FAROLFADZICHM258 | OCT23 – FEB24

FARIDAML ARMAL BINM

A4AS1203-2
TUTORIAL 2
2022468464
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 v
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
 a
C
C C

(a) is
n -nexune

/ metyl
" 5
p

3
2

· pentane
2 metylpetane

(b - -

=
(b) CHyCH2CH(CH ,)CH2CHy +

102 720 +

6202

C =
6

H 14
=

-paling
- -
-

R
bykhawan . . ->
alley group .

C) major product .

C1 -CHION

X-penthane s chlow - a
metyl pettane
I metyl
,

minor product
.

chloro-Cl
Cis I STIS 5 3
Cl - chloro

pentane -N N pentanc
I
3

metyl
6 I Mein
2 , chloro-3 metylpehtane 1, chlow - 4 metylpentance
 -

#
R-AgX H-OH ,
RIH + MgCOH) x
+

↓ I
Alkyl magnesium water alkane
hand

CH3CH2CH(CHz) CHzCH
#
, MgCl + H-OH
CHzCHzCH(CH, J CHCH, + MgCOH)D

Br

I
C I 3
e - -

- -
-

Cis Initiation step .

yU light
CHg + Brz - C HyBr +

HBr
·
the chain is intiated (started by urlight breaking a bromine

molecule into free radide .

The process is called

photochemical
homolytic fission/deqreage .

· a xX
nu 08 xX

xBrY Br
·
Br Br
⑧
X + .
· - ②

00 - X X 66
X X

Bromine atomS
hV =

radiation energy <free radide)

-> -movement of single electron Cradide)
 CTS Propogation Step -

·
Free radide species produce another free radical species .

~free radical is highly reactive species

·
Propyl radicle will react with another bromine molecule producing
bromopropane and a bromine free radical
I HH

Bre ne X
I 1 I
I H C H - HB C :

Hy
-
- -
- +

,
S
it i it propyl
radide .

propane

Bromine radide produced will then react with another

prophane
·

molecule and the recycle is repeated .

CzHq + Brz ->

<zAyBr +

Brx

(ii) Termination .

Br x +

Brx ->
Brz
CyHyo+ Brx -> CHyBr
CyHy" C3H, HyC3 CH7
"
+
-> -

(by products

Free radical substitution Reaction

 (a) ↑
M
CHCH(CH3)CH2CH2CHs 7H20 +6002
, 02
1
+ ->

c =
6 0 =
7 +
6x2

A 14 19
=

W
I
i
CHz(CH) CH(CH, ) CH2CHzz
+
02 -9H20 +8002

C =

8 0 =

9 + (8x2)
H 18
=
=

25

a
C (c eb
-
-
-

Cis Initiation step

.

unlight
CH3CH, + C2 -> CH(C)2 CHz
+
Has

- The chain initiated (started) by yr

light breaking a chlorine
molecule into free radicals
. This process is called photochemical
homolytic fission/dequege
.
 XX
⑧0
~ hu D ⑧ x X

Cl Y
+x
·
Clo
⑧

Cl -> ·

X
I
O ⑧ xx 00

chlorine atoms
free radicals)
&H = +

242 R5MOS-1
hy
=

radiation energy
-> movement of single electron Cradical)

CTi) Propagation .

chain reaction
·
ethyl radical propagates .

V
ethyl radical will react with another chlorine molecule
producing chlowethane and a chlorine thee radical
HH
- I
1
Clo
% H HG CHzCH2
:
I
H - - C ->
+

I I
H H ethyl
radical
ethane

·
Chlorine radical produced will then heat with another ethane
molecule and the cycle is repeated .

C2H , 42 C3Ci4 Cl
+

·
->
+

ethyl clow ethane

radical

(T Termination .

when two free radicals collide and combine

· The stop
C10 +

40 -
C2

CHyCH, + Co ->
CHzCHzC
CH3CH2 +CHyCHY ->
CHyCHzCizCH,
Cby product) &

A
 exhibit Bueyer's strain which is of
Caj'cylopropane , a
type
ings strain ,
because its unique geometric and structural

propertis .
Bueyer's strain is also sometimes referred to as

angle strain
.

· In cyclopropane ,
the strain ,
the carbon-carbon bond in
the three membered ring are
significantly smaller than the
ideal tetrahedral bond angle of approximately 109 50
.
.

In cydepropane -c bond approximately 60'which smaller

than ideal
angle
.

- - -

1II
Cyclopropane cyclobutane
-

Bond 60° -Bond 888

angle angle
-

highly reactive than - lower than cyclopropane

cycobutane to ringopening to ring opening .

Cylopentane > Cyclobutane >

cyclopropane .
 CHM258 | OCT23 – FEB24

QUESTION 6 v
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

QUESTION 7
Compound X with the molecular formula of C4H10 produces two structural isomers, isomer D and
isomer E. Isomer D is known to possess higher boiling point compared to isomer E. Isomer D is
then reacted with Br2 with the presence of light to produce 2-bromobutane.
a) Illustrate and indicate the IUPAC name of isomer D and isomer E 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
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 10
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.
as ↑
N
↓ I

b al X-
I I
N
-

1 I
 CHM258 | OCT23 – FEB24

QUESTION 11
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 12
a) Determine the IUPAC name for Compound A. (3 marks)

F
H2N

Compound A

b) Outline a balanced chemical equation for the preparation of 2,2-dimethylpropane from

suitable Grignard reagent. (2 marks)

QUESTION 13

a) Outline the stepwise mechanism (initiation, propagation(s) and, one termination step) for
chlorination of 1-methylcyclopentane to produce its major product.

b) Identify the structural formula of the product formed when cyclopropane react with Br2, CCl4.

QUESTION 14
a) Determine the IUPAC name for Compound A.

NO2

Cl
Compound A
b) Outline a balanced chemical equation for the preparation of 2,2-dimethylbutane from
suitable Grignard reagent.

QUESTION 15
a) Outline the stepwise mechanism (initiation, propagation(s) and one termination step) for
bromination of 2-methylhexane to produce its major product. (3 marks)

b) Compare the stability of cyclopropane and cyclobutane based on the Baeyer Strain Theory.
(2 marks)
 CHM258 | OCT23 – FEB24

QUESTION 16
a) Write a balanced chemical equation for combustion of 3-ethylhexane.
(2 marks)

b) Briefly explain which compound 2,3,4-trimethylpentane or 2-isopropylpentane possesses a

higher boiling point.
(3 marks)
QUESTION 17

c) Determine the IUPAC name for Compound A.

Br

Compound A
(3 marks)
d) Sketch the condensed structure for 5-chloro-4-ethyl-2-methylheptane.
(2 marks)
QUESTION 18
Consider the following reaction scheme.

Br

Reagent L

H2O Cl2
Compound K Compound M + Compound N
uv (minor product)
H+ (major product)
Compound B

H2, Pt

Compound J

a) Write the structural formula for Compound J, K, M and N.

b) Identify the Reagent L.
c) State the physical state of Compound B at room temperature.
d) Write a balanced chemical equation to synthesize Compound B from Compound K.
e) Predict the solubility of Compound B in water.