Allen oaperc

ORGANIC CHEMISTRY
ENTHUSIAST QUESTION BANK

(ENGLISH)
CONTENT
SR. NO. TOPIC NAME PAGE NO.
01. ISOMERISM .................................................................................... (1-13)
02. ALKYL & ARYL HALIDE ................................................................ (14-32)
03. ALCOHOL & ETHER ..................................................................... (33 - 47)
04. OXIDATION & REDUCTION........................................................ (48 - 53)
05. ALDEHYDE & KETONE ................................................................ (54 - 78)
06. CARBOXYLATE ACIDS ................................................................. (79 - 93)
07. NITROGEN CONT. COMPOUND................................................. (94 - 98)

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Path to success KOTA (RAJASTHAN)
QUESTION BANK
JEE (Main + Advanced): Enthusiast Course
ISOMERISM
SINGLE CHOICE CORRECT
1. How many primary amines are possible for the formula C4H11N ?
(A) 2 (B) 3 (C) 4 (D) 5
2. A pure sample of 2-chlorobutane shows rotation of PPL by 30° in standard conditions. When above sample
is made impure by mixing its opposite form, so that the composition of the mixture becomes 87.5% d-form
and 12.5% l-form, then what will be the observed rotation for mixture.
(A) – 22.5° (B) + 22.5° (C) + 7.5° (D) – 7.5°
3. How many benzenoid structure are possible for molecular form C7H8O :
(A) 3 (B) 4 (C) 5 (D) 6
4. Optical & geometrical isomerism both can be shown by -
(A) (B)
(C) (D)
5. On chlorination of propane number of products of the formula C3H6Cl2 is :-

(A) 3 (B) 4 (C) 5 (D) 6
6. Total number of stereoisomer of following compounds are respectively :-
OH OH
OH
(A) 4, 6 (B) 8 (C) 6,6 (D) 8, 8
Me
7. Possible mono chlorinated product obtained on monochlorination of
(A) 12 (B) 8 (C) 10 (D) 6

8. What is the value of p & q of following conformer of 2,3-dimethyl butane ? p
(A) p = H, q = H H3C CH3
(B) p = CH3, q = CH3
(C) p = CH3, q = H H CH3
(D) p = H, q = CH3 q
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9. Molecular formula C5H10O can have :-

(A) 6–Aldehyde, 4–Ketone (B) 5-Aldehyde, 3-Ketone
(C) 4-Aldehyde, 3-Ketone (D) 5-Aldehyde, 2-Ketone
10. Which one of the following is the most stable conformer ?
CH3 CH3 CH3

HO CH3 OH
H H H OH H CH3
(A) H (B) (C) (D)
OH H OH H OH H
CH3 OH CH3
CH3 OH
11. Number of possible conformations of n-butane is :
(A) 2 (B) 4 (C) 6 (D) infinite
12. What observed rotation is expected when a 1.5 M solution of (R)-2-butanol is mixed with an equal volume
of a 0.75 M solution of racemic 2-butanol and the resulting solution is analysed in a sample
container that is 1 dm long ? The specific rotation of (R)-2-butanol is – 13.9° ml gm–1dm–1.
(A) –1.54° (B) –0.77° (C) –7.70° (D) –15.4°
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13. The structural formula on the right is that of camphor.Which of the following statements is correct?
(A) This compound has two stereogenic centers and exists as a pair of enantiomers.
(B) This compound is achiral.
(C) This compound has three stereogenic centers and exists as a pair of enantiomers and
a meso isomer.
(D) This compound does not have an enantiomer O
HH
H H
H H
H H
14. The compound shown is

H H
H H HH HH
(A) (B) (C) (D)
15. Select the pair of chain isomers.

COOH OH
(A) COOH (B) OH
and and
Et NH2
(C) and Et (D) N
and
16. One of the following is not the pair of functional isomers.
O O
(A) O (B)
and C—O—H and H—C—O—
OH
O
H
(C) and (D) &
O O
O
17. Tautomer of which of the following can show geometrical isomerism
O
(A) CH3–CHO (B) CH3CH2–CHO (C) (CH3)2CH–CH=O (D)
18. The antimalarial alkaloid quinine, C20H24N2O2, is optically active. An ethanol solution of 8g quinine in
100mL displays a rotation of -13.6º in a 1dm polarimeter tube. What is the specific rotation of quinine?
(A) -85º (B) -170º (C) -43º (D) -26º
19. Which of the following is (R)-3-hexanol?

H OH
H H C2H5
C2H5 H OH
H OH
(A) C H (B) (C) (D)
2 5 H H C2H5
OH C2H5 C3H7
20. The R/S configuration of these compounds are respectively.

HO H
CF3 H NH2 H CH3
HS CHO
COOH
(A) R,R,R (B) R,S,R (C) R,S,S (D) S,S,S
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21. Which of the following represents (E)-3,6-dichloro-6-methyl-3-heptene?
Cl Cl Cl
(A) (B) (C) (D)

Cl Cl Cl Cl Cl
22. Which of the following compounds has two stereogenic centers (asymmetric carbons)?
Cl O
Cl Cl H
O
(A) (B) (C) (D)

Cl H3C H
Cl
23. Which of the following compounds is (S)-4-chloro-1-methylcyclohexene?
CH3 CH3 CH3 CH3
(A) (B) (C) (D)

Cl Cl
Cl Cl
24. Which two of the following compounds represents a pair of enantiomers?
HO OH HO OH
HO OH HO OH
I II III IV
(A) I & II (B) II & III (C) III & IV (D) II & IV
25. Which of the following is properly classified as a meso compound?
C2H5 C2H5
H OH H
OH HO H H OH
OH H H
(A) (B) OH (C) H (D) H OH
HO H
H C2H5
26. Which two of the following compounds are diastereomers?
OH OH OH OH
OH HO OH OH
O
OH O O O
OH OH
OH
(A) I & II (B) II & IV (C) III & IV (D) I & III
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27. Which two of the following compounds are identical?
OH OH OH OH
OH HO OH OH
O
OH O O O
OH OH
OH
(A) I & II (B) II & IV (C) III & IV (D) I & III
28. Which of the following sugars has the configuration (2S, 3R, 4R)?
CHO CHO CHO CHO

H OH H OH HO H HO H
H OH HO H H OH HO H
(A) (B) (C) (D)
H OH H OH H OH H OH
CH2OH CH2OH CH2OH CH2OH
29. How many stereogenic carbon centers are there in morphine, structure shown below?
HO
O H
N
CH3
H
HO
(A) 4 (B) 5 (C) 6 (D) 7
30. Which of the following compounds has a S configuration?
CH3 Cl
CH3 Br H CH3
Br CH3 H
Cl
(A) OH (B) (C) H (D) CH
H 3 H
H C2H5 CH3 CH2CH2CH3 H
31. Which of the following structures represents a chiral compound?
CH3 CH3 CH3 CH3

H H
(A) CH3 CH3 (B) CH3 CH3
H OH H CH3
CH3 CH3 CH3 OH
H H
(C) CH3 CH3 (D) CH3 CH3
H OH H CH3
32. Which of the following statements must be true for two pure chiral isomers ?
(A) they must be enantiomers (B) they must be diastereomers
(C) they must be stereoisomers (D) they must be optically active
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MULTIPLE CHOICE CORRECT

33 Which of the following statements is/are not correct :
(A) Metamerism belongs to the category of structural isomerism
(B) Tautomeric structures are the resonating structures of a molecule
(C) Keto form is always more stable than the enol form
(D) Geometrical isomerism is shown only by alkenes
34. Which of the following molecules is/are identical with that represented by :
CH3
H 3C OH
HO H
H
H OH CH3 OH
H CH3 H3C H H H 3C OH
H 3C
(A) (B) (C) (D)
H3C OH H CH3 H H CH3
OH
OH OH OH H
35. Which of the following will show optical isomerism as well as geometrical isomerism :
H3C CH3 H3C CH3
(A) C (B) C
H CH3
H3C CH3 H3C CH3

(C) C (D) C
H CH3
H3C H3C
36. Which of the following statements is/are correct?
(A) A meso compound has chiral centres but exhibits no optical activity
(B) A meso compound has no chiral centres and thus are optically inactive.
(C) A meso compound has molecules which are superimposable on their mirror images even though they
contain chiral centres
(D) A meso compound is optically inactive because the rotation caused by any molecule is cancelled by an
equal and opposite rotation caused by another molecule that is the mirror image of the first.
37. Which of the following statements is/are not correct for D-(+) glyceraldehyde?
(A) The symbol D indicates the dextrorotatory nature of the compound
(B) The sign (+) indicates the dextrorotatory nature of the compound
(C) The symbol D indicates that hydrogen atom lies left to the chiral centre in the Fischer projection diagram
(D) The symbol D indicates that hydrogen atom lies right to the chiral centre in the Fischer projection diagram
38. Which of the following statements for a meso compound is/are correct?
(A) The meso compound has either a plane or a centre of symmetry
(B) The meso compound has at least one pair of similar stereocenters
(C) The meso compound is achiral
(D) The meso compound is formed when equal amounts of two enantiomers are mixed
39. Which of the following states are correct:
(A) Any chiral compound with a single asymmetric carbon must have a positive optical rotation if the
compound has the R configuration
(B) If a structure has no plane of symmetry it is chiral
(C) All asymmetric carbons are stereocentres.
(D) Alcohol and ether are functional iosmers
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40. Which of the following are correct representation of L–amino acids
(A) (B) (C) (D)
41. Which compound(s) will show Geometrical isomerism ?

H
H3C Cl Cl N O
CH 3
(A) N–H (B) C=C=C (C) H3C (D)
H H O N
H
42. Which will show geometrical isomerism -
Cl Cl D D D D
T T
(A) (B) (C) (D)
HH H H
43. Select the correct statement for the following species.
Me Me
Me Me
(I) Me (II) (III) (IV) Me
Me Me
(A) I & II are geometrical isomers (B) II & III are geometrical isomers
(C) III & IV are conformers (D) I & IV are conformers
44. Which of the following can show geometrical isomerism :
OH
CH3
(A) (B)
C(CH3).N(OH)
Me
Me
(C) C (D)
Me
COMPREHENSION BASED QUESTIONS
Comprehension - 01
S(+) Mono sodium Glutamate (MSG) is a flavour enhancer used in many foods. Fast foods often contain
substantial amount of MSG and is widely used in Chinese food. If one mole of above MSG was placed in
845 ml solution and passed through 200 mm tube, the observed rotation was found to be + 9.6°.
1 Å
COO Na
1
OOC–CH2–CH2–C
Å
NH3 H
45. Find out the specific rotation of (–) MSG :

(A) + 24° (B) +56.8º (C) –48° (D) None of these
46. Find out the approximate percentage composition of (–) MSG in a mixture containing (+) MSG and (–) MSG
whose specific optical rotation is –20° :
(A) 83.3% (B) 16.7% (C) 91.6% (D) 74%
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47. If 33.8 g of (+) MSG was put in 338 ml solution and was mixed with 16.9g of (–) MSG put in 169 ml solution
and the final solution was passed through 400 mm tube. Find out observed rotation of the final solution :
(A) +1.6° (B) +4.8° (C) +3.2° (D) None of these
Comprehension - 02
(b)
HOH2C
H (c) CH3 O
O OH(a)
H (d) CH3
Cortisone
O
H
48. Cortisone contains which functional groups ?
(A) Ether, alkene, alcohol (B) Alcohol, ketone, amine
(C) Alcohol, ketone, alkene (D) Ether, amine, ketone
49. Total number of chiral center in Cortisone :-
(A) 4 (B) 5 (C) 6 (D) 7
50. Total stereoisomers of the compound Cortisone is :-
(A) 32 (B) 64 (C) 66 (D) 128
MATCH THE COLUMN
51. Column–I Column–I I
Me CH=CH–CH3 H CH3
(A) (P) Geometrical isomers
H H CH3–CH=CH H
Me CH2–CH=CH2 Me H
(B) (Q) At least one of the compound can
H H H CH=CH–CH3
show Geometrical Isomerism
(C) (R) At least one of the compound can
show Optical Isomerism

(D) CH2=CH–CH=CH–CH3 CH3–CH=C=CH–CH3 (S) Positional isomers
52. Match the column :

Column - I Column - II
COOH COOH
(A) A pair of metamer (P) H OH ; H OH
HO H H OH
COOH COOH
(B) Tautomerism (Q) CH3OC3H7 ; C2H5OC2H5
CH3 CH3
(C) A pair of geometrical isomer (R) H OH ; HO H
COOH COOH
H3C CH3 H C H
(D) A pair of distereomers (S) C=C ; 3 C=C
H H H CH3
O
(E) A pair of optical isomer (T) CH3CH2CH2CH ; CH3CH2CH=CH–OH
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53. Match the column I with column II.

Column-I (reaction) Column-II (stereoisomers)
(A) & Cl (P) Homologs

Cl
OCH2–CH3 OCH3
CH3
(B) & (Q) Functional isomers
OCH3 OH
CH3
(C) & (R) Metamer
(D) CH3–CH2– –O–CH3 & CH3– –O–CH2–CH3 (S) Position isomers
54. Column - I Column - II

Compounds Relation
CH2OCH3 OCH2CH3
(A) Me Me Me H (P) Metamers
H H
H H H Me
D D D D
(B) (Q) Functional

OCH3 CH2OH
D D D D
(C) (R) Geometrical isomer
14
CH3 CH3
(D) H D D H (S) Enantiomer
D H H D
CH3 CH3
14
(T) Diastereomer
55. Column-I Column-II
H CH3
(A) (P) cis-form

CH3
CH3
(B) (Q) trans-form
CH3
CH3
(C) (R) Keq is greater than one when compound undergo
CH3
flipping.
CH3
(D) (S) Keq is less than one when compound undergo
CH 3
flipping
(T) Keq is equal to one when compound undergo
flipping
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SUBJECTIVE TYPE QUESTIONS

56. Considering rotation about the C3–C4 bond of 2-methylhexane :
(a) Draw the Newman projection of the most stable conformer
(b) Draw the Newman projection of the least stable conformer
57. Comment on the relationship among the following compounds.
CH3 H CH3 CH3
CH3 T T CH3 CH3 H T CH3
(I) (II) (III) (IV)
D H D CH3 H D H D
H H T H
58. Write the structure of
(i) (E) penta-1,3-diene (ii) (2Z,4E) hexa-2,4-diene
(iii) (2E,4E)-3-ethylhexa-2,4-diene (iv) (R)-2-Bromopentane
(v) (S)-3-bromo-3-chlorohexane (vi) (2S, 3R)-2,3-dibromobutane
59. Draw the two chair conformers of each compound and indicate which conformer is more stable :
(a) cis-1-ethyl-3-methylcyclohexane (b) trans-1-ethyl-2-isopropylcyclohexane
(c) trans-1-ethyl-2-methylcyclohexane (d) trans-1-ethyl-3-methylcyclohexane
(e) cis-1-ethyl-3-isopropylcyclohexane (f) cis-1-ethyl-4-isopropylcyclohexane
60. Calculate the total number of chrial carbon atoms in.
O
H
(i) (ii)
H H HO
O
(Progesterone)
61. Determine whether each of the following compounds is a cis isomer or a trans isomer.
H Br H
H
Cl H CH3
Br H
(a) (b) (c)
CH3
Br
H
H H
H
Cl CH3
Br
(d) (e) CH3
CH3 CH3 (f)
H H H
62. Calculate total number of geometrical isomers in each case? (excluding enantiomerism)
(i) H3C CH CH CH CH CH3 (ii) CH3–CH=CH CH2–CH3
CH=CH–CH3
(iii) CH3–CH=C (iv)
CH=CH–CH 3
(v) Cl–CH=CH–CH=CH–CH=CH–CH3 (vi)
(vii) (viii)
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(ix) CH3–C º C–CH=CH–CH3 (x) CH3–CH=CH–CH=N–OH
Me
(xi) CH2=C=CH–CH2–CH=C=C=CH–Me (xii)
D
(xiii) Br–CH=C=C=CH–CH=CH–Br
63. How many monochlorinated products of methyl cyclohexane are optically active.
64. With reasons, state whether each of the following compounds I to VII is chiral
Cl Cl
H H
(I) Cl (II) H
H Cl
Cl CO2H
(III) (IV) C=C=C
HO2C CO2H Cl Me
Ph
O O
(V) (VI)
CO 2H
Me
(VII) S=O
Ph
65. How many cyclopentane structures (including stereo) are possible for C7H14.
66. How many pair(s) of geometrical isomers are possible with C 6H12 (only in open chain structures)
67. The number of diastereoisomers (excluding optical) for 1-bromo-2-chloro-3-iodocyclopropane.
68. Identify molecules which usually can show geometrical isomerism (at room temperature):
Cl
H3C Me
(I) (II) (III) (IV)
Cl Br Cl
H D
Cl
Br
(V) (VI) N (VII) (VIII)
HO
Cl
H H
Cl
(IX) (X) (XI) (XII)
Me Me
(XIII) (XIV) (XV)
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69. In what stereoisomeric forms would you expect the following compounds to exist ?
(a) EtCH(CO2H)Me (b) MeCH(CO2Et)CO2H (c) (d)

O
Ph CO2H I
H H
(e) C=C=C=C (f) Et(Me)C=C=C(Me)Et (g) (h)
H H Ph CO2H
Br
CH3 Cl
(I) (J) (k)
O
H
70. A 0.1 M solution of an enantiomerically pure chiral compound. D has an observed rotation of +0.20° in a
1 dm sample container, the molecular mass of the compound is 150.
(a) What is the specific rotation of D
(b) What is the observed rotation if this solution of D is diluted with an equal volume of solvent ?
(c) What is the observed rotation if this solution is mixed with an equal volume of a solution that is 0.1 M
in L, the enantiomer of D
(d) What is the specific rotation of D after the dilution described in part (b) ?
(e) What is the specific rotation of L, the enantiomer of D, after the dilution described in part (b) ?
(f) What is the observed rotation of 10 ml of a solution that contains 0.01 mole of D and 0.005 mole of L
? (Assume a 1 dm path length).
71. Total number of stereoisomers of following compounds
(i) CH3 - CH - CH - CH3 (ii) CH3 – CH – CH – CH – CH3 (iii) CH3 – CH – CH – CH – CH3

| | | | | | | |
OH Br Br Br Br Cl Br OH
Cl
Cl
Cl
(iv) CH3 - CH = CH - CH - CH = CH - C 2H5 (v) (vi)
|
Cl Cl
(vii) CH 3 - CH - CH = CH - CH - CH 3 (viii)
OH OH
OH
O OH
(ix) (x) (xi)

HO O
HO
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ANSWER KEY
1. (D) 2. (B) 3. (C) 4. (C) 5. (C) 6. (A) 7. (C)
8. (C) 9. (B) 10. (C) 11. (D) 12. (B) 13. (A) 14. (C)
15. (A) 16. (D) 17. (B) 18. (B) 19. (B) 20. (A) 21. (C)
22. (D) 23. (A) 24. (C) 25. (A) 26. (D) 27. (B) 28. (C)
29. (B) 30. (B) 31. (D) 32. (D)
MULTIPLE CHOICE CORRECT:

33. (BCD) 34. (AB) 35. (ACD) 36. (AC) 37. (AD) 38. (ABC)
39. (CD) 40. (A) 41. (A,C) 42. (A,B,C) 43. (B,C) 44. (B,D)

Comprehension - 1
45. (D) 46. (C) 47. (C)
Comprehension - 2
48. (C) 49. (C) 50. (B)
MATCH THE COLUMN

51. A ® P, Q; B ® Q, S; C ® Q, R, S; D ® Q, R, S
52. A ® Q; B ® T; C ® S; D ® P,S; E ® P, R
53. A ® P; B ® R; C ® Q; D ® R
54. A ® P; B ® Q; C ® R, S; D ® S
55. A ® P, T ; B ® Q,S ; C ® P, T; D ® Q, R
SUBJECTIVE TYPE QUESTIONS
H H
H Isopr H
56.
H Et Et
H Isopr H
H
(I) (II)
57. II, III & IV are Identical ; I is Enantiomer of these.

C2H5
58. (i) (ii) (iii)
Me
Pr C3H7 CH3
H Br
(iv) H Br (v) Br Cl (vi)
H Br
CH3 C 2H 5 CH3
59. More stable conformer are :
i-Pr C2H5
(a) diequatorial, (b) (c)
H5C2 H3C
H
C2H5 CHMe2
C2H5 CHMe2
(d) (e) (f)
CH3
(trans) C2H5
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60. (i) 6, (ii) 8

Explanation
O
* *
* *
H *
* *
*
*
* * * *
(i) H H (ii) *
O HO
61. (a) cis (b) cis (c) cis (d) trans (e) trans (f) trans
62. (i) 3 (ii) 4 (iii) 4 (iv) 2 (v) 8
(vi) 2 (vii) 2 (viii) 2 (ix) 2 (x) 4
(xi) 2 (xii) 0 (xiii) 4
63. (8)
64. achiral : I, III , IV ; chiral : II,V, VI, VII
65. (8)
66. (4)
CH3–CH2–CH2–CH=CH–CH3 Þ cis and trans
CH3–CH2–CH=CH–CH2–CH3 Þ cis and trans
CH3–CH2–C=CH–CH3 Þ cis and trans

CH3
CH3–CH–CH=CH–CH3 Þ cis and trans

CH3
67. (4)
Br H H Br
Cl H Cl Br H Br H H
H H H H Cl H Cl H
68. II, III, IV, V, VI, VIII, IX, XI, XIII, XIV
69. Optical : a,b,c,d,f,g,i,j,k ; Geometrical isomer : c,g,j ; None : e, h
70. (a) +13.3 ; (b) 0.10 ; (c) zero ; (d) unchanged ; (e) unchanged; (f) 1
71. (i). (4) (ii). (4) (iii). (8) (iv). (8)
(v) (3) (vi) (2) (vii) (6) (viii) (8)
(ix) (4) (x) (3) (xi) (4)
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ALKYL AND ARYL HALIDES

1. Pick the correct statement for monochlorination of R-secbutyl chloride.
Cl
¾¾®
¾2
300°C
(A) There are four possible products ; three are optically active one is optically inactive
(B) There are five possible products ; three are optically inactive & two are optically active
(C) There are five possible products ; two are optically inactive & three are optically active
(D) There are four possible products ; two are optically active & two are optically inactive
2. ¾HBr
¾¾® Major product is
1 eq ., 40°C
Br Br
(A) (B)
(C) (D)
Br
Br
3. The reaction of SOCl2 on alkanols to form alkyl chlorides gives good yields because
(A) Alkyl chlorides are immiscible with SOCl2
(B) The other products of the reaction are gaseous and escape out
(C) Alcohol and SOCl2 are soluble in water
(D) The reaction does not occurs via intermediate formation of an alkyl chloro sulphite
SOCl
4. ¾¾¾2 ® (A)
Pyridine
Major product (A) is:

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(A) (B) (C) H2C = CH2 (D)
SOCl
5. ¾¾¾2 ® (A)
Major product (A) is:
(A) (B) (C) H2C = CH2 (D)
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Å
O O H3 O
[y]
2 3
6.
[x]
Select correct statement about [x] & [y].
(A) [x] has gauche from more stable than its any other conformation across C 2–C3
(B) [x] has gauche from less stable than its any other conformation across C 2–C3
(C) [y] has gauche from more stable than its any other conformation across C 2–C3
(D) Both option (B) & (C) are correct
7. Select the most reactive Alkene for hydration.
MeO Ph
(A) (B) (C) (D)
8. Correct reactivity order for SN1 reaction.

O
O Cl Cl O
(I) (II) (III) (IV)
Cl
Cl
(A) I > II > IV > III (B) II > IV > III > I (C) I > II > III > IV (D) II > IV > I > III
9. Mg / ether
R — Br ¾¾ D O
¾¾¾® A ¾¾2¾® CH3–CH2D
R — Br by Wurtz reaction forms :
(A) CH3 –CH2 –CH2 –CH3 (B) CH3 –CH2 –CH2 –CH3 , CH3 –CH3
(C) CH3 –CH2 –CH2 –CH3, CH3 –CH3, CH2 = CH2 (D) CH3 –CH2 –CH2 –CH3, CH2 = CH2
10. Mg / ether D O Na / ether

¾¾ ¾¾¾® ¾¾2¾® ¾¾ ¾¾¾® (A), A is
(A) Br CI (B) D
(C) D (D)
11.
Above compound contains four functional groups, correct rate of reaction with RMg-X will be :
(A) I > III > III > IV (B) I > II > III > IV (C) IV > I > II > III (D) I > IV > III > II
CH MgBr
3 ¾ ¾®
12. ¾¾¾ (A)
1( eq.)
(A) (B) (C) (D)
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13. Which one of the following compounds will be most reactive for SN1 reactions:
I Cl Br Cl
O O O
(A) (B) (C) (D)
14. Among the bromides I–III given below, the order of reactivity in S N1 reaction is:
(I) (II) (III)
(A) III > I > II (B) III > II > I (C) II > III > I (D) II > I > III
15. Product,
Identify the major product :
(A) (B) (C) (D)
16. Compound CH3–O–CH2–Br gives which one of the following reactions:

(A) Only SN1 (B) Only SN2
(C) SN1 as well as SN2 (D) E1
17. In the following reaction the most probable product will be :
(A) (B) (C) (D)
18. SOCl
¾¾ ¾¾2
® Product,
Identify the product
(A) (B) (C) (D)
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EtONa
19. ¾¾ ¾¾® The product is :
(1 mol ), D
NO2
(A) (B) (C) (D)

EtO Cl
Cl
20. D
I¯ + CH3ONa ¾¾®
I
OCH3
(A) + (B) O¯CH3
O2N
+ OCH3
I
–
I
(C) (D)
O2N
21. The best yield of given product can be obtained by using which set of reactants X and Y respectively :
CH3
|
Ether
X + Y ¾¾ ¾
¾® CH2 – C – CH3
|
CH3
(A) PhLi + Neopentyl chloride (B) PhMgBr + Neopentyl bromide
(C) t-Bu – MgBr + Benzyl bromide Na
(D) Benzylchloride + t-Butyl chloride ¾¾¾®
MgBr OH
22. + ¾® A
O – Ph
(A) (B) (C) (D)
23. Compounds are shown with the no. of RMgX required for complete reaction, select the incorrect option
(A) CH3COOC2H5 1
(B) CH3COCl 2
(C) HOCH2COOC2H5 3
(D) 4
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24. Compare the two methods shown for the preparation of carboxylic acids:
Mg (i ) CO
Method 1: RBr ¾¾ ¾® RMgBr ¾¾ ¾
¾2 ® RCO2H
diethyl ether (ii ) H3O +
NaCN H O , HCl
Method 2 : RBr ¾¾¾® RCN ¾¾
2
¾¾® RCO2H
heat
Which of the following statements correctly describes this conversion?
¾¾¾®
(A) Both method 1 and method 2 are appropriate for carrying out this conversion.
(B) Neither method 1 nor method 2 is appropriate for carrying out this conversion.
(C) Method 1 will work well, but method 2 is not appropriate.
(D) Method 2 will work well, but method 1 is not appropriate.
25. Which reaction conditions (reagents) is suitable for the following reaction:
?
¾
¾®
(A) Br2 / CCl4 (B) SOBr2 (C) HBr /conc. H2SO4 (D) PBr3
H O
26. Me 2C=CH–CH2–CH2–Cl ¾¾
¾
2
® (X)
Major product of above reaction is
OH
|
(A) Me - C - CH 2 - CH 2 - CH 2
|
Me
(B) Me 2C=CH–CH2–CH2–OH
(C) Me 2C = CH - CH - CH 2 - OH
|
OH
OH
|
(D) CMe 2
27. In the given pairs, which pair represent correct order of rate dehydrohalogenation reaction.
(A) < (B) <
(C) < (D) CH3–CH2–Cl < CD3 – CD2 – Cl
I Br
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28. Consider the reaction.
CH 3
| —
OH
CH 2 = CH - CH 2 - CH - CH - CH 3 ¾¾® Product Major..
|
Cl
The major product is
CH 3 CH 3
| |
(A) CH 2 = CH - CH = CH - CH - CH 3 (B) CH 2 = C = CH - CH 2 - CH - CH 3
CH 3 CH 2
| ||
(C) CH 2 = CH - CH 2 - CH = C - CH 3 (D) CH 2 = CH - CH 2 - CH 2 - C - CH 3
—O–Cl
NBS KOH (1mole)
29.
hn
(A) ¾¾¾® (B) ¾¾¾¾¾¾ ® (C). Find C ?
D D
Cl
(A) (B) (C) (D)

OH
CH3MgX
30. O Product is
NH4Cl
(A) Enantiomer (B) Diastereomers (C) Meso (D) Achiral
CH MgBr
31. CH 3CCH 2CH 2CH 2Cl ¾¾3¾¾® A, A is
D
||
O
CH 3
|
(A) CH 3CCH 2 CH 2 CH 2 Cl (B) CH CCH CH CH CH
3 2 2 2 3
| ||
OH O
(C) (D)
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32. In the reaction sequence :
( i ) CH MgBr / CuCl
¾¾ ¾3 ¾ ¾ ¾¾® (X) Major + (Y)
( ii ) H 2O / H +
(X) & (Y) respectively are

OH CH3 OH
(A) , (B) ,
CH3
(C) , (D) ,
(2)
O OH
C
33. O (3)
¾RMgX
¾ ¾(¾2 moles )
¾ ¾®
H
H
(1)
S
C
º
CH
(4)
Deprotonation will occur from the following positions :

(A) 1,2 (B) 1,3 (C) any two positions (D) 1,4
Br
14
34. ¾Mg
¾® (A) ¾(¾ i ) CO 2
¾¾® (B) ¾NaHCO
¾ ¾¾3 ®
(C) gas
( ii ) H + / H 2O
Product C is :
(A) CO (B) 14CO2
(C) CO2 (D) A mixture of 14CO and CO2
2
35. Which of the following is incorrect.
O
O
C ||
(A) Cl OC2H5 ¾CH3MgX
¾ ¾ ¾ ® CH 3 - C - OC2 H 5
(1 eq )
O
OC2H5 ||
(B) CH3–C OC2H5 ¾C 2 H5MgX
¾ ¾ ¾¾® CH 3 - C - OC2 H 5
(1eq )
OC2H5
S S
|| H3O +
||
(C) CH3MgX + C = S ¾¾¾® CH 3 - C - SH
O O
|| + ||
H3O
(D) CH3MgX + C = O ¾¾ ¾® CH 3 - C - OH
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O
||
H3O +
36. CH3MgBr + CH2=CH - C - H ¾¾ ¾® Product (1, 4 addition). It is %
OH
|
(A) CH 2 = CH - C - H (B) CH 2 CH = CH - CH 3
| |
CH 3 OH
(C) CH3CH2CH2CHO (D) none
CH MgBr (1 eq .)
37. ¾¾3¾ ¾ ¾¾® ?
The product is :
(A) (B) (C) (D)
( i ) CH CN RMgX
38. RMgX ¾¾ ¾3 ¾® (A) ¾¾ ¾® (B) will be %
(ii ) NH 4Cl NH 4Cl
(A) 1° ROH (B) 2° ROH (C) 3° ROH (D) Alkene
39. In the given reaction
C7H12 (A) ¾HBr

¾¾®
(A) can be
(A) (B) (C) (D)

Cl
CH3
40. ¾¾
X
®
X is/are ?
(A) SOCl 2 (B) SO 2 Cl 2 /hv (C) Cl 2 /hv (D) HCl

41. Select the correct statement/s
(A) (2Z)-But-2-ene on reaction with Br2 / CCl4 yields d-l pair of vicinal dibromide.
(B)(2E)-But-2-ene on reaction with Br2 / CCl4 yields meso vicinal dibromide.
(C) (2E)-But-2-ene on reaction with Cl2 / H2O yields d-l pair of erythro isomers. .
(D) But-1-ene on reaction with Br2 / CCl4 yields d-l pair of vicinal dibromide.
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42. Which of the following is/are the chain termination step during photochlorination of ethane?
· · · ·
(A) CH3 CH 2 + Cl ¾® CH3–CH2–Cl (B) CH 3 CH 2 + CH 3CH 2 ¾® CH3CH2CH2CH3
· · · ·
(C) Cl + Cl ¾®Cl2 (D) Cl+ H ¾® HCl
43. Point out the incorrect Grignard reaction.
(A)
(B)
(C)
(D)
OH O
+
N -
O
é * 14 ù
44. + ¾¾® X + H2O + Salt êë C = C úû
gas
+
- N
O O
Mg / ether X /H O
CH2 = CH – Br ¾¾ ¾ ¾ ¾ ¾® Y ¾¾¾¾¾® ( gas ) 2 Z
Which of the following statement is /are correct
(A) Z can give CO2 gas with NaHCO3 (B) Y, on reaction with propyne gives ethene
14 14
(C) X = CO 2 (D) Z can give CO 2 gas with NaHCO3
45. A teritary alcohol can be prepared by grignard reagent and

(A) O2 (B) Epoxide
(C) Ketone (D) Acid derivatives specially acid halide
46. Which are possible products in following
moist Ag O
¾¾ ¾¾
¾
2
®
CH3 OH
(A) (B) (C) (D)
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47. Which of the following statements is / are true?

(A) CH3–CH2–CH2–I will react more readily than (CH3)2 CHI for SN2 reactions.
(B) CH3–CH2–CH2–Cl will react more readily than CH3–CH2–CH2–Br for SN2 reaction.
(C) CH3–CH2–CH2–CH2–Br will react more readily than (CH3)3C–CH2–Br for SN2 reactions
(D) CH3–O–C6H4– CH2Br will react more readily than NO2–C6H5–CH2Br for SN2 reaction
48. Correct statement(s) for the product(s) of following reaction.
CH2 = CH – CH2 – Ph ¾¾ ¾ ¾®
Cl 2 / 500°C
(A) Four different products are formed

(B) Two optically active products are formed
(C) The optically active compound formed here can also be made by the reaction of HCl
(D) The reaction path is free radical substitution.
49. In which of the following given pairs the first compound is more reactive than second to S N2 reaction.
Cl
(A) Cl CH2Cl (B)
Cl
Cl Cl
(C) (D)
Cl Cl
50. Select the correct order of reactivity towards Grignard reagent for nucleophilic attack.
O O
|| ||
(A) R - C - R > R - C - H
(B) Cl - CH 2 - C - H > CH 3CH 2 - C - H

|| ||
O O
O O
|| ||
(C) CH 3 - C - O NO2 < CH 3 - C - O
O O
|| ||
(D) R - C - OR > R - C - NR 2

Comprehension - 1 (Q.51 & Q.53)
Consider the following figure representing variation of heat of combustion of isomeric butenes.
Based on this answer the following questions:
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51. Minimum dipole moment is of isomers.

(A) P (B) Q (C) R (D) S
52. Which gives fastest reaction with HBr?
(A) P (B) Q (C) R (D) S
53. Which will give product showing no optical activity, when treated with HBr.
(A) P (B) Q (C) R (D) all of these
Comprehension - 02 (Q.54 & Q.56)
+
(A) ¾¾¾
H3O
® (B)+(C)
(C) ¾¾
H+
Δ
® (D) ¾¾¾¾
Br2 /CCl 4
® Meso-2,3-dibromobutane
(B) ¾¾
Na
® (E) ¾¾¾
Et-Br
® CH 3 -CH 2 -O-CH 2 -CH 3
54. Structure of (A) is
H3C H3C
CH3 O CH3
O
(A) (B)
H3C H3C
CH3
H3C CH3
(C) (D) All of these
O
55. Structure of (C) is
CH3
OH H3C
(A) H C (B)
3
OH
H3C H3C
H3C OH CH3
(C) (D)
H3C HO
56. Structure of (D) is
H3C H3C
H3C CH3 H2C
CH3
(A) (B) (C) (D)
CH3
CH3 H2C
INTEGER / SUBJECTIVE TYPE

57. LIST-1 (Reagents)
(A) Br2/CCl4 (B) Br2 / H2O Or (HOBr) (C) I-Cl (D) I-N3 (E) NOCl (F) H + /H 2 O
LIST-2 (Alkenes)
(1) CH 2 =CH 2 (2) CH 3 -CH=CH 2 (3) CH 3 -CH=CH-CH 3
CH3
(4) CH3 -CH=CH-CH 2 -CH 3 (5) (6)
Pick a alkene one by one from list-2 and find major product(excluding stereoisomers) when the alkene react
with each reagent given in list-1 ?
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58. Draw the major 1,2- & 1,4-products from each of the diene reactions shown below.
H3C
CH3
(1) + ? + ?
HBr (1 eq.) 1, 2-Product 1, 4-Product
(2) + Br2 ? + ?
(1 eq.) 1, 2-Product 1, 4-Product
(3)
? + ?
1, 2-Product 1, 4-Product
+ HBr (1 eq.)
CH2
(4)
+ Br2 ? + ?
(1 eq.) 1, 2-Product 1, 4-Product
CH2
59. Arrange the isomers of molecular formula C4H9Cl in order of decreasing rate of reaction with sodium iodide
in acetone.
60. Draw the product for each of the following SN 2 reactions:
(A) (S)-2-Chloropentane and NaSH
(B) (R)-3-Iodohexane and NaCl
(C) (R)-2-Bromohexane and sodium hydroxide
61. Consider the following SN2 reaction:
Br SH
¾¾¾
NaSH
DMSO
® + NaBr
(A) Draw the mechanism of this reaction.
(B) What is the rate equation of this reaction?
(C) What would happen to the rate if the solvent is changed from DMSO to ethanol?
(D) Show the transition state in energy profile diagram considering exothermic reaction.
62. Identify the product in each of the following reactions :
NaI (1mole )
(a) ClCH 2 CH 2 CHCH 2 CH 3 ¾¾ ¾ ¾ ¾® C5H10ClI
acetone
|
Cl
(b) BrCH2CH2Br + NaSCH2CH2SNa ¾® C4H8S2

(c) ClCH2CH2CH2CH2Cl + Na2S ¾® C4H8S
63. For each of the following substrates, determine whether an SN1 process will require a proton transfer at the
beginning of the mechanism:
H3C H3C
H3C
H3C I H3C OH CH3
(A) (B) (C)
H3C H3C H3C Br
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CH3
O
OH Cl
CH3
(D) (E) (F)
64. Will an SN1 process involving each of the following nucleophiles require a proton transfer at the end of the
mechanism?
(A) NaSH (B) H2S (C) H2O (D) EtOH (E) NaCN (F ) NaCl
(G) NaNH2 (H) NH3 (I) NaOMe (J) NaOEt (K) MeOH (L) KBr
65. Consider the following substitution reaction:
H3C H3C
CH3 CH3
H3C ¾¾ ¾
HBr
® H3C + H 2O
OH Br
(a) Determine whether this reaction proceeds via an SN 1 or SN2 process.
(b) Draw the mechanism of this reaction.
(c) What is the rate equation of this reaction?
(d) Would the reaction occur at a faster rate if sodium bromide were added to the reaction mixture?
(e) Draw an energy diagram of this reaction considering reaction exothermic.
66. Choose the compound of molecular formula C7H13Br that gives each alkene shown as the exclusive product
of E2 elimination when treated with alc.KOH?
(a) (b) (c) (d)
(e) CH = CH2 (f) (g) C(CH3)3
67. Write the structures of all the isomeric alkyl bromides having the molecular formula C5H11Br.
(A)Which one undergoes E1 elimination at the fastest rate ?
(B)Which one is incapable of reacting by the E2 mechanism ?
(C)Which one can yield only a single alkene on E2 elimination ?
(D)For which isomers does E2 elimination give two alkenes that are not constitutional isomers ?
(E)Which one yields the most complex mixture of alkenes on E2 elimination ?

68. Choose the alkyl halide(s) from the following list of C6H13Br isomers that meet each criterion below.
(1) 1–bromohexane (2) 3–bromo-3-methylpentane
(3) 1-bromo-2, 2-dimethylbutane (4) 3-bromo-2-methylpentane
(5) 2-bromo-3-methylpentane
(a) the compound(s) that can exist an enantiomers
(b) the compound (s) that can exist as diastereomers
(c) the compound that gives the fastest SN2 reaction with sodium methoxide
(d) the compound that is least reactive to sodium methoxide in methanol
(e) the compound (s) that give only one alkene in the E2 reaction
(f) the compound (s) that give an E2 but no SN2 reaction with sodium methoxide in methanol
(g) the compound (s) that undergo an SN1 reaction to give rearranged products
(h) the compound that gives the fastest SN1 reaction
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69. Examine the ten structural formulas shown select those that satisfy each of the following conditions.
Which compounds give an E2 elimination reaction on treatment with alcoholic KOH?
A B C D E
Br CH3 CH2– Br CH3– I CH2– Br
|
H3 C - C - Cl
|
CH 3
F G H I J
CH3 HC CH–Cl
Cl | 2 2
Br Cl
C
H 3 C - C - CH 2 - Cl
|
CH3 CH3
70. A hydrocarbon C8H10 (A) on ozonolysis gives compound C4H6O2 (B) only. The compound (B) can also be
obtained from the alkyl bromide C3H5Br (C) upon treatment with magnesium in dry ether followed by CO2 and
acidification. Identify (A), (B) and (C) and also give equations for the reactions.
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ANSWERS
1. (C) 2. (C) 3. (B) 4. (B) 5. (A) 6. (C)
7. (C) 8. (A) 9. (C) 10. (B) 11. (B) 12. (A)
13. (A) 14. (A) 15. (A) 16. (C) 17. (B) 18. (A)
19. (A) 20. (A) 21. (C) 22. (A) 23. (A) 24. (C)
25. (D) 26. (D) 27. (A ) 28. (A ) 29. (A) 30. (A)
31. (C) 32. (B) 33. (A) 34. (C) 35. (B) 36. (C)
37. (D) 38. (C)
39. (ABC) 40. (BC) 41. (ABCD) 42. (ABC) 43. (AB D)
44. (ABC) 45. (ABCD) 46. (AB) 47. (AC) 48. (AB D)
49. (B D) 50. (B D)
Comprehension - 01
51. (D) 52. (B) 53. (D)
Comprehension - 02
54. (C) 55. (A) 56. (B)
INTEGER/SUBJECTIVE TYPE QUESTIONS
57. Reagents Alkenes
CH 2 =CH 2 CH 3 -CH=CH 2 CH 3 -CH=CH-CH 3
H2 C CH2 H3 C CH CH2 H3 C CH CH CH3

Br2/CCl4
Br Br Br Br Br Br
Br2 / H2O Or (HOBr)
OH Br OH Br OH Br
I-Cl
Cl I Cl I Cl I
I-N3
N3 I N3 I N3 I

NOCl
Cl NO Cl NO Cl NO
H + /H 2 O
OH H OH H OH H
CH3
CH3 -CH=CH-CH 2 -CH 3
Br Br
H3 C CH CH CH2 CH3
Br2/CCl4
Br Br Br Br
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OH OH
H3 C CH CH CH2 CH3
Br2 / H2O Or (HOBr)
OH Br Br Br
Cl Cl
H3 C CH CH CH2 CH3
I-Cl
Cl I I I
N3 N3
H3 C C H C H CH2 C H3
I-N3
N3 I
I I
Cl Cl
NOCl H3 C CH CH CH2 CH3

NO
Cl NO NO
OH OH
H3 C CH CH CH2 CH3
H + /H 2 O
OH H H H
58. Problem 1, 2-product 1, 4-product
Br
1.
Br Br
Br
Br
2.
Br Br
3.
Br Br
Br
Br
4.
Br
C
|
59. C–C–C–C–Cl > C - C - C - Cl > C - C - C - Cl > C - C - Cl
| | |
C C C
SH CH3
60. (A) (B) H3C

H3C CH3
Cl
OH
CH3
(C)
H3C
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61. (A) SH (B) Rate=K [ ] [NaSH]

Br
Br SH + HBr
Et
d- d-
HS Br
H H
(C) The rate would be slower : (D) E
Reaction coordinate
62. (a) ICH 2 CH 2 - CH - CH 2 CH 3 ; (b) ; (c)

|
Cl
63. (A) NO (B) Yes (C) No (D) Yes (E) Yes (F) No
64. (A) NO (B) Yes (C) Yes (D) Yes (E) No (F) No
(G) No (H) Yes (I) No (J) No (K) Yes (L) No
65. (a) SN1 (tertiary substrate)
H-Br Br Br
:
(b) O H O- H
+ | +
:
( c) Rate = k OH
(d) No. The rate is not dependent on the concentration or strength of the nucleophile.
(e)
E Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\01\ Alkyl & Aryl Haides
Reaction coordinate
66. (a) ; (b) ; (c) ; (d) ; (e)
(f) , (g)
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C C
| |
67. (A) C - C - C - Br ; (B) Br - C - C - C ; (C) C–C–C–C–C–Br ; (D) C - C - C - C - C
| | |
C C Br
(E) C - C - C - C - C
|
Br
68. (a) 4&5 (b) 5 (c) 1 (d) 3 (e) 1 (f) 2 (g) 4 & 5 (h) 2
69. BCF.
Mg (i) CO2 ozonolysis

70. Br ether
MgBr (ii) H3O
C—OH CºC
O
Cyclopropyl (C) Cyclopropane (B) Dicyclopropyl (A)
bromide carboxylic acid acetylene
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IMPORTANT NOTES
Path to success
KOTA (RAJASTHAN)
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ALCOHOL, PHENOL & ETHER

1. [C2H5OH + CH2N 2] leads to the product :
(A) Higher alcohol (B) Simple ether (C) Lower alcohol (D) Mixed ether
2. Ethanol cannot be dried by anhydrous CaCl2 due to the formation of the following solvated product-
(A) CaCl2. 2C2H5OH (B) 2CaCl2. 3C2H5OH
(C) CaCl2. 4C2H5OH (D) CaCl2. C2H5OH
3. Phenol and ethanol are distinguished by the reaction with-
(A) Red litmus (B) NaHCO3 (C) FeCl3 (D) NaOH
4. Which of the following is least reactive towards ZnCl2 and con. HCl mixture-
(A) 2-Butanol (B) 1-Butanol
(C) 2-Methyl 2-butanol (D) All of the above
5. Primary, secondary and tertiary alcohols are distinguished by-
(A) Oxidation method (B) Lucas test
(C) Victor meyer test (D) All of the above
6. The relative rate of acid catalysed dehydration of following alcohols would be,
(A) III > I > II > IV (B) III >IV > I > II (C) I > III > IV > II (D) III > IV > I > II
7. In the given reaction ,
Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\02 \Alcohol, Phenol & Ether
B H , THF H O , NaOH TSCl t -BuO ¯ K +

¾¾2 ¾
6
¾¾® ¾¾2 ¾2 ¾ ¾¾® ¾¾¾® ¾¾ ¾¾ ¾ ¾® (Y)
The product ‘Y’ is

(A) A positional isomer of X (B) Identical to X
(C) Chain isomer of X (D) An oxidation product of X.
8. Mixed ether will not be formed in the reaction-
(A) CH3OCH2Cl + C2H5MgBr (B) CH2N2 + C2H5OH
(C) C2H5ONa + CH3I (D) C2H5OH + H2SO4 (140ºC)
PClMg / ether H O O ,D
9. ¾¾¾
5
® ¾¾ ¾ ¾ ¾ ¾® ¾¾ ¾
2
¾® ¾¾2¾® (X), compound X is
(A) D-2-Butanol (B) L-2-Butanol (C) Both A & B (D) Nither A nor B
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SOCl Mg
10. ¾¾ ¾¾ 2
® ¾¾ ¾ ¾¾® Product
pyridine, D ( C2H5 )2 O
Product of the reaction is
(A) (B)
(C) (D)
MeOH
11. CH2 = CH - CH - CH = CHMe ¾¾ ¾¾®
H2SO 4
|
OH
H
|
(A) CH 2 = CH - CH = CH - C - Me (B) CH2 = CH – CH = CH – CH2 – CH2 – O – Me
|
O - Me
CH2 - CH = CH - CH = CH - CH3
(C) (D) CH2 - CH = C = CH - CH2 - CH3
|
|
O - Me
O - Me
12. HÅ
¾¾
¾®
(A) (B) (C) (D)
HÅ
13. ¾¾
¾®
H2O
(A) (B) (C) (D)
34 E
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14. H+
¾¾
¾®
(A) (B) (C) (D)
CH CH OH
15. ¾¾ ¾
3
¾2¾¾®
H2SO 4
(A) (B) (C) (D)
16.
(A) (B) (C) (D)
17.
(A) (B) (C) (D)
2 Br
18. ¾¾ ¾¾® X
CH3NO2
(A) X is (B) X is (C) X is (D) X is
Å
H¾®
19. CH3 – CH2OH + CH2 = C = O ¾¾ ?
(A) CH3 - O - CH2 - C - CH3 (B) CH3 - CH2 - C - O - CH3

|| ||
O O
(C) CH3 - O - CH2 - CH2 - C - H (D) CH3 - CH2 - O - C - CH3

|| ||
O O
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¾Alc
¾.¾ KOH
20. ¾® Major product is
(A) (B)
(C) (D)
I / NaOH
21. ¾¾
2
¾¾® ¾H¾®
+ D
¾¾® A, A is
D
(A) (B) (C) (D)
22. Dehydration of the alcohols
will be in order
(A) IV > III > II > I (B) I > II > III > IV (C) IV > II > III > I (D) II > IV > I > III
23. In the following reaction, final product is
14
ClCH 2CH - C H 2 ¾NaOC H
¾ ¾2¾5 ®
\ /
O
14 14
(A) ClCH 2CH C H 2 OC 2 H 5 (B) ClCH 2CH C H 2 ONa Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\02 \Alcohol, Phenol & Ether
| |
OH OC2 H 5
14 14
(C) C H 2 - CHCH 2 OC 2 H 5 (D) CH 2 - CH C H 2 OC 2 H 5
\ / \ /
O O
24. The correct structure for compound B will be :
(i) PBr3 CH3CH2 CHO
[A] B
(ii) Mg
OH
OH
(A) (B) (C) (D)

OH
OH OH
36 E
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OH
conc.H2SO4
25. Major product :
(A) (B) (C) (D) None of these
26. Sodium tertiary butoxide forms ether only with :
X X
(A) CH3—CH2—Br (B) CH3—X (C) H3C—CH—CH3 (D) H3C—C—CH3
CH3
27. Find out correct product of following reaction.

Ag2O, dry
CH3CH2Br
(A) (B) CH2 = CH2 (C) O (D) CH3CH2OH
28. In the reaction :
Me3C—O—CH 2CH3 + HI
(1 Mole)
(A) Me3C—OH + CH3CH2I (B) Me3C—I + CH3CH2OH

(C) Me3C—I + CH3CH2I (D) Me3C—OH + CH3CH2OH
29. Which of the following ethers is the most unreactive to cleavage with conc. HBr ?
(A) Ph–CH2–O–CH3 (B) Ph—O—Ph (C) O (D) O
(i) CH3MgCl
30. H2C—CH 2 X. The product obtained in this reaction is :
(ii) H2O
O
(A) CH3CH2OH (B) (CH3)2CHOH

(C)CH3CH2CH2OH (D) HO—CH2—CH2—CH2—CH2—OH
31. Consider the reaction of HI with the following:
(I) (II)
Which forms di-iodide on reaction with HI (excess)?

(A) I and II both (B) II only (C) I only (D) none
32. Glycol on treatment with PI 3 mainly gives–
(A) Ethylene (B) Ethylene iodide (C) Ethyl iodide (D) Ethane
33. Organic product formed when diethyl ether reacts with PCl5.
(A) Ethyl chloride (B) Phosphorous oxy trichloride
(C) Ethenol (D) Ethene
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HO
HI
Products
34.
Which of the following will be not fitted as product.
(A) (B) (C) (D) I

I
H3C
LiAlH4
35. CH2 A, A is :
H3C
O
CH3
(A) CH3CHCH2OH (B) CH3CH2CH2CH2OH (C) CH3C—OH (D) no reaction
CH3 CH3
O MgBr +
H3C—C—Cl + 2 H 3O
36. A, A is :
O OH OH OH
(A) H3C—C (B) H 3C—C (C) H3C—C (D) H 3C—C—H
Cl
37. If phenyl magnesium bromide and acetaldehyde are the reactants, the product formed after hydrolysis would be:
(A) benzyl alcohol (B) 1-Phenylethanol (C) 2-Phenylethanol (D) Acetone
38. In the given reaction
H3C (i) Hg(OAc)2/CH3OH
C = CH—CH3 [X] , [X] will be :
H3C (ii) NaBH4
OMe OMe
(A) H3C—C—CH2—CH3 (B) H3C–CH–CH–CH 3 (C) H 3C–CH–CH2–CH 3 (D) H 3C—CH—CH 2—CH 3
CH CH3 CH3 CH3
3
39. In the following reaction
H3O+
Product
The major product is :
OH OH
OH OH OH
(A) (B) (C) (D)
38 E
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O
H +/H2O HBr Mg HCHO
40. + CH3MgBr P Q Ether R S, S is :
H +/H2O
OH
OH
OH
(A) (B) (C) (D) OH
PCl5 Alc.KOH 1 Conc. H SO4

41. Z X Y. 2 H O, boil2 Z; Z is :
2
(A) CH3–CH2–CH2–OH (B) H3C – CH – CH3

OH
(C) (C2H5)3C – OH (D) CH3 – CH = CH2
42. Find out correct product of reaction :
HBr
(Excess)
O
Br
(A) (B) (C) (D)
Br Br Br OH
O OH Br
43. + HI Product, Product is :

(1 eq.)
O
(A) (B) (C) (D)

HO I I OH I I I OH I
HO
44. Ethylene glycol (HO OH) on heating with conc. H2SO4 (catalytic amount) gives mainly :
O O O
(A) HO O OH (B) (C) (D)
O H H
O
H O+ HBr Mg / ether HCHO

45. CH3MgBr + ¾¾
3
¾® A ¾¾¾® B ¾¾ ¾¾® C ¾¾ ¾ ® D ¾¾®
HI E,
H O+ 3
' E ' is
(A) (B) (C) (D)
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46. Which one of the following can not be the product during dehydration of following alcohol.
+
¾H¾®
D
(A) (B) (C) (D)
X -
47. (CH3)2C = C(CH3)2 ¾¾®
2
A ¾¾¾
OH
D
®B
H 2O
(A) (CH3)2C–C(CH3)2 (B) (CH 3)2C––—C(CH3)2

O OH Cl
(C) (CH 3)2C––—C(CH3)2 (D) None
OH OH
H 2O dil. H SO H
48. In the reaction sequence, CaC2 ¾¾¾® A ¾¾ ¾
2
¾4 ® B ¾¾®
2
C, true about the product C is
Hg + 2 Ni
(A) 2º alcohol (B) 1º alcohol (C) 3º alcohol (D) Phenol

49. Which method is not useful for the synthesis of ether?
(A) ¾aq
¾. NaOH
¾¾®
(B) C2H5ONa + (CH3)2SO4 ¾®
(C) CH3ONa + CH3CH2OSO2 ¾®
(D) (CH3)3CBr + CH3CH2ONa ¾® Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\02 \Alcohol, Phenol & Ether
50. Reduction of R—CH2OH ¾® RCH3 can be carried out by :
(A) LiAlH4 (B) H2—Ni (C) Red P + HI (D) NaBH4 / AlCl3

51. When 2-chloroethanol is warmed slightly with NaOH, the major product formed is :
(A) CH3–CH2–CH2–O–CH2–CH2–Cl (B) HO–CH2–CH2–CH2–CH2–OH
(C) HO–CH2–CH2–OH (D)

O
52. Which set of the following reagents (A to D) would you select to convert C6H5COCH3 (acetophenone) to the
following alcohol ?
CH3 CH3
C6H5—C — CH—CH 3
OH
(A) CH3CH2CH2MgBr and hydrolysis (B) CH3CH(Br)CH3.AlCl3
(C)(CH3)2CHMgBr and acid hydrolysis (D) CH3CHCHCH3, Zn
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H 3C (X) H 3C
53. C—CH2—CH3 C—CH—CH 3
H3C H 3C
OH O (Y)
H 3C
C—CH—CH 3
H 3C
OH
(X) and (Y) are respectively :
(A) LiAlH4 and NaBH4 (B) LiAlH4 / AlCl3 and LiAlH4
(C)LiAlH4 and LiAlH4 / AlCl3 (D) H2 / Ni and H2 / Pt
– +
(i) CH3 C Na
54. H3C—CH—CH 2 Product, Product is :
(ii) CH3I
O
(A) H3C—CH—CH2—CH = CH2—CH3 (B) H3C—CH—CH2—C C—CH3
OMe OMe
(C) H3C—CH—CH2—C C—CH3 (D) H3C—CH—CH—C C—CH 3
OH O
–
O
PhCH2—I PhCH2—I
55. A CF3CH2OH DMSO B
A & B are respectively :
O—CH2—Ph OH OH OCH2Ph
(A) A = ;B = (B) A = ;B =
CH2Ph CH 2Ph
OCH2Ph OH
(C) A = B = (D) A = B =
CH2Ph
+
H2O/H
56. 'X'
O O
CH3
'X' will be :
(A) OH (B) (C) (D) All of these

HO O O OH
O CH3 O CH3 CH3 O HO
57. The product of the reaction is :
O
1. KH
HS 2. H2O
OH OH
S S O
(A) (B) (C) HS 5O (D) HS 4
OH
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58. Which combination of reagents will bring about the following conversion ?
O
Br
(A)MeMgBr/HÅ, H2SO4/D, HBr/H2O2 (B) MeMgBr/HÅ, H2SO4/D, HBr
(C) MeMgBr/HÅ, HBr/CCl4 (D) HBr/H2O2, MgMgBr/HÅ

59. Select the major product of following reaction :
O
–
CH3CH2O
Cl
OCH2CH 3
O O – O
(A) (B) (C) O (D)
Cl CH3CH2–OCH2 CH 3
OCH2CH 3
CH3
OH PBr3 +–
KCN
60. CH3CH2 DMF
final product
H
CH3 CH3 CH3 CH3 H
H C=C CN CH 3
(A) CH CH (B) (C) CH CH (D) NC
3 2
CN H H 3 2
H CH3CH2

Paragraph for Q. No. 61 to 64.
One of the important methods of preparation of alcohols is the reaction of Grignard reagent with aldehydes,
ketones, esters or epoxides. Grignard reagents are nucleophilic reagents and undergo nucleophilic addition to
carbonyl group. They undergo SN2 reaction with epoxides.
61. Which of the following halides is not suitable for preparing Grignard reagents by reaction with magnesium?
(A) CH3CH2Br (B) HOCH2CH2Br (C) CH º C – CH2Br (D) Both (B) and (C)
62. For preparing the alcohol
OH
C – Ph
CH3
Ph
which pair of carbonyl compound and Grignard reagent will be a wrong choice ?
(A) CH3COOC2H5 and PhMgBr (excess) (B) PhCOCH3 abnd PhMgBr
(C) PhCOPh and CH3MgBr (D) PhCOOC2H5 and CH3MgBr (excess)
OH
63. By whichj of the following methods the alcohol C – CH3 can be synthesised ?
PhCH2 CH3
(A) CH3COCH 3 + PhCH 2 MgBr ® (B) PhCH 2 COOCH3 + CH 3 MgI(excess) ®
CH3
(C) CH3 + PhMgBr ® (D) All of these
O
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64. By which of the following reactions can the Grignard reagent CH 3C º C - MgBr be prepared ?
(A) CH3C º C - Br + Mg ¾¾¾

Et 2 O
heat
® (B) HC º CH + CH 3MgBr ¾¾¾
Et 2 O
®
(C) CH 3C º CH + CH 3 MgBr ¾¾¾

Et 2 O
® (D) All of these
MATCH THE COLUMN
65. Match the column I with column II.
Column-I (Reaction) Column-II (Possible products)
(i) H g(OAc) 2 /H 2 O
(A) —C H 3 (p) —C H 2 O H
(ii) N aB H 4
OH
(i) B 2 H 6/T H F
(B) CH2 (q) —C H 3
(ii)H 2 O 2 O H
OH
Å
H /H 2 O
(C) —C H 3 (r) —C H 3
OH
(i) H g(OAc) 2 /H 2 O
(D) —C H 3 (s) —C H 3
(ii) N aB H 4
66. Column - I (Conversions) Column - II (Reagents)
R H
(A) R – C º C – R ® = (p) BH3/THF; H2O2/OH–
H R
R R
(B) R – C º C – R ® = (q) Na/NH3(1)
H H
(C) R – C º CH ® RCH2CHO (r) Aq. H2SO4/HgSO4

(D) R – C º CH ® RCOCH3 (s) H2/Pd-BaSO4, quinoline
67. Match the chemical transformations given in Column – I with the appropriate reagents given in Column II.
Column - I Column - II
(A) CH3CH = CH2 ® CH3CH2CH2OH (p) H2O/H2SO4, HgSO4
(B) CH3CH = CH2 ® CH3CH(OH)CH3 (q) Sia2BH, followed by H2O2/NaOH
(C) CH3C º CCH3 ® CH3CH2COCH3 (r) BH3 followed by H2O2/NaOH
(D) CH3C º CH and CH3CH2CH2CHO (s) Hg(OAc)2/H2O followed by NaBH4/NaOH
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SUBJECTIVE TYPE
68. Give the product of the following reaction.
(i) Hg(OCOCH 3 ) + CH3OH

(i) ¾¾¾¾¾¾¾¾ -
® (ii) ¾¾¾¾¾¾
(i) Hg(OAc)2 ,H 2 O
-
®
(ii) NaBH 4 ,OH (ii) NaBH 4 ,OH
CH3
¾(¾
i ) Hg (CF3COO )2 ,CH 3OH
¾¾ ¾ ¾¾ ¾ ¾® (i) Hg(OAc)2 ,CH 3 - O - H
(iii) ( ii ) NaBH 4 , HO ¯ (iv) ¾¾¾¾¾¾¾® -
(ii) NaBH 4 ,OH
CºCH
OH
(v) ¾¾¾¾¾¾
(i) Hg(OAc)2 ,H 2 O
-
® (vi) ¾¾¾¾¾¾
(i) Hg(OAc)2 ,H 2 O
-
®
(ii) NaBH 4 ,OH (ii) NaBH 4 ,OH
69. How could each of the following compounds be synthesized from an alkene by OMDM?
OH OCH2CH3 CH 3 CH 3
| |
(i) (ii) (iii) CH 3CCH 2 CH 3 (iv) CH 3CCH 2 CH 3
| |
OH OCH 3
70. Give the product of the following reaction.
(i) CH2 = CH2

(i ) BH
¾¾ ¾3 ¾¾® (ii) ¾¾¾¾
BH 3 ,THF
-
®
H 2O/ OH
(ii ) HO ¯,H 2O 2 , H 2O
(iii)
(i ) BH
¾¾ ¾3 ¾¾® (iv) ¾¾¾¾
BH 3 ,THF
-
®
H 2O/ OH
(ii ) HO ¯,H 2O 2 , H 2O

CºCH
BD3, THF
(v) CH3COOH (vi) ¾¾¾¾®
(i)BH 3 ,THF
-
(ii )H 2O 2 / HO
BH3, THF
CH3COOD
BT3, THF
CH3COOD
71. Find the major product in the following reactions ?
OH
H+/D
(A) (B) H+ /D
OH
OH
(C) H+ /D (D) H+ /D
HO
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OH
CH3
(E) H+ /D (F) H+ /D
OH
OH OH
(G) Al 2 O3 / D (H) ThO2 / D

¾¾¾¾ ® ¾¾¾®
OH OH
+ Al 2 O3 / D
(I) H /D
¾¾¾ ® (J) ¾¾¾¾ ®
OH OH
ThO2 / D +
(K) ¾¾¾® (L) H /D
¾¾¾ ®
Ph
(N) Ph
+ +
(M) ¾¾
H
® ¾¾
H
®
HO OH HO OH
Et + Ph Ph +
(O) ¾¾
H
® (P) ¾¾
H
®
HO OH HO OH
OH OH HO OH
(Q) Ph ¾¾
H+
® (R) ¾¾
H
®
+
Ph
HO Cl HO NH2
(S) ¾¾¾¾
Anhy.AlCl3
® (T) ¾¾¾
HNO 2
®
72. Find the organic products formed when following compounds completely react with HIO4(Periodic acid)?
OH CHO
OH
OH OH
(A) (B) (C)
OH
OH OH
CHO
CH3
OH OH
OH
(D) (E) (F)
OH OH
CHO
CH3
OH OH
(G) (H)
OH
CH3 OH
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ANSWER KEY
Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
A ns. D C C B D A A D C B A C B D A
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
A ns. B C A D D A C D B B B C B B C
Que. 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
A ns. C A A A C C B A B B B B A C D
Que. 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60
A ns. C A B D C D C C B B A A A D C

61. (D) 62. (D) 63. (D) 64. (C)
MATCH THE COLUMN 65. (A) ® q ; (B) ® p ; (C) ® q,r,s ; (D) ® r

66. (A) ® q ; (B) ® s ; (C) ® p ; (D) ® r
67. (A) ® q,r ; (B) ® ps ; (C) ® p,q,r,s ; (D) ® q
SUBJECTIVE TYPE
COCH3
OCH3 OH H3C OCH3 OCH3
O
68. i. ii. iii. iv. v. vi.
OH
OCH2CH3
69. (i) ¾(¾

i ) Hg ( OAc ) 2 , H 2O
¾ ¾¾ ¾ ¾® (ii) ¾(¾
i ) Hg ( OAc )2 ,CH3CH 2OH
¾ ¾ ¾¾ ¾¾ ¾®
r
(ii ) NaBH 4 ,OH ( ii ) NaBH4 ,OH r
CH 3 CH 3 Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\02 \Alcohol, Phenol & Ether

| |
(iii) ¾(¾
i ) Hg ( OAc ) 2 , H 2O
¾ ¾¾ ¾ ¾® CH 3CCH 2CH 3 (iv) ¾(¾
i ) Hg ( OAc ) 2 ,CH 3OH
¾ ¾ ¾ ¾ ¾® CH 3CCH 2CH 3
(ii ) NaBH 4 ,OH r | (ii ) NaBH 4 ,OH r |
OH OCH 3
H H
70. (i)CH3CH2OH (ii).
H OH
CH3 H OH CH3
H CH3 CH3 OH
(iii) OH , H (iv) CH3 , H
H OH H CH3
CH2D CH2D
(v) (a) CH 3 - CH - CH 2 , (b) CH 3 - CH - CH 2 , (c) H T T H
| | | |
D H H D CH3 CH3
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CH2CHO
(vi)
71. (A) (B) (C) (D)
(E) (F) (G) (H)
(I) (J) (K) (L)
Ph Ph
(M) (N) Ph (O) (P) Ph

O O O Et O
O
O O O
Ph
(Q) (R) (S) (T)
Ph
72. (A) 2HCHO (B) 2HCHO, HCOOH (C) HCHO, 2HCOOH (D) 3HCOOH
O
O
CHO
(E) (F) (G) (H) No reaction
CHO CHO
O
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OXIDATION & REDUCTION

1. Compound ‘X’ on ozonolysis followed by iodoform reaction produces 4 moles of CHI 3 and a tetrabasic acid.
The structural formula of ‘X’ can be
H3C CH3
CH3
CH3 H3C H3C CH3
CH3
(A) (B) (C) (D)
H3C H3C CH3 CH3
H3C
CH3 H3C CH3
2. The correct statement about main reduction products is
(Ignore ethyl alcohol formed in any reaction as a side product)

(A) p, q, r are identical compounds (B) q, r, s are identical compounds
(C) r, s, t are identical compounds (D) p, r, t are identical compounds
3. The end product of following reaction is
(1) O3 (3) LiAlH
3 (5 ) PBr ( excess ) Mg / ether 1 eq. HCOOEt
¾¾ ¾¾ ¾¾ ¾® ¾¾¾¾Å¾
4
¾ ®¾¾ ¾ ¾ ¾ ¾ ¾ ¾®
¾¾ ¾ ¾ ¾®¾¾ ¾ ¾ ¾ ¾¾®
( 2) Me2S,H2O ( 4) H (6) HÅ (7 )
(A) (B) (C) (D)
4. The structure of the starting material X is
3, 4 - Dimethyl - 3 - hexanol
(3,4 - MkbZesfFky - 3 - gsDlkukWy½
Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\03\Oxidation & Reduction
(A) (B) (C) (D)
5. In which of the following reaction the product will also be optically active
(A) (B)
(C) (D)
6. The reaction among following produces meso-compound
Me H Me H
KMnO4/OH /H2O (cold) KMnO4/OH /H2O (cold)
(A) (B)
Me H H Et
Me H Me H
KMnO4/OH /H2O (cold) KMnO4/OH /H2O (cold)
(C) (D)
Et H H Me
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7. Which of the following is/are the proper sequence of reagents for the conversion
(A)
(B)
(C)
(D)
8. The product which is not formed in the following reaction :
CH3 CH3
| | HIO4 ( excess )
Ph - C - CH - CH - CH - CH2OH ¾¾ ¾ ¾ ¾ ¾ ¾ ¾®
| | |
OH OH OH
(A) HCOOH (B) Ph - C - CH3

||
O
CH3 CH3
| |
(C) OHC - CH - CH2OH (D) OHC - CH - CHO .
Me HOCl aq.AgNO 3 H SO / D
9. Ph ¾¾ ¾¾® ¾¾ ¾ ¾ ¾¾ ®¾¾2¾ ¾4 ¾¾® (W)
(P)
‘W’ is also obtained by
–
BH3 – THF H2 O2/OH CrO3
(A) P ¾¾ ¾ ¾ ¾¾®
(1) (2) (3)
HBr / R O 2 KOH / DMSO Pyridinium Chloro Chromate

(B) P ¾¾ ¾ ¾2¾¾ ® ¾¾ ¾ ¾ ¾ ¾¾® ¾¾ ¾ ¾ ¾ ¾ ¾ ¾ ¾ ¾ ¾ ¾ ¾
¾®
(1) ( 2) (3 )
(C) Ph – CH2 – C – OEt + CH3MgBr
O
(D) Ph – CH2MgBr + Et – O – C – CH 3
O
10. Which of the following will give yellow precipitate with NaOH / I 2
(A) Ph - CH - Me (B) CI3CHO

|
OH
(C) Me - C - C - OH (D) EtOH

|| ||
O O
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11. Observe the following sequence of reaction
Cl / hn
H / Ni ¾¾2¾¾®
¾¾2 ¾¾® (Q) monochlori nation
n products (structurally isomeric)
(P)
CH3–CHO + (R)
Correct statements about R

(A) It gives yellow ppt with I 2/OH– (B) It gives silver mirror with ammonical silver nitrate.
(C) It has total four stereoisomers (D) Only two stereoisomers of R are optically active.
Paragraph for Q. No. 12 to 14.
12. The groups oxidised by using dilute cold KMnO4 solution is ?

(A) x, s, r (B) r only (C) s only (D) r, s both.
13. The oxidising agent which cannot oxidise x, y, z is
(A) CrO3 / (B) CrO3/pyridine/CH2Cl2 (C) HIO4 (D) Cu powder
14. The dehydrogenation reaction on heating with Cu powder takes place at
(A) x y z (B) x y z w (C) r y (D) y z
Paragraph for Q. No. 15 to 17
From molecular formula C9H10, Total 4 Structural isomers [having monosubstituted benzene ring] are possible.
Some structural isomer of molecular formula C9H10 decolourises Bayer's Reagent and Br2/CCl4 (Test of
unsaturation). Unsaturated compounds having same C-skeleton give same product on catalytic hydrogena-
tion.
15. How many structural isomers give test of unsaturation ?
(A) 2 (B) 4 (C) 3 (D) 1
16. How many structural isomer can show Geometrical isomerism ?
(A) 2 (B) 1 (C) 3 (D) 4
17. How many structural isomers give same product on catalytic hydrogenation at room temperature.
(A) 1 (B) 2 (C) 3 (D) 4
MATCH THE COLUMN
18. Matrix-I Matrix-II
(Pair of compounds) (Reagent can be used to differentiate the given pair of compounds)
(A) HCHO,CH 3CHO (P) NaOH + I2
(B) PhCHO,CH3CHO (Q) Fehling solution
(C) CH 3 OH,CH 3CH 2 OH (R) Tollen’s reagent
Cl
Cl
(D) , (S) Aq. AgNO3
(E) HCOOH, CH 3COOH
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(Reactions) (Regents)
O
(A) CH3–CH2–C–CH3 Carboxylic acid (P) H2/Pd, BaSO4
O
(B) CH3–CH2–C–NH2 Primary amine (Q) LiAlH4, / Mild H+
(C) CH3–CH 2–C–Cl Aldehyde (R) NaOBr, / Mild H+
O
(D) CH2=CH–C–CH 3 Saturated alcohol (S) H2/Ni, D
O
(T) Diisobutylauminium hydride (DIBAL–H)
20. Observe the following natural product and match the members of list I with list II
Functional Groups
Reducing Agent (I)
reduced are (II)
(A) LiAlH4 x
(B) NaBH4
z
(C) (CH3)2CHOH + [(CH3)2CHO]3Al, D
(MPV) w
(D) Na / C2H5OH r
(A) CH3–CHO (P) Iodoform test positive
(B) H–COOH (Q) Soluble with NaHCO3
(C) CH3–CH2–OH (R) Produces alkane when treated with EtMgBr
(D) CH3–CH2–Br (S) Red colour in victor mayer's test
(T) Silver mirror test positive
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22. Match the column.

Column I Column II
(Conversions) (Reagents)
O
(A) (P) Zn – Hg / HCl
O OH
(B) (Q) LiAlH4
O O
(C) (R) NH2–NH2 / EtONa
O
(D) (S) H2Ni
(T) NH2–NH2 / H2O2

SUBJECTIVE TYPE
For question no. 23 & 24
Write answer of part (a), (b), (c) & (d) in the same order and present the four digit number.
For example : If all these answer are 9 then correct answer will be 999.
LiAlH4 CH3COCl
P4 P5
CH = CH2 NaOH
P3
Å CaO/D
23. H /KMnO4 Lime
D
P1 + P2(gas) Milky
Water
NaHCO3
(a) The number of carbon atoms present in the principal carbon chain of product P3 obtained when
P1 is heated with sodalime.
(b) How many moles of gas P2 released when one mole of P1 is treated with sufficient amount of
NaHCO3?
(c) How many moles of CH3COCl reacts with 1 mol of P4?
(d) What is the D.B.E. (Double bond equivalent) for P 1.
24. ¾OsO
¾¾4 ®
NaOH , H 2O
(a) Number of organic product formed during this reaction.

(b) Number of stereoisomers possible for major organic product of this reaction are.
(c) Oxidation state of Os before reaction.
(d) Oxidation state of Os after reaction.
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ANSWER KEY
1. (C) 2. (C) 3. (A) 4. (B) 5. (D)
6. (A) 7. (D) 8 . (D)
9. (ABCD) 10. (ABCD) 11. (ABC)
12. (D) 13. (C) 14. (A) 15. (C) 16. (B) 17. (B)
MATCH THE COLUMN
18. A ® P ; B ® P,Q ; C ® P ; D ® P,S ; E ® Q,R
19. A ® R ; B ® QRS ; C ® PT, D ® S
20. A ® x, z, w, r B ® r; C ® r; D ® r,, w
21. A ® P, T ; B ® Q, R, T ; C ® P, R, S ; D ® P, R, S
22. A ® P,R ; B ® Q,S ; C ®T ; D R
SUBJECTIVE TYPE
23. 4333
24. 2486
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ALDEHYDES AND KETONES

1. Periodiate oxidation of 1, 2–cyclopentanediol is :
O O
(A) (B) (C) (D) CHCH2CH2CH2CH

|| ||
O O O O O
2. The reaction of ethyl alcohol and bleaching powder gives
(A) acetaldehyde (B) chloroform (C) chloral (D) All of these
O O
|| || (Y)
(X )
3. (C H 3 ) 2 C = CH C H 2 C H 2 CC H 3 ¾ ¾¾ ® (CH 3 ) 2 C H CH C H 2 C H 2 C C H 3
|
OH
O O O
|| ||
(Z)
¬¾ ¾ (C H 3 ) 2 C H C CH 2 C H 2 C CH 3
(CH3)2CH
X Y Z
(A) H2CrO4 B2H6, THF OH Q
(B) B2H6, THF H2CrO4/CrO3 OH Q / D
(C) B2H6, THF OH Q H2CrO4/CrO3
(D) H2CrO4 OH Q B2H6, THF

4. Predict product (C) for the following :
y
H2O[O] HIO4 [O] OH/ D
¾¾¾¾
(KMnO )
® A ¾¾¾¾ ® B ¾¾¾¾ ®C
4
O
CH3 Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\04\ (Aldehydes & Ketones)
CH3 CH3
C – CH3
(A) (B) (C) (D)
O CH3
O O
O O y
5. H (i) OAc
O (ii) Ph – CH = O
H
O O
O O
(A) (B)
Ph CO2y Ph CO2y
O O O O
(C) (D)
y CO2y
Ph
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6. Identify the compound ‘E’
HC º CLi (i) LiNH2 H2

Br(CH2)8CH3 C11H20 C13H24 E
(ii) C2H5Br Lindlar’s catalyst
H 5C 2 (CH2)5CH3 H 5C 2 (CH2)6CH3
(A) C=C (B) C=C
H H H H
H5C2 H H 5C 2 (CH2)8CH3
(C) C=C (D) C=C
H (CH2)8CH3 H H
7. Given a set of reactions. Identify the compound W
LiNH2 1-Chloro-3-bromopropane (i) Mg

1-heptyne S
(ii) n-C10H21CHO/HÅ
CrO3 H2, Lindlar's catalyst

W V
(n)-C5H11 (CH2)3 – C – C10H21–(n) (n)-C5H 11

H O
(A) C=C (B) C=C
O (CH2)3–C–C 10H21–(n)
H H H
H C5H 11-(n) H C5H 11-(n)

O OH
(C) C=C (D) C=C
H (CH2)3–C–C10H21–(n) H (CH2)3–C–C10H21–(n)
8. An optically active compound 'X' has molecular formula C 4 H 8 O 3 . It evolves CO 2 with NaHCO 3
'X' reacts with LiAlH4 to give an achiral compound. Find 'X'
Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\04\ (Aldehydes & Ketones)
(A) CH3CH2CHCOOH (B) CH3CHCOOH

| |
OH Me
(C) CH3CHCOOH (D) CH3CHCH2COOH
| |
CH2OH OH
HIO4 KMnO4 D
9. + OsO4 + NaHSO3 ¾¾® X¾¾¾¾ ® Y¾¾¾¾ ® Z ¾¾® W
¾
X, Y, Z, W are respectively -
OH C H =O C O 2H
(A) , , ,
OH C H =O C O 2H
OH C H =O C O 2H
(B) , , ,
OH C H =O C O 2H
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O
OH
(C) , O=CH–(CH2)4–CH=O , HO2C(CH2)4–CO2H ,
OH
O
OH
(D) , O=CH–(CH2)4–CH=O , HO2C(CH2)4–CO2H ,
OH
O
(i) EtO–
10. + CH2 (COOEt)2 Product
(ii) H3O+
Which of the following will never form duing the above reaction
O O O O
(A) (B) (C) (D)
CH(COOEt)2 CH(COOEt)2 EtOOC COOEt HOOC COOH
aq. KOH Cu / D NaOH D

11. CH3–CH2–Cl A B C D . Find ‘D’.
OH
(A) CH3–CH–CH2–CHO (B) CH3–CH=CH–CHO
(C) CH3–CH2–CH=CH–CHO (D) Both (A) & (B)
NH 2 - NH 2
12. O ¾¾¾
LiAH PCC
® A ¾¾¾
4
® B ¾¾¾¾ ® C, Product (C) is :
O
O OH
NH NH2
N N
(A) (B) (C) (D)
NH N N NH2
O OH
CH2
HCHO (A) . Product (A) is :
13. CH3–CH–CH–CH2–OH
TsOH, 93%
OH
CH3
Ph CH2–Ph CH2–Ph CH3
CH3 CH3 Ph
(A) (B) (C) (D)
O O O O O O O O
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14. The final product of the following sequence of reaction is :

+
Mg H 2C=0 H 3O
(CH3O)2CHCH2CH2CH2Br
heat
O O
(A) CH3O C CH2CH2CH2CH2OH (B) CH3 C CH2CH2CH2CH2OH
O O O
(C) H C CH2CH2CH2CH2OH (D) H C CH2CH2CH2 C H
KCN [O] CH3OH+ NaOH
15. X(C7H6O) ¾¾¾¾
C2H5OH
® Y(C14H12O2 ) ¾¾¾ ® Z(C14H10O2 ) ¾¾¾¾¾¾
H3O+
® W(C15H14O3 )
W is sweet smelling compound and liberates H2 with Na metal. Identify the correct option.
O O
CHO CH2 — C CHO CH2 — C
(A) X = Y= (B) X = Y=
OH OH
COOH OH O O O
O
HO – C HC C C–C
CH2 — C
(C) Y = OH W= (D) Y = Z=
CH3
16. Which one of the following is not correct to get cinnammic acid :
(B) C 6 H 5 - CH = O ¾¾¾¾¾¾ ®
CH 2 (COOC 2H 5 )2
(A) C6 H5 - CH = O ¾¾¾¾¾¾¾¾
(CH3CO) 2 O/ CH3COONa
® Pyridine
- D
(D) C6 H5 - CH = O ¾¾¾¾¾¾¾¾ ®
- (i) BrCH2 COOC2 H 5 / Zn /
(C) C6 H 5 - CH = O ¾¾¾¾¾¾®
CH 3COOC2 H 5 / OH
(ii) H 2O / H + / D
- - +
OH OH H
17. PhCOCHBr2 ¾¾¾ ® A ¾¾¾ ® B ¾¾® C . The compound ‘C’ is :
(A) PhCH(OH)CHO (B) PhCH(OH)COOH (C) PhCOCBr2 (D) None of these

|
H
CH2OH
O H
CH3OH HIO4
OH X Y+Z
18. dry HCl
OH OH
OH
CH2OH
O H
O OH
(A) CHO (B) CHO

OCH3
CHO OCH3
CHO
(C) HCOOH (D) HCHO
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OHy H3O+
19. CH3 COCHO P Q
H2SO4
2Q ¾¾¾¾
D
® R . The product R is :
O
C O
(A) CH3 CH(OH)COOH (B) CH3 CH CH CH3
O C
O
(C) CH3 CH=CH–COOH (D) CH3 CH C CH3
O OH
CH3COONa HBr
20. PhCHO + (CH3CO)2O A B. The product B is :
(A) PhCH = CHCH2Br (B) PhCH - CH 2 - COOH

|
Br
(C) PhCH2CH(Br)COOH (D) PhCH = CH–COBr
O
O C OC2H5 +
(1)HCl (i)LiAlH 4/Et2O H3 O
21. X Y Z Identify X, Y and Z
(2) CH2OH (ii) H2O
CH2OH
X Y Z
O O Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\04\ (Aldehydes & Ketones)
O O CH2OH
(A) C–OC2H5 O COC2H5
O
O
O O COOH HO CH2OH
C–OC2H5
(B)
O O
O
O CH2OH O CH2OH
O C–OC2H5
(C)
O
O
HO CH2OH HO COOH
(D) O CH2OH
O
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22. Arrange the following compounds in decreasing orders of Keq for hydrate formation.
O O O O
CCH3 CCH3 CCH3 CCH3
(X) (Y) (Z) (W)
Cl NO2 OCH3
(A) Z > Y > X > W (B) Z > X > Y > W (C) Z > W > X > Y (D) Z > X > W > Y
23. Give the correct sequence of reagents for the following conversion :
O O
?
Br C – CH3 HO – CH2 – CH2 C – CH3
O
Å
(A) CH3OH (large excess) Mg / ether H2C — CH2 H2O / H3O
H2SO4 (traces)
O
(B) Mg / ether H2C — CH2 H2O / H3OÅ CH3OH (large excess)

H2SO4 (traces)
O
(C) H2C — CH2 H2O / H3OÅ CH3OH (large excess) Mg / ether

H2SO4 (traces)
O
Å
(D) H2O / H3O CH3OH (large excess) Mg / ether H2C — CH2
H2SO4 (traces)
H 2 (1 eq.)
O A
Pt
LiAlH4
24. B
H 2, Ni
C
Find A, B, C ?
O OH
(A) in all cases (B) in all cases
OH O OH OH
(C) in all cases (D) =A =B =C
CH 2OH
|
25. Acetaldehyde can be converted into HO CH 2 - C - CH 2OH by which reagent?
|
CH 2 OH
(A) KOH (B) KOH followed by LAH

(C) excess of HCHO and KOH (D) KCN followed by SBH
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26. In the reaction
EtONa/EtOH
+ CH3COCH3 heat
X
the product (X) is
H3C CH3 H 3C CH3

CH3
OH CH3
(A) (B) (C) C (D) HO—C—C—OH
CH 3 CH3
27. Which step is not feasible in the following loop ?
Br
EtOH, H+
CH2(Br)CH2CHO a
CH2 – CH2CH(OEt)2
d alc. KOH b alc. KOH
+
H2O, H
CH2 = CHCHO c
CH2 = CHCH(OEt)2
(A) step - a (B) step -b (C) step - c (D) step - d

28. Product ‘C’ is :
O
– CrO
CH3—C—H OH A H2/Pt B H SO3 C
2 4
(A) CH3–CH2–CH = CH2 (B) CH3–CH2–CH2–CHO

(C) CH3–CH2–CH2–COOH (D) CH2 = CH – CH = CH2
29. An unknown compound on oxidative cleavage forms one mole each of cyclo pentanone and methanal. The
compound is :
OH
OH
OH Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\04\ (Aldehydes & Ketones)
(A) (B)
OH
OH
(C) HO (D) None
C 4H9Li R'X C4H9Li R''X HgCl 2, CdCO3

30. P Q S T U
S S H 2O
The final product U is
O
S S S S S y S
(A) (B) (C) Å (D) C
Li R' R''
H R' R' R'' H
31. The cyanohydrin of a carbonyl compound on hydrolysis gives lactic acid. The carbonyl compound is :
(A) HCHO (B) CH3CHO (C) CH3COCH3 (D) CH3COCH2CH3
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32. ?
The product is :
(A) (B) (C) (D) All of these
33. Find the product ‘Y’.
CH3MgBr/Cu 2I2
Å (Y)
H2O/H
O
(A) (B) OH (C) (D)

O CH3
O 1. BuLi
|| HS H
Å
2. CH3Br
34. H3C - C - H + A Å B
HS 3. HgCl2/H3O
Find ‘B’.
O O
O ||
(A) (B) (C) (D) H - C - H
O
O
y
35. + OH, D
¾¾¾¾ ® ' X' . Find ‘X’.
O O
(A) (B) (C) (D)

OH O O O
O O OH
O
OHy
36. D A . Find ‘A’ ?
O O
O
O
(A) (B) (C) (D)
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O
SeO2 KOH
37. CH2–C–H X Y
Find “Y”.
O OH O O O O
|| | || y || ||
(A) Ph - CH2 - C - OH (B) Ph - CH - C - OKÅ (C) Ph - C - C - H (D) Ph OH
Cl
2Ph3P 2CH3CHO
38. X Y . Find ‘Y’ ?
PhLi D
Cl
Å
CH = CH – CH3 CH =PPh3 CH2 – PPh3 CH = CH – CH3
(A) (B) (C) (D)
Å
CH2 – CH = CH2 CH =PPh3 CH2 – PPh3 CH = CH – CH3
KOBr 1. HÅ
39. X+Y 2. D
Z
O
Find ‘Z’.
O O yÅ
COOH COOK
(A) OH (B) O (C) (D)
OH Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\04\ (Aldehydes & Ketones)
CH2OH
O O
O
I2 + Ca(OH) 2 D CH3MgBr
40. C – CH3 X+Y Z Å A. Find ‘A’.
H3O
OH
| O
O
Ph - C - Ph
(A) CHI3 (B) (C) || (D) C – OH
|
Ph - C - Ph
CH3
41. Which one of the following reaction will not produce hydrocarbon as final product -
O
(i) NH2–NH2 Zn-Hg/HCl
(A) CH3–CH2–C–CH3 (B) CH3–C–CH3
(ii) KOH,D 300ºC
O
O
NaOH (i) H2/Ni
(C) CH3–CH2–C D (D) CH3–CH=O
(ii) Red P/ HI
H
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42. Number of optically active products obtained during ozonolysis of following compound.
(A) 2 (B) 3 (C) 4 (D) 5

43. Identify alkenes which on hydrogenation give racemic mixture :
Me Me
Me H
(A) (B) (C) (D)
COOH
44. Compound among following produces only oxalic acid as major product on reaction
COOH
with O3 / H2O -
(A) (B) (C) H2C = CH2 (D)
LiAlH4 H3PO4
45. C–OH X Y (Major product),
(conc.)
O
Y is :
CH3 H3C
(A) C = CH–CH 2CH3 (B) CH – CH=CH2
H3C H3C
H3C H3C
(C) C = CH–CH 3 (D) C = CH2
H3C H3C
O O
C–Cl C–H
R
46.
Which of the following can be used as R in the above reaction :

(A) LiAlH4 (B) Ni/H2 (C) Pd/BaSO4/CaCO3/H2 (D) NaBH4
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47. Which of the following represent correct major product formation -
OH
dil.H2SO4
(A) CH3–CH–CH=CH2 CH3–CH–CH–CH3
CH3 CH3
OH
(i) Hg(OAc).H2O
(B) CH3–CH–CH=CH2 (ii) NaBH 4/OH
– CH3–C–CH2=CH3
CH3 CH3
(i) B2H6
(C) CH3–CH–CH=CH2 (ii) NaOH/H 2O2
CH3–CH–CH2–CH2–OH
CH3 CH3
OH
(i) B2H6
(D) CH3–CH–CH=CH2 (ii) H2O/AcOH
CH3–CH–CH–CH3
CH3 CH3
48. Identify the final product of given reaction
( i ) B2 H 6 ,THF conc . H PO 4
¾¾ ¾ ¾¾® X ¾¾ ¾3¾ ¾® Y ¾dil
¾. H¾
2SO 4
¾® Z ; Z is :
-
( ii ) H 2O 2 / OH D
(A) (B) (C) (D)
COOH
1. PCl5 NH2OH.HCl H2SO4

49. H Ar X Y Z. X, Y, Z are : Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\04\ (Aldehydes & Ketones)
2. (CH3)2Cd
Et
OH NHCOCH3 NHCOCH3
H 3C
COCH 3 C N
H Ar
(A) H Ar (B) H Ar (C) (D) H Et
Et Et Et
Ar
50. Given the statements for a compound C10H16O which on vigrous oxidation yields acetone, oxalic acid and
CH3COCH2CH2COOH, are true
(A) It reacts with hydroxylamine to give C10H17ON
(B) It reduces Tollen’s reagent to give a compound C 10H16O2
(C) It has 2 stereoisomers
(D) It is optically active
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O CH3
C NH2
51. The suitable reagents of the following reaction are :
CH3 CH3
PCl5 NaOH D
(A) ¾¾¾
(1)
® ¾¾¾
(2)
¾
® ¾¾
(3)
¾®
+
I 2 /NaOH H Br2 +KOH NH /Δ
(B) ¾¾¾¾ (1)
® ¾¾®
(2)
¾¾¾®3
(3)
¾¾¾¾®(4)
NH OH PCl dil.NaOH/Δ N H/Δ
(C) ¾¾¾¾ ® ¾¾¾ ® ¾¾¾¾¾ ® ¾¾¾®
2 5 3
(1) (2) (3) (4)
NH 2 OH Δ
(D) ¾¾¾¾
(1)
® ¾¾®
(2)
52. Which of the following reactions will produces acetone
O3
O3 Hg
+2
B 2 H6
(A) Zn-H2O (B) CH3–C º CH H2 SO4
(C) CH3–C º CH –
OH /H 2O2
(D) Zn-H2O
H
53. Anhydrous acids bring about formation of acetals where as aqueous acids bring about hydrolysis of acetals
because
(A) High alcohol, low water concentration shift the hemiacetal-acetal and aldehyde-hemiacetal equilibria in
the direction of the acetal.
(B) Low alcohol, high water concentrations shift the equilibria in the direction of aldehyde.
(C) Reverse statements of A and B are true
(D) None of these
54. Which compounds will be oxidised by HIO4 ?
CH3 CH2 - OH
| O OH
|| | |
CH - NH2
(A) CH3 - CH - C - H (B) | (C) CH3 - C - CH2 - CH2 (D) C = O
| || |
CH2 - OH CH2 - OH
OH O
55. By which compound's reductive ozonolysis the following products are obtained
O
O O O
H—C—H ; CH3—C—C2H5 ; + CHO
I II |
(2 mole) (1 mole) O CHO
(1 mole) (1 mole)
(A) (B)
(C) (D)
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56.
?
O OH
Reagent used for the above conversion.
–
(A) LiAlH4 (B) NaBH4 (C) conc. OH (D) H2 / Pt

Para graph for Question 57 to 59
O3 Ca(OH)2 + I2 D
C = CH – Ph A+B C+D E + CaCO3
Me2S
CH3
NaOH
57. A + B ¾¾¾
D
¾
® Product. Find product.
O O
(A) C – CH = CH (B) C – CH = CH – Ph
O O
||
(C) C – CH2 – CH – Ph (D) Ph - CH = CH - C - Ph
OH
58. Find correct structure of E :
O
O O
(A) C – O Ca (B) (C) (D) None of these
C – Ph C
2
CF3CO3H
59. E ¾¾¾¾® Product . Find product.
O O
(A) (B) O
C O C
O Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\04\ (Aldehydes & Ketones)
(C) (D) None of these

O C
Par agraph for Quest ion 60 to 62.
Compounds –X (C8H14)
O3/Zn
Cyclic ketone –ve Tollen's test
C5H8O + C3H6O
(1) Mg–Hg
(A) (1) MeMgCl (1) EtMgCl
(2) H2O (2) H2 O (2) H2O
HÅ (C) (D)
Conc.
(B) H2SO4/D conc. HBr
E
Br2/hn
An Alkane
Z
66 E
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60. Identify total number of monochlorination product for Alkane 'Z' ?
(A) 4 (B) 6 (C) 3 (D) 5
61. Identify structure of 'C' compound ?
OH
(A) (B) OH (C) OH (D)

OH
62. Identify structure of compound D ?
OH
(A) (B)
OH
(C) (D)
OH
OH
Paragraph for Q.63 to Q.65.
(F) (G) (Major bromo product)
SO2Cl2 hv NBS D
(C) + (D) + (E) (Alkene)

Major Disproportionation
products
Na Et2O
Br2/hn KCN NaOH
(A) (B) (H)
(2) H3O+
Major Electrolysis
(D)
(C)
Major
On the basis of reactions involved in above interconversions answers the given questions.
63. Find out the incorrect statement?
(A) Product G is a racemic mixture
(B) Product F is 3° halide
(C) Product A,B, C & F are optically active.
(D) No product (A to H) can show geometrical isomerism.
64. Reaction which does not involve free radical mechanism in above reactions is :
(A) D to A (B) H to C
(C) A to C, D, E (D) B to H
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65. Which one of the following reaction is not involved in above interconversions.
(A) Nucleophilic substitution (B) Kolbe's electrolysis
(C) Markownikov addition (D) Wurtz reaction
Paragraph for question nos. 66 to 68.
Me
| (i) Mg/Et2O HÅ
B¾¾®
¾ C (Product without rearrangement)
Cl
Me - C - Me¾¾2 ® A (major product) O D
hn
|
H (ii) O3,
Zn / H2O
D+ E
66. Select the correct statement.
(A) D is a bicyclo compound and doesn't give Aldol condensation with NaOH
(B) D is a bicyclo compound and it give Aldol condensation with NaOH at two different a-position.
(C) E is an open chain compound and doesn't give Aldol condensation with NaOH
(D) E is an open chain compound and will give Aldol condensation with NaOH
67. How many enantiomeric pairs are formed when C is treated with NBS.
(A) 3 (B) 2 (C) 1 (D) None of these
68. How many deuterium atoms are present in the compound which is formed when compound D is kept with dil.
KOD for long time and than heated.
(A) 1 (B) 2 (C) 3 (D) 4
SUBJECTIVE TYPE
69. The compound among following which can give 2,4-DNP test (2,4-dinitrophenylhydrazine test)
O
(i) (ii) (iii) (iv)
O NH
NH2 O
H
(v) (vi) (vii) (viii) HCHO Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\04\ (Aldehydes & Ketones)
O
O
O–H
(ix) (x)
O
70. Relation between P & Q in following reaction sequence.
OH
Jones reagent (i) LiAlH4(excess) PCC

O (excess)
V U+T
(ii) H2O CH2Cl2
HC CH2OH (xs)
Zn–Hg H2–Pd
S HCl
R (1 eq.)
P or Q
Only
(excess)
product
68 E
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ALLEN REVISION TECHNIQUE

(A.R.T. # 01)
Find unknown compounds :
O
+
(i) Hg(–O–C–CH3)2/H2O H Bayers PDC (i) N2H4
A B Reagent C D –
(ii) NaBH4 CH2Cl2
(ii) OH,
(i) CH3MgBr PCC (i) Mg Cu (i) B H H2–Pd

E F CH G (ii) NH Cl H I (ii) H 2O 6/OH J
(ii) NH4Cl 2Cl 2 4 300ºC 2 2 CaCO 3
+
HgSO4 H2–Pd H O HBr N2H4 (i) LiAlH4
K H2SO4
L (1 eq.)
M N ZnH3 O O H2O2
P H2O2 Q R
2 (ii) H2O
(i) CH3–CH2MgBr RCO3H (i) DIBALH Jones

S T U V W
(ii) H2O (ii) H2O Product with Oxidation
(Fruity Smell)
higher oxidation
state of carbon
SOCl2 H2–Pd NBS

X Q Z
BaSO 4
(A.R.T. # 02)
(i)O
A 3 /Z
Cl 2 (ii) Z nH2 O
hv n-H
g
HCl K
B –
Cl /
OH P 2 O
nc. (1 e H
H
+
Co
/
q .)
Na
O 2
O
Et
Q
J
H
4
PD
Al
Li
C S
T
H 2/Pd
(ii) N2H4/OH , D
+
(i) KMnO4/H
HO
–
N
(i) EtMgBr
OH
(ii)NH4Cl
O3 Zn
(ii ) NH3 gBr
Br2/hv
H2O HO
OH I
4 Cl
M
–
OH
(i ) CH
Hg +2
U ++ V
M
/H S
D R (i )
2 O
Na
(ii OH
(i )Cl /C OH H
4
(iv ii) A 2 hv
aO
Na
Al OH
D
L
K
) H lc.
c.
2
H
O B KO
aN
r H
N
E HBr
G
Br / alc.
2 CC
l
F KOH
4
E 69
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(A.R.T. # 03)
* Find the unknowns?
O
Z (Major)
O 3
HN
O
SOCl2 Zn - Hg Anhy. AlCl3 SO 4

O
H2
A B C D
Anhy. AlCl3 HCl
N
Zn - Hg
O3 /Ag 2O
HCl
O 3/Zn AlC. KOH N.B.S.
L K F E
(1 e.q.)
O 3/L.A.H.
Mg/ether
H 2O HCHO CO 2 H+ CH3 OH
T S G H I Y
Cl
CH
NaOH-CaO
Alc. KOH N.B.S. N.B.S.

R Q P O
(Excess), D
KMnO4 /H +
HNO3 -H 2SO 4 Pd/C

V U J
1.AgOH
W X
2.Br2 /CCl4 , D
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(A.R.T. # 04)
Column I (Reaction) Column II (Name of reaction)
O O
RCO3 H
(A) (1) Preilschaive reaction
(B) Cu/D (2) Baeyer villiger oxidation
OH
(1) Hg(OAc)2 , H2 O
(C) (3) Fridel craft alkylation
(2) NaBH 4
N 2H 4/OH-
(D) H H 3C CH 3 (4) Clemmensen reduction
O
CH 3CO3 H O
(E) H 2C CH2 + CH 3CO 2H (5) Haloform reaction
Br2
(F) RCO 2 Ag ¾¾®
D
R - Br + CO 2 + AgBr (6) Finkelstein reaction
(G) C 2 H 5Cl + AgF ® C2 H5 F + AgCl (7) Wurtz-fittig reaction
dry Ether
(H) 2C2 H 5 Br + 2Na ¾¾¾¾ ® + 2NaBr (8) Fridel craft acylation
(I)
Isopropyl Alcohol
R2CO+[(CH3)2CHO]3Al
R2CHOH+Me2CO (9) Reed’s reaction
(J) RCO2Ag + I2 D
¾¾ ® RCO2 R+ CO2 + AgI (10) Elb’s persulphate
oxidation
O
||
(1)RSH - BF3
(K) CH 3 - C - H ¾¾¾¾¾
(2)H - Ni
® CH3CH3 (11) Oppenauer oxidation
2
electrosysis
(L) CH3CO2K + H2O ¾¾¾¾® CH3–CH3+CO2+H2+KO4 (12) Borodine hunsdiecker
reaction
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OH OH OH
CHO
(1) CHCl3+NaOH
(M) + (13) Birch reduction
(2) H+
(Major)
CHO
(N) ROH+SOCl2 ® RCl+SO2+HCl (14) Swarts reaction

Na
(O) C6H5Br+C2H5Br ¾¾¾
ether
® C6H5C2H5+NaBr (15) Wolff kishner reduction
OH
|
(P)
Al(OCMe3 )3
R2.CHOH+(CH3)2CO
R2CO+CH3 CH - CH3 (16) Hydroboration oxidation
OH OH
K2 S 2 O 8
(Q) (17) Kolbe’s electrolysis
OH-
OH
(R) acetone
R–Cl+NaI ¾¾¾ ® RI+NaCl (18) Meerwein ponndorf
verley reduction
Me Me Me
| | H+(dil.H2 SO4 ) |
Me - C - C - Me Me - C - C - Me
(S) | | | || (19) Wurtz reaction
OH OH D Me O

OH
O D
(T) (20) Claisen rearrangement
O
(U)
|| -
O Na+ (21) Birnbaum simonini
NaOH - I 2
CH 3 - C - CH 2CH3 ¾¾¾¾ ® CHI 3 + H3C
O
reaction
Zn - Hg - HCl
(V) CH3COCH3 ¾¾¾¾¾
reflux
® CH 3CH 2CH 3 (22) Reimer - Tiemann
reaction
(1) BH3 - THF

(W) RCH=CH2 ¾¾¾¾¾
(2) H O - OH -
¾® RCH 2 CH 2 OH + H 3BO3 (23) Oxy mercuration -
2 2
demercuration reduction.
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Cl
(X) + HCl (24) Mozingo reduction
AlCl3
Na/liq.NH 3
(Y) CH 3 - C º C - CH 3 H 3C (25) Ullamann reaction
CH 3
(Z) RCOCl + H2 H 2 /Pd/BaSO4

¾¾¾¾¾ ® RCHO + HCl (26) Darzen reaction
- +
(A') R O N a + R - X ® R - O - R + NaX (27) Williamson synthesis
CH3COCl
(B') C6H6 ¾¾¾¾
Anhy.AlCl
¾
® C6H5COCH3+HCl (28) Rosenmund reduction
3
Cl
CH3
SO 2Cl2
(C') + SO2+HCl (29) Pinacol-pinacolone
hn
rearrangement
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ANSWER KEY
1. (D)
2. (D)
3. (B)
O OH O
B2H6, THF
(CH3)2C = CH – CH2 – CH2 – C – CH3 (CH3)2CH – CH – CH2 – CH2 – C – CH3
O
HO
y
H2CrO4/CrO3
(CH3)2CH – C – CH2 – CH2 – C – CH3
O
O O
O
(CH3)2CH – C – CH2 – CH2 – C – CH2 D
OH
O CH(CH3)2
CH(CH3)2
4. (A)
5. (D)
Å
HC º C Li LiNH2
y
6. (D) Br(CH2)8CH3 H – C º C –(CH2)8 – CH3 LiC º C(CH2)8CH3
H5C2 (CH2)8–CH3
C=C H2 C2H5Br
C2H5C º C(CH2)8CH3
H H Lindlar
LiNH2 BrCH2CH2CH2Cl
7. (A) nC5H11C º CH nC5H11C º C – Li nC5H11C º CCH2CH2CH2Cl
(i) n-C10H21CHO Mg Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\04\ (Aldehydes & Ketones)

nC5H11C º C(CH2)3MgCl
(ii) H
Å
H
H2 n-C5H11 (CH2)3 – C – C10H21 - (n) CrO3

nC5H11C º C(CH2)3CHC10H21 - (n) C=C
L.C. HO
H H
OH
{n}-C5H11 (CH2)3 – C – C10H21-(n)
C=C
H H O
8 . (C) 9 . (C) 10. (A) 11. (B)

12. (B) 13. (B) 14. (C) 15. (D)
16. (C)
O
y
OH OH - - OH +
17. (B) PhCOCHBr2 ¾¾¾ ® PhCOCHO ¾¾¾® Ph – C – C H
¾¾¾® PhCH(OH)COOH
H O
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CH2OH CH2OH CH2OH
O H O H O H
CH3OH HIO4
HCOOH +
18. (C) OH dry HCl OH CHO
OH OH OH OCH3 OCH3
CHO
OH OH
19. (B) Benzil-benzilic acid rearrangement take place and finally lactide forms.
20. (B) Perkin’s reaction take place.
O O
O C – O – C2H5 (1) O C – O – C2H5 (1)

(2) (2)
O
21. (C) (X)
O CH2 – OH H3OÅ O CH2OH
O
(Z) (Y)
22. (A) More electron withdrawing group on phenyl ring more is Keq.
O OCH3
C – CH3 CH3OH (large excess)
23. (A) Br Br C – CH3
H2SO4 (traces)
OCH3 Mg Ether
OCH3 O CH3
H2O H2C — CH2 H3CO–C–OCH3
Å BrMgOCH2CH2 C – CH3
H3O
OCH3
O
MgBr
OH – CH2 – CH2 C – CH3 + 2CH3OH
24. (D) 25. (C) 26. (C) 27. (D)

28. (C) 29. (B) 30. (D) 31. (B)
32. (A) 33. (A) 34. (C) 35. (D)
36. (A) 37. (B) 38. (D) 39. (B)
40. (B) 41. (C) 42. (A) 43. (C)
44. (B) 45. (C) 46. (C) 47. (C)
48. (A)
49. (ABC) Bakemann’s rearrangement.
CH3 H
50. (ABC) C=C CH2 H
H3C CH2 C=C
H3C CHO
E ® C10H16O
Other isomer is Z
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O CH3 O O
C C OH C NH2 NH2
I 2 /NaOH /D
51. (BC) HÅ ¾ NH
¾3¾ ® Br2 / KOH
Me Me Me Me
HO
O CH3 N O O
C C CH3 C NH CH3 C OH NH2
NH 2 - OH
¾¾¾¾ ® ¾¾¾
PCl5
® ¾¾¾
NaOH
® ¾¾¾
N 3H
®
D D
Me Me Me Me Me
52. (AB) 53. (AB)
54 . (ABD) 55 . (A, B, C) 56 . (A,B,D)

57. (B) 58. (C) 59. (A) 60. (B)
61. (B) 62. (B) 63. (C) 64. (D)
65. (C) 66. (C) 67. (D) 68. (B)
SUBJECTIVE TYPE OH
(E) CH3
69. [0005]
(R)
O
O
(F)
70. (V)
(P) & (Q)
HOOC COOH
OH
(G)
(U) & (T)
OH Br
O
(H)
Relation between P & Q
HOH2C CH2OH (Enantiomer)
Br
ART : 01
OH OH
(A) (I)
OH
Br
HOH 2C CH2OH (B)
(J)
O OH
(C) CH3
H + Image Br
(S) OH
HOC CHO (K)

OH
(D) CH3
+ Image
O
76 E
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Br O
(V)
C
(L) H
O O
Br C
(W)
OH
(M)
O
OH
C
(X)
Br Cl
(N) (Z)
OH
Br
ART:02
(O)
(A) ¾¾
® CH4
(O) ¾¾
® CH3–CH2–CH=O
O
(B) ¾¾
® CH3Cl
Cl O
(P) | ||
(C) ¾¾
® CH3–CH3 (P) ¾¾
® CH—C—C—H
3
O
(D) ¾¾
® CH3–CH2–Br OH O
| ||
(Q) (Q) ¾¾
® CH—C—C—H
(E) ¾¾
® CH2=CH2
3
O (R) ¾¾
® CH3–CH2–COOH
(F) ¾¾
® CH2–CH2
| |
(R) Br Br (S) ¾¾
® CH3—CH2—CH2
|
(G) ¾¾
® CH2=CH–Br OH
OH
(T) ¾¾
® CH3–CH=CH2
(S) ® HCºCH
(H) ¾¾
O
(U) ¾¾
® CH3–CH=O
(I) ¾¾
® CH3–CHO
(T) CH2 = CH2
(V) ¾¾
® CH2=O
O (J) ¾¾
® CH3CH2OH
(U)
O (K) ¾¾
® CH2=CH2
(L) ¾¾
® CH2–CH2
| |
Br OH
(M) ¾¾
®
O
(N) ¾¾
® CH3–CH2–CH2–OH
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ART :-03
O O
O
(A) = O (B) = O (C) =
Cl
OH Cl
Br
(D) = (E) = (F) =

O
MgBr COOMgBr COOH
(G) = (H) = (I) =
CHO
CHO
(J) = (K) = (L) =
CH 3
CH 2 OH COOH
CH 2 OH COOH
(M)= (N)= (O) =
CH 3
CH 3 Br CH 3
Br
(P)= (Q) = (R) =
Br
CH 2OMgBr CH 2 OH
(S) = (T) = (U) = Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\04\ (Aldehydes & Ketones)
-
O + O
O OH
N Br
(V) = (W) = (X) =
COOCH 3
-
O
(Y) = (Z) = N
+
O O
(A.R.T. # 04)
(A) (2) (B) (25) (C) (23) (D) (15) (E) (1) (F) (12)
(G) (14) (H) (19) (I) (18) (J) (21) (K) (24) (L) (17)
(M) (22) (N) (26) (O) (7) (P) (11) (Q) (10) (R) (6)
(S) (29) (T) (20) (U) (5) (V) (4) (W) (16) (X) (3)
(Y) (13) (Z) (28) (A') (27) (B') (8) (C') (9)
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CARBOXYLIC ACIDS & IT’S DERIVATIVE

1. In the reaction sequence:
D
CH 3 - CH - COOH ¾¾® [Y]
|
OH
[Y] will be:
(A) (B) CH2=CH–COOH
OH
|
(C) CH 2 - CH 2 - COOH (D)
2. In a set of the given reactions, acetic acid yielded a product C.

C H (i) C H MgBr / ether
CH3COOH+PCl5 ¾® A ¾¾¾
6 6
AlCl3
® B ¾¾¾¾¾¾¾
¾ 2 5
Å
¾
® C ; product C would be:-
(ii ) H3O
C 2H 5
(A) CH3CH(OH)C2H5 (B) CH3COC6H5 (C) CH3CH(OH)C6H5 (D) C H 3 C (O H )C 6 H 5
Me
COOH
(i) P/Br2 Resolution NaOH/heat
3. D-isomer X , X is
(ii) H2O
Me Me Me Me
COO COO COO COO
Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\05/ Carboxylic Acid & Derivatives
(A) OH (B) OH (C) OH (D) OH
(L) (D) (D+L) (D or L)
(i) THF
4. + BrMgCH2CH2CH2CH2MgBr X. X is
O O (ii) H3O+
(A) CH2CH2CH2OH (B)

HO HO CH3CH2 O CH3
CH3CH2CH2OH
(C) (D)
HO CH 3CH2CH2OH
HO
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5. Consider the following sequence of reactions.
A B
The products (A) and (B) are, respectively,
OH
(A) and (B) and
(C) and (D) and
6. The relative order of esterification of alcohols is :-

(A) 1° < 2° < 3° (B) 1° > 2° > 3° (C) 1° > 3° > 2° (D) 1° < 3° < 2°
7. In the given reaction:
¾HBr
¾¾® [X]
[X] will be:

(A) (B) (C) (D)
8. An optically active compound 'X' has molecular formula C4H8O3. It evolves CO2 with aq. NaHCO3. 'X' reacts
with LiAlH4 to give an achiral compound. 'X' is :
(A) CH 3CH 2CHCOOH (B) CH 3CHCOOH

| |
OH Me
(C) CH 3CHCOOH (D) CH 3CHCH 2 COOH

| |
CH 2OH OH
80 E
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·· + ether
X , X is
9. H3C CO2H + Ph2C – N º N
Ph
(A) CH 3 C – O – CH (B) CH3 C – O – CH2 – Ph
Ph
O O
Ph
Ph Ph
(C) CH3 C – O – CH3 (D) CH3 C – O – CH3

O O
Ph Ph
1. LiAlD4
10. CO2H 2. H2O
X , X is
HO D DO D
(A) CH (B) CH2
D
D OD
(C) C – OH (D) C–H
O
NH2
11. + Cl – C – Cl X , X is -
CO2H
O
OH
NH–C–Cl NH
C
(A) (B)
COOH CH O
OH
NH O
O NH
C
CH C=O C O
(C) (D)
OH O
COOH CH2OCOPh
(1) (2)
12.
CD3 CD3
O O
Na/liq. NH3 PhCOCl LiAlH4 CH3COCl
(A) ¾¾¾¾¾(1)
® ¾¾¾¾
(2)
® (B) ¾¾¾¾
(1)
® ¾¾¾¾®
LiAlH4 PhCOCl Zn - Hg + HCl CH3COCl

(C) ¾¾¾¾
(1)
® ¾¾¾¾
(2)
® (D) ¾¾¾¾¾ (1)
® ¾¾¾¾®
(2)
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CO2H NaOH
X
13. H Br
NaN3 H2/Ni
Y Z
Me
(D)
Identify X, Y and Z.
X Y Z
CO2H CO2H CO2H
(A) H OH H N3 H NH2
Me Me Me
(D) (D) (D)
CO2H CO2H CO2H
H OH N3 H NH2 H
(B)
Me Me Me
(D) (L) (L)
CO2H
HO H CH2 = CH – COOH CH2 – CH2 – COOH

(C)
Me
(L)
CO2H CO2H CO2H
(D) HO H H N3 H NH 2
Me Me Me
(L) (D) (D)
14. Phosgene (COCl2) + 1 mol C2H5OH ¾¾¾

NH3
® X, X is
(A) NH2 - C - NH2 (B) NH = C = O (C) NH2 - C - Cl (D) EtO - C - NH2

|| || || Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\05/ Carboxylic Acid & Derivatives
C O O
15. Consider folllowing reaction :
O O
|| ||
RCOH + SOCl2 ¾® R - C - Cl + HCl + SO2
Consider following statements about this reaction :
A : It is SN 2 at carbonyl carbon from where OH is a leaving group.
B : It is SN 2 at sulphur from where Cl is the leaving group.
Å
O–H O
··
··
··
C : Its intermediate C is resonance stabilised.

·· S
R O Cl
··
D : Reaction is spontaneous as HCl and SO2 gases escape
Select incorrect statement(s) :
(A) A, B (B) B, C (C) D (D) A
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16. Consider the following reaction :

O
OH O – CCH3
COH O COH
CH 3CCl
O O
A B
B is an ester of :
(A) salicylic acid (B) acetic acid (C) both of these (D) none of these
17. (Refer above question)
If A is heated, there is formation of another ester called salol. Salol is an ester of :
(A) benzoic acid (B) salicylic acid (C) acetic acid (D) carboxylic acid
18. Consider following ester formation from acid and alcohol. Alcohol is isotopically labelled with 18O.
O O
|| 18 ||
H+

CH3 - C - O - H + CH3CH2 - O- H
CH3 - C - O - C2H 5 + H2O
A B C D D
Select correct statement :
(A) Molar mass of C is 88 (B) Molar mass of D is 20 (C) Molar mass of C is 90 (D) none of these
O
(1) LiAlH4
19. X , X is
N (2) H2O
H
OH
(A) (B) (C) (D) NH
NH N–H N – OH
HO
CH3 O
| ||
Br2 , NaOH
20. PhCH2 - CH - CH2 - C - NH2 ¾¾¾¾¾ ® X , X is
CH3 CH3
| |
(A) CH3 - CH - CH2 - NH - Ph (B) Ph - CH2 - CH - CH - NH2
|
OH
CH3 CH3 CH3

| | |
(C) Ph - CH2 - CH - CH2 - NH2 (D) Ph - CH - CH - C - NH2
||
O

OC2H5 dil. HCl
(catalyst)
H3C C OC2H5 + H2O X+Y
21.
OC2H5
O O
(A) X is CH 3 C OC 2H 5 (B) X is CH3 CH2 C OCH3
O
(C) X is H C OC3H7 (D) Y is C2H5OH
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22. An organic compound P (C5H10O2) reacts with Br2 in presence of phosphorus to produce a resoluble compound
Q. Q on dehydrobromonation yields ‘R’, which does not show geometrical isomerism and on decarboxylation
gives an alkene (S). S on ozonolysis gives T and U. Compound T gives positive Schiff s test but U does not
CH3 CH3H
| | |
(A) P is CH3 - CH - CH2 - COOH (B) Q is CH3 - C —C - COOH
| |
H Br
O
(C) R is (D) T is
COOH H H
23. Compound (X) (C8H6O2) on treatment with aqueous NaOH followed by acidification gives (Y) (C8H8O3),
which on oxidation gives benzoic acid only.
O O
C–C–H CH(OH) – COOH
(A) X is (B) Y is
CHO
CH2 – COOH
(C) X is (D) Y is
OH
CHO
24. Compound (X) C5H8O2 liberated carbon dioxide on reaction with sodium bicarbonate. It exists in two forms
neither of which is optically active. It yields compound (Y) C 5H10O2 on hydrogenation. Compound (Y) can be
separated into two enantiomorphs.
(A) Y is CH3 - CH2 - CH2 - CH2 - COOH (B) X is CH3 - CH = C(CH3 )COOH
CH3
|
(C) X is CH3 - CH = CH - CH2 - COOH (D) Y is C2H5 - C - COOH
|
H
25. An ester (X) of the formula C4H8O2 on acidic hydrolysis gives an acid (Y) which reduces Tollen’s reagent and
an alcohol (Z), which gives iodoform test. Ester (X) can also be converted into alcohol (Z) by reaction with Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\05/ Carboxylic Acid & Derivatives
excess of grignard reagent (W). Find the correct options
(A) X is H - C - OCH(CH3 )2 (B) Y is H - C - O - H

|| ||
O O
(C) Z is HOCH(CH3 )2 (D) W is C2H5 - Mg - I
+
LAH HBr NaCN H3O ,CaO, D CaO, D
26. C4H6O4 (X) ¾¾¾ ® ¾¾¾ ® ¾¾¾® ¾¾¾¾¾¾ ® Y ¬¾¾¾ ¾ hexanedioic acid
(A) X is (B) Y is O
O
CH2 - COOH
(C) X is | (D) Y is O
CH2 - COOH O
84 E
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27. An acid (P), C8H7O2Br on bromination in the presence of FeBr3 gives two isomers, (Q) and (R) of formula
C8H6O2Br2. Vigorous oxidation of (P), (Q) and (R) gives acids (S), (T) and (U) respectively. (S), C 7H5O2Br is
the strongest acid among all of its isomers. (T) and (U) each has a molecular formula of C 7H4O2Br2. Find the
correct options
Br
CH2 – COOH COOH
(A) P is (B) T is
Br Br
COOH COOH
(C) U is (D) S is
Br Br Br
28. Compound (X) of molecular formula C8H6O4 can produce anhydride upon heating. When treated with LiAlH4(X)
produces (Y).(Y) on treatment with HCl and HCN, then H 3O+ produce (Z). Z upon heating on BaO produces
O as the product. Predict (X), (Y) and (Z).
COOH CH2 – OH
(A) X is (B) Y is
COOH CH2 – OH
CH2COOH CH2 – COOH

(C) Z is (D) Z is
CH2CHO CH2 – COOH
29. Which of the following reagents are involved in the following transformation ?
(A) H3O+ (B) LiAlH4 (C) Ethylene glycol (D) Acetone

30. Which of the following will liberate CO2 on reaction with NaHCO3
(A) OH (B) CH3COOH

CH 2OH
(C) (D) |
CH 2OH
31. Which of the following compounds will give acetic acid with KMnO4/HÅ/D:
(A) CH3–CHO (B) CH3–CH=CH–CH3
(C) CH3–CºC–CH3 (D) CH3CH2OH
32. In the given reaction:
O O
|| ||
[ X]
R - C - OH ¾¾® R - C - O - CH 3
[X] will be:

(A) CH2N2 (B) CH3OH/HÅ (C) MeCOOH (D) Me2SO4
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33. Which of the following gives silver mirror test?

(A) HCOOH (B) CH3COCHOHCH3
(C) Tartaric acid (D) Glucose
34. Consider the following reaction:
O O
|| HÅ
||
CH 3 - C - OH + CH 3 - OH ¾¾®
¾ CH 3 - C - O - CH 3 + HOH
True about the above reaction is/are

(A) Product is having smell like fruits
(B) Nucleophilic addition followed by elimination reaction
(C) follows AAC1 mechanism
(D) it is irriversible reaction
O
||
35. AlCl3 Na2Cr2O7 , H+ heat heat
Ph(CH2 )5 - C - Cl ¾¾¾ ®(X) ¾¾¾¾¾¾¾ ®(Y) ¾¾¾ ®(Z)
CH2 COOH CO CHO

(A) X is (CH2)4 (B) Y is (C) Z is O (D) Y is
C COOH
COOH CO
O
36. trans-2-methylcyclohexanol + acetyl chloride ¾® X
X + NaOH (aq) ¾¾
D
® Y + sodium acetate.
(A) X is CH3 H (B) X is H H
H O – C – CH3 CH3 O – C – CH3
O O
(C) Y is H H (D) Y is CH3 H

CH3 OH H OH
37. An organic compound X (C9H6O3) does not react with a aqueous solution of NaHCO 3 and does not change
the colour of litmus paper. X on acid hydrolysis give Y(C9H8O4) whereas X on treatment with methanol in acid
medium gives Z (C10H14O4) as the major alcoholysis product. Y on heating with excess of soda-lime produces
(W). Identify compound X, Y, Z and W.
O
COOH COOCH3
O
(A) X is (B) Y is COOH (C) Z is COOH (D) W is
O CH3
Comprehension # 1
Favorski rearragement is an excellent process to produce carboxylic acid with ring contraction, a-chloro or
bromoketone upon treatment with base like OH– and consequent treatment with acid yields carboxylic acid
with ring contraction. Carbanion forms due to stability by –I, –R effect of ketone group. Answer the followings
on the basis of the above passage
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38. Which carbanion will form PhCH2COCH2Cl

Q Q
(A) Ph - C HCOCH 2 Cl (B) PhCH 2CO C HCl
Q Q ••
(C) Ph C H - COCHCl (D) Ph - CH 2 COC H
-
(i)OH
39. What will be the product of the following reaction PhCH2COCH2Cl ¾¾¾¾
(ii) H O
®?
2
(A) PhCH2CH2COOH (B) PhCH - CH3 (C) Ph - COCH2COOH (D) none of these
|
COOH
40. Which can be the substrate to yield COOH
Cl
O O O O
(A) (B) (C) (D)
Cl O Cl
Cl Cl
Comprehension # 2
The synthetic sweetener aspartame, known commercially as Nutra sweet, is carboxylic acid.
O COOH
NH – C
COOCH3 NH2
Following questions are based on aspartame

41. Number of stereocentres present in it are :
(A) 1 (B) 2 (C) 3 (D) 4
42. Other artificial (synthetic) sweeteners are :
(A) sorbitol (B) saccharin (C) cyclamate (D) xylitol
43. In aqueous solution on standing it changes to :
O O COOH
(A) NH2 (B)
NH2 – HOC NH – C
COOH NH2
COOH COOH
O NH COOH
(C) (D) no hydrolysis is possible
NH O
Comprehension # 3
Two chemical engineers (CE) at MIT were working on the same keto ester (A)
O
O
A:
O
for the synthesis of carbonyl compounds using same Grignard reagent CH3CH2MgBr but changing some
experimental steps.
CE Steps Product
(i) CH CH MgBr(one equivalent)
Mr Petersykes A ¾¾¾¾¾¾¾¾¾¾¾
3
+
2
® X
(ii)H3O
(i) H O+
Mr Wade A ¾¾¾¾¾¾¾¾¾®
3
Y
(ii) CH 3CH 2MgBr (one equivalent)
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44. Identify the product X and Y

X Y
OH
O
(A) CH3CH3
CH2CH3
O
(B) CH3CH3 CH3CH3
O
(C) O CH3CH3
O O
(D) O O
Comprehension # 4
In a research lab, three scientists synthesised three carboxylic acids but each using two different methods.
+
Method I RX ¾¾¾¾®
Mg/Ether CO2
¾¾¾ H3O
® ¾¾¾®
+
Method II RX ¾¾¾
KCN H3O
® ¾¾¾®
Scientists :
Mr. John (X) ¬¾¾¾ ¾ CH 3 = CHBr ¾¾¾¾

Method II
®
Method I
Mr. Perkin (Y) ¬¾¾¾ ¾ CH 2CH 2 ¾¾¾¾

Method II
®
Method I
| |
Cl OH
CH3
Mr. Amit (Z) ¬¾¾¾ ¾ CH3

Method II
C Cl ¾¾¾¾ ®
Method I
CH3
Read the above approach and answer the following questions.
45. Method I gives better result in case of :
(A) X, Y (B) Y, Z (C) X, Z (D) X, Y, Z
46. Select the product of X, Y, Z by method I :

X Y Z
(A) CH2 = CHCOOH RH (CH3 )3 CCOOH
(B) CH2 = CHCOOH RH (CH3 )2 CCOOH
CH2COOH
(C) CH2 = CHCOOH | (CH3 )3 CCOOH
OH
(D) CH2 = CHCOOH RH (CH3 )3 RH
47. Following are the drawbacks faced by X, Y, Z in their syntheses either by method I or method II
A : method II used by X cannot be used as Br is attached to vinylic carbon
B : method II used by Y cannot be used as CN – replace both Cl– and OH– group.
C : method I used by Y cannot be used as RMgX is decomposed by OH group
D : method II used by Z cannot be used as CN – being a strong base.
Select correct drawbacks :
(A) A, B, C (B) A, C, D (C) A, B, D (D) A, B, C, D
88 E
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SUBJECTIVE TYPE
48. The second dissociation constant of fumaric acid is greater than maleic acid. Explain.
49. In the following reaction, trace the position of isotopic O18.
50. Identify A, B, C, D and E in the following sequence of reactions:
51. When the compound shown was heated in refluxing hydrochloric acid, a compound with the molecular formula
A(C5H6O3) was isolated. Identify this product. Along with this product, three other carbon-containing substances
are formed. What are they ?
What happens when A(C5H6O3) reacts with

(A) HCN follwed by hydrolysis (B) soda lime/D
(C) NH2NH2/glycol, OH – (D) P/Br2 (E) N3H
52. Which is more reactive in each pair towards SN reaction ?
(A) (B)
(C)
53. reacts with :
(A) NH3 (B) LiAlH4 (C) EtOH, H+ (D) NaBH4/EtOH

What are the product in each case ?
54.
(i) What are A & B ? (ii) Which reagent will convert B into A ?
PCl MeNH
55. ¾ ¾® A ¾¾
O ¾MeOH ¾3 ® B ¾¾ ¾
¾2 ® C
D D
56. ¾¾® A¾¾® B
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D
57. ¾¾® A+B
Br / PBr (i) Alc.KOH

58. CH3(CH2)14CH2CH2COOH ¾¾2 ¾¾3
® (A) ¾¾¾¾¾
(ii) H+
® (B) ¾(¾
C)
®
( i ) Ag + ( ii ) Br
CH3(CH2)14COOH ¾¾ ¾ ¾ ¾2 ® (D)
(i) 2Na D
59. HCºCH ¾¾¾¾ ® (A) ¾H / Pd
¾2 ¾¾® (B) C¾¾® D
(ii) 2CO 2
BaSO 4
(iii) H+
D
60. Phthalic acid + NH3 ¾® D ¾¾® E
61. MeCH(CH2COOH)2 ¾(¾

CH 3CO ) 2 O
¾ ¾¾® F
D
62.
Identify A to H.
- - (i ) H O
OH OH
63. ¾¾¾® (A) ¾¾¾® (B) ¾¾ ¾
¾
2
® (C)
+
(ii ) H 3O
90 E
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ANSWERS
SI NGLE CHOICE CORRECT
1. (D) 2. (D) 3. (B) 4. (C) 5. (C) 6. (B)
7. (B) 8. (C) 9. (A) 10. (C) 11. (D) 12. (C)
13. (B) 14. (D) 15. (D) 16. (B) 17. (B) 18. (C)
19. (A) 20. (C)
MU LTI PLE CHOICE CORRECT

21. (A D) 22. (ABCD) 23. (AB) 24. (B D) 25. (ABC)
26. (BC) 27. (ABCD) 28. (AB D) 29. (ABC) 30. (B,C)
31. (ABCD) 32. (AB D) 33. (ABCD) 34. (AB)
35. (ABC) 36. (A,D) 37. (AB D)
COMP REHENSI ON BASED QUEST IONS

Comprehension - 01
38. (A) 39. (A) 40. (A)
Comprehension - 02
41. (B) 42. (B,C) 43. (C)
Comprehension # 3
44. (C)
Comprehension # 4
45. (C) 46. (A) 47. (B)
SU BJECTIVE TYPE
48. After the first dissociation, maleate ion is more stabilised due to intramolecular H-bonding, whereas fumarate
ion does not have intramolecular H-bonding.
18 18
49. O is in ester
50. A: B: (Rosenmund)
C : CH3CH=CHCHO (aldol condensation)
D: E:
51. Given compound represents

(i) acetal (ii) ester
When it is subjected to acidic hydrolysis, acetal changes to carbonyl group and ester changes to acid.
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(X), (Y) and (Z) are thus, other carbon containing product along with C5H6O3 which is the main product.
A(C5H6O3) has (i) keto group (ii) carboxylic group
(A)
(B)
D
(C) (Wolff-Kishner reduction)
(D) (HVZ-reaction)
(E) (Schmidt-reaction)
52. (A) (B) (C)
53. (A)
(B)
(C)
(D) No reaction (ester is not reduced by NaBH4).
92 E
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54. (i) A : CH3—NH2 B:

(ii) Reagent =Br2/Alc. KOH
55. (A) HOOCCH2CH2COOMe; (B) ClOCCH2CH2COOMe; (C) MeNHOCCH2CH2COOMe
56. (A) ; (B)
57. (A) (B)
58. (A) CH3(CH2)14CH2CHBrCOOH; (B) CH3(CH2)14CH=CHCOOH; (C) KMnO4;

(D) CH3(CH2)14Br
59. (A) C COOH ; (B) H - C - COOH ; (C) ; (D)

|| | ||
C COOH H - C - COOH
60. (D) ; (E)
61. (F)
62.
63. (A) ; (B) ; (C)
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NITROGEN CONTAINING COMPOUNDS

1. Which gas will be evolved out when [CH3CH2NH2 + (CH3)2CHNH2] is treated with sodium nitrite and
HCl -
(A) Chlorine (B) Ammonia (C) Nitrogen (D) NO2
2. In the following sequence of reactions the product B, will be :
CINH2 NaNO
C2H5MgBr ¾ ¾¾ ¾® A ¾ ¾¾¾
2
® B
HCl
(A) C2H5OH (B) C2H5NO2 (C) C2H2 (D) All of the above
3. Identify B, X and R respectively in the following sequence of reactions
ClCN H3 O +
C2H5MgBr ¾¾¾ ¾
® A ¾¾¾¾ ® B ,
I2
CH3COCH3 ¾¾®
NaOH
X
Ag
¾¾¾ ® Y
NaNO2 CuCN + 4H
C6H5NH2 ¾¾¾¾
HCl ® P ¾¾¾¾ ® Q ¾¾¾® R
(A) C2H5COOH, CHI3, C6H5CH2NH2 (B) C2H5COOH, CH3I, C6H5COOH
(C) C2H5CH2NH2, CH3I, C6H5COOH (D) C2H5COOH, C2H5I, C6H5CONH2
4. Which of the following compounds will dissolve in an alkali solution after it has undergone reaction with
Hinsberg reagent ?
(A) (C2H5)2NH (B) CH 3 N C6H 5 (C) CH3NH2 (D) C6H5NHC6H5
CH3
5. Maximum basic in gas phase is ?
(A) NH3 (B) CH3CH2NH2 (C) (CH3CH2)NH (D) (CH3CH2)3N
6. Identify Y in the reaction
CHCl / KOH
¾¾ ¾3 ¾¾® X ¾dil
¾HCl¾® Y
heat 300 K Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\06\Nitrogen Cont. comp.
(A) (B) (C) (D)
7. A reaction of ethyl amine & acetic anhydride leads to the formation of:
(A) CH3NHCOCH3 (B) C2H5CONHCH3 (C) CH3CONHC2H5 (D) CH3–CH=NOC2H5
8. Which is incorrect reaction:
D
(A) Cl + NH3 ¾¾® +NH4Cl (B) Cl + 2NH3 ¾® NH2+ NH4Cl
0°C
(C) Cl + NH3 ¾® + NH4Cl (D) NH2 + HNO2 ¾¾
¾®
94 E
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9. In the reaction sequence identify the functional group present in A, B, C
Sn / HCl HNO2
A ¾¾¾¾ ® B ¾¾¾¾ ® C ¾¾¾¾
C2H5 OH
¾® C6H6 -
o 0 C
(A) NO2, NH2, N=N (B) NO2, NH2, OH (C) –OH -NH2, -NO2 (D) –NH2, -NO2, -N=N
10. B ¬¾¾
A (CH3)2CHMgBr ¾¾¾¾
CINH2
® A, A and B repectively are :
(A) Position isomer of 1-propane amine and propane (B) Primary amine, alkane
(C) Isopropyl amine, propane (D) All the above
11. CH3Cl ¾¾¾

KCN +4H
® ¾¾¾ ® A ¾¾¾¾¾¾
NaNO2 / HCl
® Ethanol + ?
Apart from ethanol as the main product and the other products would be :
(A) Ethylene (B) Ethyl nitrite (C) Ethyl chloride (D) All the above
12. Least availability of lone pair of electrons on nitrogen is associated with the following compound :
(A) NH2CONH2 (B) CH3CH2NH2 (C) CH3NHCH2CH3 (D) (CH3)3N
13. The product obtained by the alkaline hydrolysis of C2H5–N = C = O when treated with t-butyl magnesium
bromide, the compound obtained will be :
(A) t-butylamine (B) n-butylamine (C) Isobutane (D) n-butane
14. N,N-dimethylacetamide is obtained in the reaction :
(A) Acetyl chloride and methaneamine (B) Acetyl chloride and ethaneamine
(C) Acetyl chloride and dimethylamine (D) Acetyl chloride and diethylamine
15. Reaction of nitrobenzene with methyl chloride in presence of anhydrous aluminium chloride
the compound formed is :-
(A) m-Nitrotoluene (B) o-Nitrotoluene (C) p-Nitrotoluene (D) None
16. Which of the following has the maximum value of dipole moment :-
Cl NO2 Cl NO2
NO2 Cl
(A) (B) (C) (D)
Cl NO2
17. Which one of the following is not an azo compound :-
Node-1\Target-2023-24\1.JEE(M+A)\Module\Enthuse\Chemistry\Organic Chemistry\Eng\QB\06\Nitrogen Cont. comp.
(A) Methyl orange (B) Benzenediazonium chloride

(C) Phenolphthalein (D) p-hydroxyazobenzene
18. A low temperature reaction of aniline with HNO 2 and subsequent treatment with alkaline b–naphthol solution
produces a precipitate whose colour would be :-
(A) Black (B) Purple (C) White (D) Orange
19. Bromo ethane ¾¾¾¾ H3 O+

® A ¾¾¾¾ ® HCOOH + B;
AgCN
CHCl
B ¾¾¾¾
KOH
3®
A ¾¾¾¾¾
Re duction
®C
A. B, C respectively in the above sequence are :

(A) Ethane amine, methane nitrile and diethyl amine
(B) Carbyl amino ethane, ethane amine and secondary amine
(C) Ethyl isocyanide, ethyl amine and methyl isocyanate
(D) Carbylamino ethane, ethane amine and ethyl methyl amine
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D CaCO3
20. CH2(COOH)2 ¾¾¾¾
- CO2
® A ¾¾¾¾
D
CH3NH2
® B ¾¾¾¾ ® C
¾
Compound C in the above sequence is :

(A) (CH3)2C = NCH3 (B) CH3CH = NCH3 (C) (CH3)3C = NCH3 (D) All of these
21. CH3COCI ¾¾
A
® CH3CONH2 ¾¾¾¾
NaOH
® CH3COONa + A
B ¬¾¾¾
COCl2
¾ A ¾¾¾
CO2
®B
A and B respectively are :

(A) NH3 . Na2CO3 (B) NH3, NaCl (C) NH3, carbamide (D) None
22. Reduction of :-
CH3
C=NOH by Na and EtOH yields
CH3
The compound :-
(A) s-Amine (B) p-Amine (C) t-Amine (D) None of these
23. Reduction of nitrobenzene with zinc and methanolic alkali gives mainly
(A) Aniline (B) p-Aminophenol (C) Azoxybenzene (D) Azobenzene
N2BF4
NaNO2
24. ¾¾¾¾
Cu, D
® Product. The product is :
(A) Nitrobenzene (B) Fluorobenzene (C) o-Di flourobenzene (D) m-Dinitrobenzene

25. When diazonium compound shows Gattermann reaction then N2 is replaced by :
(A) H-atom (B) OH-group (C) Nitro group (D) Halogen atom
ANSWERS
1. (C) 2. (A) 3. (A) 4. (C) 5. (D) 6. (D)
7. (C) 8. (B) 9. (A) 10. (D) 11. (D) 12. (A)
13. (C) 14. (C) 15. (D) 16. (B) 17. (C) 18. (D)
19. (D) 20. (A) 21. (C) 22. (B) 23. (C) 24. (A)
25. (D)
96 E
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KOTA (RAJASTHAN)
R
IMPORTANT NOTES
97
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98
JEE-Chemistr y
IMPORTANT NOTES
Path to success
KOTA (RAJASTHAN)
E
R

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ORGANIC CHEMISTRY

ENTHUSIAST QUESTION BANK

01. ISOMERISM .................................................................................... (1-13)

02. ALKYL & ARYL HALIDE ................................................................ (14-32)

03. ALCOHOL & ETHER ..................................................................... (33 - 47)

04. OXIDATION & REDUCTION........................................................ (48 - 53)

05. ALDEHYDE & KETONE ................................................................ (54 - 78)

06. CARBOXYLATE ACIDS ................................................................. (79 - 93)

07. NITROGEN CONT. COMPOUND................................................. (94 - 98)

5. On chlorination of propane number of products of the formula C3H6Cl2 is :-

(A) 12 (B) 8 (C) 10 (D) 6

9. Molecular formula C5H10O can have :-

CH3 CH3 CH3

14. The compound shown is

(A) (B) (C) (D)

15. Select the pair of chain isomers.

(A) CH3–CHO (B) CH3CH2–CHO (C) (CH3)2CH–CH=O (D)

19. Which of the following is (R)-3-hexanol?

20. The R/S configuration of these compounds are respectively.

21. Which of the following represents (E)-3,6-dichloro-6-methyl-3-heptene?

(A) (B) (C) (D)

(A) (B) (C) (D)

23. Which of the following compounds is (S)-4-chloro-1-methylcyclohexene?

CH3 CH3 CH3 CH3

(A) (B) (C) (D)

24. Which two of the following compounds represents a pair of enantiomers?

25. Which of the following is properly classified as a meso compound?

26. Which two of the following compounds are diastereomers?

27. Which two of the following compounds are identical?

CHO CHO CHO CHO

31. Which of the following structures represents a chiral compound?

CH3 CH3 CH3 CH3

CH3 CH3 CH3 OH

MULTIPLE CHOICE CORRECT

H3C CH3 H3C CH3

40. Which of the following are correct representation of L–amino acids

(A) (B) (C) (D)

41. Which compound(s) will show Geometrical isomerism ?

45. Find out the specific rotation of (–) MSG :

(C) (R) At least one of the compound can

show Optical Isomerism

52. Match the column :

53. Match the column I with column II.

(A) & Cl (P) Homologs

(D) CH3–CH2– –O–CH3 & CH3– –O–CH2–CH3 (S) Position isomers

54. Column - I Column - II

(B) (Q) Functional

(C) (R) Geometrical isomer

(A) (P) cis-form

SUBJECTIVE TYPE QUESTIONS

(i) H3C CH CH CH CH CH3 (ii) CH3–CH=CH CH2–CH3

(v) Cl–CH=CH–CH=CH–CH=CH–CH3 (vi)

(ix) CH3–C º C–CH=CH–CH3 (x) CH3–CH=CH–CH=N–OH

(XIII) (XIV) (XV)

(a) EtCH(CO2H)Me (b) MeCH(CO2Et)CO2H (c) (d)

(i) CH3 - CH - CH - CH3 (ii) CH3 – CH – CH – CH – CH3 (iii) CH3 – CH – CH – CH – CH3

(ix) (x) (xi)

MULTIPLE CHOICE CORRECT:

COMPREHENSION BASED QUESTIONS

MATCH THE COLUMN

SUBJECTIVE TYPE QUESTIONS

57. II, III & IV are Identical ; I is Enantiomer of these.

60. (i) 6, (ii) 8

CH3–CH2–C=CH–CH3 Þ cis and trans