ASSIGNMENT BOOKLET

C E3,4

Bachelors Degree Programme (B.Sc.)

ORGANIC REACTION MEC ANISM

(Las! Da!e o" S#$m%ss%o&' March ()* +,)))

Please Note
You can take electives (56 to 64 credits) from a minimum of TWO and a maximum of FOU science disci!lines" vi#$ P%&sics" '%emistr&" (ife )ciences and *at%ematics$ You can o!t for elective courses +ort% a *,N,*U* OF - ' ./,T) and a *01,*U* OF 4- ' ./,T) from an& of t%ese four disci!lines$ 0t least 253 of t%e total credits t%at &ou re4ister for in t%e elective courses from (ife )ciences" '%emistr& and P%&sics disci!lines must 5e from t%e la5orator& courses$ For exam!le" if &ou o!t for a total of 64 credits of electives in t%ese 6 disci!lines" at least 76 credits s%ould 5e from la5 courses$ You cannot a!!ear in t%e Term8.nd .xamination of an& course +it%out re4isterin4 for t%e course$ Ot%er+ise" &our result +ill not 5e declared and t%e onus +ill 5e on &ou$

School o" Sc%e&ces I&-%ra Ga&-h% Na!%o&al O.e& /&%0ers%!1 Ma%-a& Garh%* Ne2 Delh%3)),,45 (6or 7#l1* +,), c1cle) 1

Dear Student, We hope, you are familiar with the system of evaluation to be followed for the Bachelors Degree Programme. t this stage you may probably li!e to re"read the section on assignments in the Programme #uide that we sent you after your enrolment. weightage of $% percent, as you are aware, has been earmar!ed for continuous evaluation, which would consist of one tutor"mar!ed assignment. &he assignment is based on Bloc!s 1, ', $ and (. I&s!r#c!%o&s "or 6orma!!%&g 8o#r Ass%g&me&!s Before attempting the assignments, please read the following instructions carefully. 1 )n top of the first page of your answer sheet, please write the details e*actly in the following format+

,-.)/0,-& -)+1.1111111.111 - 0,+1111..1111111 DD.,SS+.1..............111111 111111111111 111111111111 2)3.S, 2)D, 2)3.S, &4&/,

+ 1..........................1111 + 1..........................1111

SS4#-0,-& -).+ 1..........................1111 S&3D5 2,-&., + 1..........................1111 6- 0, -D 2)D,7 D &,+..1111111111.

PLEASE 6OLLO9 T E ABO:E 6ORMAT STRICTL8 TO 6ACILITATE E:AL/ATION AND TO A:OID DELA8. ' $ ( 9 < 3se only foolscap si8e writing paper 6but not of very thin variety7 for writing your answers. /eave ( cm margin on the left, top and bottom of your answer sheet. 5our answers should be precise. While writing answers, clearly indicate the :uestion -o. and part of the ;uestion being solved. Please note that+ i7 /ast date for submission of ssignment is 0arch $1, '%11. ii7 &he response to this assignment is to be submitted to the Study 2entre 2oordinator within eight wee!s of the receipt of this boo!let in order to get the feedbac! and comments on the evaluated assignment. iii7 4n any case, you have to submit the assignment response before appearing in the term end e*amination. ; 9e s!ro&gl1 s#gges! !ha! 1o# sho#l- re!a%& a co.1 o" 1o#r ass%g&me&! res.o&ses.

'

Wishing you all good luc!.

T#!or Mar<e- Ass%g&me&! Orga&%c Reac!%o& Mecha&%sm

Co#rse Co-e' C E3,4 Ass%g&me&! Co-e= C E3,4>TMA>+,),3)) Ma?%m#m Mar<s' ),,

No!e' = = = 1.

&his assignment is based on all the four Bloc!s of the entire course. ll ;uestions are compulsory. 0ar!s for the ;uestions are shown within brac!ets on the right hand side. Please answer in your o2& 2or-s> do not copy from the course material.

a7 Define a nucleophile and nucleophilicity. ?ow is the nucleophilicity different from the basicity@ ,*plain with the help of an e*ample. 697 b7 With the help of e*amples e*plain the factors affecting the basicity of a molecule. 697

'.

a7 What is meant by thermodynamic and !inetic control in chemical reactions@ ,*plain ta!ing an e*ample of addition of ?2l to 1, $"butadiene. 697 b7 ,*plain how isotopic studies help in ascertaining the mechanism of reactions. 697

$.

a7 2omplete the following reactions.

i7

2?$2?'2?'2l

l2l$

@
-?'

-?' A ii7

@
-)'

6'7 6'7

b7 c7

Does pyridine undergo Briedel"2rafts al!ylation@ ,*plain your answer. ,*plain the following+ i7 ii7 ynes are more reactive towards electrophilic reagents. ddition of ?Br to conCugated diene gives 1, ( addition product as maCor product.

6$7

d7

2omplete the following reactions.

i7 2?$2?'2? 2?' B?$ ?'),)?

ii7 2?$2

22?$

B?$ ?')' ,)?

iii7 2?$2?'2?

2?'

B?$
A 2r')"' D, ?

6$7

(.

a7 ,*plain the following with suitable e*amples. i7 ii7 b7 ehyde without " hydrogen does not undergo 2anni88aro reaction. Bor 0ichael addition electron withdrawing group must be present with arbon E carbon double bond. 6(7

,*plain the following terms with suitable e*amples. i7 ii7 Schiffs base ?emiacetal 6(7

c7 9.

What do you understand by syn"elimination and anti"elimination. ,*plain with a suitable e*ample. 6'7

a7 i7 Define the Sayt8eff rule. ii7 b7 c7 d7 i7 ii7 iii7 iv7 &he elimination of ?2l from chlorofumaric acid is 9% times faster than from chloromalic acid. ,*plain. 6$7 617 6'7

2alculate the o*idation state of carbo*ylic 2"atoms in 2? $2))?. What is selective o*idation@ #ive one e*ample. nswer the following. Who got the -obel pri8e for 2hemistry in 1FD$@ What do you understand by poisoned catalyst@ What is radical ion@ 4n which year Wolff E Gishner reaction was discovered@

6(7 697

<.

a7 #ive five methods for generation of carbenes. b7 2omplete the following reactions and write down various steps involved in them. i7
2? $ -? ' + 2?2l$
G)?

) ii7 2?$2
iii7 2?'
+

-?' A Br'
2?

-a)?

2?'Br

?Br hv

?2l iv7 2 ? - ' 2l + 2u2l < 9

)2?$ v7 Br " -?'H-?$

697

D.

a7 What are the motivating factors for the Wagner"0eerwein rearrangement@ Discuss its mechanism with a suitable e*ample. 697

b7

Write down various steps involved in the following conversions+

2))? i7 -?'

O -ylon"<

ii7

697 I. a7 With suitable e*amples e*plain J'A'K and J(A'K cycloaddition reactions. b7 2omplete the following reaction and give its mechanism. 2?$
or hv

697 697

F.

a7 Draw the Labslons!i diagram showing e*citation and deactivation routes. b7

697

#ive the classification of dyes based on their chemical structures. #ive one e*ample for each case. 697

1%.

a7 2omplete the following reactions+ i7

( 2? $ ) ' 2
)

= 2? ' + ( 2 < ? 9 ) ' 2 = )

ii7

2?$22?'2)2'?9

617 -a)22?9H2'?9)? 6'7 Br62?'7( Br 6$7 ?AH?')H

iii7 0alonic ester A 3rea

)? iv7 A ?2?)
)? v7
617 -a)?, 2)' 6'7 ?AH?')
?

-a)2'?9H2'?9)?
$I$ G

697

b7

Discuss the role of activating, deactivating and protecting groups briefly in organic synthesis. 697

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