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XII (ALL)
HALOGEN DERIVATIVES
CONTENTS
EXERCISE-I (A)
EXERCISE 1(B)
EXERCISE-II
EXRECISE-III
EXRECISE-IV(A)
EXERCISE IV(B)
ANSWER KEY
EXERCISE-I (A)
(Choose the correct option. Only one is correct)
Qlf Which one is liquid at room temperature:
^
(A)CH3C1
(B)C2H5C1
(C)CH3Br
^L
Q?f
Q.4
Q. 6
(D)C2H5Br
The correct order ofmelting and boiling points ofthe primary (1 ), secondary (2) and tertiary (3) alkyl
halidesis:
(A)P>S>T
(B)T> S>P
(C) S > T > P
(D)T>P>S
Pick up the correct statement about alkyl halides:
(A) They show H-bonding
(B) They are soluble in water
(C) They are soluble in organic solvent
(D) They do not contain any polar bond
What would be the product when neopentyl chloride reacts with sodium ethoxide:
(A) 2-Methyl-2-butanol
(B) Neo pentyl alcohol
(C) Both 1st & 2nd
(D) 2-Methyl-2-butene
Reduction of alkyl halide by LiAlH4 is the type of reaction:
(B) Electrophilic substitution reaction
(A) Nueleophilic substitution reaction
(D) None of these
(C)Electrophilic Addition reaction
2-methyl butanoic acid is formed by the reaction CHC13, NaOH and
(A) Propene
(B)Ethene
(C)l-Butene
(D)2-Butene
Q.7
o
Q.12 CH3MgBr + CH2 = CH - C - H
OH
(A) CH2 = C H - C - H
CH3
(C) CH3-CH2-CH2-CHO
faBansal Classes
OH
(D) None is correct
Halogen Derivatives
[2]
Q.31
n-CjgH^Br + HC =CNa
n BuLi
>A
> B
H /Imc ar scat
Q.32
(i)
CHjCH^CHjOH
(ii)
CH3CH2CH2I
PBr
3 > (A)
Alc K0H
h+/h
> (B)
2 > (B)
HBf
socl
p6roxybenzoicacid
>F
NH
> (C)
? > (D)
2 > (C)
(D)
LiAlH4
(iii)
Alc K 0 H
> (B)
HBr
> (C)
Light
(iv)
CHgCH^MgBr
CH CHQ/H
AlcKOn
> (C)
> C^-CHj-CHj-Cl
(b) CHg-CHj-CHj-Cl
> CH3-CH-CH3
in single step
CI
CH Br
(c)(^J
C1
(d) ^ J j
> j^j
/"\^ C H 2 C 1
> [^J
O
I!
(e) Ph - CH2 - C - CI
Ph - CH^ - CI
O
(QPh-CHj-Cl
(!Bansal Classes
> Ph - CH2 - C - CI
Halogen Derivatives
[19]
EXERCISE-III
Q.l
A primary alkyl halide (X) C4H4Br reacted with alcoholic KOH to give (Y). (Y) reacts with HBr to give
(Z) an isomer of (X). On reacting with alkali metal such as sodium/dry ether gives (S) CgHj8 which was
differentfromthe compound produced when n-butylbromide was treated with Na. What (X), (Y), (Z)
and (S).
Q.2
On electrolysis an aqueous ethanoilc solution of so dium chloride gives sweet smelling liquid (X). (X)
gives isocyanide test and condenses with acetone tofromhypnotic (Y). What are (X) and (Y)?
Q.3
The alkyl halide C4H9Br (A) reacts with alcoholic KOH and gives an alkene (B), which reacts with
bromide to give dibromide (C). (C) is transformed with KOH & sodamide to gas (D) which forms a
precipitate when passed through an ammonical silver nitrate solution. Give the structure formulae of the
compounds (A), (B), (C) and (D) and explain reactions involved.
Q.4
An unsaturated hydrocarbon (A) C6H10 readily gives (B) on treatment with NaNH2 in liquid NH3.
When (B) is allowed to react with 1 -chloropropane, a compound (C) is obtained. On partial hydrogenation
in the presence of Lindlar catalyst, (C) gives (D), C9H18. On ozonolysis (D) gives 2,2-dimethylpropanal
and 1 -butanal. Give structures of (A), (B), (C) and (D) with proper reasoning.
Q. 5
One mole of each bromoderivative (A) and NH3 react to give one mole of an organic compound (B).
(B) reacts with CH3I to give (C). Both (B) and (C) react with HN02 to give compounds (D) and (E),
respectively. (D) on oxidation and subsequent decarboxylation gives 2 -methoxy-2-methylpropane.
Give structures of (A) to (E) with proper reasoning.
Q.6
A chloro derivative (A) on treatment with zinc-copper couple gives a hydrcarbon withfivecarbon
atoms. When 'A' is dissolved in either and treated with sodium, 2,2,5,5-tetramethylhexane is obtained.
What is the original compound A?
Q.7
A primary alkyl halide (A) C4HjBr reacted with alcoholic KOH to give (B). (B) reacts with HBr to give
(C) an isomers of (A). (A) on reacting with sodium gives (D) CgHlg which was differentfromthe
compound produced when n-butylbromide was treated with Na. What are (A), (B), (C) and (D).
Q. 8
One mole of a hydro carbon (A) reacts with 1 mole of bromine giving a dibromo compound C5HJ0Br2.
(A) on treatment with cold dilute alkaline KMn04 solution forms a compound C5H1202. on ozonolysis
(A) gives edquimolar quantities of propanone and ethanal. Deduce structure of (A).
Q.9
A hydrocarbon (A) was found to contain 85.7% carbon and 14.3% H. This compound consumes 1
molar equivalent of hydrogen to give a saturated hydrocarbon. 1 g of (A) just decolourised 3 8.05 of 5 %
solution by weight of Br2 in CC14. Compound (A) on oxidation with conc. KMn04 gave a compound
(C), C4HgO and (B) acetic acid. Compound (C) can easily be prepared by the action of acidic aqueous
mercuric sulphate on 2-butyne. Deduce (A), (B) and (C).
Q. 10 When a hydrocarbon (A) is treated with excess of hydrogen chloride, a dihalogen derivative (B) is
obtained. The compound (B) is treated separately with aqueous and alcoholic KOH to give compounds
(C) and (A) respectively both having three carbon atoms. Compound (C) does not reduce Tollen's
reagent and compound (A) give white precipitate with ammonical silver nitrate. Assign structures to
compounds (A) to (C).
^Bansal Classes
Halogen Derivatives
[20]
Q.ll
An organic compound (A) C7H)5C1 on treatment with alcoholic caustic potash gives a hydrocarbon (B)
C7H14. (B) on treatment with ozone and subsequent hydrolysis gives acetone and butyraldehyde. What
are (A) and (B). Explain reactions.
Q.12 A dihalogen derivative (A) of a hydrocarbon having two carbon atoms react with alcoholic potash and
forms another hydrocarbon which gives a red precipitate with ammonical cuprous chloride. Compound
(A) gives an aldehyde when treated with KOH (aq). What is (A)?
Q.13 A white precipitate was formed slowly when AgN03 was added to a compound (A) with molecular
formula C6H13C1. Compound (A) on treatment with hot alcoholic KOH gave a mixture of two isomeric
alkenes (B) and (C) having formula C6H,2. The mixture of (B) and (C) on ozonolysis furnished four
compounds (i) CH3CHO, (ii) C2H5CH0, (iii) CH3COCH3, (iv) (CH3)2CH. CHO
What are (A), (B) and(C).
Q.14 0.369 g of a bromo derivative of a hydrocarbon (A) when vaporized occupied 67.2 mL at NTP. (A) on
reaction with aqueous NaOH gives (B). (B) when passed over alumina at 250 C gives a neutral compound
(C) while at 3 50C it gives a hydrocarbon (D). (D) when heated with HBr gives an isomer of (A). When
(D) is treated with dil. F^SO^j, (E) is obtained. Identify (A) to (E) and explain the reactions.
Q.15 An organic compound (X) on analysis gives 24.24 % C, 4.04% H. Further sodium extract of 1.0 g of
(X) gives 2.90 g ofAgCl with acidified AgN03 solution. The compound (X) may be represent by two
isomeric structures (Y) and (Z). (Y) on treatment with aqueous KOH solution gives a dihydroxy compound,
while (Z) on similar treatment gives ethanal. Find out (X), (Y) and (Z).
Q.16
0)
(ii)
(Hi)
(iv)
(I%Bansal Classes
Halogen Derivatives
[21]
EXERCISE-IV (A)
Q.l
, Qrf
^
Chlorination oftoluene in the presence of light and heat followed by treatment with aqueous NaOH gives
(A)o-cresol
(B)p-cresol
(C) 2,4-dihydroxytoluene
(D) Benzoic acid
[IIT 1990]
Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl halides due to
(A) The formation ofless stable carbonium ion (B) Resonance stabilization
(C) The inductive effect
(D) sp2 hybridised carbon attached to the halogen
[IIT 1990]
1-Chlorobutane on reaction with alcoholic potash gives:
(A) 1-butene
(B) 1-butanol
(C)2-butene
(D)2-butanol [ITT 1991]
The products of reaction of alcoholic AgN02 with ethyl bromide are
(C) Nitroethane
(A) Ethane
(B) Ethyl nitrite
Q.5
Q.7
<^8
Q.9
[ITT 1991]
(D) Ethyl alcohol
When nitrobenzene is treated with Br2 in presence ofFeBr3 the major product formed is:
m-bromonitrobenzene. Statements which are related obtain the m-isomer are
(A) The electron density on meta carbon is more than on ortho and para position
(B) The intermediate carbonium ion formed after initial attack of Br+ at the meta position is least
destabilized.
(C) Loss of aromaticity when Br+ attacks at the ortho and para position and not at meta position
(D) Easier loss of H+ to regain aromaticityfromthe meta position thanfromotho and para positions.
[ITT 1992]
Arrange the following compounds in order ofincreasing dipole moment
Toluene
m-dichlorobenzene
o-dichlorobenzene
p-dichlorobenzene
I
II
III
IV
(C) IV<I<III<II (D) IV<II<I<III
(A) I < IV < II < III (B) IV<I<II<III
[IIT 1996]
In the reaction of p-chloro toluene with KNHj in liq. NH3, the major product is:
(A) o-toluidine
(B) m-toluidine
(C) p-toluidine
(D)p-chloraniline
[IIT 1997]
(CH3)3CMgCl reaction with D 2 0 produces:
(A) (CH3)3CD
(B)(CH3)3OD
(C)(CD3)3CD
(D) (CH3)3OD [IIT 1997]
Benzyl chloride (CgHjCH^C^canbe preparedfromtoluene by cMorinationwith:
(B) SOClj
(C)C12
(D)NaOCl
(A) S02CI,
[IIT 1998]
0.10
Toluene, when treated with Br2/ Fe, gives p-bromotoluene as the major product, because the CH3
group
[IIT 1999]
(A) is para directing
(B) is meta directing
(C) activates the ring by hyperconjugation
(D) deactivates the ring
0Cfl
The order ofreactivity ofthe following alkyl halides for a S ^ reaction is:
(A) RF > RC > R-Br > R-I
(B) R-F > R-Br > R-Cl > R-I
(C) R-Cl > R-Br > RF > RI
(D) R-I > RBr > R-Cl > R-F
^Bansal
Classes
Halogen Derivatives
[ITT 2000]
[22]
Identify the set of reagents / reaction conditions 'X' and 'Y in the following set of transformation:
CH3 - CH2 - CH2Br
>
Product
[IIT 2003]
CH,
CH2CH3
(A) HO-
[IIT 2002]
" CH2CH2CH3
(B) HO-
-CH 2 CH 3
CH2CH3
CH2CH3
CHjCH^
CH3
(C) HO-
CH 3 '
(D) HOCH,
CH,
Column II
(P) El reaction
(Q)E2 reaction
(R) El cb reaction
(S) First order reaction
EXERCISE-IV
Q.l
(a)
jvf
Q.2
(B)
[IIT 1992]
Amongst three isomers of nitrophenol, the one that is least soluble in wateris_
[IIT 1992]
[IIT 1993]
CI
CgHj CH2 CH - CH3
KOH A
(ii)
C6H5COOH + CH 3 MgI-
Q.3
An alkyl halide X of formula CfiH]3Cl on treatment with potassium tertiary butoxide gives two isomeric
alkenes Y and Z (C6H12). Both alkenes on hydrogenation give 2,3-dimethylbutane. Predict the structures
ofX, YandZ.
[IIT 1996]
faBansal Classes
>9+ ?
Halogen Derivatives
[23]
Q. 4
Predict the structure of the intermediates/products in the following reaction sequence - [ET 1996]
Br
HMeOPh
Q.5
_AicohaiicKOH^
Heat
(b)
H1(excess)
(CH3)2CHOCH3
[IIT 1998]
Heat
Q. 6
[DT1998]
CH=CH2
Br2
(i)NaNH 2 (3equi.)
(II)CH 3 I
Q.7
[IIT 2000]
CH,
CH 3 -C-CHBr
CH3
"
c H OH
2 5
>9
Q. 8
How would you synthesis 4 methoxyphenol from bromobenzene in NOT more thanfivesteps? State
clearly the reagents used in each step and show the structures of the intermediate compounds in your
synthetic scheme.
[IIT 2001]
Q.9
An alkene A (C16H16) on ozonolysis give only one product B (C8HgO). Compound B onreaction with
NaOH/I2 yields sodium benzoate. Compound B reacts with KOH/NT^NF^ yielding a hydrocarbon C
(CgHj Q). Write the structure of compound B and C. Based on this information two isomeric structures
can be prepared for alkene A. Write their structures and identify the isomer which on catalytic
hydrogenation (t^/Pd-C) gives a racemic mixture.
[IIT 2001]
Q.10
[IIT 2004]
CH2-C1
K C N
DMF
> / a\
( A )
(i)NaOEt/EtOH
r m
(ii)PhCHO/A
>
( B )
H3Oe
.
'
c(i)SOCl2 I
V^v (ii)CH3NH2
^Bansal
Classes
Halogen Derivatives
[24]
ANSWER KEY
EXERCISE-I
Q.l
Q.8
Q.15
Q.22
Q.29
Q. 36
Q.43
Q.50
Q.3
Q.10
Q.17
Q.24
Q.31
Q.38
Q.45
D
B
C
C
B
A
A
B
Q.2
Q9
Q.16
Q.23
Q.30
Q.37
Q.44
A
C
B
D
C
C
B
Q.l
Q5
Q9
Q.13
Q.17
Q.21
Q.25
Q.27
Q.29
D
Q.2
A,C
Q.6
A,C,D
A,B,C, P
B,C,D
Q.10 B,D
A,C,D
Q.14 A,C,D
A,B
Q.18 A,B,C
A,C
Q.22 B,C
A
3, B
2 ,C
1,D > 2
A>2, B>!, C>4, D - 3
( A ) - Q ; ( B ) - S ; ( C ) - R; (D) - P
C
C
A
C
B
C
A
Q.4
Q.ll
Q.18
Q.25
Q.32
Q.39
Q.46
D
C
D
D
B
A
D
EXERCISE-I
Q.3
Q.7
Q.ll
Q.15
Q.19
Q.23
Q.26
Q.28
Q.30
(A)
Q.5
Q.12
Q.19
Q.26
Q.33
Q.40
Q.47
A
C
C
B
C
B
B
Q6
Q.13
Q.20
Q.27
Q.34
Q.41
Q.48
D
A
D
B
C
A
A
Q7
Q.14
Q.21
Q.28
Q.35
Q.42
Q 49
A
D
B
A
A
A
C
(B)
B,C
Q.4
A,B
B
Q.8
A,B,D
A,D
Q.12 A,C,D
B,D
Q.16 A,B,C,D
A,B
Q.20 A,B,C
A,B,C,D
Q.24 B,C,D
A -> 4, B
3,4, C - > 3, D -> 1,2
( A ) - S ; ( B ) - -Q; ( C ) - R ; ( D ) - P
(A)-Q;(B)-- R ; ( C ) - P ; ( D ) - Q
EXERCISE-II
Q.l
(i) CH 3 - CH - CH,,
OH
Q.4
(ii)
Q-5
(A)\TSJ
H
Me
Me
Me
I
I
I
(c) (A) Me - C = CH - Me, (B) Me-C-CH 2 -Me, (C) Me-C-CH 2 Me
OEt
(d)(A) n
1
Me
faBansal Classes
, (B) | 0 | ,(c) | O j
1
OTs
Me
Me
Br
Halogen Derivatives
[25]
OH
OH
Et
Q.6
(b) Ph-C-<^>
^CH2-CH2-OH
(c) Et-CH-Et
o
Q.7
(d)
Q.9
A=
Q.8
O L - C H - C H = CH9
Conversion
Bs
C - C - C = C-C1
CH3
(l)NaNH2
(a)AsEt-I
(b) B = CH3 - CH - OH
(c) Me2C=CH2
OH
(d) Me2C=CH2
C1CH2CH2CH2CN
(ii)
PhCHF2
(iii)
FCH2CH = CHC02Me
(iv)
Efl
(v)
no reaction
Q.13 (i) Chloroform responds carbylamine test while ethyl alcohol does not. Carbylamine test- The compound
is heated with aniline and alcoholic caustic potash-an obnoxious smell of phenyl isocyanide (C6H5NC)
is produced.
(ii)
Chlorine atoms of chloroform can be easily replaced by - OH group s on treatment with NaOH. Hence
chlorine atoms come in the form of sodium chloride. The solution thus when treated with silver nitrate
solution gives white precipitate of silver chloride. Chlorine atom in vinyl chloride is not readily replaced
by NaOH, hence it does not give precipiatet with AgN03 solution.
(iii)
The two compounds are hydrolysed with aqueous NaOH when 1,1 -dibromoethane form acetaldehyde
while 1,2-dibromoethane gives glycol.
(iv)
Chlorine atom in chlorobenzene is very less reactive, while chlorine in cyclohexyl chloride is very reactive.
Hence the two can be differentiated as above in (ii)
(v)
Apply test (ii) as above; when benzyl chloride gives white precipitate with AgN03 solution, while O
chlorotoluene does not give precipitate. Alternately, the compounds are oxidised when o chlorotoluene
give o-chlorobenzoic acid when benzyl chloride gives benzoic acid (having non chlorine.)
(vi)
n - Hexane does not respond CI" ion test even after fusion with Na and treatment with acidic AgN03.
the remaining three compounds are distinguished by their reactivity with alcoholic AgN03 solution.
^Bansal Classes
Halogen Derivatives
[26]
(a)
(b)
(c)
CH3 -CH=CHC1 (a
CH, = CHCHjCl (an
cHravcivci
H3C-CH-CH-CH3
CH3 CI
CH3
ch3
shydrogenated carbon.
faBansalClasse
Q.22 The strong -1. E offluorineatom in F3C - C < produces partial +ve charge on C atom of CF3 which
ultimately increases+ve charge on 2nd carbon atom to destabilize it
F
+5
i
F
In F3C+, the unshared pair of electrons in the p orbitals of each of thefluorineatom are shifted to C+ via
p-p orbital overlapping and thus stablizing F3C+ ion
Q.23 Dry gaseous hydro halogen acids are better electrophile. Also in aqueous solution F^O acting as nucleophile
may produce alcohol.
Q.24 KI reacts with RC1 to form RI. This RI molecule now hydrolysed easily to give ROH because alkyl
iodide are more reactive than alkyl chloride.
RC1 + KI - RI
H0H
Q.25 The more pronounced the nucleophilic activity ofthe attacking reagent, then the more the SN2mechasnism
will be favoured. Since in SN1 mechanism the raegent doesnot enter into the rate determining step of
ionisation How ever it can also be expected that as the nucleophilic activtiy is so slow that the mechanism
will changefromSN2 to SN1
Q.26 The dielectric constant of water is greater than that of aqueous acetone, and so ionisation of benzyl
chloride is facilitated.
Q.27 On movingfrom3 to 1 alcohol rate of ^ 2 reaction decreases and reaches to minimum and mechanesm
changesfromSN2 to SN1, Then rate of SN1 rate of reaction increases.
Q.28 Anhydrous A1C13 is used as a catalyst infriedelcrafts alkylation.
Q.29 tert-Butyl chloride, sec butyl chloride and CC14 with ale. silver nitrate
Me3C - CI >
">CHC1>CC1 4
c2H^
Br
Q.30
(a)As Q
-10
1=
C ^
CuLi
2
j]
D.
Q f
Hs
o
Q
faBansal Classes
[28]
Me
Me
Pr, (B) Pr
H
Q.31
EtO
H
e
B e C10H21-C^CLi
A = CjqHjj-C^CH
D = C 1Q H 21 - C = C - (CH 2 ) 4 - CH - CH 3
C-C-C-C-C-C-Br
C
E e C1qH21 - C = C - ( C H 2 ) 4 - C H - C H .
H
CH
CH
CH
F-C10H21-C-C-(CH2)4-CH-CH3
H 0
Q.32
(ii)
(iii)
(iv)
C, CH 3 CHBrCH 3 ;
D, CHgCHNE^CHg
(i)A,CH 3 CH 2 CH 2 Br;B, CH 3 CH = CH 2 ;
B, CH 3 CHOHCH 3 ;
C, CH3CHC1CH3;
D, CH 3 CH 2 CH 2
A, CH 3 CH = CH^
A, CH 3 CHBrCH = CIi 2 ; B, CH2=CH-CH=CH2; C, CH 3 CHBrCH=CH 2 & CH 3 CH = C H - C ^ B r
A, CH 3 Clr^CHOHCH 3 ; B, CH 3 CH 2 CHBrCH 3 ; C, CH 3 CH = CH - CH 3
EXER
CISE-III
Br
Q.L
CH3-CH-CH2-CI
CH 3 - C = CH 2
CH.
(X)
CH3-C-CH
CH 3
2 - Bromo - 2 - methyl propane
(Z) (isomer of X)
Q.2
(Y)
Chloretone (Hypnotic)
Q.3
CH 3 CH 2 CH 2 CH 2 Br
CH 3 CH 2 CH = CH,
(A)
Br
(C)
(B)
CH 3 - CH2- C = CH
<P)
<!SBansal
Classes
Halogen
Derivatives
[29]
Q.4
(CH 3 ) 3 C - C 3 CH
(A)
(CH 3 ) 3 C - C =C"Na+
(CH3)3C-C = C H ^ ^ C T ^
(b)
(C)
OCH 3
Q.5
CH 3 - C(CH 3 ) - CH 2 - CH 2 NH 2
CH3-C(CH3)-CH2-CH2-Br
(B)
(A)
OCH 3
OCH 3
CH 3 - C(CH 3 ) - CH 2 CH 2 - OH
CH 3 - C(CH 3 ) - CH 2 CH 2 - NHCH 3
(D)
(C)
OCH,
CH3-CH-CH2-CH2-N-N = O
CH,
(E)
Q.6
(CH 3 ) 3 C - C ^ C L
Q.7
CH,
CH,
CH 3
C H 3 - C = CH
H 3 C C CH 3
Br
CH3-CH-CH2Br
(B)
(Q
CH,
(A)
CH,
CH 3 - CH - CH 2 CH 2 - CH - CH 3
(D)
Q.8
CH,
^CH,
C=C
"H
CH,
(A)
CH3 CH 2
Q.9
CH^ CH2
CH 3 -COOH
C = CH - CH,
CH3X
(B)
(A)
<!SBansal Classes
Halogen
Derivatives
;c = o
CH,
(Q
[30]
CI
Q.10 CH3- C = CH
CI
(A)
Q.ll
(B)
CH 3 -(CH 2 ) 3 C-C1
I
CH3
(C)
CH3(CH2)2CH = C(CH3)3
(A)
(B)
CH3.
Q.13
(CH3)2CH-CHCH2CH3
(CH3)2CH CH = CH CH3
(A)
(B)
.C2H5
^ C =C
(C)
Q.4
Q.ll
C
D
EXERCISE-IV
Q.l
(A)
Q.5 A,B
Q.12 B
Q.6 B
Q.13 D
Q.7
(B)
Q.2
^Bansal Classes
Halogen Derivatives
[31]
ch3 ch3
Q.3
ch3
ch3
CI
HQ.4
-Ph
MeOPh
CH 3
Q.5
Br
Q.6
G=CCH3
C=CNa
,CH-CH 2 Br
CH-J
NaNH,(liq.)
(A)fQ
*(B)
CH,
Q.7
CH 3 -C-CH 2 CH 3
oc2h5
ONa
Br
OMe
NaOH
conc.H,SOd
I C 3 J A high pressure^ [ o )
MejSO^ [ o ]
OMe
OMe
OMe
NaOH
'
SO,H
-Co)-
->(0)
ONa
OH
OMe
OMe
Alternative rout
Br
Br
Br
Br
naoh
o j - ^ ^ i o j
> [ q j ^ l o j - . .
OMe
ONa
SOiH
n a o h
> [ o j - ^ l q .
OH
ONa
Q.9
(A) PhC(Me)=C(Me)Ph
KOH
KU
NH3-NH3
CN
Q.10 (A)
mBansal Classes
COOH
CONHCH,
!
CH = C
(D)[OJLOj
Halogen Derivatives
[32]
Q.13
Q.14
->is:
Br
Br
(A)
Br
(C)
(D)
Br
Me
f5
Me
HO|H
Me
H|CI
11
Et
B
Steps I and II are
(A) both SN1
-OH
-> H1
Et
Et
A
(B) both SN2
(i)CH3CHO ^
f Jj
(ii)aq.NH4Cl
.
J\.
.^-Br
CHOHCH3
MgCl
(A)
Br
CI
*{S
V
MgCl
CI
&
(B)
MgBr
^-Br
CHOHCHi
MgCl
(C)f|
&
Br
H,0 +
> C4H10O
(alcohol)
(B)
Alcohol B reacts fastest with Lucas reagent. Hence A and B are
O
II
II
(C) C H 3 - C - 0 - C 2 H 5 , ( C H 3 ) 2 C H 0 H
faBansal Classes
NOMENCLATURE
(D) H - C - O - C 3 H 7 , ( C H 3 ) 3 C O H
OFORGANIC
COMPOUND
[3]
Mg
CI
ET,0
Qc
CI
MgCi
(B)
(A)
\JX*
MgBr
H
i
^CH3
H,C'
(A) SE2
1
B r
(B) SN1
V~V
.(CH2)5CH3
HO-C
X-Br
V^
(Q
C H 3
(D) SN2
(C) SN
OH-
H A _ A H
Ais:
HOV
(A)
,CH 3
h/LAH
(B)
H\/
\/
oh/V_AH
(D) None
(C) Both
HCOO"
CHCI3 + OHIntermediates ofthis reaction are
(A) :cci:
J&
(B) :CCL
(C) both
(D) None
(D)BothA&B
> CH3OH + Br
For CH3Br + OH"
the rate of reaction is given by the expression:
Q.24 (A) rate = k [CH3Br]
(B) rate = k[OH"]
(C) rate = k [CH3Br][OH_]
(D) rate = k[CH3Br] [OH"]
Which will give white ppt. with AgN03?
Q.25 (A) \
)CI
(B) ( O V - C I
(C) ( O / ~ c h 2 c i
The reaction of SOCl2 on alkanols to form alkyl chlorides gives good yields because
(A) Alkyl chlorides are immscible with SOCl2
(B) The other products of the reaction are gaseous and escape out
(C) Alcohol and SOCI2 are soluble in water
(D) The reaction does not occurs via intermediate formation of an alkyl chloro sulphite
<!Bansal
Classes
Halogen Derivatives
[194]
CH,
Q.34
H-
H_
c H O-
Br
> ? Major product is:
C2H5OH
CH
h3Cx
/H
(A)
H3Cv
/CH 3
(B)
H3Cx
^ch3
(C)
>
H3Cx
(D)
IK
<!Bansal Classes
^D
/
D
Halogen Derivatives
<
^H
C = C
X
\
CH3
[5]
Q35
(A)
Q.36
u O
H - A CH 3
BRH
(A)
Q.39
(B)
LaJ
(B)
(D),
(C)
E2
JJ
S ) E ^ ^ n e 0 S 8 e n e ^EAylcWoTde
CH3 - C - CH3 - i s
il
tij
> (A)
Agp<nvder
> (B)
H s0
(A)]
(C)]
Q.40
(D)]
^r^Trrtiztir
Q.41
042
( A ) Q
CB)|)
( C ) ^
.(D) I
Q. 43 The appropriate naming for the second step in the haloform reaction is:
(A) Halogenation
(B) Dehydrohalogenation
(C) Reduction
(D) Dehydrogenation
Q. 44 Which product is obtained when bleaching powder is distilled with acetone:
(A) CC14
(B) CHClg
(C) CH2C12
(D) CH3C1
Q.45 What will be the reduction product of following reactions:
+2H
Zn/HCl (ale)
CHCI3-
+4H
Zn/HCJ (aq.)
+6H
Zn/H 2 0
(C) CHoCl
(D)CHC13
/^Y3
is converted into
I
by:
(A) (i) CH3~ Mgl, H30+ (ii) H2S04, A, (lii) HBr, R202
(B) (i) CH3- Mgl, H30+ (ii) H2S04, A, (iii) HBr
(C) (i) CH3-MgI, H30+ (ii) HBr
(D) (i) HBr, R ^ (ii) CH3-MgI, H30+
Q. 49 To form Malonic acid, by shortest possible route, we have to start a reaction from:
(A) Ethyledine chloride (B) Methyl chloride (C) Methylene chloride (D) Chloro ethan
Q. 5 0 Frankland reagent is:
(A) Dialkyl lithium
(B) Dialkyl Zinc
<!Bansal
Classes
Halogen Derivatives
[197]
EXERCISE-I
(B)
(Choose the correct option. One or more than one are correct)
Q.l
[X]is:
H
Br
(A)kXJ
(B)rN
(C)
(D)
Br
Br
Q.2
Q.3
A solution of (R)-2-iodobutane, [a] = -15.9 in acetone is treated with radioactive iodied, until 1.0% of
iodobutane contain radioactive iodine, the specific rotation of recovered iodobutane is found to be
15.58, which statement is correct about above information.
(A) It has optical purity 96%
(B) % of R in solution is 99%
(C) Racemic mixture is 2%
(D) Final solution is dextrorotatory
Q. 4
. A
moistAg,U
2
>
CH 2 OH
CH,
CH 2 OH
Xchoh <&< 1
CH
(C)C >
(D)
OH
Q.5
(A) CH 3 CH 2 - CH - CH 3
t B
0
CH C
(B) CH 3 CH 2 - CH - CH 3
Br
3 ^OK >
Br
CH 3
(C)
&/
CH 3 CH 2 -CH-N
CH,
faBansal Classes
CH 3
oh
>
CH,
NOMENCLATURE
(D) CH CH C H - C H
S
011
>
S(CH3V
OFORGANIC
COMPOUND
[8]
Q.6
(i)Et2
A+B
> Alcohol
H2Cr 4
> Ketone
CH
(D) Ais isopropyl magnesium iodide
(C)Bis CH3-CHCOCI
H
CH
Q.7
I
H
CH3
CH 3
(A) C H 3 - C H - C H 2 B r
(C) CH3CH2CH2Br
Q. 8
(D) C H 3 - C H - C H33
Q. 9
^Bansal Classes
Halogen Derivatives
(D)R-Br
[9]
H-C-OTS
NaCN
CH3CH2CH-CN
Benzoyl chloride is less reactive than acetyl chloride for nucleophilic acyl substitution reaction because
0
(A) - C - group ofbenzoyl chloride is in conjugation with benzene ring. This makes benzoyl chloride
more stable than acylchloride.
(B) CH3- group of acetyl chloride make C-Cl bond stronger due to the +1 effect.
(C) C6H5- group ofbenzoyl chloride make C-Cl bond weaker due to +R effect.
(D) Carbonyl carbon in benzoyl chloride is less electron deficient than acetyl chloride
(C)3
(B)5
(A)L
(D)4
(B) CH3CH2CH-CH3
CI
II
s
<!Bansal
Classes
CH3
Halogen Derivatives
[10]
N-^OH
(C) C H 3 - C H - C = O
Br
le
O0
(A)
CMe3
(B)
CMe,
CMe,
<P)
(C)
Br
Q.18 3-Phenyl-3-pentanol can be prepared from grignard reagent & other component which can be
(A) 3 -pentanone
(B) Ethylbenzoate
(C) Ethyl phenyl ketone (D) Propanoyl chloride
Q.19 In which of following reaction inverted product will obtained.
(A) SN1
(B)Sn2
(QSnNgp
(D)V
(A)
<!Bansal
Br
Br
(B)
Classes
(C)
0>
Halogen Derivatives
Br
"0
[11]
Q.21
Q.22
(A)
Q.23
Q.24
(D) H ^ C H - C I V C L
(C) Ph-Cl
(B)
CH 3 CI
NaOI
(D) Ph - C H - CH - CH 3
(Q
yellnw solid
G can be
(B) C H 3 - C - C H 2 - C " C H 3
(A)CH3-C-OCH3
II
O
(D)
(C) CD3COH
CCH3
o
Q.25
Match the List I (reaction) withList II (reaction intermediate) and select the correct answer using the
codes given below the Lists.
Listn
List I
(A) CF3-CHC12
alc.KOH/A
>
CF2 = CC12
(1)
Transition state
(2)
Carbocation
(3)
Carbanion
(4)
Free radical
CH3
(B) CH3 - C - OH
CH,
(C) CH3-CH2-Br
> CH 2 -CH 2
Br
(D) C H 3 - C - C H 3
CH,
^Bansal Classes
aq.KOH/A
>
CH,
Halogen Derivatives
P2J
Q.26
Match the List I with List II and select the correct answer using the codes given below the Lists.
List I
Listn
(A)E1CB
(1)
Quaternery Amine oxide
(B) Saytzeff alkene as major product
(2)
Xanthate
CI
Q.27
(C)E2
(3)
CH3-CH2-CH-CH3
(D)E C
(4)
C6H5-CH2-CH-CH3
Match List I with List II and select the correct answer from the codes given below:
ListI
List II
(A)
CH 3 -O-SO 2 CH 3 + C 2 H 5 O
(1)
CH3CI^P H 2
(B)
CH 3 -CH2-I + PH 3
(2)
CH 3 -O-C 2 H 5
Q.28
(C)
HC = CNa + CH 3 -CH2-Br
(3)
CH 3 -O-CH 3
(D)
CH 3 -CI + CH 3 -O
(4)
CH=C-CH 2 -CH 3
Match List-I with List-II for given S n 2 reaction & select the correct answer from the codes given below
Z-CHJBR + CH 3 0
List-n
(P)0.1
List-I
(A)H(B) CH 3 (C)C 2 H S -
(R)l
Q.29
\
CH
iftcdl'i
(0)3
CH 3
(D)
Z-CH 2 -OCH 3 + Br
CH
(S)100
(P) Ketone
(B)R-MgX + (CH2) 2 0
n-carbon
(C) R - M g X + C 0 2
n-carbon
Adduct
>
(Q) 1 Alcohol (n+ 1) carbon
Adduct
faBansal Classes
H,O
> Adduct
List-n
H3
Adduct
>
3 >
Halogen Derivatives
[13]
Q.30
List-n
List-I
/OCH
W-
-C>
(A)
CH,CH 2 Q
CH,0
CH,0
>
(P)E1
CH3O
0
II
CB)
CH33
W
CH 3 CH 2 O
CH22CH2Br
(Q)E2
CH,CH,OD
(C)
(R)Elcb
Br
CD)
feBansal Classes
Br
ale. KOH
(S)Ec
Halogen Derivatives
[14]
EXERCISE-II
Q.l
(i)
(ii)
(iii)
(iv)
(a)
(b)
(v)
Although ethers are weakly polar, are used as solvent of choice for Grignard reagents.
(vii)
Treatment of either CH3-CH - CH-CHjBr or CH3-CH -CH - CH2 with aqueous HO~ gives the
O
same product. Also write down mechanism involved, & IUPAC name of product.
Q.2
(a)
(b)
(c)
(d)
(e)
On reaction between an alkyl halide and KOH in a mixture of water and ethanol, compare the two
mechanisms SNj and SN2:
relative rates of CH3X,C2H5X,iso-C3H7X&tert-C4H9X
relative rates for RC1, RBr and RI
effect on rate of a rise in temperature
effect on rate of increasing water content of the solvent.
effect on rate increasing alcohol content of the solvent.
Q.3
In the following reaction is carried out in the weakly ionizing solvent, acetone (CH3)2C=0. (Bsisbrosyl,
p-bromo benzene sulfonyl)
n-C4H9OBs + X >n-C4H9X + BsOThe order of reactivity of halide ions depends or the salt used on their source :
ifLi+X~ isused,I^r-^Clif (n-C4H))4N+ X - is used C l - > B r - > I ~
How do you account for this contrast in behavior ?
Q.4
Which of the following is the correct method for synthesizing 4,4-dimethyl-pent-2-yne, using sodamide
in liquid NH3? Given reasons.
CH3
(i) CH3C=CH + CH3 - C - Br
CH3
>
CH3
Q.5
(a)
faBansal Classes
Halogen Derivatives
[15]
C2H5O
CH3
(b)
C 2 H 5 OH
CH3-C-CH2-Br
CH3
H
Nal
H
TsCl v *
A
Pyridine
(C)
NaBr
CH, OH
Q.6
(a)
H3 +
> A
MgCl
(b)
Ph-OCl +
o
(2 eq)
(c)
H - C -OEt + CHgCHjMgBr
h3o+
(2 eq)
(d) QCMgI +
(1 eq.)
CH2
HCl
H3C
> E
Ph
C2H5
Q.7
(a)
OH
<J)MgBr + (C2H5)2CO
(b)
C2H5MgBr +
^>C =0
H
(c)
H,0
C2HsMgBr + <j>-COOCH3
<!SBansal
>
5C2
Classes
z >
Halogen Derivatives
[16]
(d)
H2
<f>MgBr + C2H5COOCH3
>
I
H
Ci
Q9
Zn
.
Zndust' A n
I
CH3-CH-CH-C
CH
H 2, -- C
C 1I
--
convert?
CH3
Q.10
(a)
(b)
(c)
(d)
What is/are the limitation in the formation of Grignard reagent by RX+Mg dryether >
R should not contain any acidic group
R should not contain any electronegative group
Alkyl halide should not be vicinal dihalide
Alkyl halide can't be Tertiary.
Q.ll
(a)
CH^jCHjCl + 1 ~ - A
(b)
(c)
(d)
CH 3 -CH-CH 2 -OH
Conc NaUH
) E,
C l C ^ O ^ C H ^ r + KCN
(ii)
PhCHO
Oii)
BrCH2CH = CHC0 2 Me
(iv)
(v)
EtOH + HI
>D
EtOH + HCN
>E
>A
SF
* >B
^
>C
Q.13
C 2 H J O H f r o m CHC1 3
(ii)
(iii)
(iv)
(v)
(vi)
<!SBansal
Classes
Halogen Derivatives
[17]
CH? - OH
- ^ A - ^ B
J.IMID4
^ q)Li a ^
(ii) CuF
+B
NBS
C
1 C
ale.KOH.
CH,
(b)
OH
CH3CH2CH2
H
(i)TsCl
kii)C2HsO"K+
(A)
Hi) K
kii)C2H5OTs
(B)
[18]