[This question paper contains 8 printed pages.

Your Roll No .............. .

Sr. No. of Qurstion Paper : 140 l C

Unique Paper Code 32171302

Name of the Paper Organic Chemistr y - II

(Oxygen Containing Functional
Groups)

Name of the Cours~ B.Sc. (H) Chemistry

Semester III

Duration : 3 Hours Maximum Marks : 75

J Instructio ns for Candidate s

1. Write your Roll No. on the top immediately on receipt

of this question paper.

2. Attempt five questions in all.

1. (a) An organic compound A (C 5H 10 0) on reduction

with lithium aluminium hydride (LiAIH 4) forms
organic compounds B (C 3H 80) and C (C 2H 6 0).
B on oxidation followed by heati'ng with ·calcium
oxide gives D (C 5H10 O). C on reaction with NaOH/

P.T.O.
 l

b forms E and a yellow precipitate of Cl·{J J•

ldrnttf~ the organic compounds A. B. C. D and B.
Gl\e the name reaction involved durin g the
con, ersion of C to E al ong. with mechanist\\ .

t\ ,.,...,t t,) ldentif~ /\ ha, ing mt1 lccular formula (C 1/t C\)
12
, ~""t I
,J..l"'- m the follo" ing reacti 1.1. n. Gin~ the name of the
-,""I • , -
1, 1~ reaction and mec hani sm inYolYed. Write down the
~ ,...
l~,. .,~ role of cyani de ion in the fol lowing reaction :

0-CHO + -cN - - - - . . A (9,6)

(a) Carry out the foll owing conversions (any three) :

...

(i) 0--0-0
(ii) Propanal ➔ Propan-2-ol.

(iii) Ethane nitrile ➔ Butan-2-one.

(iv) Ethanal ➔ Butane.

(b) Identify A and B in the following reaction and

·b justify your answer :
/
 "').._....""l,

3
t40l Ut~~
eonc.H~ A ~~-">-
100°C

cH3CH~H (9,6)
cone, HiS()4
B

(a) carry out the synthesis of ~~ollowing

3. compounds either from EAA (Ethyl acetoacetate)
or DEM (Diethyl malonate) :

(i) Methyisuccinic acid

(ii) 4-0xopentanoic acid

(iii) Crotonic acid

(iv) Antipyrine

(b) Differentiate between the following (give visible

test only) and write down the reaction involved
(any three) :

(i) Acetaldehyde and acetophenone

(ii) Ethanol and propan-2-ol

(iii) Benzoic acid and p-cresol

(iv) Ethylchloride and chlorobenzene (9,6)

P.T.0.
 4
1401
a) Give reason for the following (any four):
4. (
\A;{lf",.\Y (il The rate of hydrolysis of the carboxylic
+"~c id derivatives is:
~t ~ CH 3COCI > (CH 3CO)iO > CH3CONH
2
"\.,-

sN\~ (ii) s~ 1 rea~tions . are acco~panied by

\- ~ > racemizat1on, while SN2 react10ns result in
')....- ~ • the inversion of the configuration.

(iii) 2.2-Dimethylpropanal gives Cannizzzaro's

reaction, while 2-methylpropanal does not.

~ - (iv) Carboxylic acid does not form oxime though

--1-!),•
\- 6. . they have carbonyl group (>C=O) in their
-,...- ~
structure.

'y;;,. (v) Malanie acid and P-keto carboxylic acid

• ' ~ v,1..,1-
~\J ;,...,J.. decarboxlate readily on heating 200°C.
~L~~ 9-
""" t.y
~ • (vi) Ketones cannot be prepared from acid
,, / -:C"'-~;- chloride and RMgX although they can be
~~.: prepared from acid chloride and R2Cd/
~ - R2CuLi .

(b) Prepare the following organic compound using

Wittig reaction :
1401 5

(12,3)

•
s. (a) Identify the organic compounds (A, 8) and explain@r'
their formation with the help of mechanism. . . D..

,
0- OCH3+HI ~ A + B
l ,t- I
'l-- vvJ1J' '

OR
/'--==-
Identify the organic compound (A) formed in the (9.)
C following re.action and explain its formation wit~ @) J
the help of m_echanism. . l --- ~ "'
5

(i) CH3CH2COO·Na•
_ _____ A

(b) Benzene on reacti?n with propene in the presence

of a Lewis acid /orms A (C 9H 12). A on aerial {§)
oxidation forms B (C 9H 12 OJ. B on acidic ).+)..}U.\..
)-- )-- >- )-
hydrolysis gives C (C 6H6 O) and D (C 3 H O).
6
Identify the organic compound s A, B, C and D.

P.T.O .
 RFWDYtteN:tfi e ft: ,. rT "' _

1401
6
• (c)
(i) Write down the products obtained on heating
\ 4-1-+ I
a. p and y-hydr6xycarboxylic acid separately.

(ii) Tertiary alkyl halides are not good substrates

for nucleophilic substitution reactions. Explain.

(iii) r-Chlorotoluene on reaction with NaNH in

2
liq. NH~ forms m-toluidine along with p-
toluidine. Explain. ( 4,2,3,3,3)

6.
Complete the following reactions :

(i) CH3CH2COOH Cl2'Red P ► ~'i <.>vi ~"1

.. J.
f
(ii)
0- C-NH2 Br2"alc. KOH
D.

(iii) O-o~ __ 2~-;:-o_cu____.,_

(iv)
------- I
~J-- -

ut , o-; J

V '}
7
7

Zn-Hg/HCI
.. u\..CH
_..s "J.-M.'l,~

N
• OH
CH30H/H♦
(vii)
~COOH

(ix)

~Q Dil. NaOH ► Ul\~'{,w -o -

(x) CH3CH2CHO (ii) /J. 0

CH3 u; ....
' >
I ► ~-~~y
(xi) H3C-C-Br + NaSH
I y4
H

0
Jif .
(xii)
6 CF3COOOH
.,'-

P.T.0 .
1401 8

CH
l 3
H3C-y-Br t CH30 Ne• _ _ _
..,

~xv) CHO
Cone. NaOH (15)
I
CHO
14 i, 1 ►

(1500)
 . " .. Pl,~~~-\'
[This qucst1on pnpcr contains 4 printed pages)
Ntn;' 'la
Your Roll No. : ························
J
( ~)
SI. No. of Q. Paper : 7394

Unique Paper Codt' : 32171302

Nrune of the Cou1 sc : D.Sc.(Hons.) Chemistry

Nrune of the Paper : C VI - Organic Chemistry - II

Sc1ncstcr : 111
Time : 3 Hours Maximum Marks : 75

Instructions for Candidates :

(a) Write your Roll No. on the top immediately
on receipt of this question paper.
(b) Atten1pt any five questions.
(c) All questions carry equal marks.

· 1. {a) An organic compound A (C9 H 100l reacts ,vith

iodine and aq. Sodium hydroxide to give
iodofarm and sodium salt of an acid B
(C 8HsO 2). B on reaction with chlorine and
red phosphorous forms compound C
(C 8H 7 O 2Cl). Hydrolysis of C followed by
acidification gives compound D. Identify A,
B, C, & D with the reactions involved. ;Name
the reaction by which B is converted to C.
Write the mechanism for conversion of A to
B. 10

P.T.O.
7394

(b) Write one test along with reaction involved

for distinction behveen the following pairs
of compounds : 2.Sx2=5
(i) 1-Pcntanol and 2-pentanol "
(ii} Acetaldchydc and bcnzaldehydc

2. HO'w ,vill you prepare the con1pounds a, b, & c

from ethyl acetoacetate and d & e from diethyl
malonate ? 3x5= 15
(a) 3-Methylpentan-2-one
(b) Succinic acid
(cl 2-Methylhexanoic acid
(d) Cinnaniic acid
(e} 5-Ethylbarbituric acid

3. Exl)laln the follo,.,-ing : 3x5= 15

(aJ The rate of hydrolysis of the carboxylic acid
derivatives is
CH3 COC1>(CH3 CO) 2 O>CH3 CONH2 •
(bJ SN: reactions are accompanied by
racemization as we!: as inversion of
configuration.
(c) o-Nitrophenol is a weaker ac1d than
p-nitrophenot
(d) Reactivity of aryl halidas towards ~ucleophilic
substitution increases with the sub&titution
of nitro group at ortho-and para positions.
2
 7394

(e ) t -Bu tyl methy l ether is prepar ed by reactio n

of m ethyl chlori de and sodium t-buto xide
rather than from t-buty l chlorid e and sodium
m ethoxi d e.
4. Write the produ cts for the follow ing along with
equat ions: 3x5=15
(a) When oxalic acid, succin ic acid and adipic
acid are heated separa tely.
(b) Ethyl aceta te is treate d with sodiu m
ethox ide fallow ed by reacti on with one mole
of ethyl iodide in the prese ~e of sodium
metal .
(c) Pheno l is heate d with carbo n dioxid e under
presu re in the presen ce of sodium hydrox ide
fallow ed by reacti on \Vi th acetic anhyd ride
in the presen ce of acid cataly st.
(d) Aceto ne \vhen reacte d \Vith hydro xyl amine
followed by treatment \\ith Cone. }\SO •
4
(e) Malei c acid a..~d fumar ic acid are treate d
separ ately \Vith dil. KMnO ~·

5. How will you carry out the follo\\-ing conve rsions ?

3x5=15
(a) Ethan oic acid to Propa noic acid
(b) Benze ne to ethox ybenz ene
(c) Aceto ne to 2-met hyl-2 -butan ol
{d) Benza ldehy de to benza mide
{e) Anilin e [O fluoro benze ne

3 P.T.O.
739 4

6. Com plet e the foJlo wing reac tion s. Writ e the

n1ec hani sn1 of the reac tion invo lved . Sx3= 15
I Jil. Nu OJ I ?
(a) Cl l,1Cl I1 C'l JO - ---
Aq. /\k. KCN ,1
(b) C6 H~Cl l0 r I

7. Writ e shor t note s on any thre e of the follo wing

with emp hasi s to (i) the func tion al grou p that
unde rgoe s thes e reac tion s, (ii) prod ucts form ed,
(iii) reac tion cond ition s and (iv) mec hani sm.
5x3= 15

(a) Baey er-V illig et oxid ation

(b) Can nizz aro reac tion
(c) Frie s rear rang eme nt
(d) Benx il-be nzili c acid rear rang eme nt
(e) Mich ael addi tion

4 180 0
[This qm.'stion papl't contains 4 printed pages.]

Your Roll No ......•.•.. •···

JC
Sr. No. of Question Paper : 4 2

Unique Paper Code 32 171302

Name of the Paper C VI - Organic Chemistry -

II

Name of the Course B.Sc. (Hons.) Chemistry

Semester III

Duration : 3 Hours Maximum Marks : 75

Instructions for Candidates

1. Write your Roll No. on the top immediate'ly on receipt

of this question paper.

2. Attempt any five questions.

3. All questions carry equal marks.

1. (a) An organic compound A (C 4H 80) reacts with

hydroxylamine to give two isomeric compounds B
and C (C 4 H 9 0N). Compound B and C when /\'
treated with sulphuric acid separately, give
compounds D and E (C 4H 9 0N) respectiv~ly.
Identify A, B, C, D & E and write all the reactions
involved. Name the reaction by which B is
converted to p along with the mech~nism.
(10)

P.T.O.
42 2

(b) Write one test with reaction involved for distinction

between the following pairs of cmnpounds.
(i) Benzyl alcohol and phenol

(ii) Acetaldehyde and acetone

(2x2.S)

2. How will you prepare the con1pounds a, b, & c

from ethvl acetoacetate and d & e from diethyl
malonate? (5X3)

(a) 3-Methylpentan-2-one

(b) Pentane-l.5-dioic acid

(c) n-Butyric acid

(d) Adipic acid

(e) 5.5-Diethylb2.rbituric acid

3. Explain the follow:ng: (5X3)

(a) Maleic acid is stronger than fumanc acid. However

the second dissociation of fumanc acid occur more
readily than maleic acid.

(b) SN2 reactions invoive complete inversion of

configuration.

(c} Phenol is a weaker acid than p-nitrophenol.

(d) Vinyl chloride is less reactive than ethyl chloride

. towards nucleophilic substitution reactions .
\) Per~ -=- !4 Q~ .,. · o-SP
.
 42 3

(e) Methoxy benzene is prepared by reaction of methyl

chloride and sodium phenoxide rather than from
chlorobenzene and sodium methoxide.

4. Write the products for the following along with

equations : (5x3)

(a) When a.-, ~-, and y- hydroxy acids are heated

separately. •

(b) Ethyl acetate is treated with sodium ethoxide

followed by reaction with one mole of methyl iodide
in the presence of sodium metal.

( c) Phenol is heated with chloroform in the presence

n -r....
re I ~fl\,, of sodium hydroxide followed bv reaction with
J

sJ. ~~ alkaline KMnO4 •

.,. . ,I. 0.. µ
. dil. NaOH.
, is treated ,v.hh
¢WI.,,l.)k'<u, (d) 2-Phenyl-1-ethancrl
1·"
0
v· (e) Formic acid and malonic acid ar e heart ed
separately. j~'-dO ,

5. How will you carry out the follo\.ving conversions:

(5'><3)
(a) Propanoic acid to lactic acid
(b) Phenol to aspirin

( c) Prop anal to 2-butanol

(d) Phenylacetaldehyde to phenylacetamide

(e) Aniline to iodobenzene.

P.T.O.
 •

42 4
6. (\'11lpktc thr follnw111g reactions. Write the mechanism
of thl' H'action involved. (3/5)

(b) ~HO Con£;,_~aOH >?

CHO

7. Write short notes on any three of the following with

emphasis to (i) the functional group that undergoes
these reactions, (ii) products formed, (iii) reaction
conditions and (iv) mechanism. (3x5)

(a) Benzoin condensation

(b) Perkin reaction

( c) Wittig reaction

(d) Claisen rearrangement

( e) Dieckmann reaction

(1800)
 ::!7r, M ~ ~ Ntf'S'J,ol 1
I l'his que:--tion pnpc-1 contnins <, ptintcd pa ges. I ,· fl,t S

Your Holl No .............. .

Sr. No. of Qurstion Pnpcr : c, 4 H4 11 C

Unique Pap(.'t Code 321 ·11102

Name or the Paper O, ganic Chemistry JJ (Oxygen

Containing Functional Groups)

Na1ne of the Course B.Sc. (lions.) Chemistry

Sem,ester III

Duration : 3 Hours Maximum Marks : 75

Instructions for Candidates

1. Write your Roll No. on the top immediately on receipt of

this question paper.

2. Attempt any six questions.

---...
3. ~Question No. 1 carries 15 marks.

I•

1. (a) An organic compound ' A' (C4H9 Cl) on hydrolysis with

aq. alkali fo rms compound ' B' (C 4H 10 0). 'B' on
oxidation forms another compound 'C' which does not
reduce Fehling's solution. On treatment with iodine and
NaOH both 'B' and 'C' form iodoform. 'B' on
dehydration with cone. H2 S0 4 forms mainly 'D' which

l -;.. rJt ) 'I

P.T.O.
 tln tl onol} sis forms h, o molecules of
ldentif, A, R. C' and D. "ntc
. the react"acc1a1 de hydc
and gl\e mechamsm • ~
of formation of i,,
•011sr ittv Ivcd·
0
compound C'. t (10 • Or111 fro
111

(b) \\'rite one test with reaction involved to dislj .

folio" 1ng pairs of l'Olnpounds. , ngll1sh th c
"t
(i) Ethyl alcohol and llll'thyl alcohol

(ii) Acetaldchydc and acetophenone.

(I I ,4)

2. (a) Complete the following and give the name of the reaction
in each case.

CH3 Ph r v\-G--(.;
1! P
) ,, I
(i) CH 3 - C - C - Ph dilute H,SO4
- ►
..) u'S
I I

OH OH Heat

CH3C00 Na
(ii) Q-cHo + (CH,COJ,O -----·►

J- '"'~'\

H C OH
'__j=✓
(iv) 0 2 ND
 3
484

Con NaOH
►
(v) o,-Q-cuo
- ',/
,;,.

0 CH3COCH2COCH3
II ►
(vi) IJ3C- C =CH --- C -- C6H,s C2H50Na
II 'l _, I
~
I" _,
'I
(b) Write the structure of alcohol formed from Cfl3-CH2-
CII=CH on oxymercuration-demercuration and give the
2 ~
mechanism involv~d. ~ '{!A....- (9,3)
I'- ,
. /
j '-. t.,_ Vf
-;1 -otipnr·
f'"v1.1'r, v.
( 1,\,(/ ,._ ,,;r I
t,
),,( ,._t'l,
.,

3. (a) Give and explain the relative reactivity order of the

following derivatives of carboxylic acid towards
nucleophilic substitution reaction

(b) Give the products formed on heating the dicarboxylic

acids with the formula HOOC-(CHJn-COOH where
n = 0, 1,3,5. ,,,.,. ,l.. -

'I "LI' Jv\"(J.",_ ~'- fl.\-¼ .J

ii 'l_

(c) (i) Hydrolysis of CH3CH2 SCH2CH 2Cl proceeds at a

much faster rate than that 1 n case of
CH 3CH20CH2tCH2Cl.
.., ... A,\ "I
('-

l t- , l
,. ~
' '\ ,., ,. .... c '
I
• . \
\. \ P.T.O.

)
 6484 4

Jaj' How do you explain the formation of

1-
methylcyclopcntan-l-ol on hydrolysis of
f Vt
)
t) V'I
CH 2l
r ~''tr'
t,.tt~ (9C¥j
(4X3)
'3, l(
I0

4. (a) \Vrite the sequence of reactions for the preparation of

J9 Isopropyl iodide fron1 n-propyl bromide

OCH
f '(
- (ii)
N...___-U

2
P .

by Wittig reaction
,,1 ... •'-, ,

-< -1 Ph .. ', h.".PCAr. P.r JJ,1.i, Ph. p-t,. , ~

-(b) Write the reaction sequence involved in the ring ope ning

f"~ n
\(., tJJ\f> rt'~
' with 111cthanol
4Xr o'f' 111 acidic medium. Al so explain the
formation of a different product ov reaction with sodium
'
mcthoxidc. t\ '- (6x2)

5. Explain why

(i) Aryl halides undergo nuckoplultc d1sp.acen1ent reaction

easily if a strong electron" 1thdraw1ng group is p ~s 1t
at ortho or para position .
•
6484 I~
~ , f J
(ii) . Vinyl chloride is less reactive than ethyl chloride
towards nucleophilic substitution reactions.

(iii) Ketones cannot be prepared from RCOCl and RMgX

although they can be prepared from RCOCl and R2Cd.

(iv) o-Hydroxy benzaldehyde has lower boiling point and

decreased water solubility as compared to that of its
meta or para isomers. (3x4)

6. (a) Write the synthesis of the following compounds using

either ethylacetoacetate or diethylmalonate

(i) 3-0xobutanoic acid

(ii) Cyclohexyl methyl ketone

(iii) II exane-2,5-dionc w

(b) o-13romoanisole and m bromoanisole both give the same

product on reaction with NaNII 2 in liquid ammonia.
Explain with mechanism. (9,3)

7. (a) Write the structure of the compound~ A, B and C. Give

mechanism of formation of compound A. C/..A
O w..~ C.>-:: Cl~ ,.f.,_ ~I/
I

II i) Zn •
H3C-C-CH3 - - - ~ A _J}_I..L.9 ~ B

I'
ii) Heat

w
Vt
l H,/Pt
I ,I

' ... C -
P.T .O.
 6484
( y I ~
I
(.h) \\'1 itc do" 11 the 1ncclrn111sm fcH the following rcacticm
Heat
► RCI t- S02 + HCJ

(c) E:\plain why

(i) Enol form of ethylacetoacetate 1s more stable

"'
'r v\ than that of ethyl acetate
u/\ '-- ,1 ,. '
~ 'CM,-:: L --01 ½
C 1

(ii) Recemization is observed in reactions following

1
SN pathway. (4x3)

Q
v.
~'rite short r _ : - ~- -- any THREE of the following:

(i) Claisen-Schmidt reaction

(ii) Base catalys e~ amide hydrolysis

\
(iii) Michael addition l
(iv) Curtius reaction
(4x'J)

(1800)