B.Sc. EXAMINATION
Decernber.
20O5
CHE-I : ATOMS AND MOLECULES
&
CHE-2 : INORGANICCHEMISTRY
Instructions :
7. Studentsregistered both CHE-1& CHE-z courses
Jor
should answer both the questionWpers in two
separoteanswer books entering thelr enrclment
number, codeand course
course title cleorlyon both
the onswerLaoks.
2. Students who haueregistered CHE l or CHE-2
Jor
shouldonswerthe relevont quiition poper after
entering their enrolmentnumbet coursecodeand
coursetitle on lhe answerbook
s.wfr. qfret
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fr.qfl.f.-z , ir+rriFmwrqt
fitn:
1. A qi dca.{-r eft el.sq.l.-z crEs*it
--:+ / ---:---j-:----+cH,- c cHr
L_9J ?
K
(iii) cH,- cH- cH" ct2/733 > ' 9i99
'z '--->t
tl Na2co' )
Na2corbqj_ laq
(b) Arrange the following in the increasing order of their
acid strengih :
Fluoroethanoic acid, ethanoic acid and
methoxyethanoic acid
Cive reasonin supportof uour answer.
Assign R or S configuration to
D-(+)-glycenldehyde.
(d) Which one is more stable - a t€rtiary carbocation
or a primarv carbocalion ? Exnlain using
hyperconjugation.
(e) Assign ihe conliguration as E or Z lo the following
.. H .,- ,.CHz
(r,
Br - i c = c a\Ct
Cl
,'n '
'-- \. ,- cooH
- ".\ c H :
ar/
(fl What happenswhen glycolis treatedwith 2
(i) Na at 327 K ?
{n) Na at 423 K ?
(g) Define iodine valueand saponification
!alu€.
3. Attempt any /iue of th€ lollowingqu€srrons
I
(a) D€fine chemicalshift. Using LR. and N.M.R. spectral
techniques, differentiat€ bet'rreen :
CHE-5 P.T.O.
h) What happens when 1x3
{i) 4-chloropyridine is keated with ammonia ?
(ii) Pyrrole is treated with acetic anhldride ?
(iii) Pnmary amine is reacted unih chlotoform in
presence of alkali ?
tc, Give one example of each ot the following reactjons :
(i) Oppenaueroxidation
(ii) Witbg reaction
(iii) Gattermann - Koch synthesis
(d) Give the r€action of
(i) chloroform with silver powder
(ii) chlorom€thane with sodium metal.
{iii) 1-bromo-1-butene wiih HBr in the presence of
peroxide.
(e) Give one example for each of ihe following categori€s
(i) dlsaccharide
(ii) antibiotic
{iii) alkaloid
Electrophilic substitution in pyridine iakes place at
3'position- Explain.
CHE-5
(g) The nitraiion of nitrobenzene gields miinikobenzene
as major product as shown below :
'i" lro, NO, NO,
HNO3 '/ H2SO4
t o l
Ao A+ - o
t t t
l1ol (91%) ""? NO2
(2%)
Explain giving reason.
4. Attempt any ttoe of the following:
(a) An organic compound A reacis with soda-amide
followed by methyl iodid€ and produced '8. B on
treatment wiih 40o/o H2SO4 in the presence of
mercuricions yields'C'. On treatmentwith iodineand
'C' yields
alkali, iodoform and a carboxylicacid 'D'
whose molecular
massis 60. ld€ntifuA, B, C and D.
{b) An organic compound A on ozonolysis gives two
products B and C. Both B and C give positive Toll€n's
test. B gives iodoform and carboxylic acid D when
treated with iodine and alkali. Acid D is the oxidation
product of compound C. Acid D gives Tollen's tesi.
IdentifyA, B, C and D. 4
{c) Give one example ol the lollowing reactions : 4
{i) Perkin reaction
(ii) Benzoincond€nsation
(iii) Riemer - Tiemann reaction
(iv) Williamsonsynthesis
CHE-5 P.T.O.
{d) How are primary, secondary alld tertiary amines
wiLhihe help of Hinsbergreagent )
differentiaied
What is Micha€] addition ? How will you synthesize
s-oxohexanoic acid using it ? 4
Attempt any t&o of the following : 4
Explain the mechanism of
(i) Birch reduction
(ii) Kolbe's electrolytic method for the preparation
of alken€s
(iii) Aldolcondensation
(gj Giv€ the producis of the following reaciions (attempt
any four) .
CH,CH"
t - "
,.':\ Crol 373 K
{t t(rt--------=-,------------>
-.-_./
40% H2SO4
(i)
(ii) CH?MsBr Coz
- >
(ii)H*/tl2o
3?!5
(iii) cH3cooH + (6H3)2NH
(iv) {i) LiAlHa , eth€r
CH3COOH
lii) H* /H}O
- +
SOlH
t -
. . ra\ (i) NaOH
-----:---------->
lv, I l) | ..........
\,-./ {ii)H'i+tro
t -
cHr
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cH3-cH2 -c- cH2- cH = cH - cH2- c - oH
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CHE.5 12 4,000
tr^:l
I rnL-o I
BACHELOR oF SCIENCE (B.sc,)
' Term-End Examination
December. 2O05
CHEMISTRY
CHE-6: ORGANIC MECHANISM
REACTION
Time : 2 hours M(lximum Marks : 50
Note t Attempt ony fout questions.AII questions corry
equol rnarks.
r. {a) Aftarge Ihe lollowjng haldes in ibe mdeasing order
of their reacdvitylowardsSN2 reaction: 't l
1
CH, = CH - CHrBr; CHrBr
CuHrCHrBr;
{b) What is lsoiopic labelling? How is it us€dto probe
the mechanism a r€action? Explainwith example.
of
lc) Why is 2-chlorcethyl ethyl sulphide hydrotysedin
acetone10,000 tim€s fasterthan the corresponding
etlp'r ?
CHE-6 P.T.O.
(d) (i) Nitrobenzene upon niiraiion with fumlng
HNO3/H2SO4 mixture forms m-dinitrobenzene
as the major product.Explatnwiih m€chanism.
(ii) Why are alkenes more reaciive ihan alkynaq
towards€lectrophilic
additionreactions?
2. la) What are siereospecific and stereoselectivereaciiohs ?
Explain with one example in each case.
(b) Write a detailed ilote on any tuio o{ ihe {ollowing
r€arangements:
(i) Pinacolpinacolonerearangem€nt
(ii) Benzil'b€nzilic acid reanangement
(m) Hofmann rearrangement
3. (u) What is the product obtained when neopentyl bromide
is h€aied with dilute ethanol ? Wnte all the steps
involv€d. , 23 I -
'
(b) Give structurei and names of the h,vo sornerrc
products obtained \rhen C6H5CH2CHCIC6H5 reacts
with alcoholic KOH. Giv€ mechanism ol the reaction-
{c/ Gve mechanism for the reaction of propene with
N-bromosuccinimide.
(d) What are singlet and triplet carbenes ? Draw their
CHE-6
4. (a) How wilf you prepareanv tr.uoo[ rhe lallowtog' 2!.2
{i) Propanone from diethyl malonate
(ii) Acetvl d.etone (penrdne
2.4-dionej trom ethyl
(iti) p-bromoaniliae from aniline
(b) Wriie shod notes on any ahree ol ihe following , 2x3
(i) Fluotesc€nce
1ii) Photosensitisation
(iii) Radical anion
{iv) Intersystemcrossing
(c) Arrange following radicals in the increasing order of
their stabiiity: ti
.cH", .cH(cH3)2' .C(CH3)3' .CH2CH3
5. {a) Compl€le rhe {ollowrngreacirons:
( i ) { c H r ) r c c H 2 () t r o Lr"
(,t) -l5c
O
__--_, cHo
t';'t L9J *i",o,n,
cH.,(oo..H(r^
v _
E
c.H.{Hc,o,cl
(iv) cHi{cH,J.cH,oH
*:# r
CHE-6 P.T.O.
{b) What is the paihway {or ihe photolysis of acetone ?
Give various products form€d. '1
^2
{c) Comment on the r€lative inertness of benzene
Lowards
additionreacLions.
6. {a) How are dyes classified on &€ basis of application ?
Give the method o{ prepara'iion o{ an azo dye. A1
5
{b) How is aspirin produced from phenol ? 2
(c) What are addition and condensation polymers ? Give
the preparationof one polymer of €ach kind. 4
(d) State Ma*ownikoff's rule with suitable examplg. 2
4
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