Electronic Displacement Effects

8/16/2019 Electronic Displacement Effects

1/13

NNHN

NH

CH2 = CH ——CH3

CH2 = CH —O—CH = CH2

CH2 = CH —C N:

CH2 = CH —CH = O

CH2

OO

OCH3 —C—CH2

O

H—C—CH = CH —CH2

C+H2

O–

: NH

OO

CH3 — CH = CH — CH = CH — C+H — CH3

CH3 — CH = CH — CH = CH — C+ H3

CH3 – C = CH2 (b) H – C = CH – CH = CH2

O— O—

(c) CH2 CH2 CH2 C+H2

+

+

+

(d)

+

(e)

O— O O O

(h)(f) N+H (g)

O+

O—

CH3 – CH – CH = CH – CH = CH – CH3 (j) CH3 – C+H—CH = CH – CH = CH2

1. In which of the following lone!"i# indic"ted i$ in%ol%ed in #e$on"nce :

(") (b) (c) (d)

Ans: (b) (d)

2. In which of the following lone!"i# indic"ted i$ not in%ol%ed in #e$on"nce:(")(b)

(c) (e ) (f)

(d)

Ans : (b) (d) (e)3. "w the #e$on"nce fo#'$ to $how the deloc"li"tion of ch"#ge$ in the

following ion$

(") (f)

(b) (g)

(c) (h)

(d)(i)

(e) (j)

Ans:

R.K.SHUBHANKER Phone: 9350928856 PAGE 1

*C,ONIC &I-*/C0N C-


2/13

H2C – N N H2C = N = N H2C – N – N

() (C)

(I) CH3 – CH—CH3 "nd (II) CH3 —N— CH3

CH3 —C—CH3 CH3—C—CH3

"nd (II)

C+H2C+H2

O

. Con$ide# $t#4ct4#"l fo#'4l"$ /5 "nd C :

(") /#e /5 "nd C con$tit4tion"l i$o'e#$5 o# "#e the6 #e$on"nce fo#'$7(b) 8hich $t#4ct4#e$ h"%e " neg"ti%el6 ch"#ged c"#bon7

(c) 8hich $t#4ct4#e$ h"%e " !o$iti%el6 ch"#ged c"#bon7(d) 8hich $t#4ct4#e$ h"%e " !o$iti%el6 ch"#ged nit#ogen7(e) 8hich $t#4ct4#e$ h"%e " neg"ti%el6 ch"#ged nit#ogen7(f) 8h"t i$ the net ch"#ge on e"ch $t#4ct4#e7(g) 8hich i$ " 'o#e $t"ble $t#4ct4#e5 / o# 7 8h67(h) 8hich i$ " 'o#e $t"ble $t#4ct4#e5 o# C7 8h67

Ans: ! Resonn"e #o$%& b ! A& "!'& d!A B& e !B '& #!0& !B& h!B

9. In e"ch of the following !"i#$ of ion$ which ion i$ 'o#e $t"ble:(") (d)

(b)

(c)

Ans: () *& (b) *& (") **. (d) **

. Identif6 le$$ $t"ble c"nonic"l $t#4ct4#e in e"ch of the following !"i#$:(") (d)

(I) CH9 – C+H2 "nd (II) CH2 =

(I) CH3 – C+H2 "nd (II) CH2 =

N—H O—

C C

H H H H H

+ Ó


3/13

O— O

C C

H CH2H C— H2

+CH2

(b)

(c) (e)

Ans+ () *& (b) **& (") **& (d) *& (e) **


4/13

N

"nd CH2 = CH – CH = CH – CH = CH2

NO2

CH2D

"nd

OH

"nd

NO2"nd

O

O

O

o

"nd

N

H

"nd

O

(f) – %e ch"#ge i$ on 'o#e elect#oneg"ti%e "to' th"n if – %e

Ans: () (b) (") (#)

1E.Identit6 elect#on – don"ting g#o4!$ in #e$on"nce "'ong the following :

(") – CONH2 (c) – OCOCH3 (e) – CHO (f) —NHCOCH3(b) – NO2 (d) – COOCH3

Ans: (") &(#)

11.Identit6 elect#on – withd#"wing g#o4!$ in #e$on"nce "'ong the following :

(") —COOH (c) – COCl (e) – Ó – CH = CH2 (f)

(b)— CONHCH3 (d) – CN

Ans: ()& (b)& (")& (d)& (#)

12.8hich of the following g#o4!$ c"n eithe# don"te o# withd#"w " !"i# ofelect#on$ in #e$on"nce de!ending 4!on $it4"tion :(") – NO2 (b) –NOF (c) – CH = CH2F (d) – CHO (e) – NH2 (f) – N

= NHF/n$: (b5 c5 f)

13.8hich of the following !"i#$ h"$ highe# #e$on"nce ene#g6 :(") CH3COOH "nd CH3COON"(b) CH3 – CH O

D "nd CH2 = CH – OH(c) "nd

(d)"nd

(e)

Ans: () ** (b) * (") * (d) * (e) *

1.8hich of the following !"i#$ h"$ le$$ #e$on"nce ene#g6 :(")

(b) (d)

(c) (e)

Ans: () **& (b) **& (") **& (d)**& (e) *


5/13

"nd CH2 = CH – CH2

N N

H

"nd

CH2

12

3

12

3

12

3

O

O

O

O

CH2

C

CH2 CH2

O

C

NH2 H

O

C

NH2H2N

"nd

O

C

NH2H2N

O

C

NH2CH3

"nd

O

C

ClCl

O

C

ClCH3

19.8hich of the following !"i#$ h"$ highe# #e$on"nce ene#g6 :(")

(b) CH2 = CH – O – CH = CH2 "nd CH2 "nd CH2 = CH – NH – CH2(c) CH2 = CH NH "nd HN = CH – NH(d) CH2 = CH – "nd CH2 = CH – #

(e)

Ans: () *& (b)**& (") ** &(d) * &(e) *

1.he$e "#e th#ee c"nonic"l $t#4ct4#e of n"!hth"lene. >"'ine the' "nd Gndco##ect $t"te'ent "'ong the following :

(") /ll C – C bond$ "#e of $"'e length(b) Cl – C2 bond i$ $ho#te# th"n C2 – C3 bond. F(c) C1 – C2 bond i$ longe# th"n C2 – C3 bond

(d) None1


6/13

I

NH2

CHO

NH2

II

NH2

III I

CH2 = NH

1 2C CH 1 2CH2 = CH31 2CH= CH2 1 2C CH

CHO

NH2

(e)

Ans: () * (b) * (") ** (d) * (e) * (#) *

19.

/'ong the$e co'!o4nd5 the co##ect o#de# of C – N bond length$ i$:(") I J I JIIJIII (c) III J I J II J I(b) III J II J I J IF (d) III J I J I J II

2E.C1 – C2 i$ $ho#te$t in(") (b) (c)

(d)

21./'ong the following 'olec4le$5 the co##ect o#de# of C –C bond lenght i$(") C2H J C2H J CH J C2H2 (c) C2H J C2H J

C2H2 J CH(b) C2H J CH J C2H J C2H2 ( CH i$ benene ) (d) C2H J C2H J

C2H2 J CH22.CH3O – CH = CH – NO2

CH2 = CH – NO2CH2 = CH – Cl

CH2 = CH28hich of the following i$ the co##ect o#de# of C – C bond length$ "'ong the$eco'!o4nd$ :(") I J II J III J IF (c) I J III J II J I(b) I J III J II J I (d) II J III J I JI

23.In which of the following 'olec4le$ #e$on"nce $t#4ct4#e "#e eB4i%"lent :(") HCOOD F(b) CH2 = CH – CH = CH2(c) (d)

2.(I) CH3 – O – CH = CH – CH = CH2(I) CH3 – O – CH – CH = CH CH2(II) CH3 – O = CH CH = CH CH2

/'ong the$e th#ee c"nonic"l $t#4ct4#e ( th#o4gh 'o#e "#e !o$$ible ) wh"two4ld be thei# #el"ti%e cont#ib4tion in the h6b#id :(") I J II J III (b) III J II J I (c) I J III J II

(d) III J I J II29.Co'!"#e the C – N bond – length in the following $!ecie$ :

"nd

⊝

⊝


7/13

H2N

O

H2NH2N

NO

i$o>"ole

N -

153thi"ole

O

!6#"n

+

O

H

6#6li4' ion

O

O

6#one

NH

152 dih6d#o!6#idine

NH2

N

NH

O

c6to$ine

C

/

&

+ 3H2dKC

(i) (II) (III)

Ans : /// // /

2.o# 1 – 'etho>6 – 15 3 –b4t"diene5 which of following #e$on"ting $t#4ct4#e i$the le"$t $t"ble 7(") H2 C – CH – CH = CH – O – CH3 (c) H2C = CH – CH – CH – O

CH3 F(b) H2 C – CH = CH CH = O – CH3 (d) H2 C = CH – CH CH = O –

CH32!l"in wh6 e"ch co'!o4nd i$ "#o'"tic5 "nti"#o'"tic o# non"#o'"ntic.

(") (c)

(b) (d)

(e) (f)

(e)

Ans : .() A (b) A (") N.A (d) A (e) A (#) N.A.() A

2A.Con$ide# the gi%en #e"ction :

R.K.SHUBHANKER Phone: 9350928856 PAGE

ΘΘ

ΘΘ


8/13

"nd

"nd

CH2

CH3

"nd

CH3

CH3

NO2

NO2

NO2

#

9

31

In the "bo%e #e"ction which one of the gi%en #ing will 4nde#go #ed4ction7

Ans:A

2. /##"nge the following in thei#(I) $t"bilit6 o#de# "nd (II) he"t ofh6d#ogen"tion.(") (b) (c) (d)

Ans: (*) d " b +3E. /'ong the following !"i#$ identif6 one which gi%e$ highe# he"t of

h6d#ogen"tion :(")

(b)

(c)(d)

Ans : .() * & (b) *& (") ** & (d) *

31.8hich of the following $t"te'ent$ wo4ld be t#4e "bo4t thi$ co'!o4nd :

(") /ll th#ee C – N bond$ "#e of $"'e length.(b) Cl – N "nd C3 – N bond$ "#e of the $"'e length b4t $ho#te# th"n C9 – N

bond.(c) Cl – N "nd C3 – N bond$ "#e of the $"'e length b4t longe# th"n C9 – N

bond.(d) Cl – N "nd C3 – N bond$ "#e of the die#ent length b4t both "#e longe#

th"n C9 – N bond.

CH3 – CH = CH – CH3 "nd CH3 – CH2 –


9/13

(b)in CH2 = CH – OCH35 the#e i$ $ingle bond ch"#"cte# d4e

H2C = CH – OCH3 CH2 – CH = O+ CH3(c)Conj4g"te b"$e of CH3-H ie5 Ch3- i$ 'o#e $t"ble th"n c"#bon –

(d)in CH2 = CH – NH2 lone !"i# of N i$ deloc"lied CH2 = CH – NH2 CH2 – CH = NH2

() e 4o $esonn"e H2' ! 'H '- ' H2 'H ! '-

CH3 – CH2 CH3 – CH – CH3

(b)(") (c)

CH3 – C

CH3

CH3

(") (b) (c)

(") (b) (c)


(b)(") (c)

CH3 – C

CH3

CH3

(") (b) (c)

(") (b) (c)


(b)(") (c)

CH3 – C

CH3

CH3

32.&i$c4$$ the following ob$e#%"tion$ :(") C – Cl bond in %in6l chlo#ide i$ $t#onge# th"n in chlo#oeth"ne.(b) C"#bon – c"#bon bond length in eth"ne i$ $ho#te# th"n in CH2 = CHOCH3(c) CH3-H i$ $t#onge# "cid th"n CH3OH(d) CH3CH2NH2 i$ $t#onge# b"$e th"n CH2 = CHNH2

/n$:

33.8#ite $t"bilit6 o#de# of following inte#'edi"te$ :(i)

(ii)

(iii)

(i%)

(%)

(%i)

(%ii)



10/13

b (//) " b (///) b " (/7) " b (7) " b (7/) b" (7//) b"(/) b" () d"b (/) b" (//) "b

(") (b) (c)

Cl

CH2

N

CH2

O O

CH2

CN

(d)CH2

(") (b) (c) CH2CH2

O0eN

CH2

O O

(%iii)

(i>)

(>)

(>i)

(>ii) o

Ans :

3.8#ite the $t"bilit6 o#de# of following inte#'edi"te$:(i)


11/13

(") (b) (c) CH2

OH

CH2

OH

CH2

OH

(") (b)

CH2 CH2

Cl

(")

CH2—CH

O

(b)

CH2—CH2

(c)(") (b)O O O

(c)(") (b)C2 – CH2 – CH2 C3 – CH2 C3

C3 CCl3(") (b)

C3 CCl3(") (b)

CH2

(")

CH2 – CH2

(b) (c)

(") (b) (c)

(ii)

(iii)

(i%)

(%)

(%i)

(%ii)

(%iii)

(i>)

(>)

(>i)



12/13

(") (b)

(d)(b) (c)

(") (b)(c)

(") (b) (c)

C

CH2H

HH

CH2

CH

HH

C

CH2

HHH

(") (b) (c)CH2

CH3

CH2

CH20e

CH2

CH 0e2

(d)CH2

CH 0e2(/) b " (//) b"d (///) "b (/7) b (7) b (7/) b" (7//) "b (7/

() b" (/) b" (//) b (/7) "bd (7) "b (7/)

(b)(")

(") (b) (c)(d)

(>ii)

(>iii)

(>i%)

(>%)

(>%i)

ANS:

39.8#ite inc#e"$ing o#de# of he"t of h6d#ogen"tion :(i)

(ii)

(")


13/13

(HOH !e# benene #ing

(") (b) (c)(d)

(e)

(") (b) (c)

(HOH !e# L bond )

(") (b) (c)

(") (b) (c)

(") (b) (c)

(") (b) (c)(d)

(") (b)

(") (b) (c)

(iii)

(i%)

(%)

(%i)

Ans: (/) b (//) b d " (///) b " d e (/7) " b

(7) b " (7/) b "

3.Mi%e dec#e"$ing o#de# of he"t of co'b4$tion (HOC):(i)

(ii)

(iii)

(i%)

Ans: (/) " b (//) b " d (///) b (/7) " b

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Electronic Displacement Effects