BATCH XII & DROPPER’S 2022 (Mains + ADV)

TOPIC HALOALKENES DPP 8

Marking Scheme : Single Correct (+3,-1) M M: 39 Time : 30 min

SCQ
1. In which of the following reactions an optically active single product is formed :

(a) CH3ONa + (b)

(c) + (d)

SH CH3
(i) NaOH / 
2. C2H5 D W; Identify W
+
(ii) H
H I
SH CH3 SH D
SH CH3 SH D
(a) C=C (b) C2H5 D (c) C=C (d) C2H5 CH3
C 2H 5 D C2H5 CH3
H OH HO H

3. The major product of following reaction is :

CN
H2C
CN

(a) (b) (c) (d)

MCQ

4. The correct statement/s about the following reaction is / are : NaI / Acetone
 ‘Y’

(a) The product is achiral compound

(b) The product does not have isotopic iodine
(c) It is an allylic bimolecular nucleophilic substitution reaction
(d) Ozonolysis product of ‘Y’ give positive iodoform test

1
5. Observe the following reaction and tick correct option (s) :
r1 .................. (I)


CH3 – I + r2 ................. (II)

 

(a) r1 < r2
(b) Transition state in reaction (I) is less stable then transition state in reaction (II)
(c) Substrate of both the reactions are equally reactive to a perticular nucleophile
(d) r1 and r2 both are directly proportional to the concentration of nucleophile CH3ONa
6. Which of the statements regarding E2 reaction is correct ?
(a) It leads to a five membered transition state
(b) Increase in branching of  carbon stablizes the transition state
(c) it is found to be accompained by rearranged products
(d) The more stable alkene is produced and it is known as Saytzeff alkene provided stereochemical
requirement of elimination is fulfilled
 H O 
H O
7.  CH3 – O H2 ............... (I); CH3 – Br 2
CH3 – Br 2  CH3 – O H2 ............... (II)
KI
Statement : 1 Reaction (II) is much faster than reaction (I)
Statement : 2 Both the reactions are SN2 and is a poor nucleophile and better leaving group in reaction
(II)
(a) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(b) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1
(c) Statement-1 is True, Statement-2 is False
(d) Statement-1 is False, Statement-2 is True
8. Statement-1 : The anti-periplanar transition state is most commonly seen in E2 reactions.
Statement-2 : The transition state for the anti-periplanar arrangement is a staggered conformation,
with the base far away from the leaving group. In most cases, this transition state is higher in energy
than that for the syn-periplanar elimination.
(a) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(b) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1
(c) Statement-1 is True, Statement-2 is False
(d) Statement-1 is False, Statement-2 is True
Comprehension (Q.No. 9 & 10)
When optically active 2-iodooctane was allowed to stand in acetone solution containing Na I131
(radioactive iodide), the alkyl halide was observed to lose optical activity and to exchange its ordinary iodine
for radioactive iodine. The rate of each of these reactions depended on both [RI] and [I–], but loss of optical
activity was exactly twice as fast as gain of radioactivity. Combining as it does kinetics and stereochemis try,
the experiment, reported in 1935 by E.D. Hughes, is considered to have established the stereochem istry of
the SN2 reaction : that each molecule undergoing substitution suffers inversion of configuration.

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9. In the above reaction the rate of reaction depends upon
(a) only on concentration of alkyl halide.
(b) only on concentration of NaI131
(c) it is independent of concentration of both the reactant
(d) Rate of reaction depends upon both (2-Iodooctane) and (NaI131)

10. Which of the following statement is correct for the above reaction
(a) Lose of optical activity will be exactly equal equal to gain of radioactivity.
(b) Loss of optical activity will be half of gain of radioactivity
(c) Loss of optical activity is exactly twice as fast as gain of radioactivity
(d) Loss of optical activity is four times as fast as gain of radioactivity.

Comprehension (Q.No. 11 to 13)

Observe the following reactions and given answers

11. Which of the following structure represents the transition state of slow step of reaction I.

(a) (b) (c) (d)

12. Which of the reaction (I – IV) involves rearrangement of reaction intermediate.

(a) I only (b) I, III (c) II, III, IV (d) I, II, III
13. Planar reactive intermediates are formed in reactions :
(a) I, III (b) II, III (c) I, II (d) I, III, IV

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All students are advised to solve DPPs within allowed time only.
All discussions are scheduled in every 4th doubt discussion class
–MKA Sir (Guruji)

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BATCH XII & DROPPER’S 2021 (ADV)
TOPIC HALOALKENES DPP 9

Marking Scheme : Single Correct (+3,-1) M M: 36 Time : 30 min

SCQ
1. The correct order of SN2 / E2 ratio for the % yield of product of the following halide is –

(P) (Q) (R) CH3 – CH2 – I (S)

(a) R > S > Q > P (b) R > Q > S > P (c) P > R > S > Q (d) Q > P > R > S
CH3CH2 C2H5 Et Me Et Me
| I CH2
C–I CH3
2. (a)  (b) CH3 
|
CH3 Et Et
H H
The possible set of reagents for the reactions (a) and (b) are
(a) Alcoholic KOH/ in preaction (a) and EtONa / DMF/ in reaction (b)
(b) Alcoholic KOH in both the reactions
(c) EtOH /  in reaction (a) and EtO -/  is reaction (b)
(d) EtOH /  in reaction (a) and reaction (b) is not possible

–
3. EtoO [X] ; Product x will be

(a) (b) (c) (d)

4. In the given reaction, the percentage of (+) enantiomer formed is :

CH3 – CH – CH2 – CH3  


O
CH3 – CH – CH2CH3
()obs. = – 15.90º ()obs. = – 15.26º
(a) 2% (b) 4% (c) 96% (d) 98%
I

Mg
5. O O 
 Y ; What is the structure of y ?

O O
(a) IMgO O (b) O O O O (c) IMg O O (d)
MgI

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6. The major product of the following reaction is :

(a) (b) (c) (d)

MCQ
7. Observe the following structure and select the correct option :

(a) SN1  X, Y, Z (b) SN2  X, Y, W (c) SN1  Z, T (d) SN2  W, T

8. In which of the following reactions the correct major products are mentioned :
Br
H3C H 3C CD3
CH3 CD3
(a)  EtO 
(b) EtO



NaOEt
(c) EtOH
(d) H2 SO 4 , 
  

9. In which reaction D-exchange in compound is observed.

Ph Ph

(a) NaOEt / EtOD

   
 (b) NaOEt / EtOD
  
O Br O OH

(c) NaOEt / EtOD

   (d) N

10. Select the reaction in which one organometallic compound produces another organometallic compound.
Ether
(a) CH3MgBr + HC  C – Ph  (b) Ether
+ CH3MgBr 
 
H H
OH SH

(c) + Ether (d) CH3CH2Na + Ether

 
  


MgI

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11. Match the column :

12. Match the processes observed in Column-II with the reactants (for which these process will
take place) in column-I
Column-I Column-II

(a) (p) Upon Reaction with C2H5O–/C2H5OD deciterium

exchange is observed.

(b) (q) Upon reaction with NaSH / DMSO SN2 reaction

is observed

(c) (r) Upon reaction with C2H5ONa / C2H5OH

E2 reaction is observed

(d) Ph — CH2 — CH2 (s) Upon reaction with H2O/ either E1 or SN1
|
Br product is obtained

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All students are advised to solve DPPs within allowed time only.
All discussions are scheduled in every 4th doubt discussion class
–MKA Sir (Guruji)

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BATCH XII & DROPPER’S 2021 (ADV)
TOPIC HALOALKENES DPP 10

Marking Scheme : Single Correct (+3,-1) M M: 69 Time : 1 hr

1. Match the following:

Compound H3C–X (p) CH3–F (q) CH3–Cl (r) CH3–Br (s) CH3–I
carbon-halogen bond length (Å) (i) 1.78 (ii) 2.14 (iii) 1.39 (iv) 1.93
2. Arrange the following compound in the increasing order of their dipole moment
(a) CH3–F, CH3–Cl, CH3–Br, CH3–I (b) CH3–F, CH2–F2, CH–F3, CF4
3. Arrange the following alkyl halide in increasing order of their boiling point
(A) (i) CH3–CH2–F (ii) CH3–CH2–Cl (iii) CH3–CH2–Br (iv) CH3–CH2–I
(a) (iii) < (iv) < (i) < (ii) (b) (i) < (ii) < (iii) < (iv) (c) (iv) < (i) < (ii) < (iii) (d) (ii) < (iii) < (iv) < (i)
(B) (i) CH3–X (ii) CH3–CH2–X (iii) CH3–(CH2)2–X (iv) CH3–(CH2)3–X
[X is halogen atom]
(a) (ii) < (iii) < (iv) < (i) (b) (iii) < (iv) < (i) < (ii) (c) (i) < (ii) < (iii) < (iv) (d) (iv) < (i) < (ii) < (iii)
4. Decreasing order of relative nucleophilicity of the following nucleophile in protic solvent is:
SH , ACO , PhO , OH , Cl , H2O

(a) SH > OH > Cl > H2O > ACO > PhO (b) SH > OH > PhO > ACO > Cl > H2O
(c) SH > PhO > OH > Cl > H2O > ACO (d) SH > OH > PhO > Cl > ACO > H2O

5. When the concentration of alkyl halide is tripled and the concentration of OH ion is reduced to half, the
rate of SN2 reaction increased by:
(a) 3 times (b) 2 times (c) 1.5 times (d) 6 times
6. (CH3)3C–CH2CH2Br [excess] + NH3 

(a) [(CH3)3C–CH2–CH2]4N Br (b) (CH3)3C–CH2–CH2–NH2
(c) (CH3)3C–CH2–CH2–CH3 (d) [(CH3)3C–CH2–CH2]3N
7. The decreasing order of rate of SN2 is:
(i) Br–CH2–CH2–Br (ii) NC–CH2–Br (iii) CH3–CH–CH3 (iv) CH3–CH2–Br
|
Br
(a) (ii) > (i) > (iv) > (iii) (b) (ii) > (iii) > (i) > (iv) (c) (ii) > (i) > (iii) > (iv) (d) (iv) > (i) > (ii) > (iii)
8. Which of the following reaction will go faster if the concentration of the nucleophile is increased?
H Br H OCH 3

(a) + CH3O

(b) Br + CH3S SCH 3

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Br
Ph Cl Ph
(c) + HCOO
HCOOH (d) + AcO
AcOH

Ph tB4 Ph tBu
H O
C

O
9. In the following reaction the most probable product will be:
Br OH CH3 C2H5 CH3

H CH 3 OH H CH 3 H OH H CH 3 OH H
SN
2 (a) (b) (c) (d)
H 3C H H 3C H H 3C H H 3C H H 3C H

C2H5 C2H5 C2H5 OH C2H5

10. Which of the following reaction is not correct?
(a)

(b)

Et2O 
(c) 4-Chloro-1-butanol + NaH C4H8ClONa O

(d)
11. Product and mechanism of the given reaction are respectively:
H Cl H I I H I H H I
NaI / Acetone
50°C
(a) , SN1 (b) , SN2 (c) , SN2 (d) , SN1
H t-Bu t-Bu H t-Bu H H t-Bu H t-Bu
12. Which configuration will be adopted by the product at carbon atoms marked (1) and (2) respectively in
the given reaction.

(a) D, D (b) D, L (c) L, L (d) L, D

13. The insecticide chlordane is warmed with dilute NaOH solution for some time. The expected product
would be:
Cl Cl HO OH HO OH HO OH O
Cl Cl OH OH Cl OH Cl Cl Cl Cl
dil. NaOH
Cl OH OH OH OH
sol n
(a) (b) (c) (d)
Cl OH OH Cl Cl
Cl OH Cl Cl Cl
Cl OH OH OH OH

14. The following reaction is descdribed as:

CH3
–

(1) NaOH
H2C–CH 2–CH 2–CH–Br
(2) 
–

HO O CH 3

(a) S with racemisation

N
1
(b) intramolecular SN2 with walden inversion
(c) intramolecular SN2 with retention of configuration (d) intramolecular SN1 with recemisation

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15. Which statement is incorrect about the following reaction
CH 3 (a) The rate of each of these reactions depended on both [R–I] and [131I ]
131
NaI
H I Acetone (b) Loss of optical activity was exactly twice as fast as gain of radioactivity
C 6H13 (c) Each molecule undergoing substitution suffers Inversion of configuration
2-Iodooctane (+) (d) Final solution has radioactive iodine only

16. tBuO Mechanism of reaction is possible by

tBuOH
NH
CH3
Br

(a) SN2 (b) ArSN2 (c) E2 (d) SN1

17. The product of the given reaction:
Br OH

OH
NaOH
(a) (b) (c) (d)
O O
OH OH OH

18. A solution of pure (R)-2-iodobutane, [] = –15.9° in acetone is treated with radioactive iodide, until 1.0%
of the iodobutane contains radioactive iodine, the specific rotation of the recovered iodobutane is found to
be –15.58°, which statement(s) is/are correct about the above informations.
(a) It has optical purity 96% (b) Percentage of R in the solution is 99%
(c) Recemic mixture is 2% (d) Final solution is dextrorotatory
CH 3 CH3
CH3OH, 30°C
19. What will be the major product of the reaction: H 3C C C CH CH3
H CH3 Br

CH 3 CH3 CH 3 CH 3 CH3 CH 3 CH 3 CH3 CH 3 CH 3 CH3

(a) H 3C C C C CH 3 (b) H C3 C C CH CH3 (c) H C 3 C C CH CH3 (d) H C3 C C CH CH2
H 3CO H H H OCH 3 H H CH3

20. The increasing order of reactivity of the following isometric halides with alcoholic AgNO3 is:
(i) C6H5–CH == CH–CH 2–CH 2–Cl (ii) C6H5–CH == CH–CH–CH 3
–

Cl
CH 3
– –

(iii) C6H5–C == CH–CH 2–CH 3 (iv) C6H5–C–CH == CH2

–

Cl Cl
(a) (iii) < (iv) < (ii) < (i) (b) (i) < (iii) < (iv) < (ii) (c) (iii) < (i) < (ii) < (iv) (d) (i) < (ii) < (iv) < (iii)
21. In the following compound, rate of reaction with aqueous KOH solution is:

(i) –CH–OCH 3 (ii) –CH–CH 3 (iii) –CH 2–CH 2–Cl (iv) –CH–CH 2–CH 3
–

Cl Cl Cl
(a) (i) > (ii) > (iv) > (iii) (b) (i) > (iv) > (ii) > (iii) (c) (ii) > (i) > (iv) > (iii) (d) (iv) > (i) > (ii) > (iii)
22. Which of the following order of decreasing rate of reaction in CF3COOH is correct
Ph Ph

(i) (ii) (iii) Ph (iv)

Cl
(a) (iii) > (i) > (ii) > (iv) (b) (iii) > (i) > (iv) > (ii) (c) (i) > (iii) > (iv) > (ii) (d) (i) > (iii) > (ii) > (iv)

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23. Which of the options is/are correct for the given reaction:

Cl HCOOH
HCOO , (k 1)

HCOOH
Ph (k 2)

OCOH OCOH
(a) and K1 > K2 (b) and K1 = K2
Ph Ph
OCOH
(c) Ph and K1 = K2 (d) Ph , and K1 = K2
OCOH OCOH Ph

All students are advised to solve DPPs within allowed time only.
All discussions are scheduled in every 4th doubt discussion class
–MKA Sir (Guruji)

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