ORGANIC CHEMISTRY

(JEE-ADVANCED)

Single Correct :
1. The product(s) of the following reactions sequence is(are)
NH2
(i) Acetic anhydride/pyridine
(ii) KBrO3/HBr
+
(iii) H3O , heat
(iv) NaNO2/HCl, 273-278 K
(v) Cu/HBr

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

2. The correct order of acidity for the following compounds is

CO2H CO2H
HO OH OH
I. II.

CO2H CO2H

III. IV.
OH
OH

(A) I > II > III > IV (B) III > I > II > IV (C) III > IV > II > I (D) I > III > IV > II

3. The major product of the following reaction sequence is:

O
(i) HCHO (excess)/NaOH, heat
+
(ii) HCHO/H (catalytic amount)

O O O O OH

(A) (B)

O O O OH
HO
(C) (D)

OH
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4. The major product of the following reaction is
OH
(i) NaNO2, HCl, 0°C
(ii) Aq.NaOH

NH2
OH –
ONa+

(A) (B)

Cl N2Cl

OH N=N OH

(C) (D)

N=N

5. The order of basicity among the following compounds is

NH NH2
I. H3C NH2 II. N NH III. HN N IV. H2N NH

(A) II > I > IV > III (B) IV > II > III > I (C) IV > I > II > III (D) I > IV > III > II

6. Aniline reacts with mixed acid (Conc. HNO3 and Conc. H2SO4) at 288 K to give P(51%),
Q(47%) and R(2%). The major product(s) of the following reaction sequence is(are)
1. Ac2O,pyridine 1. Sn/HCl
2. Br 2, CH3CO2H 2. Br2/H2O (excess)
R + S Major product(s)
3. H3O 3. NaNO2,HCl/273-278 K
4. NaNO2, HCl/273-278 K 4. H3PO2
5. EtOH,

Br Br
Br Br
(A) (B)
Br Br
Br Br

Br Br

(C) (D)
Br Br Br Br
Br

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7. The Fischer presentation of D-glucose is given below :
CHO
H OH
HO H
H OH
H OH
CH2OH
D-glucose
The correct structure(s) of -L-glucopyranose is (are)
H H CH2OH H
O O O O
HO OH HO OH HO OH HO H
CH2OH CH2OH H CH2OH
(A) H HO
(B) H H
(C) OH HO
(D) H HO
H H H H H H H OH
OH H OH OH H H OH H

8. The correct order of acid strength of the following carboxylic acid is

O
O H OH
I. H II.
OH H
O OH
III. MeO IV. H3C
OH O
(A) III > II > I > IV (B) I > II > III > IV (C) I > III > II > IV (D) II > I > IV > III

9. Newman projections P, Q, R and S are shown below.

CH3 OH CH3 CH3

H CH3
HO CH3 C2H5 H C2H5 CH(CH3)2
H H

H3C C2H5 HO CH3 H H

H C2H5
CH3 C2H5 OH
CH3
P R S
Q
Which one of the following options represents identical molecules ?
(A) P and Q (B) Q and S (C) Q and R (D) R and S

10. Which one of the following structures has the IUPAC name
3-ethynyl-2-hydroxy-4-methylhex-3-en-5-ynoic acid?
OH OH OH
HO2C CO2H CO2H
(A) CO2H (B) (C) (D)
OH

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11. The desired product X can be prepared reacting the major product of the reactions in List-I
with one or more appropriate reagent in List-II.
(Given, order of migratory aptitude : aryl > alkyl > hydrogen)
O
Ph
OH
Me Ph
X
List-I List-II
Ph
HO
(P) Me + H2SO4 (1) I2, NaOH
Ph
OH
Me
Ph
H2N
(Q) H + HNO2 (2) [Ag(NH3)2]OH
Ph
OH
Me
Ph
HO
(R) Ph + H2SO4 (3) Fehling solution
Me
OH
Me
Ph
Br
(S) H + AgNO3 (4) HCHO, NaOH
Ph
OH
Me
(5) NaOBr
The correct option is
(A) P  1; Q  2, 3; R  1, 4; S  2, 4 (B) P  1, 5; Q  3, 4; R  4, 5; S  3
(C) P  1, 5; Q  3, 4; R  5; S  2, 4 (D) P  1, 5; Q  2, 3; R  1, 5; S  2, 3

12. List contains reactions and List-II contains major products.

List-I List-II
+
(P) ONa Br (1) OH

+ HBr
(Q) OMe (2) Br

+ NaOMe
(R) Br (3) OMe

+ MeBr
(S) ONa (4)
O
(5)
Match each reaction in List-I with one or more products in List-II and choose the correct
option.
(A) P  1, 5; Q  2; R  3; S  4 (B) P  1, 4; Q  2; R  4; S  3
(C) P  1, 4; Q  1, 2; R  3, 4; S  4 (D) P  4, 5; Q  4; R  4; S  3, 4

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13. The Fisher projection of D-erythrose is shown below.
CH3
H OH
H OH
CH2OH
D-Erythrose
D-Erythrose and its isomers are listed as P, R, R and S in Column-I. Choose the correct
relationship of P, Q, R and S with D-erythrose from Column II.
Column-I Column-II
OHC HO H
(P) 1. Diastereomer
H OH
OH
OHC OH
(Q) 2. Identical
HO H
H OH

OHC H OH
(R) 3. Enantiomer
H OH
OH
OHC OH
(S)
HO OH
H H
(A) P-2, Q-3, R-2, S-2 (B) P-3, Q-1, R-1, S-2
(C) P-2, Q-3, R-1, S-3 (D) P-2, Q-3, R-3, S-1

One or more than one correct :

14. Choose the correct option(s) for the following set of reaction
(i) MeMgBr Conc.HCl
C6H10O Q S
(ii) H2O
(major)
20% H3PO4, 360 K

(i) H2, Ni HBr, benzoyl peroxide

T R U
(major) (ii) Br2, h (major)  (major)
CH3 H3C H3C Br CH3
Br
Cl Cl
(A) (B)

S T U S
H3C Cl CH3 CH3 H3C Br
Br Br
(C) (D)

S U U S

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15. Choose the correct option(s) for the following reaction sequence
2+
CHO (i) Hg , dil.H2SO4
(ii) AgNO3,NH4OH (i) SOCl2 pyridine Zn-Hg conc. HCl
Q R S
(iii) Zn-Hg, conc.HCl (ii) AlCl3
MeO

Consider Q, R and S as major products

OH

CO2H
(A)
MeO MeO
Q S

(B)
MeO MeO
O
R S

CO2H
(C)
MeO MeO
Q R O

(D)
MeO MeO
O
R S

16. Choose the correct option(s) form the following

(A) Natural rubber is polyisoprene containing trans alkene units
(B) Nylon-6 has amide linkage
(C) Teflon is prepared by heating tetrafluoroethene in presence of a persulphate catalyst at
high pressure
(D) Cellulose has only -D-glucose units that are joined by glycosidic linkages

17. With respect to the compounds I-V, choose the correct statement(s).

H
H
H
H-CH3 H H

I II III IV V
(A) The acidity of compound I is due to delocalization in the conjugate base.
(B) The conjugate base of compound IV is aromatic
(C) Compounds II becomes more acidic, when it has a-NO2 substituent.
(D) The acidity of compounds follows the order I > IV > V > II > III.

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18. Consider the following four compounds I, II, III and IV.
H3C CH3
H3C CH3 NH2 N
NH2 N O2N NO2 O2N NO2

NO2 NO2
I II III I
Choose the correct statement(s).
(A) The order of basicity is II > I > III > IV.
(B) The magnitude of pKb difference between I and II is more than that between III and IV.
(C) Resonance effect is more in III than in IV.
(D) Steric effect makes compound IV more basic than III.

19. The reaction(s) leading to the formation of 1, 3, 5-trimethylbenzene is (are)

O Conc.H2SO4 Heated iron tube
(A)  (B) Me H 873 K

O CHO
1. Br2,NaOH
Zn/Hg, HCl
2. H3O+
(C) 3.sodalime, (D)
OHC CHO
O O

20. Positive Tollen's test is observed for

O OH O
H CHO Ph
(A) (B) (C) Ph (D) Ph Ph
H O
H
H

21. The correct statement(s) about the following reaction sequence is(are)
(i) O2 CHCl3/NaOH
Cumene (C9H12) +
P Q(major) + R(minor)
(ii) H3O

NaOH
Q S
PhCH2Br

(A) R is system volatile

(B) Q gives dark violet coloration with 1% aqueous FeCl3 solution
(C) S gives yellow precipitate with 2, 4-dinitrophenylhydrazine
(D) S gives dark violet coloration with 1% aqueous FeCl3 solution

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22. Reagent(s) which can be used to bring about the following transformation is (are)

O O O O
C O C

H OH
O O
COOH COOH
(A) LiAlH4 in (C2H5)2O (B) BH3 in THF
(C) NaBH4 in C2H5OH (D) Raney Ni/H2 in THF

23. Among the following reaction(s) which gives (give) tert-butyl benzene as the major product
is(are)
Br Cl
(A) (B)
NaOC2H5 AlCl3
OH
(C) (D)
H2SO4 BF3OEt2

24. The IUPAC name(s) of the following compound is(are)

H3C Cl

(A) 1-chloro-4-methylbenzene (B) 4-chlorotoluene

(C) 4-methylchlorobenzene (D) 1-methyl-4-chlorobenzene

25. The correct statement(s) for the following addition reactions is(are)
H3C H Br 2/CHCl3
(i) M and N
H CH3

H3C CH3 Br2/CHCl3

(ii) O and P
H H
(A) O and P are identical molecules
(B) (M and O) and (N and P) are two pairs of diastereomers
(C) (M and O) and (N and P) are two pairs of enantiomers
(D) Bromination proceeds through trans-addition in both the reactions

26. For the following compounds, the correct statement(s) with respect to nucleophilic substitution
reaction is (are)
CH3
CH3
Br Br Br
I. II. III. H3C–C–Br IV.
CH3
(A) I and III follows SN1 mechanism
(B) I and II follows SN2 mechanism
(C) Compound IV undergoes inversion of configuration
(D) The order of reactivity for I, III and IV is IV > I > III

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27. Compound P and R upon ozonolysis produce Q and S, respectively. The molecular formula of
Q and S is C8H8O. Q undergoes Cannizzaro reaction but not haloform reaction, whereas S
undergoes haloform reaction but not Cannizzaro reaction.
(i)O 3 /CH2Cl2
(i) P  
(ii) Zn/H O
Q
2 (C8H 8O)

(i)O 3 /CH2Cl2
(ii) R  
(ii) Zn/H O
S
2 (C8H 8O)

The option(s) with suitable combination of P and R, respectively, is (are)

H3C
CH3 CH3
(A) H3C and (B) and
CH3 CH3
H3C
H3C CH3
CH3 CH3
(C) and (D) H3C and H3C
CH3 CH3
CH3

Paragraph # 1
Answer Q.28 and Q.29 by appropriately matching the lists based on the information
given in the paragraph.
List-I includes starting materials and reagents of selected chemical reaction. List-II gives
structures of compounds that may be formed as intermediate products and or final products
from the reactions of List-I.
List-I List-II
(i) DIBAL-H
CN (ii) dil. HCl CHO
(I) O
(P)
(iii) NaBH4
CO2H
(iv) Conc.H2SO4
O
(i) O3
OH
(ii) Zn, H2O
(II) (Q)
(iii) NaBH4 OH
CO2H (iv) Conc.H2SO4
(i) KCN
+
Cl (ii) H3O ,
(III) (R)
(iii) LiAlH4 O
CO2CH3 (iv) Conc.H2SO4
OH
CO2Me (i) LiAlH4
(IV) (S)
CO2Me (ii) Conc.H2SO4 CO2H

CO2H
(T)
CO2H

(U)
O

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28. Which of the following options has correct combination considering List-I and List-II ?
(A) (I), (Q), (T), (U) (B) (II), (P), (S), (T) (C) (II), (P), (S), (U) (D) (I), (S), (Q), (R)

29. Which of the following options has correct combination considering List-I and List-II ?
(A) (III), (S), (R) (B) (IV), (Q), (U) (C) (III), (T), (U) (D) (IV), (Q), (R)

Paragraph # 2
Answer Q.30, Q.31 and Q.32 by appropriately matching the information given in
the three columns of the following table.
Columns 1, 2 and 3 contain starting materials, reaction conditions and type of
reactions, respectively.
Columns-1 Columns-2 Columns-3
(I) Toluene (i) NaOH/Br2 (P) Condensation
(II) Acetophenone (ii) Br2/h (Q) Carboxylation
(III) Benzaldehyde (iii) (CH3CO)2O/CH3COOK (R) Substitution
(IV) Phenol (iv) NaOH/CO2 (S) Haloform
30. For the synthesis of benzoic acid, the only CORRECT combination is
(A) (II) (i) (S) (B) (IV) (iii) (P) (C) (I) (iv) (Q) (D) (III) (iv) (R)

31. The only CORRECT combination that gives two different carboxylic acid is
(A) (II) (iv) (R) (B) (IV) (iii) (Q) (C) (III) (iii) (P) (D) (I) (i) (S)

32. The only CORRECT combination in which the reaction proceeds through radical mechanism is
(A) (II) (ii) (P) (B) (IV) (i) (Q) (C) (II) (iii) (R) (D) (I) (ii) (R)

Paragraph # 3 (Q.33 to Q.34)

The reaction of compound P with CH3MgBr (excess) in (C2H5)2O followed by addition
of H2O gives Q. The compound Q treatment with H2SO4 at 0°C gives R. The reaction
of R with CH3COCl in the presence of anhydrous AlCl3 in CH2Cl2 followed by
treatment with H2O produces compound S. [Et in compound P is ethyl group]
(H3C)3C
CO2Et
Q R S

P
33. The product S is
H3C CH3 COCH3
(H3C)3C (H3C)3C CH3
(A) (B)

COCH3
H3COC HO3S
(H3C)3C H3C CH3 (H3C)3C O CH3
(C) (D)

COCH3

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34. The reactions, Q to R and R to S, are
(A) Dehydration and Friedel-Crafts acylation
(B) Aromatic sulfonation and Friedel-Crafts acylation
(C) Friedel-Crafts acylation, dehydration and Friedel-Crafts acylation
(D) Friedel-Crafts alkylation and Friedel-Crafts acylation

Paragraph # 4 (Q.35 to Q.36)

Treatment of benzene with CO/HCl in the presence of anhydrous AlCl3/CuCl followed by
reaction with Ac2O/NaOAc gives compound X as the major product. Compound X upon
reaction with Br2/Na2CO3, followed by heating at 473 K with moist KOH furnishes Y as the
major product. Reaction of X with H2Pd-C, followed by H3PO4 treatment gives Z as the major
product.
35. The compound Y is
OH
COBr Br
(A) (B)
HO O
Br
COBr
(C) (D) Br

36. The compound Z is

OH

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

O O O

Paragraph # 5 (Q.37 to Q.38)

An organic acid P (C11H12O2) can easily be oxidized to a dibasic acid when reacts with
ethyleneglycol to produce a polymer dacron.Upon ozonolysis, P gives an aliphatic
ketone as one of the products. P undergoes the following reaction sequences to
furnish R via Q. The compound P also undergoes number another set of reactions to
produce S.
1. H2/Pd-C
2. NH3/ 1. H2/Pd-C 1. HCl
3. Br2/NaOH 2. SOCl2 2. Mg/Et2O
S P Q R
4. CHCl3,KOH, 3. MgMgBr,CdCl2 3. CO2(dry ice)
+
5. H2/Pd-C 4. NaBH4 4. H3O

37. The compound R is :

HO2C

(A) CO2H (B)

(C) CO2H (D) CO2H

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38. The compound S is :

H
N
NH2
(A) (B) (C) (D)

HN
NH2

Numerical value :
39. In the following monobromination reaction, the number of possible chiral products is
CH2CH2CH3
Br2(1.0 mole)
H Br
300°C
CH3
(1.0 mole)
(enantiomerically pure)

40. Among the following, the number of aromatic compound(s) is


 

 

41. For the given compound X, the total number of optically active stereoisomers is_____.
HO
HO
This type of bond indicates that the configuration at the specific
carbon and the geometry of the double bond is fixed
This type of bond indicates that the configuration at the specific
carbon and the geometry of the double bond is NOT fixed
HO
HO
X

42. In the following reaction sequence, the amount of D (in g) formed from 10 moles of
acetophenone is______ .
(Atomic weights in g mol–1 : H = 1, C = 12, N = 14, O = 16, Br = 80. The yield (%)
corresponding to the product in each step is given in the parenthesis)
O

NaOBr Br2 (3 equiv)

A NH3, B Br2/KOH C D
H3O+ (60%) (50%) (50%) AcOH (100%)

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43. Schemes 1 and 2 describe the conversions of P to Q and R to S, respectively. Scheme 3
describes the synthesis of T from Q and S. The total number of Br atoms in a molecule of T
is_________ .

Scheme 1 :
NH2 (i) Br2(excess), H2O
(ii) NaNO2, HCl, 273 K
(iii) CuCN/KCN
Q
(iv) H3O+, 
(v) SOCl2, pyridine (major)
P
Scheme 2 :
(i) Oleum
(ii) NaOH, 
(iii) H+
S
(iv) Br2, CS2, 273 K (major)
R
Scheme 3 :
(i) NaOH
S (ii) Q T
(major)

44. In the following reaction, compound Q is obtained from compound P via an ionic intermediate.
CO2CH3
C6H5 C6H5
conc. H2SO4
Q (A colored compound)

C6H5
P
What is the degree of unsaturation of Q ?

45. Total number of isomers, considering both structural and stereoisomers, of cyclic ethers with
the molecular formula C4H8O is________.

46. Consider the reaction sequence from P to Q shown below. The overall yield of the major
product Q from P is 75%. What is the amount in grams of Q obtained from 9.3 mL of P ?
(Use density of P = 1.00 g mL–1 ; Molar mass of C = 12.0, H = 1.0, O = 16.0 and N = 14.0 g
mol–1)
(i) NaNO2 + HCl / 0-5 ºC
NH2 Q
OH
P (ii) + NaOH

(iii) CH3CO2H/H2O

47. An organic compound (C8H10O2) rotates plane-polarized light. It produces pink colour with
natural FeCl3 solution. What is the total number of all the possible isomers for this
compounds?

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 ANSWER KEY

1. (B) 2. (A) 3. (A) 4. (C) 5. (C)

6. (D) 7. (D) 8. (A) 9. (C) 10. (D)

11. (D) 12. (B) 13. (C) 14. (AD) 15. (AD)

16. (BC) 17. (ABC) 18. (CD) 19. (ABD) 20. (ABC)

21. (BC) 22. (CD) 23. (BCD) 24. (AB) 25. (BD)

26. (ABC) or (ABCD) 27. (AB) 28. (B) 29. (A)

30. (A) 31. (C) 32. (D) 33. (A) 34. (D)

35. (C) 36. (A) 37. (A) 38. (B) 39. 5

40. 5 41. 7 42. 495 43. 4 44. 18

45. 10 46. 18.6 47. 6

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