Aromatic Compounds

ENTHUSE
IIT CHEMISTRY
ORGANIC CHEMISTRY
AROMATIC COMPOUNDS
Paracetamol
- Paracetamol is non narcotic analgesic drug which is also known as

acetaminophen and APAP
Aspirin
- Aspirin is non narcotic analgesic drug which is also known as

acetylsalicylic acid (ASA) and 2-ethanoyl oxy Benzoic acid.
- It is also used as antipyretic and anti inflammatory agent.
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AROMATIC COMPOUNDS
EXERCISE # I
Q.1 Which of the following is not an aromatic compound :
(A) (B) (C) (D)

+
Q.2 Which of the following group is divalent:

(A) Benzoyl (B) Benzyl (C) Benzal (D) p-Tolyl
Q.3 Benzene is a resonance hybrid mainly of two Kekule structures. Hence:

(A) Half of the molecules correspond to one structure, and half of the second structure
(B) At low temperatures benzene can be separated into two structures
(C) Two structures make equal contribution to resonance hybrid
(D) An individual benzene molecule changes back and forth between two structures
Q.4 How many p electron are there in the following species :
(A) 2 (B) 4 (C) 6 (D) 8
Q.5 The number of benzylic hydrogen atoms in ethylbenzene is:

(A) 3 (B) 5 (C) 2 (D) 7
Q.6 Which one of the following is the most basic compound in water :
(A) C6H5–NH2 (B) C6H5–NHCH3 (C) C6H5–N(CH3)2 (D) C6H5N(C2H5)2
AlCl
Q.7 + CH 3CH 2CH 2CH 2Cl ¾¾¾3 ® hydrocarbon (X) major product X is:
CH 3
|
(A) CH 2CH - CH3 (B) C - CH 3
| |
CH3 CH 3
(C) CH2CH2CH2CH3 (D) None is correct
Q.8 In the sulphonation, acetylation and formylation of benzene the group of effective electrophiles
would be :
+ + + +
(A) SO 3+ ,CH 3C º O, HCO (B) SO 3 , CH 3 - C º O, HC O
(C) SO3, CH3CHO, CO + HCl (D) HSO3, CH3CO, HCO
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Q.9 o/p ratio in highest for nitration of which of the following compound ?
(A) Ethyl benzene (B) Toluene
(C) Isopropyl benzene (D) Tertiarybutyl benzene
Q.10 Which can be used to generate NO2+ in nitration of benzene ring
(A) HNO3 + H2SO4 (B) HNO3 + HClO4 (C) N2O5 (D) All
Q.11 Product obtained when benzoyl acetic acid is heated with soda-lime is:
(A) (B) (C) (D)
Q.12 For the electrophilic substitution reaction involving nitration, which of the following sequence
regarding the rate of reaction is true?
(A) k C6 H6 > k C6 D6 > k C6 T6 (B) k C6 H6 < k C6 D6 < k C6 T6
(C) k C6 H6 = k C6 D6 = k C6 T6 (D) k C6 H6 > k C6 D6 < k C6 T6
Q.13 For the electrophilic substitution reaction involving sulphonation, which of the following sequence
regarding the rate of reaction is true?
(A) k C6 H6 > k C D > k C (B) k C6 H6 < k C D < k C

6 6 6 T6 6 6 6 T6
(C) k C6 H6 = k C6 D6 = k C6 T6 (D) k C6 H6 > k C6 D6 < k C6 T6
Zn -Hg
Q.14 C6H6 ¾CH COCl
¾3¾¾® A ¾¾ ¾ ¾® B
AlCl 3 HCl
The end product in the above sequence is:

(A) Toluene (B) Ethyl benzene (C) Both the above (D) None
Q.15 p-Nitrotoluene on further nitration gives:
(A) (B) (C) (D)
Q.16 Reaction of SO3 is easier in:

(A) Benzene (B) Toluene (C) Nitrobenzene (D) chlorobenzene
Q.17 Which order is correct for the decreasing reactivity to ring monobromination of the following
compounds:
(I) C6H5CH3 (II) C6H5COOH (III) C6H6 (IV) C6H5NO2
(A) I > II > III > IV (B) I > III > II > IV (C) II > III > IV > I (D) III > I > II > IV
Q.18 The highest yield of m-product is possible by the electrophilic substitution of the following:
(A) C6H5CH3 (B) C6H5CH2COOC2H5
(C) C6H5CH(COOC2H5)2 (D) C6H5C(COOC2H5)3
Q.19 Which of the following will undergo sulphonation at fastest rate ?
(A) (B) (C) (D)
Q.20 Aniline under acidic medium, when chlorinated, produces:

(A) o-Chloro aniline (B) m-Chloro aniline
(C) p-Chloro aniline (D) Mixture of ortho and para-chloro aniline
Q.21 When sulphonilic acid (p-H2NC6H4SO3H) is treated with excess of bromine water, the product is:
(A) Tribromo product (B) Dibromo product
(C) Monobromo product (D) Tetrebromo product
Q.22 In a reaction of C6H5Y, the major product (>60%) is m-isomer, so the group Y is:
(A) –COOH (B) –Cl (C) –OH (D) –NH2
Q.23 An aromatic compound of molecular formula C6H4Br2 was nitrated then three isomers of formula
C6H3Br2NO2 were obtained. The original compound is:
(A) o-Dibromobenzene (B) m-Dibromobenzene
(C) p-Dibromobenzene (D) Both A & C
Q.24 Which of the following substituted benzene derivatives would furnish only three isomers in significant
amount when one more substituent is introduced:
Cl Cl
Cl Cl
(A) (B) (C) (D)
Cl
Cl Cl
Q.25 Which of the following is most reactive towards sulphonation?
(A) m-Xylene (B) o-Xylene (C) Toluene (D) p-Xylene
Q.26 Ring nitration of dimethyl benzene results in the formation of only one nitro dimethyl benzene. The
dimethyl benzene is:
CH3
CH3
(A) (B) (C) (D) None of these
CH3 CH3
Q.27 If meta-nitroaniline is chlorinated, the major product is:
NH2 NH2 NH2 NH2
Cl Cl
(A) (B) (C) (D)
NO2 NO2 Cl NO2 NO2
Cl
Q.28 If p-methoxy toluene is nitrated, the major product is:
CH3 CH3
NO2
(A) (B) (C) (D) No reaction
NO2
OCH3 OCH3
CrO Cl H O
Q.29 C6H5CH3 ¾¾ ¾¾® A ¾¾
2 2
¾2
®B
The functional group present in B and name of the reaction would be
(A) –CHO, Gattermann aldehyde synthesis (B) –CHO, Etard reaction
(C) –COCH3, Friedel Crafts reaction (D) –CHO, Oxo reaction
Q.30 Etard reaction in the following is:

(A) Oxidation of toluene to benzaldehyde by chromylchloride
(B) Oxidation of toluene to benzaldehyde by alkaline KMnO4
(C) Dry distillation of calcium benzoate
(D) Reaction of benzene with Cl2 in the presence of UV light
Br KMnO
Q.31 A ¬¾2¾ ¾¾ ¾
¾4 ® B
Compound A and B respectively are:

(A) o-Bromostyrene, benzoic acid (B) p-Bromostyrene, benzaldehyde
(C) m-Bromostyrene, benzaldehyde (D) Styrene dibromide, benzoic acid
Q.32 If the mixture of the following four aromatic compounds on oxidation by strong oxidising agent
gives:
, , and
(A) Mixture of C6H5CH2OH + C6H5COOH (B) Mixture of C6H5CHO + C6H5COOH

(C) Only C6H5COOH (D) None of the above
Q.33 Methyl group attached to benzene can be oxidised to carboxyl group by reacting with:
(A) Fe2O3 (B) AgNO3 (C) KMnO4 (D) CrO3
Q.34 Which of the following is/are produced when a mixture of benzene vapour and oxygen is passed
over V2O5 catalyst at 775 K?
(A) Oxalic acid (B) Glyoxal (C) Fumaric acid (D) Maleic anhydride
Q.35 Benzene on reaction with 'A' forms which on reaction with 'B' forms
'A' and 'B' are:
(A) Zn(Hg) + conc. HCl, (B) , LiAlH4
(C) , NaBH4 (D) , Zn(Hg) + conc. HCl
Q.36 Which chloroderivative of benzene among the following would undergo-hydrolysis most readily
with aq.NaOH to furnish the corresponding hydroxy derivative.
(A) O2N (B) O2N Cl (C) Me2N Cl (D) Cl
Q.37 Major product of this reaction will be :
CH Cl
¾¾3¾®
AlCl3 , D
(A) o-Xylene (B) p-Xylene (C) Both (D) m-Xylene
Q.38 For preparing monoalkyl benzene, acylation process is preferred than direct alkylation because
(A) In alkylation, a poisonous gas is evolved
(B) In alkylation, large amount of heat is evolved
(C) In alkylation, polyalkylated product is formed
(D) Alkylation is very costly
Q.39 Phenol and ethanol are distinguished by the reaction with

(A) Red litmus (B) NaHCO3 (C) FeCl3 (D) Na
Q.40 An aromatic compound 'A' C7H6Cl2, gives AgCl on bonding with alcoholic AgNO3 solution, and
yields C7H7OCl on treatment with sodium hydroxide. 'A' on oxidation gives a mono chlorobenzoic
acid which affords only one mononitro derivative. The compound A is:
CHCl2
(A) (B) (C) (D)
Q.41 + H2 ¾¾¾¾¾
High pressure ®
Ni, high temp.
(A). Which of the following can be isolated as the product of this
reaction.
(A) (B) (C) (D)
Q.42 Chloral + Cl ¾Conc

¾¾ ¾
. H 2SO 4
¾® product. The product is:
(A) Lindane (B) DDT (C) Teflon (D) Ethaneperchlorate

+
Pthalic Anhydride
HCO 3H H3O
Q.43 Acetophenone ¾¾ ¾¾® A ¾¾ ¾® B + C ¾¾ ¾ ¾ +
¾¾® Indicator (D) ; C & D are
H
(A) CH3OH & (B) PhOH &
(C) PhOH & (D) CH3OH &
Q.44 Select the reaction giving correct major product :
NO2 NH2 CH 3
Br Br
(i) Fe or Sn / HCl (i) Red hot Fe tube
(A) (B) C2H2 (ii) Me–Cl / AlCl
(ii) Br2 / water 3
(iii) Cl2 / hv
Br Cl
OH NH2 OH
:
OMe
(i) NaHCO3 (i) (NaNO2 + HCl) / 0-5ºC

(C) (ii) Me–I (D) (ii) H3PO2
+ Al O
H / H 2O
Q.45 Phenol ¾(¾
i ) NaOH
¾¾® A ¾¾ ¾¾ ® B ¾¾2¾3 ® C
( ii ) CO 2 / 140°C CH 3COOH , D
In this reaction, the end product C is:

(A) Salicylaldehyde (B) Salicylic acid (C) Phenyl acetate (D) Aspirin
Q.46 AlCl
¾¾¾3 ® ? Major Product is :
(A) (B) H3COC OH
(C) (D)
Q.47 D ? Product is:

¾¾®
(A) (B)
(C) (D) No reaction
Q.48 m-Aminophenol on treatment with NaOH and CO2 gives which of the following as major product?
NH2
(A) (B) (C) (D)
Q.49 Stability order of following singlet halocarbene is
(A) CF2 > CCl2 > CBr2 > CI2 (B) CI2 > CBr2 > CCl2 > CF2
(C) CCl2 > CF2 > CBr2 > CI2 (D) CF2 > CI2 > CCl2 > CBr2
CHCl3 / KOH
Q.50 Trans-Butene-2 Product
Solvent
Cl Cl Cl Cl
H3C Cl
(A) H3C CH3 (B) H3C H (C) (D) Both (A) & (B)
H H H CH3 H H
CHCl2Br
Q.51 Product ; Product is :
KOH
Br Cl
Br Cl
(A) (B) (C) (D)
EXERCISE # II
Q.1 In which of the following reaction t-butylbenzene is formed:
BF . HF
(A) Benzene + iso-butyl chloride, AlCl3 (B) Benzene + (CH3)2C = CH2 ¾¾3¾
¾®
(C) Benzene + t-butyl alcohol ¾H¾2SO

¾
¾4 ® (D) Benzene + (CH3)2 C= CH2 ¾AlCl
¾¾3 ®
Q.2 The replacement of a hydrogen atom in benzene by alkyl group can be brought about with the following
reagents :
(A) Alkyl chloride and AlCl3 (B) Alkene and AlCl3
(C) Alkanol and alkali (D) Alkanol and acid
Q.3 Benzene reacts with n-propyl chloride in the presence of anhydrous AlCl3 to give predominantly:
(A) n-Propylbenzene (B) Isopropylbenzene
(C) 3-Propyl-1-chlorobenzene (D) Cumene
Q.4 The structure of the compound that gives a tribromo derivative on treatment with bromine water is:
(A) (B) (C) (D)
Q.5 Electrophilic attack of NO Å

2 at meta position is observed in:
(A) (B) (C) (D)
Q.6 Which of the following will undergo nitration faster than benzene?
(A) (B) (C) (D)
Q.7 The good method for converting benzene into n-propyl benzene is:
(A) C6H6 + CH3CH2CH2Cl + Anhyd. AlCl3
(B) C6H6 + CH3CH2COCl + Anhyd. AlCl3 and then treatment with Zn/Hg/HCl
(C) C6H6 + CH3CH2COCl + Anhyd. AlCl3 and then treatment with H2 Ni
(D) C6H6 + Anhyd. AlCl3 + cyclopropane
Q.8 Which of the following can be used as reagent in Friedel Crafts reaction?
NO2
(A) (B) CH2=CH–Cl (C) CH3CH2Cl (D) CH2=CH–CH2–Cl
O O
|| ||
Q.9 Of the species PhSR, PhSR , PhSR and Ph - S - OR the meta-substituted product is obtained from
|| || ||
O O O
O O
|| ||
(A) PhSR (B) PhSR (C) PhSR (D) Ph - S - OR
|| || ||
O O O
Q.10 Amongst the following, the moderately activating group is
R
||
(A) —NHR (B) —NHCOCH3 (C) – O – C – R (D) —CH3
Q.11 False statement is / are :

(A) Although benzene contains three double bonds, normally it does not undergo addition reaction.
(B) m-Chlorobromobenzene is an isomer of m-bromochlorobenzene.
(C) In benzene, carbon uses all the three p orbitals for hybridization.
(D) An electron donating substitutent in benzene orients the incoming electrophilic group to the
meta position.
Q.12 Benzoic acid may be prepared by the oxidation of:
(A) (B) (C) (D)
Q.13 Identify reactions give ketone product ?

OEt O O
1. BF3 Anhydrous
(A) + R—C —OEt + (B) + O
2. H3O AlCl3
OEt
O
Me–C–O
+
H3O Dry distillation
(C) PhMgBr + Me–C N (D) Ca
Me–C–O
O
Q.14 Which of the following reaction(s) will give aromatic product ?
H
Cl
C=O H 2N + SbCl5
(A) H (B)
+
C=O H 2N
H
O O
HBr H
+
(C) (D) + H2N–OH
Q.15 Which of the following statements is/are not true?

(A) All ortho-para directing groups activates the ring towards electrophilic substitution.
(B) Halobenzene is ortho para directing but deactivating in nature
(C) All meta-directing groups have p-bond on the atom directly attached to the ring
(D) All meta directing groups are deactivating.
Q.16 Which of the following is not an ortho-para directing group?

r
(A) CF3 (B) CCl3 (C) –CH=CH–COOH (D) – N = C
Q.17 Which of the following does not gives Fridel-Crafts reaction?
(A) (B) (C) (D)
Q.18 Which of the following reactions of benzene proves the presence of three carbon–carbon double
bonds in it :
(A) Formation of a triozonide
(B) Hydrogenation of benzene to cyclohexane
(C) Formation of C6H6Cl6 by addition of chlorine
(D) Formation of nitrobenzene on heating benzene with a mixture of concentrated nitric acid and
sulphuric acid
Q.19 Which of the following are classified as aromatic ?

(A) 1, 2, 3-Triphenylcyclopropenium cation (B) Cyclooctatetraenyl dianion
(C) Azulene (D) Annulene [10]
Q.20 Which of the following is/are name of 1,2,3,4,5,6 - hexachloro cyclohexane :

(A) Lindane (B) Gammexane (C) 666 (D) BHC
Q.21 Among the following reaction sequences identify incorrect step :
COOMe COOMe COOMe CH2–OH Br
Cl Cl Cl Cl Cl
NaOH NaH/Me–I LiAlH4 PBr3
(I) (a) (b) (c) (d)
Cl OH OMe OMe OMe
Cl Cl Cl Cl Cl
+ –
NO2 NO2 NH2 N2Cl I
Br2+FeBr3 H2/Pd NaNO2+HCl KI

(II) (a) (b) (c) (d)
Br Br Br Br
Me Me Me Me COOH
Br +
Br +
Br
SO3 NBS/hv H / KMnO4 / H
(III) H2SO4 (b) (c) (d)
(a)
SO3H SO3H
O O
Br COOH C–OMe C–OMe
Br2 + Fe (1) Mg/Dry-ether + Na / Liq. NH3
H / MeOH
(IV) (a) (2) CO / H+
2
(c) (d)
(b)
(A) I–a ; II – b ; III – c ; IV – d (B) I–b ; II – a ; III – d ; IV – d

(C) I–a ; II – a ; III – b ; IV – d (D) I–b ; II – a ; III – d ; IV – c
Q.22 How many of following compounds are less reactive than benzene for sulphonation by
conc. H2SO4 :
O
+
OH CH3 NO2 Cl COOPh NMe3 NH–C–CH3 D
D D
D D
D
(A) 2 (B) 4 (C) 6 (D) 8
Q.23 Decide the correct order of reactivity of following compounds towards halogenation with (Cl2 + AlCl3).
COOPh CH3 Et
I II III IV
(A) I > II > III > IV (B) II > III > IV > I (C) III > II > IV > I (D) II > III > I > IV
Q.24 Which of the following method(s) is/are not used to prepare p-bromo aniline as major product :
NH 2 NH2 NH 2 NH2
Br2 CH3COCl Br2 NaOH/H2O
(A) H2O
(B) FeBr3 D
Br Br
NH 2 NH2 NH 2 NH2
H2SO4 Br2 KCN LiAlH4 Br2

(C) FeBr3 (D) NaNO2/HCl CuCN FeBr3
0-5°C D
Br Br
OH OH OH
COOH
(i) NaOH
Q.25 + X +
(ii) Acidification
COOH
X is/are -
(A) CHCl3 (B) CCl4 (C) CO2 (D) HCOOH
Q.26 Which product is/are not obtained in following reaction.

(i) CH3COCl/Anhy.AlCl3
(ii) Ph3P = CH–CH3
(iii) BH3 / THF
–
(iv) H2O2 / OH
(A) (B) (C) (D)

OH OH OH
OH
NH2
Ac2O HNO3 Chromatographic
Q.27 A B + C separation B
Pyridine + H2SO4
(Major)
+
H3O
Zn
E + HCl D + Acid
E is :
NH2 NH2
(A) (B)
NH2 NO2
(C) H2N NH–C–CH3 (D) NH2

O NH2
O2 conc.
Q.28 Cumene A Acetone + B C.
hv H2SO4 O
C +
O, H
C
O
Identify correct statement :
(A) Product C is phenophthalein indicater
(B) Product B gives CO2 effervescence with NaHCO3
(C) Product A formation involves carbocation intermediate
(D) Product B gives no colour with neutral FeCl3
Paragraph for Q.29 to Q.30
Identify reagent used and intermediate products in following conversion.
SO 3 HNO3
H2SO4 H2SO4
II I
A
Br
C B
CO2H
Mg
+
D then H
+
H
E F heat
III + IV
major minor
CH2OH CHO product product
HO
alkenes
Q.29 Identify II product -
NO2 SO3H CH3 N=O
(A) (B) (C) (D)
Q.30 (III) major product is ?

COOH
(A) (B) (C) (D)
Q.31 Match the following :

Column-I Column-II
(Properties) (Compound)
O–H
(A) CO2 is evolved from NaHCO3 (P)
OH
O2N NO2
(B) Gives libermann nitroso test (Q)
NO2
:
H–N–Me
(C) Gives yellow oily liquid with NaNO2+HCl (R)
H
(D) Evolve a colourless gas with active metals (S) N
:
Q.32 Match the column-
Column - I Column-II
(Compound) (Properties)
NO2
(A) (P) Group attached with phenyl ring is + M.
N
(B) (Q) Rate of electrophilic aromatic substitution is less than benzene ring
CH3
(C) (R) Group attached with phenyl ring will show (+H) (Hyperconjugation)
(S) Group attached with phenyl ring will show (–H) effect (Hyperconjugation)
Q.33 Match the following :

Column I Column II
(Compound) (Properties)
Cl
(A) (P) o-p directing
CH3
(B) (Q) m-directing
SO3H
(C) (R) Activating towards electrophile
ONa
(D) (S) Deactivating towards electrophile
Q.34 Match the column :
Column I Column II
(Reaction) (Product & its property)
(A) + CrO3 in CH3COOH ¾® ? (P) Tropylium ion
(B) + Ph3CÅ ¾®? (Q) Benzaldehyde
(C) + n-Pr Br + ZnCl2 ¾® ? (R) Product can oxidise by KMnO4/H+
AlCl
(D) C6H6 + CO + HCl ¾¾¾3 ® ? (S) Aromatic product obtained
Q.35 Column - I Column - II

(Reactions (Intermediate formed or type of reaction)
O – O
OH
(A) (P) Product obtained as racemic mixture
O
+ H+
(B) OH OH O O (Q) Substitution reaction
(R) Nu– Addition takes place during reaction

conc conc
(C) + HNO + H SO
3 2 4
NO2
O OH
(1) LAH
(D) (2) H2O (S) Carbocation intermediate
(T) Carbanion intermediate
EXERCISE # III
\ Q.1 Write the most stable resonating structure for the cyclohexadienyl anion formed by reaction of
methoxide ion with o-fluoronitrobenzene.
Q.2 Write the principal organic product in each of the following reactions:
H NNH
(i) + C6H5CH2SK ¾® A (ii) ¾¾2 ¾¾2 ® B
triethylene
glycol
( i ) HNO , H SO
(iii) ¾¾ ¾ ¾ ¾¾4 ® C
3 2
(iv) + CH3CH2ONa ¾® D
( ii ) NaOCH 3 ,CH 3OH
(v) + C6H5CH2SNa ¾® E
Cl NH2
(i) NaNO2 , HBr ( i ) NBS, Benzoyl peroxide ,CCl , heat

Q.3 (i) ¾¾ ¾¾ ¾¾® E (ii) ¾¾ ¾ ¾ ¾ ¾ ¾ ¾ ¾ ¾
4
¾® F
( ii ) CuBr ( ii ) NaSCH 3
NaOCH
Q.4 ¾¾ ¾¾3 ® I
CH 3OH
Q.5 Reaction of 1,2,3-tribromo-5-nitrobenzene with sodium ethoxide in ethanol gave a single product,
C8H7Br2NO3, in quantitative yield. Suggest a reasonable structure for this compound.
Q.6 Offer an explanation for the observation that 4-chloropyridine is more reactive toward nucleophiles
than 3-chloropyridine.
Q.7 The dichlorocarbene reacts with phenol in base where as it doesn’t reacts with benzene explain.
Q.8 Find out the products in given reaction sequence :
CH3–C–H mcpba (A) (B)

(i) CH2N2/D
(C)
CH2N2
(D)
CH3–MgBr
(E)
SOCl2 (ii) HOH (1 eq.)
O
1
Q.9 CHCl3/OH
N D
H
Q.10 Compare the given characteristics of aniline and cyclohexanamine :

(i) Both are primary amine
(ii) Both can be acylated by RCOCl
(iii) Both reacts with CHCl3/KOH
(iv) Both reacts with NaNO2 + HCl at 0-5ºC
(v) Both reacts with PhSO2Cl to give a compound which is soluble in KOH
(vi) Both gives coupling reaction with phenol
(vii)Both gives electrophilic substitution reaction
How many of the given characteristics are correct?
Q.11 Number of compounds which can show faster rate of nucleophilic substitution of halogen
Br
than
NO2
NO2 F Cl NO2
Cl I
(i) (ii) (iii) (iv)
NO2 NO2
NO2
F
Br
NO2
(v) (vi)
NO2
NO2
Q.12 Number of possible monochlorinated isomer of R.

O
COONa
C
Cl in
Zn–Hg
P Q R
Anhy-AlCl3 HCl
Q.13 Identify total number of reactions incorrectly match with its product ?
+
(a) N2Cl + NO2 N=N
NO2
NH2 NH2 NH2

Me
AlCl3
(b) + Me–Cl +
Me
conc.
(c) Et–OH + NaI H2SO4 Et – I
Me Me Me
Br
+ Br2 Fe +
(d)
Me Me Me
Major
product Br
Minor
product
(e) M e–CºCH + Na/Liq NH3 ¾® Me–CH = CH2
O O Br
(f) + Br2 / CCl4
Br
100 % product [Stereo specific reactions] /
Me Me + Me Me
H /
(g)
SO3H
(h) Conc.
H2SO4, 150ºC
Major product
Paragraph for Q.No. 14 to 15
For given reaction sequence molecular formula for compound 'U' is C7H6O2 & P gives negative
Fehling test.
NaOH O3
P + Q R S + P
Zn, H2O
HgSO4
H2SO4 CrO2Cl2
KMnO4
W HotRed
Fe tube
V NaOH
CaO,
U T
Q.14 Compound which is not a hydrocarbon

(A) W (B) R (C) T (D) V
Q.15 Compound S is :
CH = O
(A) CH3 – CH = O (B) Ph – CH = O (C) (D) CH – CH2 – CH
CH = O
O O
EXERCISE # IV (MAIN)
Q.1 Reaction - [AIEEE-2002]
Primary amine + CHCl3 + KOH ® product, here product will be -
(1) Cyanide (2) Isocyanide (3) Amine (4) Alcohol
Q.2 The compound formed in the positive test for nitrogen with the Lassaigne solution of an organic
compound is - [AIEEE-2004]
(1) Fe4[Fe(CN)6]3 (2) Na3[Fe(CN)6]
(3) Fe(CN)3 (4) Na4[Fe(CN)5)NOS]
Q.3 Which one of the following methods is neither meant for the synthesis nor for separation of amines
(1) Hofmann method (2) Hinsberg method [AIEEE-2005]
(3) Curtius reaction (4) Wurtz reaction
OH
– +
O Na
Q.4 + CHCl3 + NaOH ¾®
CHO
The electrophile involved in the above reaction is [AIEEE-2006]

Q
(1) dichlorocarbene ( :CCl2) (2) trichloromethyl anion (C Cl3 )
Å Å
(3) formyl cation (C HO) (4) dichloromethyl cation (C HCl2 )
Q.5 In the chemical reaction,

CH3CH2NH2 + CHCl3 + 3KOH ® (A) + (B) + 3H2O,
the compounds (A) and (B) are respectively - [AIEEE-2007]
(1) C2H5CN and 3KCl (2) CH3CH2 CONH2 and 3KCl
(3) C2H5NC and K2CO3 (4) C2H5NC and 3KCl
Å
Q.6 The electrophile, E attacks the benzene ring to generate the intermediate s –complex. Of the
following, which s –complex is of lowest energy? [AIEEE-2008]
NO2 NO2 NO2
H
H
(1) + (2) + E (3) + E
(4) + H
E
H E
Q.7 In the chemical reactions, [AIEEE-2010]
NH2
NaNO2 HBF 4
HCl, 278 K
A B
the compounds 'A' and 'B' respectively are :-

(1) Nitrobenzene and chlorobenzene (2) Nitrobenzene and fluorobenzene
(3) Phenol and benzene (4) Benzene diazonium chloride and fluorobenzene
Q.8 In the chemical reactions

NH2
¾¾¾¾
NaNO2
HCl,278K
® A ¾¾¾
CuCN
D
® B, the compounds A and B respectively are : [AIEEE-2011]
(1) Fluorobenzene and phenol (2) Benzene diazonium chloride and benzonitrile
(3) Nitrobenzene and chlorobenzene (4) Phenol and bromobenzene
Q.9 An organic compound A upon reacting with NH3 gives B. On heating, B gives C. C in presence
of KOH reacts with Br2 to give CH3CH2NH2. A is :- [JEE(Main)-2013]
(1) CH3COOH (2) CH3CH2CH2COOH
(3) CH3–CH–COOH (4) CH3CH2COOH
CH3
Q.10 The gas leaked from a storage tank of the Union Carbide plant in Bhopal gas tragedy was:-
(1) Methylisocyanate (2) Methylamine [JEE(Main)-2013]
(3) Ammonia (4) Phosgene
Q.11 On heating an aliphatic primary amine with chloroform and ethanolic potassium hydroxide, the
organic compound formed is :- [JEE(Main)- 2014]
(1) An alkyl cyanide (2) An alkyl isocyanide

(3) An alkanol (4) An alkanediol
Q.12 Sodium phenoxide when heated with CO2 under pressure at 125ºC yields a product which on
acetylation produces C. [JEE(Main)-2014]
ONa
+
125º H
+ CO2 5 atm.
B Ac2O
C
The major product C would be :
OH OCOCH3 OCOCH3 OCOCH3
COOCH3 COOH COCH3
(1) (2) (3) (4)
COOH
COCH3
Q.13 In the reaction [JEE(Main)-2015]
NH3
NaNO2/HCl CuCN/KCN
0–5°C
D D
E+N2
CH3
the product E is :-
CN CH3 COOH
(1) (2) (3) (4) H3C CH 3
CH 3 CH 3
Q.14 In the following sequence of reactions : [JEE(Main)-2015]

KMnO 4 SOCl2 H2/Pd
Toluene A B C
BaSO4
the product C is :-
(1) C6H 5CH 2OH (2) C6H5CHO (3) C6H5COOH (4) C6H5CH3
Q.15 Which of the following compounds will significant amont of meta product during mono-nitration reaction?
[JEE (Main) 2017]
OH OCOCH3 NH2 NHCOCH3
(1) (2) (3) (4)
16. Phenol react with methyl chloroformate in the presence of NaOH to form product A. A reacts with
Br2 to form product B. A and B are respectively. IIT 2018
OH OH OH Br OH
(1) and (2) and
OCH 3 OCH 3 OCH 3 OCH 3
O Br O O O
O O O O O O O O
and
(3) O O
(4) O O
Br
Br
17. Phenol on treatment with CO2 in the presence of NaOH followed by acidification produces
compound X as the major product. X on treatment with (CH3CO)2O in the presence of catalytic
amount of H2SO4 produces IIT 2018
CO 2H O
O O CH3 O O C H3
C
O CH3 O
CO 2H OH
(1) (2) (3) (4)
O C H3
CO 2H
O CO 2H
18. The major product of the following reaction is : [JEE MAIN-2019]
(1) (2) (3) (4)
19. The compounds A and B in the following reaction are, respectively : [JEE MAIN-2019]
(1) A = Benzyl alcohol, B = Benzyl isocyanide

(2) A = Benzyl alcohol, B = Benzyl cyanide
(3) A = Benzyl chloride, B = Benzyl cyanide
(4) A = Benzyl chloride, B = Benzyl isocyanide
20. The major product of the following reaction is: [JEE MAIN-2019]
(1) (2)
(3) (4)
21. The products formed in the reaction of cumene with O2 followed by treatment with dil. HCl
are: [JEE MAIN-2019]
OH
O O
(1) and H3C CH3 (2) and H3C CH3
O CH3 OH
OH
(3) and CH3 – OH (4) and H3C CH3
22. The major product obtained in the following reaction is: [JEE MAIN-2019]
OH
(CH3CO)2O/pyridine (1 eqv.)
room temp.
NH2
COCH3 OH
(2)
(1) NHCOCH3
NH2
OCOCH3 OH
(3) NH2 (4) NHCOCH3
(1) (2)
(3) (4)
24. What will be the major product in the following mononitration reaction? [JEE MAIN-2019]
(1) (2)
(3) (4)
(1) (2) (3) (4)
(1) (2)
(3) (4)
(1) (2) (3) (4)
28. Among the following four aromatic compounds, which one will have the lowest melting point ?
[JEE MAIN-2019]
(1) (2) (3) (4)
(1) (2)
(3) (4)
(1) (2)
(3) (4)
31. The increasing order of the reactivity of the following compounds towards electrophilic
aromatic substitution reactions is : [JEE MAIN-2019]
Cl CH3 COCH3
(I) (II) (III)

(1) III < II < I (2) I < III < II (3) II < I < III (4) III < I < II
32. The major product obtained in the given reaction is : [JEE MAIN-2019]
(1) (2)
(3) (4)
33. The major product ‘Y’ in the following reaction is : [JEE MAIN-2019]
(1) (2) (3) (4)
34. The major product of the following reactions is: [JEE MAIN-2019]
(1) (2) (3) (4)
35. The major products of the following reaction are: [JEE MAIN-2019]
(1) (2)
(3) (4)
36. Benzene diazonium chloride on reaction with aniline in the presence of dilute hydrochloric acid
gives: [JEE MAIN-2019]
(1) (2)
(3) (4)
37. Coupling of benzene diazonium chloride with 1–naphthol in alkaline medium will give :
[JEE MAIN-2019]
(1) (2)
(3) (4)
(1) (2)
(3) (4)
39. Polysubstitution is a major drawback in : [JEE MAIN-2019]

(1) Friedel Craft’s alkylation (2) Friedel Craft’s acylation
(3) Acetylation of aniline (4) Reimer Tiemann reaction
(1) (2) (3) (4)
41. The major product obtained in the following reaction is : [JEE MAIN-2019]
(1) (2) (3) (4)

CH2CH3
(i) alkaline KMnO4

(ii) H3O+
CH2CHO CH2COOH COCH3 COOH
(1) (2) (3) (4)
43. Aniline dissolved in dilute HC1 is reacted with sodium nitrite at 0°C. This solution was added
dropwise to a solution containing equimolar mixture of aniline and phenol in dil. HC1. The
structure of the major product is : [JEE MAIN-2019]
(1) N = N – NH (2) N=N OH
(3) N=N NH2 (4) N=N–O
44. The increasing order of reactivity of the following compounds towards aromatic electrophilic
substitution reaction is: [JEE MAIN-2019]
Cl OMe Me CN
(A) (B) (C) (D)

(1) A < B < C < D (2) D < B < A < C (3) D < A < C < B (4) B < C < A < D
CO2Et
(1) (2) (3) (4)
46. p-Hydroxybenzophenone upon reaction with bromine in carbon tetrachloride gives:

[JEE MAIN-2019]
(1) (2)
(3) (4)
EXERCISE # IV A (ADVANCE)
Q.1 The chlorination of toluene in presence of ferric chloride gives predominatly: [JEE 1986]
(A) Benzyl chloride (B) m-Chlorotoluene (C) Benzal chloride (D) o-and p-Chlorotoluene
Q.2 Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl halide due to
(A) The formation of less stable carbonium ion (B) Resonance stabilization
(C) Longer carbon-halogen bond (D) The inductive effect [JEE 1990]
Q.3 The most basic compound among the following is: [JEE 1990]
(A) Benzylamine (B) Aniline (C) Acetaniline (D) p-Nitro aniline
Q.4 Chlorination of toluene in the presence of light and heat followed by treatment with aqueous NaOH
gives:
(A) o-Cresol (B) p-Cresol
(C) 2,4-Dihydroxytoluene (D) Benzoic acid [JEE 1990]
Q.5 When nitrobenzene is treated with Br2 in presence of FeBr3 the major product formed is
m-bromonitrobenzene. Correct statements are : [JEE 1992]
(A) The electron density on meta carbon is more than on ortho and para position.
(B) The intermediate carbonium ion formed after initial attack of Br+ attack the meta position
is least destabilized.
(C) Loss of aromaticity when Br+ attacks at the ortho and para positions and not at meta position
(D) Easier loss of H+ to regain aromaticity form the meta position than from ortho and para position.
Q.6 Reaction of R–CO–NH2 with a mixture of Br2 and KOH gives R–NH2 as the main product. The
intermediates involved in this reaction are : [JEE 1992]
(A) R–CO–NHBr (B) RNHBr (C) R–N=C=O (D) R.CO.NBr2
Q.7 Choose the correct statement from the ones given below for two aniline in: [JEE 1993]
(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
Q.8 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
Q.9 Arrange in order of decreasing trend towards SE 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
Q.10 Among the following statements on the nitration of aromatic compounds, the false one is:
(A) The rate of benzene is almost the same as that of hexadeuterobenzene [JEE 1997]
(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
Q.11 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
Q.12 Benzyl chloride (C6H5CH2Cl) can be prepared from toluene by chlorination with: [JEE 1998]
(A) SO2Cl2hn (B) SOCl2 (C) Cl2 hn (D) NaOCl
Q.13 The most unlikely representation of resonance structure of p-nitrophenoxide ion is:[JEE 1998]
(A) (B) (C) (D)
Q.14 Benzenediazonium chloride on reaction with phenol in weakly basic medium gives: [JEE 1998]
(A) Diphenyl ether (B) p-hydrooxyazobenzene
(C) Chlorobenzene (D) Benzene
Q.15 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
Q.16 Toluene, when treated with Br2/Fe, gives p-bromotoluene as the major product, because the CH3
group: [JEE 1999]
(A) is para directing (B) is meta directing
(C) activates the ring by hyperconjugation (D) deactivates the ring
Q.17 Amongst the following the strongest base is: [JEE 2000]
(A) C6H5NH2 (B) p-O2NC6H4NH2 (C) m-O2NC6H4NH2 (D) C6H5CH2NH2
Q.18 Identify the correct order of reactivity in electrophilic substitution reactions of the following
compounds:
(I) (II) (III) (IV) [JEE 2002]
(A) I > II > III > IV (B) IV > III > II > I (C) II > I > III > IV (D) II > III > I > IV
( CH ) NH NaNO 2 HCl 0°-5° C

Q.19 F NO2 ¾¾ ¾
3 2
¾¾® A ¾(i)
¾ ¾¾ ¾ ¾ ¾¾® B [JEE 2003]
DMF (ii) H 2 Catalytic Reduction
(A) O2N NH2 (B) N NH2
H3 C
(C) N NO2 (D) N NO2
H2 C
NH2
Br
Q.20 ¾¾2 ® [JEE 2004]
Fe
Major product of above reaction is:
(A) (B)
(C) (D)
Q.21 Which of the following is obtained when 4-Methylbenzenesulphonic acid is hydrolysed with excess
of sodium acetate? [JEE 2005]
—+
(A) CH3 CO O N a (B) CH3 + SO3
+
(C) CH3 SO 3- N a + CH3COOH (D) CH3 SO2O. COCH3 + NaOH
Q.22 CH3NH2 + CHCl3 + KOH ® Nitrogen containing compound + KCl + H2O. Nitrogen containing
compound is [JEE 2006]
— + + —
(A) CH3–C º N (B) CH3–NH–CH3 (C) CH 3 - N º C (D) CH 3 N º C
AlCl (i) O / D
Q.23 + Cl - CH 2CH 2 - CH3 ¾¾¾3 ® P ¾¾¾
2
¾® Q + Phenol [JEE 2006]
(ii ) H 3O +
The major products P and Q are
(A) and CH3CH2CHO (B) and CH3COCH3
(C) and CH3COCH3 (D) and CH3CH2CHO
Question No. 24 to 26 ( 3 questions)

Comprehension I
RCONH2 is converted into RNH2 by means of Hofmann bromamide degradation.
O O O
Cl Cl Cl
NH2 NH–Br N–Br
••
(i) (ii) (iii)
O–M+ O
O C
H2N Cl N Cl N Cl
H
(vi) (v) (iv)
In this reaction, RCONHBr is formed from which this reaction has derived its name. Electron donating
group at phenyl activates the reaction. Hofmann degradation reaction is an intramolecular reaction.
Q.24 How can the conversion of (i) to (ii) be brought about? [JEE 2006]
(A) KBr (B) KBr + CH3ONa
(C) KBr + KOH (D) Br2 + KOH
Q.25 Which is the rate determining step in Hofmann bromamide degradation? [JEE 2006]
(A) Formation of (i) (B) Formation of (ii)
(C) Formation of (iii) (D) Formation of (iv)
Q.26 What are the constituent amines formed when the mixture of (i) and (ii) undergoes Hofmann
bromamide degradation ? [JEE 2006]
15
CONH2 CONH2
D
(i) (ii)
15 15
(A) NH2 , NH2 , NH2 , NH2
D D
15
(B) NH2 , NH2
D
15 15
(C) NH2 , NH2
15
(D) NHD ,
Paragraph for Question Nos. 27 to 30 (4 questions)

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 salicylaldehydes as depicted below.
OH O1NaÅ OH
CHO CHO
aq. HCl
[I]
[Intermediate]
CH3 CH3 CH3
(I) (II) (III)
Q.27 Which one of the following reagents is used in the above reaction ? [JEE 2007]
(A) aq. NaOH + CH3Cl (B) aq. NaOH + CH2Cl2
(C) aq. NaOH + CHCl3 (D) aq.NaOH + CCl4
Q.28 The electrophile in this reaction is [JEE 2007]

(A) ·· CHCl (B) +CHCl2 (C) ·· CCl 2 (D) · CCl 3
Q.29 The structure of the intermediate I is [JEE 2007]
O1NaÅ O1NaÅ O1NaÅ O1NaÅ

CH2Cl CHCl2 CCl3 CH2OH
(A) (B) (C) (D)
CH3 CH3 CH3 CH3
Q.30 In the following reaction, [JEE 2007]
conc . HNO
¾¾ ¾ ¾ ¾3 ® X
conc. H SO
2 4
the structure of the major product 'X' is

O2N
O O
(A) (B)
N NO2 N
H H
O O
(C) (D)
N O2N N
H H
NO2
Q.31 Statement - 1 : Bromobenzene upon reaction with Br2 / Fe gives 1, 4-dibromobenzene as the major
product.
and
Statement-2 : In bromobenzene, the inductive effect of the bromo group is more dominant than the
mesomeric effect in directing the incoming electrophile.
(A) Statement-1 is True, Statement-2 is True ; Statement-2 is a correct explanation for Statement-1
(B) Statement-1 is True, Statement-2 is True ; Statement-2 is NOT a correct explanation for Statement1
(C) Statement-1 is True, Statement-2 is False
(D) Statement-1 is False, Statement-2 is True [JEE 2008]
Q.32 Statement-1 : Aniline on reaction with NaNO2 / HCl at 0°C followed by coupling with b-naphthol
gives a dark blue coloured precipitate.
and
Statement-2 : The colour of the compound formed in the reaction of aniline with NaNO2 / HCl at
0° followed by coupling with b-naphthol is due to the extended conjugation.
(A) Statement-1 is True, Statement-2 is True ; Statement-2 is a correct explanation for Statement-1
(B) Statement-1 is True, Statement-2 is True ; Statement-2 is NOT a correct explanation for Statement1
(C) Statement-1 is True, Statement-2 is False
(D) Statement-1 is False, Statement-2 is True [JEE 2008]
OH
Q.33 In the reaction NaOH(aq) / Br

¾¾¾¾¾¾ 2
® the intermediate(s) is(are) – [JEE 2009]
O O O O
Br
(A) (B) (C) (D)
Br
Br Br Br Br
Q.34 The compounds P, Q and S [JEE 2009]
O
COOH OCH3 C
O
HO H3 C
P Q S
were separately subjected to nitration using HNO3 / H2SO4 mixture. The product formed in each
case respectively, is
COOH OCH3 O
(A) C
HO H3 C O
NO2 NO2 O2 N
COOH OCH3 O
(B) C
HO NO2 H3C O
NO2 NO2
O NO2
COOH OCH3
C
(C) O
HO H3 C NO2
NO2
O
COOH OCH3
C
(D) O NO2
HO H3C NO2
NO2
Q.35 The correct acidity order of the following is : [JEE 2009]

OH OH COOH COOH
(I) Cl (III) CH3

(II) (IV)
(A) (III) > (IV) > (II) > (I) (B) (IV) > (III) > (I) > (II)
(C) (III) > (II) > (I) > (IV) (D) (II) > (III) > (IV) > (I)
Q.36 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 ——3C —— C —— CH3
HO H CH3
(A) CH3 at C - 4 (B) H at C - 4 (C) CH3 at C - 2 (D) H at C - 2
Q.37 Match the reactions in Column–I with appropriate options in Column–II.

Column–I Column–II [IIT-JEE-2010]
NaOH/H2O
(A) N2Cl + OH N=N OH (P) Racemic mixture
OH OH O
H2SO4
(B) H3C–C—–C–CH3 C CH3 (Q) Addition reaction
CH3 CH3 CH3 C
CH3
CH3
O OH
C 1. LiAlH 4
(C) + CH (R) Substitution reaction
CH3 2. H3O
CH 3
(D) HS Cl Base S (S) Coupling reaction
(T) Carbocation intermediate
O
(1) NaOH/Br2
Q.38 In the reaction H3C C O T.
(2) C
NH2 Cl
(i)
The structure of the Product T is : [JEE 2010]
O
(A) H3C C O (B) NH
O–C C CH3
O
O
(C) H3C NH (D) H3C C O
C NH–C
O
Q.39 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
Q.40 Match the reactions in Column-I with appropriate types of step/reactive intermediate involved in
these reactions as given in Column-II
Column-I Column-II [IIT-JEE-2012]
H3C O O
O
(A) ¾¾¾¾
aq NaOH
® (P) Nucleophilic substitution
O O
(B) CH2CH2CH2Cl ¾¾¾ ¾

CH 3MgI
® CH3 (Q) Electrophilic substitution
18 O
O
18
(C) CH2CH2CH2OH ¾¾¾
H 2SO 4
® (R) Dehydration
CH2CH2CH2C(CH3)2
(D) ¾¾¾
H 2SO 4
® (S) Nucleophilic addition
OH
H3C CH3
(R) Carbanion
Q.41 Among P, Q, R and S, the aromatic compound(s) is / are : [JEE 2013]
Cl
¾¾¾
AlCl3
® P
¾¾¾
NaH
® Q
¾¾¾¾
(NH 4 )2 CO3
100 -115ºC
® R
OO
O
¾¾®
HCl S
(A) P (B) Q (C) R (D) S
Q.42 The major product(s) of the following reaction is (are) - [JEE 2013]
OH
AqueousBr2 (3.0 equivalents)

¾¾¾¾¾¾¾¾¾¾ ®
SO3H
OH OH OH OH
Br Br Br Br Br
Br Br Br Br Br
SO3H Br Br SO3H
(P) (Q) (R) (S)
(A) P (B) Q (C) R (D) S
Q.43 In the following reaction, the product (s) formed is (are) [JEE 2013]
OH
CHCl3
¾¾¾ ®
1
OH
CH3
O OH OH
OH
CHO
OHC CHO
H3 C CHCl2 H3 C CHCl2 CH3

CH3
(P) (Q) (R) (S)
(A) P (major) (B) Q (minor) (C) R (minor) (D) S (major)
Paragraph for Question 44 and 45

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
COOH COOH COOH
(S) (T) (U)
Q.44 In the following reaction sequences V and W are , respectively -

H2 / Ni
Q ¾¾¾D ®V
AlCl3 (anhydrous) 1.Zn -Hg/ HCl

+V ¾¾¾¾¾¾¾ ® ¾¾¾¾¾¾
2.H PO
®W
3 4
O
CH2OH
(A) O and (B) and
CH2OH
O (V) (W)
O
(V) (W)
O
HOH2C
(C) O and (D) and
CH2OH CH2OH
O (V)
(W)
(V) (W)
Q.45 Compounds formed from P and Q are respectively
(A) Optically active S and optically active pair (T, U)
(B) Optically inactive S and optically inactive pair (T, U)
(C) Optically active pair (T, U) and optically active S
(D) Optically inactive pair (T, U) and optically inactive S
Q.46 In the reaction shown below, the major product(s) formed is / are : [JEE 2014]
NH2
NH2 ¾¾¾¾¾
acetic anhydride
CH 2 Cl2
¾® product(s)
H
N CH3 NH2
O
(A) + CH3COOH (B) H + CH3COOH
NH2 N CH3
O O O
H Å 1
N CH3 NH3CH3COO
O
(C) H + H2O (D) H
N CH3 N CH3
O O O O
Q.47 The reactivity of compound Z with different halogens under appropriate conditions is given
below : [JEE 2014]
OH mono halo substituted derivative when X2=l2

X2
di halo substituted derivative when X2=Br2
C(CH3)3
Z tri halo substituted derivative when X2=Cl2
The observed pattern of electrop hilic substitution can be explained by -
(A) The steric effect of the halogen (B) The steric effect of the tert-butyl group
(C) The electronic effect of the phenolic group (D) The electronic effect of the turt-butyl group
Q.48 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
(Q) (2) Scheme II

OH
(i) Sn/HCl (ii) CH3COCl (iii) conc.H2SO4

(iv) HNO3 (v) dil.H2SO4, heat (vi) HO–
? C6H6N2O2
NO2
(R) (3) Scheme III
(i) red hot iron, 873 K (ii) fuming HNO3, H2SO4, heat
(iii) H2S.NH3 (iv) NaNO2, H2SO4 (v) hydrolysis
? C6H5NO3
NO2
(S) (4) Scheme IV
CH3
(i) conc. H2SO4, 60ºC

(ii) conc. HNO3, conc. H2SO4 (iii) dil. H2SO4, heat
? C6H5NO4
Code :
P Q R S
(A) 1 4 2 3
(B) 3 1 4 2
(C) 3 4 2 1
(D) 4 1 3 2
Q.49 The major product U in the following reactions is : [IIT 2015]
+
CH2=CH–CH 3,H radical initiator, O 2
high pressure, heat T U
H
O
O H3 C CH3
CH3 O
(A) (B) O H
H
O
O CH 2
CH2 O H
O
(C) (D)
Q.50 In the following reactions, the major product W is : [IIT 2015]

OH
NH2 , NaOH
NaNO2, HCl
0º C
V W
OH
N=N OH N=N
(A) (B)
HO
OH
N=N
(C) N=N (D)
Q.51 Among the following the number of reaction(s) that produce(s) benzaldehyde is : [IIT 2015]
CHCl2
CO, HCl H2 O
I. II.
Anhydrous AlCl3/CuCl 100°C
CO2Me
COCl DIBAL-H
III. H2 IV. Toluene, –78°C
Pd-BaSO4 H2 O
Q.52 The correct statements(s) about of the following reaction sequence is(are) [IIT 2016]
(i) O2 CHCl3/NaOH
Cumene(C9H12) + P Q (major) + R (minor)
(ii) H3O
NaOH
Q S
PhCH2Br
(A) R is steam 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
Q.53 The product(s) of the following reaction sequence is(are) [IIT 2016]
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
Q.54 Among the following reaction(s) which gives (give) tert-butyl benzene as the major product is(are)
[IIT 2016]
Br
Cl
(A) (B)
NaOC2H5 AlCl3
OH
(C) (D)
H2SO 4 BF3.OEt2
Q.55 The major product of the following reaction is [IIT 2017]
OH
i) NaNO2, HCl, 0ºC

NH2 ii) aq. NaOH
+
OH O Na
N=N OH OH
(A) (B) (C) (D)
Cl N2Cl
N=N
Answer Q.56, Q.57 and Q.58 by appropriately matching the information given in the three
columns of the following table. [IIT 2017]
Q.56 For the synthesis of benzoic acid, the only CORRECT combination is
(A) (III) (iv) (R) (B) (IV) (ii) (P) (C) (I) (iv) (Q) (D) (II) (i) (S)
Q.57. The only CORRECT combination in which the reaction proceeds through radical mechanism is
(A) (I) (ii) (R) (B) (II) (iii) (R) (C) (III) (ii) (P) (D) (IV) (i) (Q)
Q.58 The onlty CORRECT combination that give two different carboxylic acids is
(A) (IV) (iii) (Q) (B) (III) (iii) (P) (C) (II) (iv) (R) (D) (I) (i) (S)
Paragraph for Q. No. 59 to 60
The reaction of compound P with CH3MgBr (excess) in (C2H5)2O followed by addition of H2O gives Q.
The compound Q on treatment with H2SO4 at 0ºC 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] [IIT 2017]
(H3C)3C CO2Et
Q R S
P
Q.59 The reactions, Q to R and R to S, are
(A) Dehydration and Friedel-Crafts acylation
(B) Friedel-Crafts alkylation, dehydration and Friedel-Crafts acylation
(C) Aromatic sulfonation and friedel-Crafts acylation
(D) Friedel-Crafts alkylation and Friedel-Crafts acylation
Q.60 The product S is
HO2S H3C CH
(A) (H3C)3C O (B) (H3C)3C 3
CH3
COCH3 COCH3
COCH3
(H3C)3C CH3 H3COC
(C) (D) (H C) C H3C CH3
3 3
PARAGRAPH Q.61 to Q.62

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 H2/Pd-C, followed by H3PO4 treatment gives Z as the major product.
[IIT 2018]
Q.61 The compound Y is
(A) (B)
(C) (D)
Q.62 The compound Z is
(A) (B)
(C) (D)
Q.63 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) Br2, CH3CO2H (2) Br2/H2O (excess) [IIT 2018]
R + S major product(s)
(3) H3O (3) NaNO2,HCl/273-278K
(4) NaNO2, HCl/273-278K (4) H3PO2
(5) EtOH
Br Br Br Br
Br Br
(A) (B) (C) (D)
Br Br Br
Br Br Br
Br
Br Br
Q.64 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) [IIT 2018]
O
NaOBr A NH3 ,  Br2/KOH Br2(3 equiv)

+ B C D
H3O (60%) (50%) (50%) AcOH (100%)
Q.65 Schemes 1 and 2 describe the conversion 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_________ [IIT 2019]
Scheme 1 :
NH2
(i) Br2 (excess), H2O
(ii) NaNO2, HCl, 273K
(iii) CuCN/KCN
Q
(iv) H3O+,  (major)
P (v) SOCl2, pyridine
Scheme 2 :
(i) Oleum
(ii) NaOH, 
S
+
(iii) H (major)
R (iv) Br2, CS2, 273 K
Scheme 3 :
(i) NaOH
S T
(ii) Q (major)
66. Choose the correct option(s) for the following reaction sequence [IIT 2019]
i) SOCl2
CHO i) Hg2+, dil. H2SO4
pyridine
ii) AgNO3, NH4OH Zn-Hg
Q ii) AlCl3
R Conc. HCl S
iii) Zn-Hg, conc. HCl
MeO
Consider Q, R and S as major products
(A)
MeO MeO
R O S
(B) CO2H
MeO MeO
Q R O
OH
(C) CO2H
MeO MeO
Q S
(D)
MeO MeO
O
R S
67. Choose the correct option(s) that gives(s) an aromatic compound as the major product
Br [IIT 2019]
NaOEt UV, 500 K
(A) (B) + Cl2 (excess)
H3C Br
i) alc. KOH
ii) Na NH2
NaOMe
(C) Br iii) red hot iron tube, 873 K
(D)
EXERCISE # IV (B)
AlCl
Q.1 + (CH3)2CH.CH2Cl ¾¾¾3 ® (A) [JEE 1992]
( i ) Br ,Heat ,Light
Q.2 C6H5C2H5 ¾¾ ¾
2
¾ ¾ ¾® [JEE 1994]
( ii ) NaCN
Q.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]
Q.4 Toluene reacts with bromine in the presence of light to give benzyl bromine while in presence of
FeBr3 it gives p-bromotoluene. Give explanation for the above observations. [JEE 1996]
Q.5 Show the steps to carry out the following transformations: [JEE 1998]
(a) Ethylbenzene ¾® benzene (b) Ethylbenzene ¾® 2-phenylpropionic acid
alcoholic KOH , heat

Q.6 C6H5CH2CHClC6H5 ¾¾ ¾ ¾ ¾ ¾¾® (A) + (B) [JEE 1998]
(Cis and trans forms)

Q.7 Normally, benzene gives electrophilic substitution reaction rather than thus electrophilic addition
reaction although it has double bonds. [JEE 2000]
Q.8 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 synthetic scheme. [JEE 2001]
Q.9 Carry out following conversions in 3 or less steps.
¾¾® [JEE 2003]
Q.10 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]
Q.11 7-bromo-1, 3, 5-cycloheptatriene is ionic compound, whereas 5-bromo-1,3-cyclopentadiene can't
ionise even in the presence of AgÅ, Explain why? [JEE 2004]
Q.12 Give reasons: [JEE 2005]
(a) (i) C2 H 5OH ( aq.) C H OH ( aq.)

¾¾ ¾ ¾ ¾® acidic solution (ii) ¾¾ ¾ ¾ ¾® neutral
2 5
¾NaOH
¾ ¾(¾aq.)
(b) (i) ¾® F (liberated) (ii) ¾NaOH
¾ ¾(¾ ¾® F is not liberated
aq.)
Conc .HNO Conc .HNO

(c) (i) ¾¾ ¾ ¾¾3 ® + (ii) ¾¾ ¾ ¾¾3 ®
Conc.H 2SO 4 Conc.H 2SO 4
¾Pd
¾¾ /C
®
3 moles of H 2
(d) is formed but not
NaBr + MnO 2
Q.13 æç pungent
Brown fumes and ö B ¬¾ Conc .HNO 3
÷ ¾ ¾¾¾ A ¾¾ ¾ ¾ ¾® C(intermediate) D(Explosive product)
è smell ø
Find A, B, C and D. Also write equations A to B and A to C. [JEE 2005]
Q.14 The maximum number of isomers (including stereoisomers) that are possible on mono-chlorination
of the following compounds, is [JEE 2011]
CH3
C
CH3CH2 CH2CH3
H
ANSWER KEY
EXERCISE-I
1. B 2. C 3. C 4. C 5. C
6. B 7. D 8. B 9. B 10. D
11. A 12. C 13. A 14. B 15. A
16. B 17. B 18. D 19. B 20. B
21. A 22. A 23. B 24. C 25. A
26. C 27. B 28. B 29. B 30. A
31. D 32. C 33. C 34. D 35. D
36. A 37. D 38. C 39. C 40. A
41. A 42. B 43. C 44. A 45. D
46. A 47. A 48. C 49. A 50. B
51. C
EXERCISE-II
1. ABCD 2. ABD 3. BD 4. BCD 5. ABC
6. ABD 7. BD 8. CD 9. CD 10. BC
11. BCD 12. AB 13. ABCD 14. ABC 15. AC
16. ABD 17. BCD 18. ABC 19. ABC
20. ABCD 21. C 22. B 23. A 24. ACD
25. BC 26. ABD 27. A 28. A 29. B
30. A
31. AQ; BPRS; CRS; DPQRS
32. AQ; BP; CR;
33. APS; BPR; CQS; DPR
34. AQRS; BPRS; CRS; DQRS;
35. ART; BRS; CQS; DPR;
EXERCISE-III
O¯ O
NO2 N
F OCH3
Q.1 F
SCH2–C6H5 NH–NH2 CF3 OCH2CH3 SCH2–C6H5

NO2 NO2 NO2 NO2
Q.2 (i) (ii) (iii) (iv) (v)
NO2
CH3 NO2 OCH 3 NO2 NO2
Cl Br
Br
Q.3 (i) (ii)
CH2 OCH3
CH3 S
Q.4
OCH3
N
Br Br
Br OC2H5
Q.5
O2N Br O2N Br
Q.7 Due to more electron density
Q.8 (A) CH3 – C – OH (B) CH3 – C – Cl (C) CH3 – CH2 – C – OH
O O O
(D) CH3 – CH2 – C – OCH3 (E) CH3 – CH2 – C – CH3
O O
Cl
Q.9
N
10. 5 11. 3 12. 4 13. 7 14. B 15. C
EXERCISE-IV (JEE-MAIN)
1. 2 2. 1 3. 4 4. 1 5. 4 6. 2
7. 4 8. 2 9. 4 10. 1 11. 2 12. 3
13. 1 14. 2 15. 3 16. 4 17. 2 18. 2
19. 4 20. 3 21. 1 22. 2 23. 1 24. 2
25. 4 26. 2 27. 3 28. 1 29. 4 30. 4
31. 4 32. 4 33. 1 34. 2 35. 3 36. 1
37. 2 38. 2 39. 1 40. 4 41. 2 42. 2
43. 3 44. 3 45. 3 46. 3
EXERCISE-IV- A (JEE-ADVANCE)
1. D 2. B 3. A 4. D 5. AB
6. C 7. C 8. D 9. C 10. C
11. A 12. AC 13. C 14. B 15. D
16. AC 17. D 18. C 19. B 20. D
21. C 22. D 23. C 24. D 25. D
26. B 27. C 28. C 29. B 30. B
31. C 32. D 33. ABC 34. C 35. A
36. D 37. A-RS; B-T; C-PQ; D-R; 38. C 39. C

40. A-RST; B-PS; C-RS; D-QR; 41. ABCD 42. B 43. BD
44. A 45. B 46. A 47. ABC 48. C

49. B 50. A 51. 4 52. BC 53. B
54. BCD 55. C 56. D 57. A 58. B
59. D 60. B 61. C 62. A 63. D
64. 495 65. 4.00 66. 1AB 67. CD
EXERCISE-IV-B (SUBJECTIVE)
Q.1
Br
Q.2 ¾¾2 ®
D ,hg ¾NaCN
¾¾®
Q.3 (A) (B) (C)
Q.4 In presence of FeBr3, Br2 produces Br+(an electrophile) which attacks the benzene ring at o-,p-position
to give p-bromotoluene. In presence of light, side chain is attacked to produce benzyl bromide.
C2H5 COOH
Q.5 (b) (i) ¾[¾®

O]
¾Soda
¾ ¾lim¾e®
CN COOH
CH2CH3 CHXCH3 CHCH3 CHCH3
2
(ii) ¾X¾® ¾KCN
¾¾® ¾HOH
¾¾®
hv
KOH ( alc.)
Q.6 C6H5CH2CHClC6H5 ¾¾ ¾ ¾® C6H5CH= CHC6H5
D
(Cis and trans forms)
Q.7 Benzene has resonance stabilization due to delocalisation of p-electrons. Also during electrophilic
addition reactions, it loses its aromaticity. In electrophilic substitution reaction aromaticity is retained.
Q.8 NaOH
¾¾ ¾¾® ¾Me
¾¾ ¾®
SO
conc . H SO
¾¾ ¾2¾¾4 ® ¾NaOH
¾¾®
D high Pr essure 2 4
H O+
¾¾
3
¾®
Alternative rout
+
conc.H2SO 4 NaOH NaOH H 3O
Me2SO 4 high
Pressure
conc . H SO HBF / KHF

Q.9 ¾¾ ¾2¾¾4 ® ¾¾ ¾
4
¾¾2 ®
D D
Q.10 l
(A) (B)
Keto Enol
Enol form is more stable due to extended conjugation
(A) ¾KMnO
¾¾ ¾4 ®
Q.11 On ionization 7-bromo-1,3,4-cycloheptatriene gives tropolium ion which is aromatic with 6p electrons.
l + Brr
5-bromo-1,3-cyclopentadiene can't ionise as it will in that case give highly unstable antiaromatic
cation with 4 p electrons.
Å
+ Brr
CH 3
|
Q.12 (a) (i) H5C6 - C - OC2 H 5 + HBr(acid) ; (ii) no reaction due to partial double bond character
|
CH 3
(b) (i) + F– is liberated ; (ii) Bimomecular mechanism is not possible in (ii) case
(c) (i) Due to presence of lone pair of nitrogen atom NO group is electron donating and ortho, para
directing
(ii) NO2 group is electron withdrawing and meta directing
(d) Due to reduction of central ring, three four membered antiaromatic rings become stable while
on recuction of terminal ring only one antiaromatic ring can be stabilized.
Q.13 (A) H2SO4, (B) Br2, (C) NO Å

2 , (D)
Q.14 (8)
2019
100 Percentile 99.99 Percentile 99.98 Percentile 99.98 Percentile 99.97 Percentile 99.97 Percentile 99.96 Percentile 99.96 Percentile
HIMANSHU GAURAV SINGH GAURAV KRISHAN GUPTA SARTHAK ROUT VIBHAV AGGARWAL RITVIK GUPTA BHAVYA JAIN AYUSH PATTNAIK SAYANTAN DHAR
2019 (*SDCCP) 2020 (DLP) 2020 (CCP) 2019 (CCP) 2020 (DLP) 2020 (CCP) 2019 (CCP) 2020 (DLP)
Child Help Line No. 1098, Hope Society Kota + 91-72443 33666

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ENTHUSE

- Paracetamol is non narcotic analgesic drug which is also known as

- Aspirin is non narcotic analgesic drug which is also known as

AIR-1 AIR-3 AIR-6 AIR-8

JEE MAIN RESULTS 2020 (January Attempt) OF NUCLEUS EDUCATION

JEE ADVANCED RESULTS OF NUCLEUS EDUCATION

AIR-10 AIR-12 AIR-23 AIR-24 AIR-37 AIR-42 AIR-66 AIR-98

AIR-20 AIR-27 AIR-32 AIR-61 AIR-67 AIR-78 AIR-61 AIR-91

AIR-2 AIR-19 AIR-33 AIR-48 AIR-51 AIR-53 AIR-86

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

Q.2 Which of the following group is divalent:

Q.3 Benzene is a resonance hybrid mainly of two Kekule structures. Hence:

Q.4 How many p electron are there in the following species :

(A) 2 (B) 4 (C) 6 (D) 8

Q.5 The number of benzylic hydrogen atoms in ethylbenzene is:

(C) CH2CH2CH2CH3 (D) None is correct

(C) SO3, CH3CHO, CO + HCl (D) HSO3, CH3CO, HCO

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

(A) k C6 H6 > k C6 D6 > k C6 T6 (B) k C6 H6 < k C6 D6 < k C6 T6

(C) k C6 H6 = k C6 D6 = k C6 T6 (D) k C6 H6 > k C6 D6 < k C6 T6

(A) k C6 H6 > k C D > k C (B) k C6 H6 < k C D < k C

(C) k C6 H6 = k C6 D6 = k C6 T6 (D) k C6 H6 > k C6 D6 < k C6 T6

The end product in the above sequence is:

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

Q.16 Reaction of SO3 is easier in:

Q.19 Which of the following will undergo sulphonation at fastest rate ?

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

Q.20 Aniline under acidic medium, when chlorinated, produces:

Q.30 Etard reaction in the following is:

Compound A and B respectively are:

(A) Mixture of C6H5CH2OH + C6H5COOH (B) Mixture of C6H5CHO + C6H5COOH

'A' and 'B' are:

(A) Zn(Hg) + conc. HCl, (B) , LiAlH4

(C) , NaBH4 (D) , Zn(Hg) + conc. HCl

(A) O2N (B) O2N Cl (C) Me2N Cl (D) Cl

Q.37 Major product of this reaction will be :

(A) o-Xylene (B) p-Xylene (C) Both (D) m-Xylene

Q.39 Phenol and ethanol are distinguished by the reaction with

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

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

Q.42 Chloral + Cl ¾Conc

(A) Lindane (B) DDT (C) Teflon (D) Ethaneperchlorate

(A) CH3OH & (B) PhOH &

(C) PhOH & (D) CH3OH &

Q.44 Select the reaction giving correct major product :

(i) NaHCO3 (i) (NaNO2 + HCl) / 0-5ºC

In this reaction, the end product C is:

(A) (B) H3COC OH

Q.47 D ? Product is:

(C) (D) No reaction

Q.49 Stability order of following singlet halocarbene is

(C) Benzene + t-butyl alcohol ¾H¾2SO

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

Q.5 Electrophilic attack of NO Å

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

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

(A) (B) CH2=CH–Cl (C) CH3CH2Cl (D) CH2=CH–CH2–Cl

Q.10 Amongst the following, the moderately activating group is

Q.11 False statement is / are :

(A) CO2 is evolved from NaHCO3 (P)