KKHK
KKHK
KKHK
PROBLEM SOLVING
IIT JEE MAIN + ADVANCED
ORGANIC CHEMISTRY
BY
NAVNEET JETHWANI
AROMATIC
CHEMISTRY
ETOOSINDIA
INDIA’S NO. 1 ONLINE COACHING
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INDIA’S NO. 1 ONLINE COACHING
JEE MAINS
1. The reaction of chloroform with alcoholic KOH and p-toluidine forms : [AIEEE-2003]
Ans. (4)
OH
– +
O Na
2. + CHCl3 + NaOH
CHO
+ +
(3) formyl cation (CHO) (4) dichloromethyl cation (CHCl 2)
Ans. (1)
3. Fluorobenzene (C6H5F) can be synthesized in the laboratory [AIEEE-2006]
(1) from aniline by diazotisation followed by heating the diazonium salt with HBF4
(2) by direct fluorination of benzene with F2 gas
(3) by reacting bromobenzene with NaF solution
(4) by heating phenol with HF and KF
Ans. (1)
4. Presence of a nitro group in a benzene ring [AIEEE-2007]
(1) activates the ring towards electrophilic substitution
(2) renders the ring basic
(3) deactivates the ring towards nucleophilic substitution.
(4) deactivates the ring towards electrophilic substitution.
Ans. (4)
5. The reaction of toluene with Cl2 in presence of FeCl3 gives predominantly : [AIEEE-2007]
(1) Benzoyl chloride (2) Benzyl chloride
(3) o–and p–Chlorotoluene (4) m–Chlorotoluene
Ans. (3)
6. The electrophile, E . attacks the benzene ring to generate the intermediate -complex. Of the following, which
-complex is of lowest energy ? [AIEEE-2008]
NO2 NO2 NO2
H
H
+ E
(1) (2) + E (3) + (4) +
H
E
H E
Ans. (1)
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7. Phenol, when it first reacts with concentrated sulphuric acid and then with concentrated nitric acid, gives :
[AIEEE-2008]
(1) o-nitrophenol (2) p-nitrophenol (3) nitrobenzene (4) 2,4,6-trinitrobenzene
Ans. (1)
8. Toluene is nitrated and the resulting product is reduced with tin and hydrochloric acid. The product so obtained is
diazotised and then heated with cuprous bromide. The reaction mixture so formed contains : [AIEEE-2008]
(1) mixture of o– and p-dibromobenzenes (2) mixture of o- and p-bromoanilines
(3) mixture of o- and m-bromotoluenes (4) mixture of o- and p-bromotoluenes
Ans. (4)
9. Phenol is heated with a solution of mixture of KBr and KBrO3. The major product obtained in the above reaction is
[AIEEE-2011]
(1) 2-Bromophenol (2) 3-Bromophenol (3) 4-Bromophenol (4) 2, 4, 6 -Tribromophenol
Ans. (4)
10. Ortho-Nitrophenol is less soluble in water than p- and m- Nitrophenols because : [AIEEE-2012]
(1) o-Nitrophenol is more volatile steam than those of m- and p-isomers.
(2) o-Nitrophenol shows Intramolecular H-bonding
(3) o-Nitrophenol shows intermolecular H-bonding
(4) Melting point of o-Nitrophenol is lower than those of m- and p-isomers.
Ans. (2)
11. A compound with molecular mass 180 is acylated with CH3COCl to get a compound with molecular mass 390. The
number of amino groups present per molecule of the former compound is : [JEE(Main)-2013]
(1) 2 (2) 5 (3) 4 (4) 6
Ans. (2)
12. Compound (A), C8H9Br, gives a white precipitate when warmed with alcoholic AgNO3. Oxidation of (A) gives an acid
(B), C8H6O4. (B) easily forms anhydride on heating. Identify the compound (A). [JEE(Main)-2013]
CH2Br
CH2Br C2H5 CH2Br
(1) (2) (3) (4)
Br CH3
CH3 CH3
Ans. (4)
13. The gas leaked from a storage tank of the Union carbide plant in Bhopal gas tragedy was :- [JEE(Main)-2013]
(1) Methylisocyanate (2) Methylamine (3) Ammonia (4) Phosgene
Ans. (1)
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14. Sodium phenoxide when heated with CO2 under pressure at 125°C yields a product which on acetylation produces
C. [JEE(Main)-2014]
ONa
125° H+
+ CO2 B C
5 atm Ac2O
Ans. (3)
15. The following reaction [Jee Main (Online) 2014]
OH
OH
Anhyd.
+ HCl + HCN
ZnCl2 CHO
is known as
(1) Perkin reaction (2) Kolbe’s reaction
(3) Gattermann reaction (4) Gattermann-Koch Formylation
Ans. (4)
16. Chlorobenzene reacts with trichloro acetaldehyde in the presence of H2SO4 [Jee Main (Online) 2014]
O
Cl
H2SO4
2 +H C CCl3
Cl
(1) Cl CH Cl (2) Cl C Cl
Cl Cl
Cl
(3) Cl C Cl (4) Cl CH Cl
CH2Cl CCl3
Ans. (4)
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17. In a set of reaction p-nitrotoluene yielded a product E [Jee Main (Online) 2014]
CH3
Br2 Sn/HCl NaNO2 CuBr
B C D E
FeBr3 HCl HBr
NO2
Ans. (2)
E + N2
CuCN/KCN
CN COOH
CH3
CH3 CH3
Ans. (1)
19. In the following sequence of reactions: [JEE(Main)-2015]
KMnO4 SOCl2 H2/Pd
Toulene A B BaSO4 C
OCH3
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OH OH
OCH3
H3CO
(1) (2)
OH OH
OCH3
H3CO
(3) (4)
Ans. (4)
21. Fluorination of an aromatic ring is easily accomplished by treating a diazonium salt with HBF4. Which of the
following conditions is correct about this reaction ? [Jee Main (Online) 2016]
(1) Only heat (2) NaNO2/Cu (3) Cu2O/H2O (4) NaF/Cu
Ans. (1)
22. The major product expected from the following reaction is : [Jee Main (Online) 2017]
CH2OH O
HO2C
NH2
HCl(g)/CCl4
OH
O O
O O
HO2C HO2C
(1) (2)
Cl OH
O
O CH2OH O
O
HO2C
NH2 NH2
(3) (4)
OH Cl
Ans. (3)
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23. Which of the following compounds will significant amount of meta product during mono-nitration reaction ?
[JEE Main 2017]
Ans. (3)
24. Which of the following compounds will not undergo Friedel Craft’s reaction with benzene ?
[Jee Main (Online) 2017]
COCl
Cl Cl
(1) Cl (2) (3) (4)
O
Ans. (1)
JEE ADVANCED
Subjective Type Questions
AlCl3
1. + (CH3)2CHCH2Cl (A) [JEE 1992]
C(CH3)
Ans.
CHBrCH3 CHCNCH3
NaCN
Ans.
2-phenylpropane nitrilile
3. An organic compound (A) C8H6 on treatment with dilute sulphuric acid containing mercuric sulphate gives a
compound (B), which can also be obtained from a reaction of benzene with an acid chloride in the presence of
anhydrous aluminium chloride. The compound (B), when treated with iodine in aqueous KOH, yields (C) and a
yellow compound (D). Identify (A), (B), (C) and (D) with justification. Show how (B) is formed from (A) ?
[JEE 1994]
C CH COCH3 COOK
4. Toluene reacts with bromine in the presence of ultravoilet light to give benzyl bromine while in presence of FeBr3 it
gives p-bromotoluene. Give explanation for the above observations. [JEE 1996]
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5. Show the steps to carry out the following transformations : [JEE 1998]
(a) Ethylbenzene benzene (b) Ethylbenzene 2-phenylpropionic acid
[O]
(a) Ethylbenzene Soda lime
Ans. Benzene
2
X KCN HOH
(b) Ethylbenzene 2-phenylpropionic acid
h
(liq.) Br2 / Fe
8. [JEE 2000]
Ans.
9. How would you synthesis 4 methoxyphenol from bromobenzene in NOT more than five steps ? State clearly the
reagents used in each step and show the structures of the intermediate compounds in your synthesis scheme.
[JEE 2001]
H3O+
ONa OH
COOH COOH
COOH COOH
Conc. H2SO4 HBF4 / KHF2
Ans.
heat heat
F
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11. A compound C9H7O2Cl exists in keto form A and enolic form B. Enolic form B predominates at equilibrium. On
oxidation with KMnO4 it gives m-chlorobenzoic acid. Give structures of A and B. [JEE 2003]
O OH
C CH2 CHO C CH CHO
Ans.
Cl Cl
(A) (B)
Keto Enol
H3C
Br C2H5OH(aq.)
CH3
C2H5OH(aq.)
(a) (i) acidic solution (ii) Br neutral
CH3 CH3
F F
NaOH(aq.) NaOH(aq.)
F (liberated) F is not liberated
(b) (i) O2N (ii) H3C
CH3 CH2NO2
O O O
N N N NO2 NO2
Conc. HNO3 NO2 Conc. HNO3
(c) (i)
+ (ii)
Conc. H2SO4 Conc. H2SO4 NO2
NO2
CH3
Ans. (a) (i) H5C6 C OC2H5 + HBr (acid) ; (ii) no reaction due to partial double bond character
CH3
OH
(b) (i) + F— is liberated ; (ii) Biomolecular mechanism is not possible in (ii) case
O2N
CH3
(c) (i) Due to presence of lone pair of nitrogen atom NO group is electron donating acid ortho, para directing.
(ii) NO2 group is electron withdrawing and meta directing.
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CH3
Brown fumes and NaBr + MnO2 Conc. HNO3
14. B A C (intermediate) D (Explosive product)
pungent smell
CH3
O2N NO2
Ans. (A) H2SO4 (B) Br2 (C) NO2
(D)
NO2
15. Among the following the number of reaction(s) that produce(s) benzaldehyde is [JEE (Advance)-2015]
I. II.
III. IV.
Ans. (4)
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20. Choose the correct statement from the ones given below for two aniline in : [JEE 1993]
+ NH3 NH3
(I) (II)
(A) II is not an acceptable canonical structure because carbonium ions are less stable than ammonium ions.
(B) II is not an acceptable canonical structure because it is non aromatic.
(C) II is not an acceptable canonical structure because the nitrogen has 10 valence electrons
(D) II is an acceptable canonical structure.
Ans. (C)
21 Most stable carbonium ion is : [JEE 1995]
(A) p–NO2 – C6H4 – +CH2 (B) C6H5+CH2
(C) p – Cl – C6H4 – +CH2 (D) p – CH3O – C6H4 – +CH2
Ans. (D)
22. Arrange in order of decreasing trend towards SNAE reactions : [JEE 1995]
(I) Chlorobenzene (II) Benzene
(III) Anilinium chloride (IV) Toluene
(A) II > I > III > IV (B) III > I > II > IV (C) IV > II > I > III (D) I > II > III > IV
Ans. (C)
23. Among the following statements on the nitration of aromatic compounds, the false one is : [JEE 1997]
(A) The rate of benzene is almost the same as that of hexadeuterobenzene.
(B) The rate of nitration of toluene is greater than that of benzene.
(C) The rate of nitration of benzene is greater than that of hexadeuterobenzene.
(D) Nitration is an electrophilic substitution reaction.
Ans. (C)
24. Nitrobenzene can be prepared from benzene by using a mixture of conc. HNO3 and conc. H2SO4. In the nitrating
mixture HNO3 acts as a : [JEE 1997]
(A) Base (B) Acid (C) Reducing agent (D) Catalyst
Ans. (A)
25. The most unlikely representation of resonance structure of p-nitrophenoxide ion is : [JEE 1998]
O O O O
O– + O– O– + O– +
+
N N N N
O– O – O
O
Ans. (C)
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26. Benzenediazonium chloride on reaction with phenol in weakly basic medium gives : [JEE 1998]
(A) Diphenyl ether (B) p-hydroxyazobenzene
(C) Chlorobenzene (D) Benzene
Ans. (B)
27. A solution of (+) -1-chloro-1-phenylethane in toluene racemises slowly in the presence of small amount of SbCl5,
due to the formation of : [JEE 1999]
(A) Carbanion (B) Carbene (C) Free-radical (D) Carbocation
Ans. (D)
28. Amongst the following the strongest base is : [JEE 2000]
(A) C6H5NH2 (B) p-O2NC6H4NH2 (C) m-O2NC6H4NH2 (D) C6H5CH2NH2
Ans. (D)
29. Identify the correct order of reactivity in electrophilic substitution reactions of the following compounds
CH3
(I) (II)
Cl NO2
(III) (IV)
(A) I > II > III > IV (B) IV > III > II > I (C) II > I > III > IV (D) II > III > I > IV
Ans. (C)
H3C
(A) O2N NH2 (B) N NH2
H3C
H3C H3C
(C) N NO2 (D) N NO2
H2C H3C
NH2
Ans. (B)
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Br2 /Fe
(A) (B)
(C) (D)
Ans. (A)
32. Which of the following is obtained when 4-Methylbenzenesulphonic acid is hydrolysed with excess of sodium
acetate ? [JEE 2005]
–+
(A) CH3 CO ONa (B) CH3 + SO3
– +
(C) CH3 + SO3 Na + CH3COOH (D) CH3 SO2OCOCH3 + NaOH
Ans. (C)
33. CH3NH2 + CHCl3 + KOH Nitrogen containing compound + KCl + H2O. Nitrogen containing compound is
[JEE 2006]
— —
(A) CH3 – C N (B) CH3 – NH – CH3 (C) CH3 N C (D) CH 3 N C
Ans. (D)
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Ans. (C)
35. In the following reaction,
O
N conc. HNO
3
X
H conc. H2SO 4
O O
(C) N (D) O N N
2
H H
NO2
Ans. (B)
Ans. (A)
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O
COOH OCH3 C
O
HO H 3C
S
P Q
were separately subjected to nitration using HNO3 / H2SO4 mixture. The product formed in each case respectively,
is
O
COOH OCH3
C
O
(A) HO H 3C
NO2 NO2 O2N
OCH3 O
COOH
C
(B) HO NO2 H 3C O
NO2 NO2
O NO2
COOH
OCH3 C
(C) HO O
H 3C NO2
NO2
O
COOH OCH3
C
O NO2
(D) HO H 3C
NO2 NO2
Ans. (C)
38. In the following carbocation, H/CH3 that is most likely to migrate to the positively charged carbon is :
[JEE 2009]
H H
1 2 + 4 5
H3C C C C CH3
3
HO H CH3
(A) CH3 at C – 4 (B) H at C – 4 (C) CH3 at C – 2 (D) H at C – 2
Ans. (D)
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O (1) NaOH/Br2
C T
39. In the reaction H3C O [JEE 2010]
NH2
(2) C
Cl
O
C O NH
(A) H3C (B)
O C C CH3
O
O
(C) H3C NH (D) H3C C O
C NH C
O
Ans. (C)
40. Among the following compounds, the most acidic is [JEE 2011]
(A) p-nitrophenol (B) p-hydroxybenzoic acid
(C) o-hydroxybenzoic acid (D) p-toluic acid
Ans. (C)
41. The major product of the following reaction is : [JEE-2011]
(A) (B)
(C) (D)
Ans. (A)
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42. Amongst the compounds given, the one that would form a brilliant colored dye on treatment with NaNO2 in dilute
HCl followed by addition to an alkaline solution of -naphthol is : [JEE-2011]
Ans. (C)
43. The major product(s) of the following reaction is (are) : [JEE (Advance)-2013]
OH
Br
Br Br
SO3H
P Q R S
(A) P (B) Q (C) R (D) S
Ans. (B)
44. In the reaction shown below, the major product(s) formed is/are : [JEE 2014]
NH2
acetic anhydride
NH2 product (s)
CH2Cl2
H
CH3 NH2
N
H
O + CH3COOH + CH3COOH
N CH3
(A) NH2 (B)
O O
O
H
+
N CH3 NH3CH3COO
H H
O
N CH3 + H2O N CH3
(C) (D)
O O O O
Ans. (A)
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45 Match the four starting materials (P, Q, R, S) given in List - I with the corresponding reaction scheme (I, II, III, IV)
provided in List - II and select the correct answer using the code given below in lists. [JEE 2014]
List - I List - II
(P) H H (1) Scheme I
+
(i)KMnO4, HO, heat (ii) H, H2O
(iii) SOCl2 (iv) NH3
? C7H6N2O3
OH
NO2
NO2
CH3
Code :
P Q R S
(A) 1 4 2 3
(B) 3 1 4 2
(C) 3 4 2 1
(D) 4 1 2 3
Ans. (C)
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OH
HO
OH
N=N
(C) (D) N=N
Ans. (A)
47. In the following reactions, the product S is [JEE (Advance)-2015]
H3C
i. O3 NH3
R S
ii. Zn, H2O
H3C H3C N
N
(A) (B)
N
N
(C) (D)
HC
3 HC
3
Ans. (A)
48. The product (s) of the following reaction sequence is (are) : [JEE (Advanced) 2016]
Br Br Br
Br
Br Br Br Br
(A) (B) (C) (D)
Br
Br Br
Ans. (B)
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H H
O H3C CH3 O CH2
O O O O H
(A) CH3
(B) O O H (C) CH2
(D)
Ans. (B)
50. The major product of the following reaction is [JEE (Advanced) 2017]
OH
NH2
ONa+ OH
(A) (B)
N2Cl Cl
OH
N=N OH
(C) (D)
N=N
Ans. (C)
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53. Benzyl chloride (C6H5CH2Cl) can be prepared from toluene by chlorination with : [JEE 1998]
(A) SO2Cl2/h (B) SOCl2 (C) Cl2/h (D) NaOCl
Ans. (A,C)
54. Toluene, when treated with Br2/Fe, gives p-bromotoluene as the major product, because the CH3 group :
(A) is para directing (B) is meta directing [JEE 1999]
(C) activates the ring by hyperconjugation (D) deactivates the ring
Ans. (A,C)
OH
NaOH(aq)/Br2
55. In the reaction the intermediate(s) is (are) – [JEE 2009]
O O O O
Br
(A) (B) (C) (D)
Br Br Br
Br Br
Ans. (A,B,C)
56. In the following reaction, the product(s) formed is(are) [JEE (Advance)-2013]
OH
CHCl3
?
OH–
CH3
P Q
R S
(A) P (major) (B) Q (minor) (C) R (minor) (D) S (major)
Ans. (B, D)
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57. The reactivity of compound Z with different halogens under appropriate conditions is given below –
[JEE 2014]
NaOH
Q PhCH2Br S
Br
Cl
(A) (B)
NaOC2H 5 AlCl3
OH
(C) (D)
H2SO4 BF3OEt2
Ans. (B, C, D)
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O O O
Cl Cl Cl
NH2 NH Br N Br
In this reaction, RCONHBr is formed from reaction which has derived its name. Electron donating group at phenyl
activates the reaction. Hofmann degredation reaction is an intramolecular reaction.
62. How can the conversion of (i) to (ii) be brought about ?
(A) KBr (B) KBr + CH3ONa (C) KBr + KOH (D) Br2 + KOH
Ans. (D)
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15
CONH2 CONH2
D (i) (ii)
15 15
(A) NH2 , NH2 , NH2 , NH2
D D
15 15 15
(B) NH2 , NH2 (C) NH2 , NH2
15
(D) NHD ,
Ans. (B)
Paragraph - 2 (65 - 67)
Riemer-Tiemann reaction introduces an aldehyde group, on to the aromatic ring of phenol, ortho to the hydroxyl
group. This reaction involves electrophilic aromatic substitution. This is a general method for the synthesis of
substituted salicyladehydes as depicted below. [JEE 2007]
OH O Na OH
CHO CHO
aq. HCl
[I]
[Intermediate]
CH3 CH3 CH3
(I) (II) (III)
65. Which one of the following reagents is used in the above reaction ?
(A) aq. NaOH + CH3Cl (B) aq. NaOH + CH2Cl2 (C) aq. NaOH + CHCl3 (D) aq. NaOH + CCl4
Ans. (C)
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ETOOSINDIA N.J. SIR
INDIA’S NO. 1 ONLINE COACHING
Ans. (B)
Paragraph - 3 (68-69)
P & Q are isomers of dicarboxylic acid C4H4O4. Both decolourize Br2/H2O, On heating P forms the cyclic anhydride.
Upon treatment with dilute alkaline KMnO4, P as well as Q could produce one or more than one from S, T and U.
[JEE 2013]
COOH COOH COOH
H OH H OH HO H
H OH HO H H OH
+ V AlCl3(anhydrous) 1. Zn–Hg/HCl
2. H3PO4
W
O CH2OH
and and
(A) (B)
CH2OH
O O
(V) (W) (V) (W)
O HOH2C
and
and
(C) (D) CH2OH
CH2OH (W)
O (V)
(V) (W)
Ans. (A)
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 25
Kota, Rajasthan – 324005 Mob. : 9214233303
ETOOSINDIA N.J. SIR
INDIA’S NO. 1 ONLINE COACHING
Pd-BaSO4 i. B2H6
C8H6 C8H8 X
H2 ii. H2O2 NaOH, H2O
H2O
HgSO4, H2SO4
i. EtMgBr, H2O
C8H8O + Y
ii. H , heat
70. Compound X is
O OH
OH
COH
(C) (D)
Ans. (C)
71. The major compound Y is
CH3 CH3
(A) (B)
CH2 CH3
CH3
CH3
(C) (D)
Ans. (D)
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 26
Kota, Rajasthan – 324005 Mob. : 9214233303
ETOOSINDIA N.J. SIR
INDIA’S NO. 1 ONLINE COACHING
(O)
72. The compound R is
NH2 Br
(A) (B) Br
NH2
O
O O
NHBr
NBr
(C) NHBr (D)
O O
73. The compound T is
(A) Glycine (B) Alanine (C) Valine (D) Serine
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 27
Kota, Rajasthan – 324005 Mob. : 9214233303
ETOOSINDIA N.J. SIR
INDIA’S NO. 1 ONLINE COACHING
COCH3
H3C CH3
COCH3 (H3C)3C
(H3C)3C CH3
(C) (D)
COCH3
Ans. (D)
76. The only CORRECT combination in which the reaction proceeds through radical mechanism is
(A) (IV) (i) (Q) (B) (III) (ii) (P) (C) (II) (iii) (R) (D) (I) (ii) (R)
Ans. (D)
77. For the synthesis of benzoic acid, the only CORRECT combination is
(A) (II) (i) (S) (B) (I) (iv) (Q) (C) (IV) (ii) (P) (D) (III) (iv) (R)
Ans. (A)
78. The only CORRECT combination that gives two different carboxylic acid is
(A) (IV) (iii) (Q) (B) (II) (iv) (R) (C) (I) (i) (S) (D) (III) (iii) (P)
Ans. (D)
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 28
Kota, Rajasthan – 324005 Mob. : 9214233303
ETOOSINDIA N.J. SIR
INDIA’S NO. 1 ONLINE COACHING
NaOH/H2O OH
+
N2Cl + +
OH N N
(A) –
(P) Racemic mixture
– –
OH OH O
H2SO4
(B) H3C C C CH3 C CH3 (Q) Addition reaction
CH3 CH3 C
CH3
CH3
CH3
O OH
1. LiAlH4
C +
CH
(C) CH3 2. H3O CH3 (R) Substitution reaction
Base S
(D) HS Cl (S) Coupling reaction
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 29
Kota, Rajasthan – 324005 Mob. : 9214233303