CH

3
CH CH
2
+ HBr CH
3
CH
2
CH
3
+ Br
2
h
H
2
C CH
2
C
H
2
HBr + CH
3
CH
2
CH
2
Cl + NaBr
acetone
Br
Br
Br Br
Br
+
acetone
HBr
soluble in acetone
Multiple choice questions with one correct alternative
1. Which of the following reactions is likely to give the greatest yield of n!ro!yl bro"ide#
$%& $B&
$C& $'&
Ans $C&
Cyclo!ro!ane "olecule is highly strained and readily undergoes addition reaction for"ing n!ro!yl
bro"ide.
2. (he increasing order of hydrolysis of the following bro"o co"!ound is
) )) ))) )*
$%& ) + )) + ))) + )* $B& ))) + ) + )* + ))
$C& )* + )) + ) + ))) $'& )) + )* + ) + )))
Ans $B&
(he ease of hydrolysis follows the order tbutylbro"ide , allylbro"ide , alkylbro"ide , arylbro"ide
(herefore o!tion $B& is correct.
3. %"ong the following the co"!ound which will not give a white !reci!itate on treat"ent with sodiu"
iodide in acetone is
$%& Br -hCH
2
$B& CBr & CH $
3 3
$C& Br CHCH CH
2 2
= $'&
Br CH CH
2 3
Ans $B&
)n !olar solvent 3 carbocation is for"ed which readily undergoes eli"ination reaction for"ing HBr.
Hence. white solid of NaBr is not se!arated.
2)BC1213CCW-07MS 1
CHEMISTRY
Class IIT-JEE Achiever BASECamp 2012 - 2013
Topics
Classor! 0" #Main$
Halo%ena&e' H('rocar)ons
Mechanism o* S
+
an' E reac&ions, or%anome&allic compo-n's
Alcohols an' e&hers phenols /anuary. 2013
1
1 1
1
1
$2&
$3&
H)
heat
H
2
1
)
)
CH
3
Br + 1H CH
3
1H + Br
CH
3
Br + 1H CH
3
1H + Br
4t1H
'561
NH
2
HN1
2
07
o
C
2 3 8
H
3
1
+
9heat $i& CCl
:
9Na1H.heat
$ii& H
3
1
+
H
1H
1
1H
1
1H
1
1H
1
1H
1H
:. $+& 1bro"oethylben;ene is allowed to react with "ethanol in ben;ene. (he "ain !roduct for"ed is
$%& $+&1!henyl"etho<yethane $B& $& 1!henyl"etho<yethane
$C& vinylben;ene $'& $& 1!henyl"etho<yethane
Ans $'&
)n 1
N
6
reaction. retention in configuration e<ceeds over inversion in configuration.
7. Which of the following is "ore likely to react both by 2 1
N N
6 and 6
"echanis"s si"ultaneously#
$%& Cl C & CH $
3 3
$B&
3 3
CHClCH CH $C& Cl CH CH CH
2 2 3
$'& CCl -h
3
Ans $B&
=enerally secondary alkyl halides "ore likely to react both by 1
N
6
and 2
N
6
"echanis"s
si"ultaneously. %"ong the given co"!ounds. 2chloro!ro!ane is "ost likely to react by 1
N
6
and
2
N
6
"echanis"s.
>. Consider the following reactions carried out at the sa"e te"!erature.
Which of the following state"ent9s is9are correct about these reactions#
$%& Both the reactions take !lace at the sa"e rate
$B& (he for"er of the two reactions is faster.
$C& (he latter of the two reactions is faster.
$'& %ddition of Na) has no influence on either of these two reactions.
Ans $C&
(he given reaction re!resents 2
N
6
and its reactivity is high in a !rotic !olar solvent like '561. Hence.
state"ent given as o!tion $C& is correct.
?. %n organic co"!ound $2& C
@
H
1@
1. does not react with sodiu". 1n being heated with hot concentrated
H). it is converted into a "i<ture of two iso"eric iodo co"!ounds. Both the iso"ers yields hydrocarbon
$3& when treated with alcoholic A1H solution. (he co"!ound $2& is
$%& $B& $C& $'&
Ans $'&

@. Consider the following seBuence of reactions
(he !roduct $8& is
$%& $B& $C& $'&
2)BC1213CCW-07MS 2
CH
3
CH
2
CH CHCH
3
CH
3
1H
CH
3
CH
2
CCH
2
CH
3
CH
3
1H
$CH
3
&
2
CCH
2
CH
2
CH
3
1H
$CH
3
&
2
CHCHCH
2
CH
3
1H
1C1CH
3
NH
2
NHC1CH
3
1H
NH
2
C1CH
3
1H
NH
2
C1CH
3
1H
-hBr
5g
4t
2
1. heat
2
1
+ 2 3
NH
:
Cl
H
2
1
8
CH
2
1H
CH
3
1H
1H
CH
2
CH
2
NH
2
NaN1
2
dil. H
2
61
:
gives "ainly
1H
-h
1H
-h
1H -h
1
-h
Ans $B&
C. (he
$%& $B& $C& $'&
Ans $C&
10. Which of the following will for" a yellow !reci!itate of iodofor" on heating with iodine and dilute
Na1H#
$%& -hCH
2
CH
2
1H $B& -hCH
2
CH1HCH
2
CH
3
$C& CH
3
CH
2
CH
2
1H $'& CH
3
CH1HCH
3
Ans $'&
11. % co"!ound $2& with the "olecular for"ula C
>
H
1:
1 !roduces hydrogen gas on treat"ent with "etallic
sodiu". )t gives an i""ediate cloudiness in the Ducas test. )t is very easily dehydrated on treat"ent with
H
2
61
:
to give a co"!ound $3& which on o<idation with alkaline A5n1
:
gives a neutral substance
C
:
H
@
1 and an acidic substance C
2
H
:
1
2
. (he co"!ound $2& is
$%& $B&
$C& $'&
Ans $B&
12. Paracetamol. an analgesic and anti!yretic. is !re!ared by "onoacetylation of !a"ino!henol with acetic
anhydride. (he structure of !araceta"ol is
$%& $B& $C& $'&
Ans $B&
13. Which of the following co"!ounds on reaction with ethyl "agnesiu" bro"ide $one "ole& and
subseBuent hydrolysis will for" 2"ethyl2butanol#
$%& CH
3
C1CH
3
$B& CH
3
C11CH
3
$C& CH
3
CH
2
CH1 $'& CH
3
CH
2
C1CH
3
Ans $%&
1:. Consider the following seBuence of reactions
(he "aEor !roduct for"ed $8& is $co"!ound $8& contains chiral centre&
$%& $B& $C& $'&
2)BC1213CCW-07MS 3
CH
3
CH
2
1H 1H )
1 CH
2
Ans $B&
17. Which of the following is "ost soluble in water#
$%& nButyl alcohol $B& )sobutyl alcohol $C& tertButyl alcohol $'& secButyl alcohol
Ans $C&
1>. When va!ours of an alcohol are !assed over hot reduced co!!er. it gives an alkene. (he alcohol is
$%& !ri"ary $B& secondary $C& tertiary $'& none of these
Ans $C&
1?. (here are four alcohols -. F. G and 6 which have 3. 2. 1 and ;ero al!ha hydrogen ato"$s& res!ectively.
Which one of the following will res!ond to Ducas test#
$%& - $B& F $C& G $'& 6
Ans $'&
1@. Which of the following !henols has the lowest boiling !oint#
$%& oHluro!henol $B& mHluoro!henol $C& pHluro!henol $'& !henol
Ans $%&
1C. Consider the following alcoholsI
). 1-henyl1!ro!anol
)). 3-henyl1-ro!anol
))). 1-henyl2!ro!anol
(he correct seBuence of decreasing order of reactivity of these alcohols in their reaction with HBr is
$%& ) , )) , ))) $B& )) , ) , ))) $C& ) , ))) , )) $'& )) , ))) , )
Ans $C&
20. (he ether when treated with H) !roduces
$%& $B& $C& $'&
Ans $C&
J J J
2)BC1213CCW-07MS 4