce T.

CHM457_OCTOBER 2020_ASSINGMENT
 (4 marks)

QUESTION 3

A reaction scheme for compound X is given below:

KOH
ethanol
stage 1
C4H10 P + Q
X 1° 3°
alkly halide alkly halide
KOH(aq), D KOH(aq), D
SN2 SN1
R S

a) Draw structure for X and give the reagents and conditions for stage 1.

CHM457_OCTOBER 2020_ASSINGMENT
 (2 marks)

b) Draw structures for P, Q and T and suggest a chemical test for T.

(4 marks)
c) Draw structures for R and S and give their IUPAC name.

(3 marks)
d) R can react with sulfuric acid to produce alkene and ether at different conditions.
State the conditions and draw structures for the alkene and ether formed.

(3 marks)

CHM457_OCTOBER 2020_ASSINGMENT
e) Give the product of when S reacted with NaH and CH 3CH2Br and indicate the type of
reaction.

(2 marks)

QUESTION 4

a) Predict the major product(s) of the following reactions:

Cl CH3CH2Cl
i)
AlCl3
ii) CO2H
HNO3
H2SO4
iii) N(CH2CH3)2
SO3
H2SO4
CH2CH2CH2CH3 KMnO4
vi)
H2O

CHM457_OCTOBER 2020_ASSINGMENT
 (6 marks)

b) How would you prepare m-chloronitrobenzene starting from benzene.

CHM457_OCTOBER 2020_ASSINGMENT
 (5 marks)

QUESTION 5

CHM457_OCTOBER 2020_ASSINGMENT
Propose an efficient synthesis of

a) Octane from 1-pentyne.

(5 marks)

b) 2-Cyclopentylacetaldehyde from vinylcyclopentane

CHM457_OCTOBER 2020_ASSINGMENT
 O

(3 marks)

QUESTION 6
CHM457_OCTOBER 2020_ASSINGMENT
a) Dialkyl ether undergoes SN2 reaction to form two equivalents of the alkyl bromide as shown
in the reaction below:

O + 2 HBr 2 Br + H2 O

Propose a stepwise mechanism with curved arrows for the substitution reaction.
(5 marks)

b) Compound V is reacted with strong nucleophile as shown below. This reaction proceeds via
SN2 reaction mechanism to give W as the final product.

H CH 3
C C H NaSH
H3 C W
Cl
C 6 H5 DMSO

V
i) Show the mechanism of the substitution reaction to produce W.
(2 marks)

ii) If NaSH was substituted with Na(OCH3)3, suggest

CHM457_OCTOBER 2020_ASSINGMENT
 ii-a) the new type of mechanism
ii-b) structure of the new products.

ii-c) trend on the reaction rates if doubled the concentration of V.

(4 marks)

CHM457_OCTOBER 2020_ASSINGMENT