FOUNDATION IN SCIENCE

AUGUST 2012 FINAL EXAMINATION

SUBJECT: CHEMISTRY 3
SUBJECT CODE: FIS0134
TIME ALLOWED: 3 HOURS
(9.30 AM 12.30 !M"
DATE: AUGUST 13# 2012
T$%& '()&*%+, -.-)/ 0+,*.%,& NINE (9" -/%,*)1 -.2)& %,03(1%,2 *$) 0+4)/ -.2).
INSTRUCTIONS TO CANDIDATE:
1. Answer ALL questions in SECTION A and ANY TWO (2" out of THREE
(3" questions in SECTION B.
INFORMATION TO CANDIDATE:
1. You are permitted to use a non-programmable electronic calculator in this
examination.
SECTION A
A,&5)/ ALL '()&*%+,&
6()&*%+, 1
A) Deduce the 0+,1),&)1 &*/(0*(/.3 7+/8(3. of the alkene ( ! ") based on the following
reaction.
(9 8./:&"
#) $hlorination of alkanes is a %er& important process. 'rite the reaction mechanism of
monochlorination of c&clohexane.
(; 8./:&"
$) i) (xplain how boiling points of an alkane increase with increasing molecular
weight.
(3 8./:&"
ii) #ranched alkanes and straight chain alkanes with similar molecular weight ha%e
different boiling point. 'hich of the two has higher boiling point) *ustif& &our
answer.
(3 8./:&"
(T+*.3: 20 8./:&"
+
6()&*%+, 2
A) ,enthene- which is a h&drocarbon found in mint plant- has the ./A$ name as 1-
isoprop&l-0-meth&lc&clohexene.
i) Draw the structural formula for menthene.
(2 8./:&"
ii) Draw the structural formula of the products formed from the o1onol&sis of
menthene.
(2 8./:&"
iii) 2i%e one chemical test that can be used to differentiate menthene from 1-
isoprop&l-0-meth&lc&clohexane. You are required to show the equation in%ol%ed.

(; 8./:&"
#) redict whether each of the following reactions proceeds predominantl& b& substitution
("31 or "3+) or elimination ((1 or (+) or whether the two compete. *ustif& &our
answer. Draw the skeletal structural formula for the ma4or organic product(s).
i)

(< 8./:&"
ii)

(< 8./:&"
(T+*.3: 20 8./:&"
5
6()&*%+, 3
A) 'rite a multi step reaction mechanism for the reaction of phen&lmagnesium bromide
(,g#r) with acetone to form an alcohol.
(< 8./:&"
#) Alkenes undergo man& reactions- mainl& electrophilic addition reactions. 6he
,arko%niko%7s rule ma& be used to predict the addition products.
i) "tate the ,arko%niko%7s rule.
(2 8./:&"
ii) redict the product formed from the h&dration of +-+-dimeth&lbut-+-ene. "how
the reagent(s) and equation in%ol%ed.
(3 8./:&"
iii) (xplain the formation of the products in the following reactions8
(3 8./:&"
(3 8./:&"
i%) 'rite the equations for the reaction of h&drogen bromide with c&clohexene and
with 1-meth&lc&clohexene. 'hich of these + reactions are faster) (xplain &our
answer.
(4 8./:&"
(T+*.3: 20 8./:&"
0
SECTION B
A,&5)/ TWO (2" +(* +7 THREE (3" '()&*%+,&
6()&*%+, 4
A) 9igure 1 shows a structure of hen&lethene (st&rene) which is used in large quantities to
make pol&(phen&lethene).
F%2(/) 18 hen&lethene (st&rene)
A possible s&nthetic route from ben1ene to phen&lethene is shown below.
i) 2i%e the name of a suitable catal&st for step 1 and gi%e the structural formula of
compound A.
(2 8./:&"
ii) 'h& is ultra%iolet light necessar& in step +)
(2 8./:&"
iii) "uggest a suitable reagent and conditions for step 5.
(2 8./:&"
i%) 6he oxidation step 0 has to be done with care to obtain a good &ield of aldeh&de.
"uggest how this is achie%ed.
(2 8./:&"
:
%) ;ow would &ou prepare the 2rignard reagent- meth&lmagnesium bromide-
$;5,g#r used in step :)
(2 8./:&"
%i) Draw the structural formula and gi%e the ./A$ name of compound B.
(2 8./:&"
#) ro%ide the products of the following reactions. .f no reaction is expected- write <3=>.

i)
(2 8./:&"
ii)

(2 8./:&"
iii)

(2 8./:&"
i%)

(2 8./:&"
(T+*.3: 20 8./:&"
?
6()&*%+, <
A) $onsider the following reaction scheme8
i. 2i%e the reagents and conditions necessar& for8
a) step 1
(2 8./:&"
b) step +
(2 8./:&"
ii. 2i%e the equation for the reaction between propanoic acid and phosphorus
pentachloride and the product(s) formed.
(3 8./:&"
iii. $ompound B reacts with +-0-dinitrophen&lh&dra1ine but not with ammoniacal
sil%er nitrate solution. 2i%e the structural formula for compound B and explain
wh& B reacts with +-0-dinitrophen&lh&dra1ine and not with ammoniacal sil%er
nitrate.
(4 8./:&"
i%. 2i%e the structural formula for compound C.
(2 8./:&"
%. "tate wh& the ether sol%ent must be dr& in the con%ersion of B to C.
(2 8./:&"

@
#) .mine formed from an aldeh&de or ketone on reaction with h&dra1ine (3;+3;+) is
unstable in base. 3ame the reaction in%ol%ed in reduction of the following compound
and propose a mechanism for the reaction.
(< 8./:&"
(T+*.3: 20 8./:&"
A
6()&*%+, ;
A) $onsider the reaction scheme gi%en below.
i) 'rite the structural formula for A- # and $.
(; 8./:&"
ii) "tate the reagents . and ...
(4 8./:&"
#) 6he structural formula of organic compounds B and Y are shown below.

B Y
%" 3ame the functional group for each compound B and Y.
(2 8./:&"
%%" "uggest a reagent that can be used to differentiate B from Y.
(2 8./:&"
%%%" 'hich of the compounds boils at a higher temperature) (xplain &our answer.
(2 8./:&"
%4" 'rite the reaction equation to show the preparation of Y from B.
(2 8./:&"
4" 'rite the reaction equation to show the preparation of B from Y.
(2 8./:&"
(T+*.3: 20 8./:&"
===END OF 6UESTION !A!ER===
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