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MSCCH-07

June - Examination 2016

M.Sc. (Final) Chemistry Examination Synthetic Organic Chemistry

Paper - MSCCH-07

Time : 3 Hours ] [ Max. Marks :- 80

Note: The question paper is divided into three sections A, B and C.

Write answers as per the given instructions.

{ZX}e : ¶h àíZ-nÌ "A', "~' Am¡a "g' VrZ IÊS>m| ‘| {d^m{OV h¡& à˶oH$

IÊS> Ho$ {ZX}emZwgma àíZm| H$m CÎma Xr{OE&

Section - A 8

×

2 = 16 (Very Short Answer Types Questions)

Note: Answer all questions. As per the nature of the question delimit your answer in one word, one sentence or maximum upto 30 words. Each question carries 2 marks.

IÊS> - "A' (A{V bKw CÎmar¶ àíZ)

{ZX}e : g^r àíZm| Ho$ CÎma Xr{OE& AnZo CÎma H$mo àíZmZwgma EH$ eãX,

EH$ dm³¶ ¶m A{YH$V‘

30

eãXm| ‘| n[agr{‘V H$s{OE& à˶oH$ àíZ

273

(2)

1) (i) Complete the following reaction

{ZåZ A{^{H«$¶m H$mo nyU© H$s{OE&

OR/

AWdm

(ii) Give the formula of Wilkinson’s catalyst.

{db{H$ZgZ CËàoaH$ H$m gyÌ {b{IE&

OR/

AWdm

Complete the following reaction.

{ZåZ A{^{H«$¶m H$mo nyU© H$s{OE&

C H6 3-C CH/ Et Cu MgBr2

(iii) Complete the following reaction.

{ZåZ A{^{H«$¶m H$mo nyU© H$s{OE&

O+_CH3 2i CuLi OR/

AWdm

2RLi + Cu CN

(3)

(iv) Give the two important characteristics of a good protecting group.

EH$ AÀN>o àmoQ>p³Q>¨J g‘yh Ho$ H$moB© Xmo ‘hÎdnyU© bjU ~VmBE&

(v) Define functional group interconversion (FGI)

{H«$¶mË‘H$ g‘yh AÝVn[adV©Z H$mo n[a^m{fV H$s{OE&

(vi) Define the term chemoselectivity.

H$s‘mogobop³Q>{dQ>r nX H$mo n[a^m{fV H$s{OE&

(vii) Define homeomorphic ligands.

hmo‘mo‘mo[’©$H$ {bJ¡ÊS> H$mo n[a^m{fV H$s{OE&

OR/

AWdm

What is Metallocone?

‘oQ>mbmoH$moZ ³¶m h¡?

(viii) Define Stereoselectivity.

ñQ>r[a¶mogobop³Q>{dQ>r H$mo n[a^m{fV H$s{OE&

Section - B 4

×

8 = 32 (Short Answer Questions)

Note: Answer any four questions. Each answer should not exceed 200 words. Each question carries 8 marks.

(IÊS> - ~) (bKw CÎma dmbo àíZ)

{ZX}e : {H$Ýhr Mma àíZm| Ho$ CÎma Xr{OE& CÎma

200

eãXm| ‘| Xr{OE& à˶oH$

àíZ

8

A§H$ H$m h¡&

2) Write short notes on:

{ZåZna g§{jßV ZmoQ> {b{IE&

(i) Epoxidation of alkenes

EoëH$sÝg H$m Bnmo³grH$aU

(4)

3) Complete the following reaction.

{ZåZ A{^{H«$¶m H$mo nyU© H$s{OE&

(i) (ii)

(iii)

(iv)

4) Write short notes on any two of the following:

{ZåZ ‘o go {H$Ýhr Xmo na g§{já ZmoQ> {b{IE…

(i) Aldol reaction

EoëS>mb A{^{H«$¶m

(ii) Stock Enamine Synthesis

ñQ´>moH$ BZEo‘rZ g§íbofU

(iii) Retrosynthetic analysis of TM (45) TM (45)

H$m [aQ´>mopñZWo{Q>H$ {díbofU

(5)

5) What is Nazarov cyclisation? Discuss with an example.

ZoOamod MH«$sH$aU ³¶m h¡? EH$ CXmhaU XoH$a g‘PmBE&

OR/

AWdm

Explain Meerwain-Ponndorf-Verley Reduction.

‘o{d©Z-nmo§S>amo’$-d}bo AnM¶Z H$mo g‘PmBE&

6) Give the retrosynthesis and synthesis of the following molecules.

{ZåZ{b{IV AUwAm| Ho$ [aQ´>mog§íbofU Ed§ g§íbofU H$mo g‘PmBE&

(i)

(ii)

OR/

AWdm

Explain the reduction of nitro group.

ZmBQ´>mo g‘yh H$m AnM¶Z g‘PmBE&

7) Using butadiene as one of the precursor how would you plan the synthesis of the following.

ã¶yQ>mS>mB©Z H$mo àrH$aga Ho$ ê$n ‘| Cn¶moJ H$aVo hþE Amn {ZåZ{b{IV H$m g§íbofU H¡$go H$a|Jo&

OR/

AWdm

Enumerate four monocylic aromatic ions studied by you.

(6)

8) Explain the reversal of polarity with suitable examples.

Cn¶w³V CXmhaUm| H$s ghm¶Vm go "Y«wdUVm H$m ~XbZm' H$mo g‘PmBE&

9) Outline the synthesis of enantiomeric - 2 - methyl butanoic acids.

EZEZñ¶mo‘a-2-‘o{Wb ã¶yQ>oZmoB©H$ Aåb Ho$ g§íbofU H$s ê$naoIm {b{IE&

Section - C 2

×

16 = 32 (Long Answer Type Questions)

Note: Answer any two questions. You have to delimit your each answer maximum upto 500 words. Each question carries 16 marks.

(IÊS> - g) (XrK© CÎmar¶ àíZ)

{ZX}e : {H$Ýhr Xmo àíZm| Ho$ CÎma Xr{OE& CÎma H$mo A{YH$V‘

500

eãXm| ‘|

n[agr{‘V H$aZm h¡& à˶oH$ àíZ

16

A§H$ H$m h¡&

10) Explain in detail about the oxidation of alcohols with atleast the oxidation of alcohols with atleast, three types of reagents.

VrZ àH$ma Ho$ A{^H«$‘H$m| H$s ghm¶Vm go EëH$mohmob Ho$ Am³grH$aU H$mo {dñVma go g‘PmBE&

11) Explain in detail the reaction of alkyl boranes with carbon monoxide.

EopëH$b ~moaoZ H$s H$m~©Z ‘m¡ZmoAm°³gmBS> Ho$ gmW hmoZodmbr A{^{H«$¶mAm|

H$mo {dñVma go g‘PmBE&

OR/

AWdm

Explain the synthesis and reactions of Phenanthrene in detail.

{’$ZoZWuZ Ho$ g§íbofU Ed§ AnM¶Z H$mo {dñVma go g‘PmBE&

(7)

12) Write the retrosynthesis and synthesis of Disparlure.

S>rgnmabwa H$s [aQ´>mog§íbofU Ed§ g§íbofU H$mo {b{IE&

OR/

AWdm

How would you explain disconnection approach?

n¥WH$Ëd ÑpîQ>H$moU H$mo Amn H¡$go g‘PmE§Jo?

13) Discuss some specific oxidation of carbonyl compounds.

H$m~«moZmBb ¶mo{JH$mo§ Ho$ {d{eîQ> Am³graUm| H$mo g‘PmBE&

OR/

AWdm

Explain enantiomer differentiation reactions and diastereomer differentiation reactions. with suitable examples.

BZEZñ¶mo‘a {d^oXrH$aU Ed§ S>m¶ñQ>r[a¶mo‘a {d^oXrH$aU A{^{H«$¶mAm| H$mo

Cn¶w³V CXmhaU XoH$a g‘PmBE&

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