EXCEL (DROPPER) 2023

GOC - MECHANISM OF REACTIONS

ELIMINATION REACTION 04P

Marking Scheme : Single Correct (+3,-1) M M: 144 Time : 90 min.

E1
Ph Me

1. Identify the final product: Ph Me H / 

Me Ph HO OH
Ph Me
(a) Ph Me (b) Ph Me (c) (d) Stilbene
Ph Me
O Me Me O

OH
2. conc. H2SO4 /  [A] (major product); conc. H2SO4 /  [A] (major product);
OH
Sum of -hydrogen in alkene [A + B] is:
(a) 17 (b) 18 (c) 19 (d) 20
3. The loss of a hydroxyl group (an alcohol) to generate an alkene is known as?
(a)A dehydrohalogenation (b) A dehydration (c) A reduction (d) An oxidation

4. What is the major product of the following reaction? conc. H2SO4 / 

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


5. Choose the major product of the following reaction. H / 

OH

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

O
6. Which is not a likely product formed when the following alcohol is treated with sulfuric acid ?

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

7. Among the following compounds which can be dehydrated very easily is:

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

OH OH OH
8. Select the major product of the dehydration of the following alcohol:
OH

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

OH

9. H /  [X] ; Possible structure of X formed is:

(a) 1 (b) 2 (c) 3 (d) 4

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10. Rate of dehydration of alcohols follows the order:
(a) 3° > 2° > 1° > CH3OH (b) 2° > 3° > 1° > CH3OH
(c) CH3OH > 1° > 2° > 3° (d) 2° > 1° > CH3OH > 3°
11. Which of the following carbocation will undergo rearrangement ?

(a) (b) (c) O (d) N

H

12. Benzamide on treatment with POCl3 gives:

(a) aniline (b) benzonitrile (c) chlorobenzene (d) benzyl amine
13. Ethyl alcohol is heated with conc. H2SO4. The product formed is
O
(a) (b) C2H2 (c) C2H4 (d) C2H46
OEt
14. Which alcohol should give the fastest reaction with sulfuric acid to produce alkene product ?
OH
(a) OH (b) (c) OH (d) (e)
OH HO

15. OH  Best method for above reaction is:

(a) conc. HCl + ZnCl2 (b) conc. H3PO4 (c) HBr (d) conc. HCl
E2

16. (i) CH3—I, (ii) Ag2O, (iii)   ; Identify major product:

NH2

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

17. Identify the major product of the reaction shown. Br KO(CH3)3

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

Cl
Cl
18. (X) alc. KOH Moles of alc. KOH consumed are:
Cl
Cl
(a) 0 (b) 1 (c) 2 (d) 3

OH   [A] , Product [A] is:


19. N (a) (b) (c) (d)

Ph Ph

H 3C H H 3C H
20. H 3C Br
(X) alc. KOH[A] ; Br CH3
(X) alc. KOH[B] ; Product [A] and [B] is:
Ph Ph

(a) [A] = cis, [B] = cis (b) [A] = trans, [B] = cis (c) [A] = trans, [B] = trans (d) [A] = cis, [B] = trans

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 CH 3 CH 3

21. NaOEt,  [P] ; NaOEt,  [Q] ; Identify product [P] and [Q] respectively:
Cl Cl
CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3

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

Ph
22. NaNH2 ; Total number of elimination products are (including stereoisomer)
Br
(a) 2 (b) 4 (c) 6 (d) 8
O
23. HEM [P] HEM [Q] ; Product [Q] is: [HEM = Hoffmann exaustive methylation]
N
H H
O O N
(a) (b) (c) (d)
H
N
24. (i) CH3I (excess), (ii) Moist Ag2O, (iii)  [X](major poroduct) ; [X] is:
(a) (b) (c) (d)
25. The most reactive conformation for an E2 reaction is:
(a) Syn periplanar (b) Anti periplanar (c) Gauche staggered (d) Gauche eclipsed
26. The major product of the reaction of 1,2-dibromobutane and excess NaNH2 is:
(a) 2-bromo-1-butene (b) 1-bromo-l-butene (c) 1-butyne (d) 1,2-butadiene.
27. Alkynes may be formed directly via elimination from which of the following ?
(a) Alkanes (b) Bromoalkenes (c) Alcohols (d) Alkenes
27. Dehydrohalogenation of an alkyl halide is a/an:
(a) Nucleophilic substitution reaction (b) Elimination reaction
(c) Both nucleophilic substitution and elimination reaction (d) Rearrangement
29. In the following sequence of reaction:
CH3CH2CH2Br KOH (alc.)[A] HBr[B] KOH (aq.)[C] ; The product (c) is:
(a) Propan-2-ol (b) Propan-1-ol (c) Propyne (d) Propene
30. The major product obtained on treatment of CH3CH2CH(F)CH3 with CH3O / CH3OH is:
(a) CH3CH2CH(OCH3)CH3 (b) CH3CH==CHCH3 (c) CH3CH2CH==CH2 (d) CH3CH2CH2CH2OCH3
31. Alcoholic potash is used to bring about:
(a) Dehydrogenation (b) Dehydration (c) Dehydrohalogenation (d) Dehalogenation
32. The major product of the reaction of 2,2-dichloropropane and excess NaNH2 is:
(a) Propyne (b) 1,2-propadiene (c) 2-chloropropene (d) 2-chloropropane
33. What will be the major organic product from the reaction shown below:


(CH3)3CO , (CH3)3COH
Br

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

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34. Predict the major product of the following reaction: (i) (excess) MeI, (ii) Ag2O, 
N
H

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

N N
Me
H
N
35. Which is not a possible product of the following reaction? (i) (excess) MeI, (ii) Ag2O, 

(a) (b) (c) (d) All the above products are possible
36. The dehydrobromination of 2-bromobutane gives CH3CH==CHCH3. The product is:
(a) Hofmann product (b) Saytzeff product
(c) Hoffmann-Saytzeff product (d) Markownikoff product
37. In which reaction last product is ‘Ph ’
Br

(a) Ph –3NaNH2, mineral oil, –NH4Cl (b) Ph –Br2, CCl4–3NaNH2, mineral oil,  –NH4Cl
Br
O
(c) –PCl5 –3NaNH2, mineral oil,  –NH4Cl (d) All
Ph

38. Which of the following dibromides would yield 2-butyne upon elimination ?
Br
Br
Br
(i) Br (ii) (iii) (iv)
Br Br
Br
Br
(a) (iii) (b) (ii) and (iii) (c) (ii) and (iv) (d) (i)
39. An alkyl bromide produces a single alkene when it reacts with sodium ethoxide and ethanol. This alkene
undergoes hydrogenation and produces 2-methyl butane. What is the identity of the alkyl bromide.
(a) 1-bromo-2,2-dimethylpropane (b) 1-bromobutane
(c) 1-bromo-2-methylbutane (d) 2-bromo-2-methylbutane
40. Give the order of reaction rate with alc-KOH

Br
(i) (ii) (iii)
Br Br
(a) (i) > (ii) > (iii) (b) (ii) > (i) > (iii) (c) (iii) > (ii)> (i) (d) (iii) > (i) > (ii)
41. Among the following compounds.
Ph Ph Ph Br Ph Ph Ph Br
(i) (ii) (iii) (iv)
H Br H Ph H Cl H Cl
Which of the following statements is correct about rate of E2 under identical conditions ?
(a) (i) > (iii) (b) (ii) > (i) (c) (iv) < (iii) (d) (ii) > (iii) > (iv)
42. What is the major product of the following reaction ?

(i) Br2 (ii) NaNH2 (3 eq.) (iii) H2O

Br Br Br

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

Br Br NH2

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 E1CB / Ei
43. What is the order of E1CB reaction?
(a) 1 (b) 2 (c) 0 (d) can't be determined
44. What is the molecularity of E1CB reaction?
(a) 1 (b) 2 (c) 0 (d) can't be determined
45. Rate of E1CB reaction is more for ? [P] Ph—CD2—CH2—Br [Q] Ph—CH2—CH2—Br
(a) [P] (b) [Q] (c) same (d) can't be determined
46. Predict the product of the following reaction.
CH 3

H2O2 
N

CH 3 CH 3 CH 3 CH 3
O
O
(a) (b) (c) (d)
N H N

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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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