DROPPERS 2022

GENERAL ORGANIC CHEMISTRY - II

ELECTROPHILIC & NEUCLEOPHOLIC ADDITION 04 I

Marking Scheme : Single Correct (+3,-1) M M: 140 Time : 1 hr 30 min

Single Correct Answer Type

1. Identify the major product in the following reaction.

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

2. Possible products have been written against the following reactions.

(I) ; (II)

Pick up the correct option regarding the above reactions.

(a) I False and II True (b) I True and II False (c) Both true (d) Both false
3. The number ofstereoisomeric tetrabromides likely to be obtained have been noted against the following
reactions.

(I) ; (II)

Pick up the correct option regarding the above reactions.

(a) I False and II True (b) I True and II False (c) Both true (d) Both false
4. We know nucleophilic addition reactions are reversible. In which of the following AdN reactions, equilibrium
will lie largely towards left?

(a) (b)

(c) (d)

5. In which of the following HCl addition reactions, Markovnikov's rule can predict the product correctly?

(a) F3C—CH==CH2 (b) H2C==CH—COOH (c) H3CO—CH==CH2 (d) —CH==CH—CH2—Br

6. Predict the product correctly.

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

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7. ; Identify A and B.

(a) A = ,B= (b) A = ,B=

(c) A = ,B= (d) A = ,B=

8. Watch the following reaction and pick up the choice showing a plausible step of its mechanism.

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

9. The hydration reaction of carbonyl compounds proceeds as follows.

Out of the followings, the extentof hydrationreaction towards the product side is highest in the case of:

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

10. Which of the following is / are example(s) of nucleophilic addition reaction?

(I) ; (II)

(a) Both are AdE reactions (b) Both are AdN reactions
(c) I is AdE and II is AdN (d) I is AdN and II is AdE
11. Choose the correct sentence about the product(s) of the above reaction.

(a) A pair of meso compounds (b) A pair of enantiomers

(c) A pair of diastereomers (d) A pair of enantiomers and a meso compound
12. Predict the correct stereoisomeric product for the following reaction.

(a) (b) (c) (d) Both (a) and (c)

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13. ; What is true about 'B' ?

(a) It contains two deuterium atoms and is optically active.

(b) It contains two deuterium atoms and is optically inactive.
(c) It contains three deuterium atoms and is optically active.
(d) It contains three deuterium atoms and is optically inactive.
14. Check the following reactions and select the appropriate answer.

(a) I = , II = (b) Both I & II are

(c) I = , II = (d) I = , II =

15. Rank the following compounds in order of decreasing amount of hydrate present at equilibrium.

(I) (II) (III) (IV)

(a) III > I > II > IV (b) III > II > I > IV (c) I > III > II > IV (d) I > II > III > IV
16. For the following conversion, choose the appropriate set of reagents to be used in the given order.
(a) HOCH2CH2OH/H+, PCC/CH2Cl2, CH3MgCl/H3O+
(b) CH3O–/CH3OH, CH3I
(c) HOCH2CH2OH/H+, CH3MgI/H3O+, PCC/CH2Cl2
(d) CH3MgI/H3O+, PCC/CH2Cl2
17. Predict the correct statement about products.
(a) I can form two stereoisomers whereas II can form one.
(b) I can form one stereoisomer whereas II can form two.
(c) Both can form one stereoisomer each.
(d) Both can form two stereoisomers each.
18. Predict the product.

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

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 Multiple Correct Answer Type
19. Predict the product.

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

20. The E-isomer of 3-methylhex-3-ene was treated with the following reagents. In which of the following
case(s), anti-addition would result?
(a) OsO4, then H2S (b) Cl2 (c) ICI (d) Br2 in CH3OH
21. What product(s) is / are expected for the following reaction?

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

22. Pick the choice(s) that correcly describe(s) the decreasing order of reactivity towards AdN.
O O O O O O

(a) CH 3 C C C CH 3 > CH 3 C C CH3 > CH 3 C CH3

(b) Br—CH2—CHO > CH3—CHO > CH3COCH3 > Br—CH2—CO—CH3

(c) (CH3)2C== OH > (CH3)2C==O > (CH3)2C==NH
(d) CH3COCH3 > Cl—CH2COCH3 > O2N—CH2COCH3
23. In which of the following reaction(s) you would not expect exclusive anti-addition to take place?
(a) R—CC—R + Br2 (1 equivalent) 
(b) R—CC—R + HCl (1 equivalent) 
(c) R—CC—R + Br2 (1 equivalent) CH3OH Pd
(d) R—CC—R + H2 (1 equivalent) Pd / BaSO4
24. Which of the following isomerisation reaction(s) is / are possible?

(a) (b)

(c) (d)

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 Assertion-Reason Type
I nstruction: Each question contains statement-1(assertion) and statement-2 (reason). Use the fol-
lowing key to select one appropriate answer:
(a) If statement-1 and 2 are true and statement-2 is a correct explanation for statement-I.
(b) If statement-1 and 2 are true and statement-2 is not correct explanation for statement-1.
(c) If statement-1 is true and statement-2 is false.
(d) If statement-1 is false and statement-2 is true.
25. Statement-1: Imines are more reactive than carbonyl compounds in AdN reactions.
Statement-2: Imines are more easily protonated than carbonyl compounds
26. Statement-1: Reactions of ammonia derivatives with carbonyl compounds slow down as pH approaches
close to 1.
Statement-2: In very strong acidic medium catalytic effect is not available.
27. Statement-1: Addition of sodium bisulphite (NaHSO3) across a carbonyl group is initiated due to attack
by SO32– on carbonyl group.
Statement-2: SO32– is a better nucleophile than HSO3–.
28. Statement-1: Addition of HBr to CH2==CH—Br proceeds at a faster rate than does CH2==CH2.
 
Statement-2: CH3—C H—Br is formed relatively slowly than CH3—C H2.
29. Statement-1: Ph—CC—CH3 when treated with dilute H2SO4 in presence of Hg2+ ion predominantly
gives PhCH2COCH3 and not PhCOCH2CH3.
Statement-2: Ph– group directs nucleophilic attack.
30. Statement-1: A highly substituted carbocation is formed faster; once formed rapidly goes on to give
the poduct.
Statement-2: Electrophilic addition preferrably gives highly substituted carbocation.
31. Statement-1: In -unsaturated nitrile, the C==C bond can undergo AdN reaction.
Statement-2: This gives the thermodynamic product.
32. Statement-1: pri-amines give imines but sec-amines give enamine when react with carbonyl compounds.
Statement-2: Enamines are generally very good nucleophiles.

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 Comprehension Type
Electrophilic addition on conjugated system basically goes behind the following generalizations.
 The initial attack always takes place on terminal carbon atom of the conjugated system. This
would give rise to a stable carbocation.
 Both 1,2 and 1,4-additions are possible. The relative proportion of the products depends upon
temperature. At low temperature, kinetic product, while at higher temperature, thermodynamic
product is formed.
 With unsymmetrical dienes and unsymmetrical reagents, the problem of orientation of addition
rises. Initial attack is still on a terminal carbon atom.
 Nonetheless, a more stable carbocation is formed preferentially in the first step, which is then
attacked by the nucleophiles in the second step.
33. Identify the product. H3C—CH==CH—CH==CH2 (1 eq. HCl)
Cl Cl

(I) CH 3 CH CH CH CH3 (II) CH 3 CH2 CH CH CH2

Cl

(II) CH 3 CH2 CH CH CH2 (IV) CH 3 CH CH CH CH3

Cl
(a) I and II (b) II and III (c) III and IV (d) I and IV
34. Identify the product. CH3

CH 2 C CH CH2 (1 eq. HCl)

CH3 CH3 Cl Cl CH3
CH 3
(I) CH 3 CH CH 3 (II) CH 3 C CH CH2 (III) CH 2 C CH CH3 (IV) CH 2 C CH CH3
Cl
Cl
(a) I and II (b) II and III (c) III and IV (d) I and IV
35. Look at the following reaction. Which is / are true among options?
Br2
H 2C CH CH CH 2 H2C CH CH CH2

Br Br

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

(cis product)

This is the Must have participated This is the most Formed only
exclusive product. as an intermediate. likely intermediate in small amount.
36. What is true? Note that Ea is the activation energy leading to the formation of the concerned product and
G° is the free energy change in the concerned path.
(a) Ea is low and G° for 1,4-product is more negative.
(b) Ea is low and G° for 1,2-product is more negative.
(c) Ea for 1,4-product is high and G° is less negative.
(d) Ea for 1,4-product is high and G° is more negative.

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 Match the Columns
37. Column-I Column-II

(i) (p) Product contains one chiral centre

(ii) (q) Crowding converts an otherwise 1,2-addition to 1,4-addition

(i) (ii) (iii) (iv)
(a) (r) (s) (q) (p)
(iii) (r) General 1,4-AdN reaction
(b) (r) (s) (p) (q)
(c) (s) (r) (p) (q)
(iv) (s) 1,4-electrophilic addition (d) (s) (q) (p) (r)

38. Column-I Column-II

(i) (p) AdN

(ii) (q) A meso product is formed. (i) (ii) (iii) (iv)

(a) (s) (r) (p) (q)
(iii) (r) Product quickly tautomerises. (b) (q) (r) (p) (s)
(c) (r) (s) (p) (q)
(d) (p) (q) (r) (s)
(iv) (s) Optically active product is formed.

39. Column-I Column-II

(i) (p) Two asymmetric C atoms in the product
produced through cyclic transition state. (i) (ii) (iii) (iv)
(ii) (q) Two asymmetric C atoms in the product (a) (r) (p) (s) (q)
produced through cyclic intermediate. (b) (r) (q) (p) (s)
(iii) (r) Six-membered ring in the product. (c) (r) (p) (q) (s)
(d) (s) (p) (q) (r)
(iv) (s) Optically inactive five-membered
ring product.
40. Column-I Column-II

(i) (p) Product contains one ring

(ii) (q) Product contains two ring (i) (ii) (iii) (iv)
(a) (s) (r) (q) (p)
(iii) (r) Product contains three ring (b) (s) (q) (r) (p)
(c) (s) (p) (q) (r)
(d) (r) (q) (p) (s)
(iv) (s) Product contains no ring

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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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