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ORGANIC CHEMISTRY
Daily Practice Problems Target IIT-JEE
CH2 Cl
KSH
1. Major product :
(SN2)
Br
SH Cl
(A) (B)
SH SH
SH SH
(C) (D)
Br Cl
2. Consider the reaction of (R)-2-iodooctane to react with radioactive iodide ion (*T-).
Rate constant Ks = The rate of substitution determined by measuring the rate of incorporation of
radioactivity into the alkyl halide
Rate constant K The rate of loss of optical activity from the alkyl halide under the same condition.
For which of the following stereochemical scenerio K°/Ks=1 ?
(A) Retention (B) Inversion
(C) Equal amounts retention and inversion (D) For all scenerio K / Ks 1
KCN H3O
C2H4Cl 2 (B) (C) (D)
3. (A)
The compound D has the characteristics
(A) It is succinic anhydride if (A) is vicinal-dihalide.
(B) It is popionic anhydride if (A) is gem dihalide.
(C) It is succinic anhydride if (A) is gem dihalide.
(D) If is propionic anhydride if (A) is vicinal-di-halide.
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4. The best sequence of reactions to prepare 2 -heptanone is
NaNH NC C Br H O, Hg2
(A) propyne
2
X
4 9
Y
2
H SO 2 4
O Cl
O C C CH3
Sum of x + y ?
(A) 4 (B) 5 (C) 3 (D) 2
OCH3
OCH3
(iii) Ph O O Ph (iv)
OCH3
CH2 OH
(v) Et-O-Et (vi)
OH
(A) 10 (B) 11 (C) 12 (D) 13
CH3
H Br NaI/acetone
7. (SN2) condition
H Cl
CH3
CH3 CH3 CH3
H I H I I H
(A) (B) (C) (D)
H Cl Cl H H Cl
CH3 CH3 CH3
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I
NBS KSH
8. A B
CH3
Product (B) is
SH I
(A) (B)
Br
SH
I SH
(C) (D)
CH2 SH Br
CH3
1 NaNH2
1mole ColdKMnO
9.
2 CH3I A 4
B
CH2OH 1mole
OH
Identify final product (B) ?
O
OH
(A) (B)
CH2OH
OH O COOH
O O
(C) (D)
COOH CHO
OH OH
O
(i) LDA
(A)
(ii) CH3I
10. (i) C2H5ONa
(B)
(ii) CH3I
What is relation between A & B
(A) Tautomer (B) Chain (C) Position (D) Geometrical
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ORGANIC CHEMISTRY
Daily Practice Problems Target IIT-JEE
2. The first demonstration of the stereochemistry of the SN2 reaction was carried out in 1935 by prof.E.D.
Hughes and his colleagues at the University of London. They allowed (R)-2-iodooctane to react with
radioactive iodide ion (*I–).
* - -
CH3CH(CH 2)5 + I CH3CH(CH 2)5 + I
I *I
2-iodooctane 2-iodooctane
(radioactive)
The rate of substitution (rate constant k s ) was determined by measuring the rate of incorporation of
radioactivity into the alkyl halide. The rate of loss of optical activity from the alkyl halide (rate constant k )
was also determined under the same conditions.
(a) What is the value of k%k s for equal amount of inversion and retention?
(A) less than 1 (B) More than 1
(C) equal to 1 (D) Can not predict
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5. Correct statement
(A) F Cl Br I Nucleophilicity in polar-protic solvent
(B) F Cl Br I Nucleophilicity in polar-aprotic solvent
(C) I Br Cl F Leaving group order
(D) R-I > R-Br > R-Cl > R-F Rate of SN1 and SN2 reaction
O
NaOH CH3 I
(C) R C OH (a) (b)
1 CH3 1HF
NaNH 2 2 2 CH I H O /HO
(D) 1-butyne
2
(a)
3
(b)
H Cl HO H
Cl HO OH
+ H Cl
(S) H2O (R) (S)
(D) +
1. NaNH2 2 eq.
2. CH3CH2
x
3. CH3
Scheme-I
4. H2 /Pd BaSO4
OH
CH
C
1. NaNH2 2 eq.
2. Ch3 CH2
3. H O mild
(y) Scheme-II
3
4. Na/NH3
CH2 OH
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8. The product (y) is
CH3CH2
CH2CH3
(A) (B)
CH2 OH CH2 OH
CH2
CH
CH3CH2 CH
(C) (D)
CH OCH3
w
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ORGANIC CHEMISTRY
Daily Practice Problems Target IIT-JEE
CH3 CH3
H2O
1.
SN1
Cl
Total number of plane of symmetry present in carbocation formed (of given compound) in rate determining
step will be?
(A) 1 (B) 3 (C) 2 (D) 4
2. How many Dichloro products of (I) are possible (including stereoisomers and neglecting rotational isomers)
Cl2
hv
?
Cl
(A) 5 (B) 6 (C) 7 (D) 4
CH3
SN1
4. C6H 5 Br Maximum racemisation takes place when :
H
(A) 100% H2O (B) 100% Acetone
(C) 80% H2O + 20% acetone (D) 80% acetone + 20% H2O
HCl
CH2
(A) (B) Cl
Cl
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(C) (D)
Cl
Cl
Br CH3 CH2 Br
7. What is the maximum number of products possible when (2R, 3R) 2-chloro-3-phenylbutane is undergone
through hydrolysis SN1
(A) 2 (B) 3 (C) 4 (D) 5
Br2
CH OH aq
hv
3
solution ‘A’
Br2
CH OH aq
Fe
3
solution ‘B’
10. Correct graphical representation of rate of SN1 will concentration of nucleophile and alkyl halide
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ORGANIC CHEMISTRY
Daily Practice Problems Target IIT-JEE
CN Br
C2 H5 O Br
C2 H5 O
CH2 A B C (?)
CN
CN CN CN CN CN
CN CN
(A) (B) (C) (D)
CN
MeO
Me
OTs
Me AcOK
AcOK
?
MeO MeO
Me Me
Me Me
MeO MeO
Me Me
OAc OAc
(C) Me
(D) Me
Racemic Racemic
(optically inactive) (optically inactive)
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Passage Q.3 to Q.4
The reaction sequence shown below gives products Q,R,S,T respectively.
OH
CH2
CH O
C C C C
(A) C (B) C (C) (D)
C C
H3C O
OH H3C
(I)
CH3
Br Br
H3C H3C
(A) H C OH (B) H C OH
3 3
CH3 CH3
OH OH
H3C H3C
(C) H C Br (D) H C Br
3 3
CH3 CH3
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Multiple Choice Questions
5. The hydrolysis of ether (x) shown below –
OR acid
OH + ROH
SOCl2
(Q) (2) SN2
OH
PCl5 /Pyridine
(R)
(3) SN1
OH
Aq. KOH
(S) (4) SN NGP
Codes :
P Q R S
(A) 3 2 1 4
(B) 1 3 2 4
(C) 2 1 4 3
(D) 1 2 3 4
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ORGANIC CHEMISTRY
Daily Practice Problems Target IIT-JEE
NO2 NO 2 NO 2
H
H
N O O
N
(A) Br (B)
Br
Br
H H
Br N O N O
(C) (D)
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NO 2
1 NaOH
3. F
2 H3O
Br
Product (A) is
NO 2
NO 2 OH
NO 2
OH
(A) (B) (C) (D)
OH
F F
F
Br
OH Br
Br
NO 2 NO 2 NO 2
6. Choose the one compound within each set that meets the indicated criterion :
List –I List-II
F
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when allowed to stand in aqueous ethanol.
Br
(S) The ether that cleaves more rapidly in HI. (4) C CH3
CH3
Codes :
P Q R S
(A) 3 2 1 4
(B) 1 3 4 2
(C) 2 1 4 3
(D) 1 2 3 4
7. List-I List-II
Cl
NaOCH3
(P) (1) Electrophilic aromatic substitution reaction
NO2
Br
NO 2
CH3
O CH3
H3O
(S) (4) SIV-Ar reaction
CH3
Codes :
P Q R S
(A) 1 2 3 4
(B) 4 3 1 2
(C) 2 4 1 3
(D) 3 2 1 4
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ORGANIC CHEMISTRY
Daily Practice Problems Target IIT-JEE
1. The product which results from antiperiplanar elimination on pyrolysis of following sulfonate ester of
menthol is
O
O
Heat
N S O ?
H O
EtO
(P)
Br EtOH
t-BuO
Br (Q)
t-BuOH
(A) Positional isomers (B) Enantiomers (C) Enantiomers (D) Chain isomers
Br
Br
alc KOH alc KOH
3. (I) (II)
O
Br
(III) alc KOH
N
H
The rate constant of which of the above reaction is highest
(A) (I) (B) (II) (C) (III) (D) (II) & (III) have same rate constant
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Cl
t-but O
(A)
t-but O
4.
O
“(A)” is
t-but O O
Cl O t-but
O O O
OH
5. SOCl 2
A
C2H5ONa/C2H5OH
A X (Alkene)
Total number of alkenes formed are
(A) 3 (B) 6 (C) 5 (D) 4
6. How many isomer of C4H9Br when reacts with NaNH2. Diastereomers will form ? (excluding stereoisomer)
(A) 0 (B) 1 (C) 2 (D) 3
ElONa/EtOH
7. A (Major), A is
Cl
OEt OEt
Br
(i) (B) Br (C) Br
(A) (i) > (ii) > (iii) (B) (ii) > (i) > (iii) (C) (iii) > (ii) > (i) (D) (iii) > (i) > (ii)
10. Which of the following compounds undergo E2 reactions with the fastest rate ?
(A) CH3 CH CH3 (B) CH3CH2CH2I (C) CH3 CH CH3 (D) CH3CH2CH2-Br
Cl I
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ORGANIC CHEMISTRY
Daily Practice Problems Target IIT-JEE
OH
H HBr
(A) (B)
CCl 4
(major)
(A) 2 (B) 3 (C) 4 (D) 6
2. Conc. H2SO 4
A + H 2O
(major)
OH
Which of the following is product “A” in the above reaction ?
(A) (B)
(C) (D)
3. In which of the following reaction product formation takes place by saytzeff rule ?
OAc Br
CH3ONa/
(A) H3C (B) H3C
CH3 CH3
H3C
Br (CH3)3COOK/
(C) OH (D) H3C
+
N CH3
H3C CH3
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4. Which one of the following will be the major product when OH is treated with H SO ?
2 4
CH 2
CH3 CH3
OH CH3 OH CH3
CH3
N
OH
5.
(B)
(A) (C)
Compound (A) do not decolories bromine and dissolve in HCl. On treatment with con H2SO4 gives B. Now
count the number of Hoffmann exhaustive methylation of B to C is
(A) 1 (B) 2 (C) 3 (D) no reaction
TsCl/Py EtO K
6. (A) (B) + (C)
EtOH/
OH
KSH
(D)
DMSO
Comment on stereo chemistry of product :
(A) B, C = Position, D=Single (B) B, C = Racemic, D = Position
(C) B, C = Racemic, D = Racemic (D) B, C Racemic, D = Single
7. Which of the following carbocations donot undergo rearrangement to give a major product.
O
O
(C) CH3 (D)
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8. Compound X, C7H13Cl is reacted with sodium ethoxide and gives a elimination product Y, C7H12. Treatment of
ozone followed by zinc and water gives the compound below. X and Y are respectively :
O O
O3, Zn
X Y
H2 O H
Cl Cl
(A) X = Y= (B) X = Y=
Cl
Cl
(C) X = Y= (D) X = Y=
Conc.H2SO4
9. Products are
OH
(A) Mirror image stereoisomers (B) Geometrical isomers
(C) Identicle (D) Diastereomers
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ORGANIC CHEMISTRY
Daily Practice Problems Target IIT-JEE
Br
alc. KOH
1. No. of products including stereoisomers are
2. Major product (X) & (Y) of the below reaction are respectively ?
CH3 CH3
CHCH3
CHCH3
EtO EtO
EtOH X ;
EtOH Y
H3C H3C Cl
Cl
(Methyl chloride) (Neomenthyl chloride)
CH3 CH3
CHCH3 CHCH3
CHCH3 CHCH3
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OH
(A)
C6H12
Terninal
Alkene
O
(i) H-Br (ii) KOH (alcoholic) (iii) O 3
(D) (E)
followed by
(F)
Zn/H2O
6. Red Brown colour of bromine water disappears when it reacts with alkene (A) Identify the product.
Br OH
(A) (B)
OH Br
Br OH
(C) (D)
OH Br
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Passage (Q.7 to Q.9)
Elimination is reaction is important to synthesize alkene. Generally more stable product (Saytzeff's alkene) is
major but in certain cases less stable product (Hoffman's alkene) can also be major.
+
N
OH Major product
7.
Et-O
Major product
8. Et-OH/
Br
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ORGANIC CHEMISTRY
Daily Practice Problems Target IIT-JEE
CH3 I
alc. KOH
1. C C CH2
CH3 CH CH3
CH3
X = Number of chiral products (including stereoisomer).
(A) 2 (B) 4 (C) 6 (D) 8
NH2
(1) CH 3 I (excess)
(2) Ag 2O
2. (3)
Identify major product
CH2
OH
H ,
3. X
4. + H
(P) Major
N
H
Major Product (P) is :
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N
N
(A) (B)
N N
(C) (D) OH
1 O3 H2 Conc. H3PO4
5.
2 Zn/H2O
Ni
Identify all the possible product(s) formed in the above reaction is/are :
CH2
TsCl/py H2SO 4
(x) (a)
OH OH HgSO 4
CH3 CH3
6.
CH3 H Conc. H2SO 4 B2H6 (THF)
(y) (b)
H2O 2, NaOH
Find the relationship in between (x) and (y), (a) and (b)
(A) Identical, (x) and (y) (B) Position isomer, (x) and (y)
(C) Identical, (a) and (b) (D) Position isomer, (a) and (b)
OCH3 O
7. NaOH, Br2,CCl 4
A Solution (B)
(major)
Correct statement(s) about the solution B is/are : -
(A) It has 2 products (B) It has 1 product
(B) It is optically inactive mixture (D) It is optically active mixture
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Br
8. Base
(P)
COOH
Br
Base
(Q)
COOH
=P =P
(A) COOH (B) COOH
=P =Q
(C) (D)
Br2 Et3CO K NBS Alo. KOH 1 H 1 mole
9.
hv
P
Q R S Ni
T
Major major
X = difference in molecular weight in reactant and product T than X = ?
Alc. KOH
10. Number of alkene obtained by E2.
Br
CH3
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ORGANIC CHEMISTRY
Daily Practice Problems Target IIT-JEE
3. List-I List-II
H2O
(P) Ph Cl (1) SN1
Cl Ph S Na
(Q) (2) SN2
F
KOH
(R) (3) Carbocation is intermediate
NO 2
Br2
(S)
CCl4
(4) Carbanion is intermediate
Codes :
P Q R S
(A) 1 2 4 3
(B) 1 2 3 4
(C) 2 1 4 3
(D) 2 1 3 4
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4. List-I List-II
CH 2 Cl
NO 2
F
NO 2
(Q) (2) Sterically inhibited resonance
NO 2
F
Codes :
P Q R S
(A) 3 2 1 4
(B) 4 3 2 1
(C) 2 1 4 3
(D) 1 2 3 4
5. Column-I Column-II
(1) Hg(OAc)2, H2O
(I)
(2) NaBH4, HO
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(C) CH CH Cl NaC CH (R) I and II are formed by addition
3 2 (I)
Br
(i) alc. KOH
CH3 C CH2 CH3 (II)
(ii) NaNH2
Br Reaction
H2O
(D) Major (I)(S) I and II are enantiomers
SN1
I
CH3 OCH3
CH3 OCH3
I
H2O
Major (II)
SN1
6. List-I List-II
(Reaction sequence) (Reagent required)
OEt
(R) (3) EtOH/H
Codes :
P Q R S
(A) 1 2 4 3
(B) 2 1 4 3
(C) 2 1 3 4
(D) 3 2 1 4
CH3
CH3OH
?
7.
Br
X = Total number of substitution & elimination product(s). Find the value of X ?
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8. How many of the following reactions will prefer following a path way which gives 1st order kinetics.
Cl
OH + NaNH2
H
(a) (b)
Cl
CH CH2
CH2 CH2 F
-
EtO /EtOH
(c) NO2
NO2
SH
Cl Cl
NaI
KOH S
(d) (e) (Acetone)
Cl
H2O
(f) (g) Base,
Cl OH
N
O
(1) PhMgBr
(h) +
(2) H
CH3 Cl , Cl , ,
O Et , OH ,CH3 CH CH2 , Cl , CH3 C N
NO2
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