Practice t

h
r e a g e n t s u e o r g a n ic r e a c ti o n s
sed. w i t h referen
2.. 'E x p l a ce to
in why U n d e r s ta n
withdraw i n spite th e d ir e c ti d th e m o v e m e n t o f
o
d i r e c t i n g i n g g r o u p , c h lo r inf b e in g a n e le c tr b y d r a w in o n o f a r r o w s . Prac 1
i e on
r e a c t i o n s n e le c tr o p h il ic a r is ortho- a n d ptml• g. tioan Pair t
. o m a ti c s u
b s ti tu 4. (a) A r r a ce the so ~
~
( Concep E) t ! U } g {Oti o n . ng
m c r e a s.m g e tdh e isfotm
t Applied
l Reson
EB} p o in ~ . o r e r o h e.r ic d ic h lO
3. Which a n c e effect.) e ir b o il in g tQ l».._ _• -
o : ~1
u n d e r g o n e o f t h e f o ll o w (b) Explain
why the e P O U \t a n
h y d r o ly s is in g d
mechanis a t a f a s c o m p o u n d s w il l i n haloar
e n e s o
lectrophil
ic s u b s ti
m ? J u s ti f y te r r a te • drastic c c cu tu ti
. by ~ 1 onditions r s lo w ly and o
a a s compar
ed to th n
Ans. (a) .
m - d ic h o lr
~~
< p-dicho o b e
lrobenze. n z e n e < om-ldl S QP~
or s y m m e tr ic icho
C H3C H 2 C a l
o r th o is o m s tr u c tu r e a n d clo
H20 e se
D]{SQP20 a s c o m p a r r h a s a s tr o n g e r dipo packing in par
20} (b) th e h a e d to m e ta . le dipole inte
' .. -
•► '_ui ..,... .. lo g e n a to ra
~~~~ '· 7
'
te n d e n c y m because
:_ . .
..- . . .
~1 r in g . As a
to w it h d r o f it
a w electro s -1 effect has l
r n
a s c o m p a r e s u lt , th e r in g gets s s from the benz
.. . _ , ..
__ ; . "f'.
·•·

. e o
' .- d to benzene a mewhat dea
c:ti
. s u b s ti tu ti o n d h e n
a n d r e q u ir r e a c ti o n s i n halo ce the electrop
n
\• ,
.• ~M '
-
e m o r e dra a
s ti c condit renes occur slo
~.

.• - •

~~pater •¥,&'
s .
th
W
o s e in benzen
e.
ions as com
pam
betide and o f f o r m ation
f a s te r w il &om'the ~~g
~
(a) Oxidat
r ite e q u a t io
ion o f chlo
n s for t h e foll
owing: .
• The benzy l be t h e ra r o f o t.
lic ~ te o f ~ o
n.
(b) R
-
e a c ti o n o f
c h
r m b y air and
lo r o b e n z e l i ~ Qlanh
. ,_ '~ . ~
.- . ' ~
. A1C4. n e w it h
. . ·• 1/.& 13 [Delhi. Sset-..,., l
( Concept .
Applied
F n e d a l cra }atio;n)
.

~~
. .0 + ft alky--~~
+ \ . .- \Ans. (~).C H :€
,
, ~ + { O J tunll&ht
b ' \ ;- · . • - ,
:·, . . • Ch + c<JOi
'"_·· .. <~)_'. ., ' . (iai} • _" '> ..
~>
lo r o f o r m Phosge+neHC?, ..
( ii if ••. .·
•I

Q • •
.
._ • •. (i v ) •; •. . ·· © a
,....,,......11,a,./½-r
~
tl . . I • · .
~- • (b). o
LV -+:~
,-: • • ' . ; • +Cl\-a
. •
~~~)
• • • •
_. ... . . . .
.
. \
'I '. ~)
\,·
•, .:. -
• ·· .. I
.- ·, · · . . .
~
•

(v) ~.
. _· - ~ C H • ·•. (w')
.
~Cl -
a
1° ~ ' w
hich
1/.&
II
-~
 tudents do

c:tlce of writing formulae helps In IVoldin

• ~ oustakeS· ,
1
baloatenes are not reactive towarc1a
6, ~c substitution reaction? Give two reaaolllldeo
n.. -
P ~- , _ ID (De~ Set-3, ~0 \-0 \•a t.
20111
,...MJfflles •are less. reac tive ·:-.. -----
• C-X (carb on and ~ ) it :-- ~ (II) V . Hlr ~ ?
l,enZe l\~ is_ ,p" hy\,ridieed hnin g.:: :
~ two aubons. . .. . . . .
arenes shows resonating Strucbue in 1'bkh\
pa ir= = :e~ thel
• it ·a stable structure and dt, not -= 1 (iil)H~
r(yO\OH + HQ NII
?
teth ~~o gen ~p. . • •. l
•,,.. i· ; · [Marking Schem .,.~, 2m3] 1+~
Delhi
\ .. ~~~....._...... . . . . . . . . .e. .__ 1 .........,_........,"

2. Draw the structures of the major monohalo product

for each of the following reactions:
CH2- CH3
f.
t' .
J t.

r·
l . ~ .
Br,,heat

(i)

(ll)
Q /4 CH3
♦---~1
3. (i) Aa:oant for lbe faDowiDg:
(a) Electrophilk
occur slowly.
ll:lbltitntlno -IUC-dlam- la 1laloarmll

(b) }laloaJkmn, tbaagh ,._ are illlohable in wallr.

(ii) AlraDge the fo1)awiDg o-op aadl bl lnaW iDg
order of IUdintJ IDWUda s,.i displace■ mt
~ O H HCl,""'1,1 1--Jromo-Z.MethJlbalaDe. 1-lii • .,-atane,
1-- 1~ :...... 1)elW c-pt t. Set-], 2, 3, 2017)
(lii) HO -CH !v
4. (a) ldaltifJ die cblnl makcale in the fallowml
m(Forei Set-1, 2, 3, 2017]
t~.-
..
;~)'1 <''"◊/'
•

w,i
...~. ,....
Br
:'. • '1
o-t-.. u..'
~-~
-· ~
.... . ·.,,
lf~• ~~f·; ,
'fllt"t,-,.,.-,

~ )y •) 0
••
(ii) .•. OH OH
,·r
(i) (II)
 <>swaal C8SE Question Bank Cha
pterwlse & Toptcwt
(b) Wr ite the str uct ure se,Cltb...._.
of the pro duc t wh en
chl oro ben zen e is tre ate 6. Write the pro dud (s) for me
the pre sen ce d wi th methyl chloride in d When -~•Clii,._
of sod ium me tal and dry eth (i) i-Bromopropane und erg
er oes deb ""\
(c) Wr ite the str uct ure 0 ruc tio n.
of the alkene formed )'~
by deh ydr oha log ena tio n (ii) Chlorobenzene und erg
oes
me thy lcy clo hex ane wi th
of t-t,romo-1• (ill) Methylbromide is tre ate nitration.,._ - - ~
alcoholic KOH. d With k O {"
r~-~-·· -•- . . .•.·._. . ,,.......,....----~~
1.1 [Outside Delhi, 2018] (!!i] ml [Outside De ~ '
• . ~ - _ Coti.Plt.,
AnL (a)
: .·. :·.
(l) •Ji •O H"
ADI, (Q Plopel\e ·: - •

: _ . ~ ; ~ t,~:; • •-/ -'.: \. • . ~

.(b,~
~
(j~
_
(Ill}~.~

'~\;'~=~~;~7!~::~~
•···

,
. . .. more reactive tow ard s SN
. ' • ·: • lVblcla
(ii) Write the pro duc t for l and why?
me d wh en
--~
(c) , •~ • • + • ben zen e is hea ted wi th aqu
eou s NP- lll ~
• tMaJorJ... . : . followed by acidification.
• (ill) Why dextro and lae
•OIi ll tll l
vo - rotatory .,;__
Butan-2--ol are dif fic ult to
separate by1..__ 11
Detailed Answer: distillation? . . .. . "' [D el hi ~ m
(a) Structure (i) contains chiral
active so it is a chiral molecu
caibon and it is optically Ant. (I) (CHa},C-1/Due
. •• :Jeaving group/Due-. to' of 1, ~ ~ ~~size ~
le. lower i"

1/ti:f f4::
(b) Wurtz-Fittig reaction
a
6 ♦CH,(l+2Na-Dry-e-ther-6 ♦2N,
Ol3
, ••;) ?. •. ~'.··•··. ::.,•. "

•. ~ ··•
~- , ' •, .. '
;-:.-_ I '·· ·--. .. : :(l) Na 0H
~ .44 3K /. , • :._. ~
Toluene • .•

.,
•' •
, # , ' \"': ff+. .. ' •. IU) '>t

·.'
"' • ,.
~'

CH3 CH

~KOH>6 ♦ c5 ~,~
(c) ~- ·:·. .• _ -.·_;:•/<~:;~~:--~.-·L _;·ri.::_·
2 !; ,:-_::.·, N, ~f ,;:··_:'':''._,
,':.;,·:,,-~??.
(Iii) •Because ~t io m er s hav
e same
1-bromo- (Major) (Minor) ., > ~ p':h,,..;.,...i .pro
"· per
,, •••ti.es~ '.'_:: : ..; ,,.
1-methylcydohexane ~
( ".,c >

• • ., . 'L
• 1' ·
,'_:-, -
.i

/
°3 9 ~
"Scheme D
, . • ••,
<•

rua rM nn
~ ' • •

5. A mm.pound is formed by the e& •~- w.. ..r, ,,;~

.-'- 'id, u!~ J:" :!~
/

substitution of two 8. Write the structures of ma -... .... -..- ,;

....... ...
dtlodne atoms for two hydrog in products whenbmm
en atoms in propane. diazonium chloride reacts
Wdte the stnactures of the wi th the foDawilg
possible isomen. Give reagents:
the IUPAC mme of the iso (i) CuCN
mer which can exhibit
enantiomerism. (ii) CH3Cli iO H
II s P 2018-191 (iii) KI
.•.·l
. , .....
.;"t, ?
·.,,... •
9. For each of the following 2, ,n~
combinations of re,gall
and conditions, sug ges t wh
a) l!lI) PJn [Delhi Set-

eth er su bt tl- .:!

elimination wi ll predominat
e. Justify your -an i
l(v nu
(a) heating CH CHiCHiBr wi th
3 aqueous NaOH
(b) heating (CH,hCBr with Na
OH in ethaJIOl
(c) heating (CH,)iOIBr wi th
(CH3)3C01'+
Concept Appli d Reactions
prima1'Y1 ~ e s
e and tem~"of' bro
&~ J moaJkan • i.-
Ans. (a) Substitution;' In polar
predominates for pri ma ry vent, sut,stitU~
sol
ha}oa}kal\es 1
OHions.
(b) ~ ti o n ; In a less po . ~
lar so lv~ t ~
e~ ti on predominates for 1
with OH ions. •
tertia1'Y
(c) Elimination; elimination pre eto std'-_
dommates du 1
effect as the base used is bulky
iluolution ;, p,o,., tltt oul <ftltt
dtqli,. group,
 A-.(1 ) Br Br
..rtftlorilY Mad e Erro r
cow
~ ¢ Ofp f,
with the reagents in different p Q 1 +1
gh
.~ pe woroalu ng with their affects on the reactions. t 1
~ don o~ ~~ --- --- --- ...- 1 (ll) Q Is the major produc
,ol&J 1.. tane is prepa red from 1-butanol u per • Due to the ltalc d!ect of dw b.om b• group ,
JIIOIIU
substitution at the ortho poaition • h!ndcred and
jO, 1.a,ro ct1on i,eJow.
tfae :•NaB r + "2SO4 ➔ C,H,Br + NaHS 04 + ffi0 prefaably oman at the pua poaitlon.
rjl'tl 1,eloW are the different stages In the (give marb If they mention Ina ffPU11ion irllla d
of stale).
Gwe:.ation.
pref' the reactants for aroun d SO minut es In the 12. An orpai c campo aad wltla the fonaa la c.H,8 w
reac:11 with CaCN ID form compoancl 'P' aad C.lk
(I) beatil18tuS shown in Figure 1.
•l'l'ara the reaction mixture to obtain the product °'
In Pl"elEDCe PJddlne at .,, JC. Comp -AM ~ - l
mctlo n with dll. H Q - - . ~ '(l' wldd
(II) clJllillb'lutane in the apparatus shown In Figure 2.
1.a,rootO reac:ta with methyl alcobol pruclaca a •••1-
~ g the distillate obtained. IDM!Ufng coaapoand T. Write tlw chank aJ -.adl M
llbowtng the abcwe caannlon&. ri (a=PQ J
(JO) lain why the reactants are heated for SO minut es
(,)~g el. Ans. The c:hemicaJ reactioN lhowing the con... erliol • arr.
Formation of P:
What is the function of condenser in stage I and In CN
tb) stage 07 How does it help the reaction? Br

-- --- ..
6 + Cu CN ..:.•6
Cyanobenzene
+ CuBr

p
Q
Compound 'P' is cyanobenzene. 1

[~ Formation of Q:
COOH

6
CN

6---~ -'--., .0-3_..

Hgaret Figure2
P-wat erin
p Q
Q-wat erout
Compound 'Q' is benzo k add.
Ana. . mD + ID [CFPQJ
Formation of R:
(a) This substitution reaction is very slow in nature
and hence takes a long time. 1 0 0
(accept any other valid answer)
~
• condenses vapours and returns liquid
lb) •Instage t , 1t
to
be te flask thus, allowing the reaction mixture to
eated at the boiling point without any loss of
No u u-a
V H:,C- 0H u
~OCH3
+Hp

thereactant. Q R
Compound 'R' l1 Acetophenone. 1
• lnsta 2 •
dis~ , it condenses vapours of the product that is 13. The table below sbowl Ille dhct al aqM W .DYa
gout. 1 +1
ll nitrate OD bramble caatafnlng iiMip -..... d l'OGa
In the reaction below. temperature.
'
Br
I
·6
~odium hn1111i,k I t--11111111l,u1.1n..-

. I~
e 1• No..- •--11 111: faint
..•tma
Flle ,..p
+ Cli3CH2Br Anhyd. AIO3 p;elf h hlff ea"41m
appe an-- •·
.(~Iden. ---~ p +Q ....a It
(if) lVbi tify P and Q.
dtoft b (i) Why cloel lilftr mlnle prod. -e DO imaed iale
e111 is the major product and why? pndpl lale w1t1a l• b11wt.l: IJM~
ml[CFPQ]
• ()sWIII CISE (1UIStlOl'I Bink Chlpterwtse &Topi~,

(ii) Suggest c;:i\ '

several ~r:::n why a precipitate a,....c:= c•~· + OH- 'tJ\ •~
Ans. (i)TheC-Brbondtnt-brcxnobu.tane1smva1ent1nnature, , !IJC,.... 'H;,C -:-. 1\c-C •
.. therefore it does mt produce Brians~ l l: '
(u) Bromine is more electronegative than cmt,on, 10 the <jl\ '-1\ ~
C-Br bond is polar. o.5 • or C_
• The partial positive charge on cut,on attracts HO.,... 6\'Ola
nucleophiles with their lone pain of electrons. o.5
• Water molecules &om silver nitrate attack the partial Here the reagent used i.e., aq. I<ott
It la 1 ~
positive carbon, and a substitution reaction takes1
place, releasing bromine ions after some time,
long ..... ,.,,......... ........., }\C/
r
10 substitution takes place.

I 'a
aq.KOH
Elimation 1-\C .....
<il\
C\,
1. Some alkyl halldee undergo eubltltution wbeffU CH., reaction , Cl\1- \t
some undergo ellmlmtlon reaction on treatmen; I •

with bases. Dt1cua1 the structural featura o OH- • .~·

alkyl halld'- with the help of examples which are -H ► HaC-c-~
respomible for this clifferenc.'e. - II[OEBJ
2-Ineth -,.. ~
( Col1C9J)t AppUed •Substibdkxtandefi minatioo~ As ale. KOH is a strong base ~t.._.
Ans. Cue I: Primary alkyl halides follow~~ completes over substitution and~ ~M

in which a nudeophlle attacb from back to the Case W: Secondary alkyl halid e • ~
halogen atom. A transition state Js formed in which substitution or elimination depen~can ~
cubon is bonded to nudeophiles and finally hal~ solvent and temperature conditions. ~- on IJJie•
atom is pushed out. In ~ mechanism, substitution I

ruckop::par::r~~
H,., I 'c (weak base) / \
►t+I
Commonly Made Error

H H H
H Answering Tip
,.,t ......... +C-
H I uH A Understand the structuralfeatures ofcom
H and correlate them with mechanisms. J)OUnda
Cue II: 1ertiary alkyl follow StJl ~ by
forming 3" carbocations. Now, if the reagent used 2. Some halogen containing compounds are-,..
is a weak base then substitution occurs while if in daily life. Some compounds of this daaa
it is a strong base then instead of substitution responsible for exposure of flora and fa1111ato •

.r
elimination occurs. 1 +1 and more of UV light which causes dema:::
to a great extent. Name the class of that ..
aq.I<OH compounds. In your opinion, what should becbt
to minimize harmful effects of these compoull.
~c,., ~c (weakbase)
0 DI+ IINCDII
COMPETENCY BASED QUESTIONS
Oljea:llu lype ~ (lmnlldl) 2. Which of the following is not correct?
mJ■ultiple Choice Questions (A) In haloarenes, the electron pain on baloge
atom are in conjugation with p-electroll ;
1. The convenion ol an alkyl halide into an alcohol b the ring.
aqueou, NaOH J, claasifted u: Y
(A) a dehydrohalogenation reaction (B) The carbon-magnesium bond is covalent and-
(B) a substitution reaction polar in nature.
(C) an addition reaction , __J 1161
(C) During SNt reaction, the carbocation ~
Am. (D) a dehydration
Option reaction
(B) J, correct.
II [Delhi Set-1, 2020] 1s ow step being sp2
hybridised is p
tanar.

~!_:_~:_~
.......
. .
~OH➔ R- OH+ NaX
..n .......-.. .,. . w.......w................1
(Dj ~.!!~v~;.~: .,~~
ID
cJlP'P
[SQP-
!
l10 ~,~ ~ ~
l
L .........." - - ~ ~
~
= I
1 = p t Applied , Chemical pro
perdd;

~;;,;;;;,,=
•....,-~_-;;;·-;...;...;.····;··-~··~···-;···;···;
Ai°nft..:..~n.~
.,;, . , . . 1 o : _ •farJl'lll.'li«IINl it, IDluHon;, pen,t • • ~
....••••~..:_;··;·-·;····~···;·~-~-~-~Li---~._;;;;;ns;_an;;d~~~~t~r_e;a~cti~·o;n-:::::
., '

•
.,,.,~

~ (f) 11;:::-um bond Is rovalent 111d non.

(A)s_.J._...
7-Lc I C
IIOPJI Dlllls.t-iaDJ
.........
f 11" ~ ; : . . , The bond between Cllbon 111d
~,cl is ionic in nature, (grignard tapnti (C) N.11..,s_1 . . s,.i..:!'2llldlorl
pv--efl~,y palar in nature due to differeuce In & - (D)S,., .......... 5-1ratlon
~~ N&-dvlty between carbon and Dllgnahun_ n-.<>,laa(A)r.--.
~flega ~ - - la LI b GC11111 mS,.1 IWtlan If
...,f11onlY Made Error -uunlllhecMraa...._
cow
,_....._.,,_av .......
I021hDIIIIIW4,mt)
-.
(A)St,llfldbl (lt~IBdlall
(C) Neither St,l nar ~ llldlall
(D) s,,iltldbl • wel • S,.1 radian
all the options carefully and than choose G'--,.,Pp.11 5,,lllldknapt!t,llacd;lly )

~~~~~-~~---------__,
'- fle'd __..... option.
of the following molecules bu a cbln1
Am. Optlaa (A) .. carnet.
In s..i ......., optkaDy iCdvt IIILyl hdda
undergo lanlaallan, forming I planar ad,catlan
5, ~c:orredlY labelled with an asterlak r)? intaa.edlate. Nudeophi1k attack can ormr l.n,m
- ~ c•HBrCH3 (B) CH3C•HCICl_iiBr either fact of the lnlmmdlate, lading to • amtme
(,\) ()OiC•H(OH)CH20H of ltatul1u1a.& and ramiutlon, thaebJ aaling
(Cl ~ c•Br2CH3 DJ~Sd-1,2013} the Initial oplbl ldl9lly.
3
(I)) (B) is correct. 9. WhlcboltMfDOowms~ art f1111Pr1z•
,,,,_ Opd:non: Chiral molecules images are non-super (A) Ol,Ol,Br+ Na·O-C(CH,), ➔ CH,Ol,-0
. .EJP..-i1ble to each other. -QCH,),
illlr--version of an alkyl halide into an alkae by (B) (Ol,),C-Q+Na•O-C(CH,), ➔ CH,Ol,-0
'-::uc KOH is class~ed as -QCH,),
(A) a substitution rea_ction (C) Both (A) and (B) (D) Neither (A) nor (B)
(8) an addition reaction. . ■ (Oatsidit DeDd 5&].. mJ]
(C) a dehydrohalogenation reaction (,--Cmapt--Appllld---~-reactions----.)
(D) a dehydration reaction
Ans. Option (A) .. canect.
DJ[Outside Delhi Sd-1,2011]
5"1..-•
f i Applied Dehydrohalogentation reaction.) hindmd by mil: hia.diaaa due ID
bulky l'Nib'ffll nar lhe mdicll rmts Tmilly
sullltlatesechilitmmehbtma, miudngtlk.IWtitla
-. Option (C) is correct. · rate amapmd to pdmazy m leCllndaly Mllltata The
.. Dehydrohalogentationreadion: As it is accompanied mdiml lmdva • pimu1 alkyl 1:awim_ wlidl ii
• by removal of one halogen molecule. IID'e reatlive in~tadionl. 1'he produ¢ I l l ~ ii
CH,-CHi-X K~H >O\=CHi+HX stable. 'etiaryalkyldlbideinoptim(B) ii 11!1.l&diie.
S. Which one of the following compounds is more 10. Foar compoandl, CB.P, CB.JJr, CJI,JJr and c,B,l
ructive towards SNt reaction? are repraadled by the ld7m M, N, 0 and P la PIie
table below (in ranc1am --,. The bafflng,...
(A) CH2 = CHCH2Br (B) CJisCH2Br are U10 pm OD tbe table.
(C) Qi5CH (CJ\)Br (D) CJ-15CH(CH3lBr
DJ [SQI: :m.1-24]
Boilin~ I :~.: (. I ; .. (.

Ans. Option (C) is correct.

Erpllll,ation: C6ffsCH(CJ1s,♦ carbocation formed is
more stable.
l'uinh 1U1'1

{ 11111rounJ aaaa
Whkh of tbe fou t,NII,.. . . . . . . 'N" --Ubly
6. The IUPAC name of the compound shown below is: . repraem?
Cl (A)~C (B)Qi>8r
(C)~r (D)C3",l
■ (AlQ Sd-]..lm-21)

Br
(A) 2-bromo-6-chlorocyclohex-1-ene •
{B) 6-bromo-2-chlorocyclohexene • tL
(C) 3-bromo-1-chlorocyclohexene balidel7 •
(I)) l-bromo-3-chlorocyclohexene (A) mi-CHOIPIP (B) ~-~-Of,
........ Br
~
n.i.~
e m[so~m>-211
i, for 1'l'tldict and its solution is given td t1tt tn4 ~ t1tt dtqlff.
 OswHI CBSE Question Bink Chlpterwfse &Topi ~

(C) CH2 = CH-o I:rBr (D) CH■ C- Br , , •• ---- ··-- ---- . ,--. . , .
Q
II [Outside Deihl Set-2, 7Am]
Ans. Optio n (B) is correct.
Q\= C-n-.., -t ••
I . 1
Br .
(Because vinyl halide s are alkyl group with formula
ROIC HX)
12. lnven ion of configuration occun in :
(A) ~ reaction (B) ~1 reaction
(q Neith er~n or~lr eacti on
(D) ~1 as well as~ reaction ' Which of the following co.,._,_,
m
[Outaide Delhi Set-3, 2023) --"~"Y I

( Conc 9pt Applied ~reac tions , ~1 reaction;) Optio n SN I rt',1ction / .

S,\' I '

Ans. Option (A) is correct. . . , graphP

happe ns in ~_reactions, ~:.; '.''''
Inversion of config uration
anucle ophile directly replace s a Jeavmggroup. ·' X graphQ
where
This results in a change in the stereoehemistry at the Y· -graphR.
reacting carbon centre. ~1 reactions do not ~ i t
inversion as they involve a carl,oc.ation intermediate. Z graph Q
13. Wblcb of the lollowing alkyl iodide W1Dot be (A) W . ~) X (q y •
produced by the reaction of Ill with an appropriate (D) 2
' ether:
• (A) (CH.,),C- CH2 - I· , (B) (CH3hCH - I [ Concept Ap}tied -~ ~I and ~ r e ~
Ans. Option (D) is correct. •• ~ •
(Q CJisCH2 -I (D) ~ - I

( CanceptAppl!ld Preparation of alkyl halide)

m1J [APQ Set-2, 2023-24)
Explanation: Identificatio n of
is based on the hydrolysis rate
~I ~d • :·• •
graphs 8t ·
secondary, and tertiary haloalkanes The
. option (D) corresponds to ~I reacti • ,
Am. Option (D) is correct. relying
Erpllauztlon: CJirI , ether having an aryl part substr ate conce ntratio n. _ons
will lead to the formation of phenol rather than 16. The table below shows some of the featma
iodobem.ene. Formation of phenyl cation will not be and SN2 reaction mechanisms. of
favoured, partial double bond character of C-0 will
Rows / S~I

-
make it less stable.
first order kinetics
Commonly Mad e Erro r
B reaction favoured
A Students get confused in the formulae. by any type of
nucleophile
Ans weri ng Tip
C reaction favoured
A Understand the structures given and than by a good leaving
choose the correct one. group
l4. Iden ~ tbe products (1) and (2) in the following D stereochemistry:
reactions: racemisation
C1 H50 + KCN ➔ (l)and
Which of the rows show s an INCORRECT lt#:
C2H50 + KN03 ➔ (2) for at least one of the mechanisms?
(A) (1) ½ffsCN (2) qisN o2 (B) B (C) C (D) D
(A) A
(B) (1) qfsN C (2) qisN o2 ■ rara
(C) (l) ~ (2) ¼ffsONO
(D) (l) qfsN C (2) ½ffsONO
( Concept Appl ied ~ reactions, Sr.J I~
Ans. Option (B) is correct. _,
Ant. Option (C) u comet. II [APQ Set-2, 1.023-UJ Explanation: SN2 reactions are favoured by IJf

Explmu,tion: Both CN- and o ~o~-bulky nucleophiles, while ~1 readfoOS

indifferent to nucleophile size. . _-dad
nucleophiles and KCN ~d KNO NO. ~ ~de nt
15. Three graphs P. Q and R have mnature.
2are 1orucdra 17• Which of the following will be the major,..,..-
been
,
represent the relative rates of h drol wn to formed in the reaction below? j
for primary, sea>nduy, and y ysis reactions
tertiary haloalkanes. CH,- CH,- CH =CH ,+ HBr->7 ___J
 .,...- ,..... .....ca.-CH,Br
r~~,--~r-cH•Ofz
al ~,,C J¼:C J{Br -Of: ,

if1 ~' ... at - cH -CffzBr IIOJtQJ

~ i;tf, ... M'eU-S l HBraddsmlheal!ne
~,. ~
~ ,.. . Jlllt addl to the alkae, ~ 1
, or:-~ tntenJlecliate,
The bromide Ion then
ingfn the lllljorPft>dact
~dO "~d on, result
~~ _ cHB r- Of:,, accord ing to elrct.oPhlc

~~ ~oawlns ~kcala mlllllo.,.....

~1
l~..A oper ttane
~ ,-tad z.inethylpropane •
(f) ~odo prop ane (D) 2-iodobutane
(Gl 1, llCFPQJ (I) 2 eo, 4
{C) 3
Appl i~. Momdesexhatingoptical ■ ICRQJ
l'.:aiust haVe a chiral centet (j
..,,.,.ll_
t~~lill
!tllliJjii. 'Dnl opnl ll )
(I)) ii correct. Am. Opllaa((')11--.
,,,. ~afi on: Molecules exhibiting optical iaomerJam .
,... ,,_ In lhe ghm l'lldlan, the ....,..,, ...
D1""'~~e a chiral cent~ • (Na) In 1hr Jllllda vi dry ether wlD d+ePn1 tr
fll~ (D) Z.iodobutane has a chiral camon, u it lhe 1-bnim o, ~ The proda d
bmed,P,wibtcydohemwthroughanellm b.,..
aptt:ched to four different groups, allowing for reaction.
~ fsOOlerism. 22.0IJaaft ... ..,.. ...,_
,bnage below shows the ball and stick model of
If. ~ t compounds.
.: Jla1' ananY of the above compounds i,/are optically
adfve7
.(Xa a
Na
Dry ether
l>P

Whicb of Ille lallowmg procladl wfll be lwwwwl

.

wO
•P1
. •H,N \ co;
H (2)
(A)l (B) 2 (Q 3 (D) 4
ll[CFPQJ
~ p t Applied Optically active )
(4)
A& Option (A) is correct.
Erpllau,tion: To be optically active, a compound
must contain a chiral cen~ In the given image, a
mily one compound has a chiral cen~ making it
(A)l (8)2 (Q3 (D)4
optically active.
I. Which of the following compounds will be (o .ap tA pp llld il~ )
hydrolyaed most rapidly under similar mdion ■ [mQJ
l'Ollditlons7
Option (C) II camd.
Al per_ the Fittig reaction, when 2 moles of Ans. In the given ..ction. 1,J,41,tlc-..c.,c ...... ,,.
~ e reacts with metals nch u aodium
p

In lhe Pretence of dry ether, it gives diphenyL

reacts with Na in the paamce of dry eds This
(B) 1-chlorobutane reaction inwlva dw eliainttion ~ two chbine
(A) 1-cltloropropane
atoms (dehalogenatkln) ID bm a double bond
~ 2-dtlo ro-2-methylp ropan e The product, 2 wil bt ~ through
111

) 2-dtlorobutane LI [CFPQ ]
elimination reaction.
io,. ~Ap plie d Fittig readioll ) l!IIA SSll1follllllll Ii 11 ,-,a t
~ on (q is correct. aw Diredlonl: m.... .... .... .. ,,
~ (A) ■ .... . bJ I ltllP!Md ol
~tio n: The reactivity in the Fittig reaction of A,aa1IOll ..... ----d lak'l •lullo wl:
COrres ds on the ease of generation of the RalCJG (ll). Mam .. L11Ha.•
P<>nding alkyl radical. In Option (C) (2-chloro-
 • ()SWIii C85E Questton sank Chapterwlse & Top1c-._, I
(A) Both A :me! R are tme and R II the a,ned
explanation of A. .
= . . : :~ ' : , . . _
_Readivity is thus controlled by o-ll1d~ . i
~
(B) Both A and R are true but R is NOT the c:orrect e«ect and orientation is contro~. ~
explanation of A. 5 A,,ertfon (A) : Nucleophillc subs"'¥
(q A is true but R is false. • 1odoetflane is easier than chlo titutto.i
(D) A is false and R is true. ~ (R): Bond enthalpy 0 ~
1. Assertion (A) : Chloro~e is resistant to nudeo· that of c:.O bond. - borict la
philic substitution reaction at ,oom tempenture- Oplloa (A) II conect. mll [Outside DelJii I,_
Reuon (R): C-0 bond gets weaker due to reson;:i· Ao& Exp_"'1Ultion: The weaker C-J hon S...i
ID [Outside Delhi Set,3, awces it more prone toth·nu~ d In
e stron~-~
Concept. Applied . , Nucleophilic substitution .
reaction ~~ctionsthanco:'~d
ouoroe • , OtoPtion A is .:':"l
and resonance 6. A,sertfon (A): 2-Methoxy-2-met h~ .
Ans. Option (A) is correct. . t to with hydrogen iodide to form YI ~
&plluumon: Chlorobenzene is resistal1 2-Iodo-2-methylpropane. lllethyJ ~ ,
nucleop~c s~titution at room ~perature~un: R~~~;~R): The reaction given in (A) ,::
the stabilizing effect of benZene J1ll8 ~ it Jess m~ucu .....m, a;, [AP .-~
resonance strengthens the C-Cl bond. 'ch ---~-- ' ---.-,, Q, Set.,
susceptible to nudeophilic attack. The el~~~ AIJa. Oplim,1 (C) J, correct.· • • •• •.- z-:·~ , .,
benzene ring hinders nucl~philes from fur the \;_,· ·_. _ ~ '. The :- (A)' reactl_oii
the chlorine atom. The primMYbili.
resistance is the enhanced sta ty. ycu ·---
rea;~.
..-1 by .\\lt_mechanism- The PfOtonated ether
,,., :' .- ~va~; to give methanol and
benz.ene's resonance. ,,~ ~:t-- ~hich _JS_ slow step•.-'.J'.he carboca •
~}:i · to form butyl iodide. •• •

,.
f,_I

I 1
Commonly Made Error
--- ';: : ·_, _-· ·,.. >' ..: .- . ™"~-c.,i.~. : ·',,~~- ~
Ut'~i::frh++;.,u1 .-.,A... -,c>4k~ ..........:Jll.t~ ...~-•~.......;;;:::..!V

lriJCase Based MCQs

L Read the passage given below and
of the following questions:
§~u-_...:....:.

•• ;- .
answer..,._
1:-;it Answering Tip Nucleophilic substitution reaction f •• " •
k.·. ·)'
~- i A Read the reason statement and find whether it can be conducted according to botho~~
is true or false than correlate it with assertion mechanisms. However, which m-"~llid ~
'~11 based on is related to such factors ;'ihe111111 i 1
1,a /t .\ statement
of haloalkane, and properties of lea • 8lr1'iii
I 2. A,serlion (A): Chlorobenzeneis less reactive towards nucleophilic reagent and solvent. :vmg P:111
I nudeophilic substitution reaction. Influences of halogen: No matter which .
I
Reason (R): Nitro group in chlorobenzene increases the nucleophilic substitution reaction i s = -
I its reactivity towards nucleophilic substitution leaving group always leave the central aiooar»,t,
reaction. lJJ (Deihl Set-1, 2021] with electron pair. This is just the opposite «8:
ADI. Option (B) is correct. situation that nucleophilic reagent attacks the•
I Exp/Jaumon: In chlorobenzene, the lone pair of carbon a!o~ with ele~on pair. Therefore, the•
I chlorine is delocalised on the benzene ring and
stabilised by resonance. Hence, a partial double
the alkalinity of leavmg group is, the more.,_..
anion formed is and it will be more easier b •
bond character develop in the bond which make it !eaving group to leav:e the central carbonatm;._
j difficult for nucleophile to cleave C-0 bond.
~ e nitro group present at ortho and para position
IS to say, the reactant IS more easier to be substitaW
The alkalinity order of halogen ion is r- < er- <a
I withdraws electrons from benzene ring and activate < p- and the order of their leaving tendenqilllll
haloarenes for nucleophilic substitution. be r > Br- > a- > p-, Therefore, in fourhaldll
j

3. Assertion (A): Aryl halides undergo nucleophilic with the same alkyl and different halogens, themdl
substitution reactions with ease. of substitution reaction rate is RI> RBr > RO>I
Reason(R): The carbon halogen bond in aryl halides In addition, if the leaving group is veryeasytoi.
, has~ d?uble bond charactei: 19 {SQP. 2020-2lJ many carbocation intermediates are ~eratedmllr
'-1-' Ans. Option (C) JS correct. ' reaction and the reaction is based on ~1 mechli!'
Explllnll~ Aryl !1aJides are less reactive towards ~ the leavin_S' group is not easy to leave, the red'
nucleophilic substitution reactions because of th IS based on ~2 mechanism.
Influences of solvent polarity: In ~1 ~
carbon halogen bond in aryl halides has partiale
~,I
double bond character. polarity of the system increases from the ~
4. Alsemon (A): Halogens are ortho and para-directin
cs·n (R): Halogens are electron-withdra •
g
to the transition state, because po~ _solvent ':,
greater stabilising effect on the transition state "
the reactant, thereby reduce activation ~
~~~ wing
Am. Option (B) is correct. m
(APQ Set~z, 2013-24] accelerate the reaction. In ~2 reaction, the~~
&plmumon: Jialogens withdra
an inductive effect (-1) and ~
~ (+R). Through Jndlldive ,./1-,, through
:=
through
of the system generally does not wangenlY cJd
reactant to the transition state and~ ent fiat'
dispersion occurs. At th.is time, polar th v ~
great stabilising effect on Nu_ ~ ~
estabila.e the intermediatecarbocation--.., ~ -_
the electrophilic substitutio formed during
resonance state, thereby increasing acovatton -xain~ ~
n Through I slows down the reaction rate. For e,,u-,
 .-,...-
~ rate C5Nl) of tertiary~ In
~ ~dan. electric amstant 79) Is 3CXXXXj tbna
I llf'f."fl.'_~ (dietJ,af!Ol (dJelectrk constant~ The
1 ~ C ~ itl 2) of 2-bromopropane and NaOH In
~ ,.~ ~ n 40~ water is twice aiowa than
Z' c:on~fL In a word, the level of IOlvent
,~1ute iiJluence on both ~1 a n d ~ ~
.. lar:iy ~"°1'eflt results, Generally spaking, Weak
•..-18' ~-Is favourable for.~ ~ whlJe
"',al\'.ent50lvent is favourable for S,.t 'action,
~ ~t,rnl under the action of polar solvent can ~~~-~-~'!!Is:~ -
fY..iJe onlYh1 ~ dissodate intocubocation l5t.lftldlaa1'111 ........ laC1NII:
!n
~~ted 1 and solvents with a strong~
~J,,l~ for salvation of ~ t i o n , ~ g
(A(I)) !-0abo.2-1t.y1 propw
"i,fOIJJ- c;enerally _s~aking, the substitution
·fodo.i.thyt J'IOIMI•
if pt,ilitY.- ertfarY haloalkane is based on S..1 A m . ~ ~
~ of ~ solvents with a strong polarity (lor CD) 1-ladabu••S!J■
~i:.nJsD'tt,anol containing water). [QB, 7.0lJJ Er,'a"'- Since, Iodine II the , - - lawing
"-';je,et group, IO !ttt 1t1C1b1 II flltat In 1-~J.awlhJI
~,._ ~pplied i Role of solvents in ~1 reaction propq, I

~.1 01
ecJtaniSDl is favoured in which of lht Dmea. ......SaJKth, Questions
t.~ ~
~) ~ d d
(Q ace
Jvents·
• (B) carbon tetrachloride
(D) carbon disulphide
--" ...........
~ . . . . ~belowllldww• . .
The obfeeta which are non-supatmpouble on lhllr
l(iji] ~ bnap (like I pair of handa) are Mid to be
011
(C)iscoaect. chiral and tllll pn,pert) 11 known u chlnllty. Cdnl
_ . ~ tu»'' Since the rate of ~1 reaction inaeases molecuJa are optlcaDy active, while the objedl.
£,plAtU' • nee ~£ polar solvents and benzene, whkh are, IU_Peltmpoeable on their minor bnapl
In the P:Cchloride and carbon dilsulphide, all are
l:r
ort,on solvents and acetic acid is a polar solvent,
non-Po~1 mechanism is favoured in acetic acid. 1
are called achiral II shown in the lmlge. Thae
molecuJes are optically inactive. The above tat
of molecular chirality can be applied to arpnlc
_, tile bilk substitution will be fastest in we of: molecules by amstructing models and lts mimlr
2. N4~oro-2,2-dimethyl propane images or by drawing three dimensional ltructuftS
(A) t-Jodo-2,2-dimethyl propane and attempting to superimpose than in our mlndl.
~ l-Bromo-2,2-dimethyl propane There are other aids, howevei:, that can Ulllt u In
(D) l-Fluoro-2,2-dimethyl propane m recognising chiral molecnla One such aid II lbe
Option (B) is correct. presence of asingle asymmetric carbon atom.
Afl. I,xpllmation: In nucleophilic reactions, the L Whatareaanl\......, ID[OEBJ
cleophile attacks on the positively charged
~~phile. And i~e is the £~test lea!ll'~ group ( Concept~ ; Stmo i1omerism and c:hinBty )
out of chlorine, bromine, fluonne and iodine. So,
nucleophilic substitution will be fastest in 1-Iodo-2,2-
dimethyl propane. 1
1 ~1 reaction will be fastest in which of the following
eolvents? l!l!] 1
(A) Acetone (dielectric constant 21)
(B) Ethanol (dielecbic constant 24)
(Q Methanol (dielecbic constant 32) Commonly Made Error
(D) Chloroform (dielectric constant 5) m .A. Number of students get confused betwem
All.Option (C) is correct. 1 stereo isomers •
• &,,ltauition: Higher the dielectric constant, more
Will ~e solvent polar and fastest _will be the ~1
: reaction. Here methanol has maxunum value fur Answering Tip
dielectric constant.
OR A Understand the concept thoroughly.
Polar solvents make the reaction faster as they: Ans. The stereoisomenrelated to each othera s ~
(A) destabilize transition state and decrease
the imposable mirror images are called~
activation energy.
(B) destabilize transition state and increase the 2. Why aracemlc mixtm caatabring two ffllRe:=
(C) acti~~tion energy. • will lalff mo....--
stabilize transition state and increase the in equl propmtiODI
rotation?
m(OEB]
(D staactivation energy
) bilize transiti~n state and decrease the
..........nb. mixture « "
~ activation energy. m Ans. A racemic mixtWe • •
15 an ~-:-due ID extanal
[;:tton (C) is correct.
bansi'7tion: Polar solvents helps to stablise the
1 and I forms. It i.1 ~
compensation as the rotatiOn
0: form is canceJed
on state and increase the activation energy. by another form.