Allen Guided Revision Organic Chemistry

JEE (MAIN + ADVANCED) 2022
GUIDED REVISION JEE (Main + Advanced) 2022

ENTHUSIAST COURSE
ENTHUSIAST COURSE
ORGANIC CHEMISTRY GR # 01 SCORE-1
SECTION–I : (i) Only One option correct Type

This section contains 6 multiple choice questions. Each question has four choices (A), (B), (C) and
(D) out of which ONLY ONE is correct. 3(–1)
O
1. MeMgBr (1 eq.)
1. 2. H2O
Me Me
O
In above reaction out of the following which will be obtained in maximum yield.
HO Me O
(A) (B)
Me Me Me Me
O HO Me
Me OH Me
(C) (D) O
Me Me Me Me
HO Me OH
2. Select reaction which does not involve formation of free radical.

(A) Hundsdicker reaction (B) Wurtz reaction
(C) Williamson's ether synthesis (D) Kolbe's electrolysis synthesis
3. Which of the following will not produce methane with MeMgBr ?
O O
(A) Ph– C –CH2– C –Ph (B) Me–C C–H (C) H2O (D)
4. Which of the following set of reagent(s) give cis-but-2-ene as a final major product starting
with (+)-2-chlorobutane.
(A) Alcoholic KOH (B) (i) CH3COOAg , (ii)
(C) (i) Alc. KOH , (ii) Br2/CCl4 , (iii) Alc. KOH ; NaNH2 , (iv) H2/Pd-BaSO4
(D) (i) Alc. KOH , (ii) Br2/CCl4 , (iii) Alc. KOH ; NaNH2 , (iv) Na/ Liq. NH3
5. Find the value of "n" in following reaction sequence :
CO2Et +
NaOEt I2 P H3O
H2C P Q R S T + nCO 2
CO2Et
(A) 1 (B) 2 (C) 3 (D) 4
ORGANIC CHEMISTRY / GR # 01 (Set-3) E-1/5

TM JEE (Main + Advanced) 2019
Path to success KOTA (RAJASTHAN )
GUIDED REVISION LEADER+ENTHUSIAST COURSE
6. CH3–CH3 CH4
Identify reagent sequence for above conversion :
(A) (i) Cl2 / hv ; (ii) Na / Et2O
(B) (i) Cl2 / hv ; (ii) Aqueous KOH ; (iii) PCC ; (iv) Red P / HI
(C) (i) Cl2 / hv ; (ii) Aq. KOH ; (iii) KMnO4 , NaOH , ; (iv) NaOH / CaO /
(D) (i) Br2 / hv ; (ii) Alc. KOH / ; (iii) O3 ,Zn ; (iv) H2, Pd
SECTION-I(ii) : One or More than one
(D) out of which ONE or MORE are correct. 4(–1)
7. Identify major product formed are correctly matched in following reactions ?

Br
O
OH NaH
HO
(A) HO
O
O
H KOH / EtOH
(B)
O
NH2
NaNO2 + HCl
(C) O
OH
+
H
(D) H2S
O O S
O
O
8. 1. CH2=CH–C–H
(P) +
(Q)
OH 2. H / H2O
Correct statements for above reaction sequence :
(A) (P) is 2º alcohol (B) (P) to (Q) involve 1,4 addition
O O
H
(C) (Q) is (D) (P) to (Q) involve 1,2 addition
E-2/4 Physics / GR # 000

GUIDED REVISION ENTHUSIAST COURSE
O
COOH NaBH4 +
H
X Y Z
9. COOH gas
Identify correct statement for above reaction sequence ?
(A) 'Z' product is sweet smelling substance
HO
+
H + O
OH OH LAH H
(B) Reaction of 'X' hemi ketal product
(C) 'Y' product librate CO2 gas with aqueous NaHCO3 and also soluble in aqueous NaOH
(D) 'Z' product is resolvable

O O
Ph O Ph +
H3O O
10. P – Q
O O MeCOO /
O
Ph
Ph
– R
OH /
Identify correct statement for above sequence ?
O
(A) Ph–C–H is 'P' product (B) Ph–CH=CH–COOH is 'Q' product
O O O
CH–Ph
(C) is 'Q' product (D) is 'R' product
SECTION–I(iii) : Paragraph Type

This section contains 2 paragraphs each describing theory, experiment, data etc. 2 or 2 questions
relate to two paragraphs . Each question of a paragraph has one OR more than one correct answer
among the four choices (A), (B), (C) and (D). 3(0)
PARAGRAPH
Paragraph for Q.No. 11 to 12
A optically active alkene (P) on reaction with H2 , Pt produces optically inactive (Q). (P) on
reaction with 1% KMnO4 followed by HIO4 produces (R) & (S). When (R) & (S) are reacted
in 1 : 2 respectively with NaOH, , it produces (T) & HCOONa.
11. Which of the following can't possible as (P) ?
(A) (B) (C) (D)
12. (T) on reaction with HCHO in acidic medium produces :

O O O O
(A) (B) (C) (D)
O O O O Ph
Ph


O O
NH2 +
H + +
H3O H
R P –gas Q R S
–H2 O Dimerise
COOH –2H2O
Se
T
13. Identify 'T' product is above sequence ?

N N N NH2
(A) (B) (C) (D)
N N NH2
14. Identify 'R' product in above sequence ?
O
NH2 H–C COOH HOOC
(A) (B) (C) (D)
O H2N O H2N O H2N O
Matching List Type
This Section contains 1 multiple choice questions. Each question has matching lists. The codes for
the lists. have choices (A), (B), (C) and (D) out of which ONLY ONE is correct. 4(0)
15. List-I List-II
(Compound) (Statements)
H O
(P) C (1) It can show tautomerism, optical isomerism but not
geometrical isomerism
Ph
H3C CHO
(Q) (2) It can show tautomerism, geometrical isomerism but
not optical isomerism
Ph
CHO
(R) (3) It can show geometrical isomerism , optical isomerism

Ph but not tautomerism
O
(S) (4) It can show tautomerism, geometrical isomerism &
also optical isomerism
Ph

Code :
P Q R S
(A) 2 1 3 4
(B) 2 3 4 1
(C) 3 2 4 1
(D) 2 3 1 4
SECTION-III : (Integer Value Correct Type)
This section contains 04 questions. The answer to each question is a single digit Integer, ranging from
0 to 9 (both inclusive) 4(–1)
1. How many of the following will give silver mirror with tollen's reagent ?
OH
O
(i) Ph–CH=O (ii) HCHO (iii) (iv) Me–C CH
OH
(v) HCOOH (vi) MeCOOH (vii) O (viii) HC CH
OH OEt
(ix) Me–CH–C–Me (x) Me–CH2–CH
OH
O
2. Total number of compounds whose molecular mass is incresed by 126 gm on reaction with
excess CH3–COCl / Pyridine :
OH
COOH
HO H
(i) CH2–CH–CH2 (ii) HO (iii) (iv) HOOC–CH–CH3
HO H
OH OH OH COOH OH
OH
NH2 OH
OH
COOH COOH
(v) (vi) (vii) CH2–—C–CH 2 (viii)

HO OH HO
COOH OH COOH OH
NH2
OH
(ix) (x)
HO H2NCH 2 CH2OH
OH
3. A tetrapeptide on hydrolysis produced glycine (gly), Leucine (Leu.), Alanine (Ala) , Valine
(Val.). Count number of possible tetrapeptides (structural isomers only) which can produce
above four amino acids with the following both conditions.
(i) Glycine is not present at N-terminal (ii) Alanine in present at C-terminal
4. A segment (X) of cellulose obtained on partial hydrolysis has molecular mass 1476 gm. On
complete acidic hydrolysis, mass of the product obtained is 1620 gm. Find out the number
of glycosidic linkage(s) present in segment (X) :
ENTHUSIAST COURSE
ENTHUSIAST COURSE

1. Amino acid (Q) obtain in following sequence is :
O
+
(i) KOH H3O
NH P Q
(ii) Br–CH2–COOEt
(A) Alanine (B) Valine (C) Glycine (D) Leucine

2. 1,4-addition polymer of CH 2=C–CH=CH 2 monomer was subjected to reductive ozonolysis.
CH 3
The product formed is :
O O O O O
(A) C (B) C—C (C) C–CH2–CH 2–C (D) All correct
H H H H H CH 3
3. In Aniline & water mixture, Aniline can be seperate by :
(A) Steam distillation (B) Fractional distillation
(C) Simple distillation (D) Distillation under reduced pressure
4. The best reaction sequence to convert 2-methyl-1-bromopropane into 4-methyl-2-
bromopentane is :
(A) (i) Mg in ether (ii) acetaldehyde (iii) NH4Cl ; (iv) SOBr2
(B) (i) NaC CH in ether (ii) H3O+ + HgSO4 (iii) HBr, heat
(C) (i) Alcoholic KOH (ii) CH3COOOH (iii) H2 / Pt (iv) HBr, heat
(D) (i) NaC CH in ether (ii) H2, Lindlar catalyst (iii) HCl , peroxide
5. The compound(s) that will NOT react(s) with hot concentrated aqueous alkali at atmospheric
pressure is/are :
Cl CHO CH2CHO Cl
NO2
(A) (B) (C) (D)
NO2 OCH3 CH3 OCH3

6. Major product (S) of following reaction is :
(i) HNO3/H2SO4 CH3COCl (i) conc. H2SO4 (i) dil. H2SO4 ,

P Q R S
(ii) Sn / HCl Pyridine (ii) HNO3 / H2SO4 (ii) NaOH
NH2 NH2 NH2 NH2

NO2 OH NO2
(A) (B) (C) (D)
SO3H NO2 NO2


7. Identify reaction correctly matched with their major product ?
OH OH
O (i) Me2SO4 / NaOH O
HO HO
(A) OH (ii) HCl, H2O OH
HO HO
OH OMe
O O
(i) Me2CuLi, Et2O

(B) +
(ii) H3O
Me
O
COOH
(i) NaOH, Br2
(C) NH +
(ii) H3O
NH2
O
Me O
OH (i) TsCl, Py.
(D) N Me–C–NH
H +
(ii) H
Ph H
Me Ph
Me
NH 2
+ – H3O
+
8. + PhN2Cl Major product Product mixture
Me
Which of the following is/are present in final reaction mixture :
OH NH2 NH2 OH
(A) (B) (C) (D)
Me Me
9. Which of the following reaction(s) / intermediate are involved in following reaction :
O
OH
Conc. O
H2SO4
(A) Nucleophilic substitution (B) Elimination

(C) Nucleophilic addition (D) Dehydration

10. Which of the following option can produce (P) as major product on reaction with dil. H2SO4
OH
(P)
(A) (2) (C) (D)

OH
11. Choose the correct option ?

(A) Cyclohexanone forms cyanohydrin in good yield but 2,2,6-trimethyl cyclohexanone does
not
(2) Tertiary amines (Me3N) have higher boiling point than primary amine (MeNH2)
(C) pKb of aniline is more than that of methyl amine
(D) PCC can oxidise 1º alcohol to aldehyde in anhydrous condition
12. Three isomeric compound M, N and P (C5H10O) give the following tests :
(i) M and P react with sodium bisulfite to form an adduct
(ii) N consumes 1 mol of bromine and also gives trubidity with conc. HCl / anhydrous ZnCl2
after prolong heating
(iii) M reacts with excess of iodine in alkaline solution to give yellow crystalline compound
with a characteristic smell.
(iv) p-Rosaniline treated with sulphur dioxide developes pink colour on shaking with P
The structures of M, N and P, respectively can be :
M N P
O OH
(A) H
O O
(B)
OH H
O H
(C)
OH O
O H
(D)
OH
O


This section contains 1 paragraph each describing theory, experiment, data etc. 2 questions relate
to two paragraphs with two questions on each paragraph. Each question of a paragraph has only one
correct answer among the four choices (A), (B), (C) and (D). 3(0)
For a long time attempts to prepare compound A ( C6H5–CH–CH=O ) in basic medium have
OH
been failed. Also hydrolysis of its diethyl acetal B ( C6H5–CH–CH(OCH2CH3)2 ) does not give
OH
compound A. Actually compound B on acidic hydrolysis gives C :
13. Compound A in basic medium converted into :
CH=O
–
(A) Ph–C—–CH–CH–C6H5 (B) Ph–C–CH=O (C) Ph–C–CH 2OH (D) Ph–CH–CO2
OH OH OH O O OH
14. Compound C is :
Ph O OH
–
(A) PhCH=CH–CH=O (B) (C) Ph–C–CH=O (D) Ph–CH–CO2
HO O Ph
O OH
Matching List Type
15. For the following sequence , match the products from list-I with correct common name in
list-II.
O O
(i) Cl2/NaOH CH3COCl
(i) 2P' + Q' (ii) P' R'
+
(ii) H Pyridine
(i) R' (i) KOH

(iii) Ph–CHO + P' + S' (iv) Phenol + Q' + T'
(ii) H3O , (ii) H
List-I List-II
(P) P' (1) Salicyaldehyde
(Q) Q' (2) Cinnamic acid
(R) T' (3) Acetic acid
(S) S' (4) Chloroform
Code :
P Q R S
(A) 4 3 1 2
(B) 3 4 2 1
(C) 4 3 2 1
(D) 3 4 1 2
16. List-I List-II
Cl
NO2
OH NO2
(P) Product (1) Product give molish test
NO2
(i) Sn + HCl
(ii) Na NO2 + HCl
(Q) OH
(T < SºC) Product (2) Product give violet colour with
–
(iii) OH neutral FeCl3
+
(R) n-glucose H Starch product (3) L.S. of product give blue colour
Polymerisation
solution with FeSO 4 solution
Polymerisation
(S) Amino acid Polymeric (4) Product give Biurate test
mixture product
Code :
P Q R S
(A) 3 2,3 1 4
(B) 2 2,3 1 3,4
(C) 3 2,3 1 3,4
(D) 3 2 4 1,3
SECTION–III : Integer Type
1. Identify reactions correctly matched with their major product ?
O O
–
O Hot
O LAH
(a) (e)
Aqueous NaOH C N C–OH
OH
O
Me Me N=N–Ph
OH OH
1. Ph–N2Cl + – Aq. NaOH
(b) (f) N C NH2
T < 5ºC
(aq. NaOH) +
+ H–COOH
2. H
O + O
1. H
COOEt OH OH
(c) 2. LAH OH
+
3. H3O
O O
NH2 Br
1. O Py.
Br Br
2. Conc. HNO3 + H2SO4
(d)
3. Aq. NaOH , 4. H2 / Pd , 5. Br2 / H2O Br
Br
6. NaNO2 + HCl (excess) , 7. CuBr + HBr
Br
2. How many of reagents can carry out following transformation :

OH O
CH3–CH–CH3 CH3–C–CH3
(a) Cu, 300ºC (b) O3 / Zn, H2O (c) NBS (d) Zn–Hg / HCl
(e) Jones reagent (f) KMnO4, NaOH, (g) Al(OCMe3)3 , O O
+
(h) Collin's reagent (i) (i) TsCl, (ii) DMSO, NaHCO3 , (j) C5H5 N HCrO3Cl (PCC)
3. Consider all possible carbonyl compounds including stereoisomers of molecular formula

C 5 H 10 O, All these isomers are independently reacted with NaCN / HCN (NOTE :
stereoisomers are also reacted separately). The total number of carbonyl compounds that
give a racemic product(s) is/are :

4. Total number of moles of CO2 evolved in following reaction per mole of compound 'M' is
KMnO4
'M'

ENTHUSIAST COURSE
ENTHUSIAST COURSE

1. Major product (Q) in following sequence is :
O
+ +
(i) Ethylene glycol , H (i) H3O ,
(P) (Q)
(ii) LAH (ii) NH2OH,
N–OH N–OH OH N–OH
(A) (B) (C) (D)
OH O N–OH N–OH
O OH O OH
2. CH3 H
Compound-I Compound-II
Correct statement about compound-I & compound-II is :

(A) Compound-I gives Tollen's test with Tollen's reagent & Compound-II gives Iodoform test
with NaOH, I2
(B) Compound-I gives Iodoform test with NaOH, I2 & Compound-II gives Tollen's test with
Tollen's reagent
(C) Both comopunds gives Tollen's test with Tollen's reagent
(D) Both comopunds gives Iodoform test with NaOH, I 2
+
3. Starch HOH / H mixture (A)
+
Glycogen HOH / H mixture (B)
+
Cellulose HOH / H mixture (C)
Which of the following mixture contain -D-glucose, after treating following polymers with
H3O for long time.
(A) Only in mixture A (B) Only in mixture B
(C) Only in mixture C (D) In all mixtures A, B & C

4. Two acyclic molecules having molecular formula C5H8 one of which shows enantiomerism &
the other shows diastereoisomerim. The two acyclic molecule are related as :
(A) Chain Isomers (B) Positional Isomers
(C) Geometrical Isomers (D) Conformation isomers
5. A certain carboxylic acid X which can be isolated form whale blubber or sardine oil on
ozonolysis with O 3 / Zn / H2O yields nonanal & 5-oxo pentanoic acid. The correct option
regarding X is :
(A) It is example of - unsaturated acid (B) Its molecular formula is C14H28O2
(C) This acid does show geometrical isomerism (D) This acid exists as (+) enantiomeric pair
COOH COOH
Reagent
6.
N C N C
NO 2 O NO 2
Above conversion is carried out with the help of :

(A) LiAlH 4 (B) NaBH4
(C) NH2–NH2 / OH / , then H (D) Zn–Hg / HCl
7. For the following sequence, choose the correct option(s) ?
COOH
Br2 NH3 N3H (i) HNO2

S R P Q
NaOH H2SO4 (ii) H2O , Boil
(X)
(A) (Q) will give positive Br2, H2O test
(B) (R) on reaction with NaNO2, HCl produces (X)
(C) Major product (P) & (S) are identical

(D) Reaction sequence involves schmidt & Hoffmann bromamide degradation reaction
8. Which of the following amino acid(s) has isoelectric point more than 7
(A) Aspartic acid (B) Phenyl alanine (C) Arginine (D) Histidine
9. Which set of reagents can carry out following conversion ?
HC CH CH3–CH2–CH2–CH3
(A) (i) HgSO4, H2SO4 ; (ii) NaOH, ; (iii) N2H4 , H2O2 ; (iv) Zn–Hg / HCl
(B) (i) NaNH2 (2 mole) ; (ii) CH3–I (2 mole) ; (iii) H2 / Pd , BaSO4 ; (iv) N2H4 , H2O2
(C) (i) H2 / Pd , BaSO4 ; (ii) HBr / H2O2 ; (iii) Na / Et2O

–
(D) (i) B2H6 ; (ii) H2O2 , O H ; (iii) Mg-Hg / H2O ; (iv) Red P / HI
10. Which of the following reaction(s) are correctly matched with their major product ?
O
O (i) LiAlH4 HO OH
(A) (ii) H2O
(B) CH3–CHO + 3Br2 + 4NaOH HCOONa + CHBr3 + 3NaBr + 3H2O
O O
NH2 –NH2
(C)
pH (4.5-6.0) N
N
H
(D)
O O
COOH
11. For the following reaction, choose the incorrect option(s) ?
CH3
HCl
H CH2–OH (P)
CH2–CH3
(–)-2-methylbutane-1-ol
(A) Formation of major product (P) involves carbocation rearrangement
(B) Major product (P) is 2-methyl but-2-ene
(C) Reaction follows bimolecular nucleophilic substitution
(D) Major product (P) is 2-chloro-2-methyl butane
12. Which of following reactions are shown with incorrect major product :
CH 3 CH 3
(A) CH3– C— ONa + CH3–Cl CH3– C— O–CH3
CH 3 CH 3
Me Me
KCN
(B) (C) D Cl
DMF
D CN
OAc H H
+
18 H3O 18
(D) O OH + OH

This section contains 1 paragraphs each describing theory, experiment, data etc. 3 questions relate
to two paragraphs with two questions on each paragraph. Each question of a paragraph has only one
correct answer among the four choices (A), (B), (C) and (D). 3(0)

Paragraph for. Q.No. 13 to 14

(i) Red-P/HI (i) Sn / HCl (i) CuCN /
D-Glucose (A) (B) (C)
(ii) Al2O3 , Cr2O3 / (ii) NaNO2 + HCl (ii) SnCl2 + HCl
(iii) Conc. 0–5ºC (iii) HOH / H
+ O
–
(H2SO4 + HNO3)
H H OH
(1 eq.)
(D) + (E)
Aromatic
compound
13. Select correct statement among following :
(A) Compound 'C' on treating with conc. NaOH show disproportionation reaction
(B) Compound 'C' form diazonium salt with aq. HNO2 or (NaNO2 + HCl) / 0–5ºC
(C) Compound 'C' give foul smelling compound with (CHCl3 + KOH)
(D) Compound 'C' is primary amine
14. Select the correct statement / reaction among following :
Cl
NO2
(i) H2O / Cl2 / AlCl3
(A) Comopund-B OMe (B) Compound-A
(ii) Na
(iii) Me–Cl
– +
(C) Compound-D is Ph–CH2–N=CH2 (D) Compound-E is Ph–COONa
SECTION–I(iv) Matching List Type
15. List-I List-II
NH2
CHCl3 + KOH
(P) (1) Aryl halide is obtained as a product
+ –
N NCl
CuCl , HCl
(Q) (2) It is electrophilic substitution reaction
Cu
(R) (3) Reaction is isocyanide test
CH3
Conc. HNO3
(S) (4) New carbon-carbon bond is formed in product
Conc. H2SO4
Code :
P Q R S
(A) 4 1 2 3
(B) 3 1 4 2
(C) 1 2 4 3
(D) 3 1 2 4
SECTION–III : Integer Type

1. "X" dichloro derivatives are possible for n-butane. What will be the value of (X – 3) :
2. Identify total number of chiral centre present in product of following reaction :
CH2OH
H O
O
H (i) Hg(OAc)2 / MeOH Me–C–Me
(ii) NaBH4 + Product
OH H
HO
H
3. Identify total number of compounds which librate CO2 gas on reaction with aqueous NaHCO 3?
OH COOH
HO O HO OH
(a) (b) OH (c) (d)

O
O O
HO
OH OH
CH3 C CH
(e) (f) ; (g) H2SO4 (h) MeCOOH
4. Identify total number of free radicals which have sp2 hybridised central atom (having free
radical) :
O
O O O
CF3 O2N–CH2 Ph–CH2
SECTION–IV : Matrix Match

This section contains ONE questions. Each question contains two columns, Column-I and
Column-II. Column-I has four entries (A), (B), (C) and (D) Column-II has five entries
(P), (Q), (R), (S) and (T) Match the entries in Column-I with the entries in column-II. One
or more entries in Column-I may match with one or more entries in Column-II. The ORS
contains a 4 × 5 matrix whose layout will be similar to the one shown below :
(A) (P) (Q) (R) (S) (T)
(B) (P) (Q) (R) (S) (T)
(C) (P) (Q) (R) (S) (T)
(D) (P) (Q) (R) (S) (T)

1. Column - I Column - II
(One of the organic product can)
(i) O3, (ii) Zn, H2O

(iii) dil. NaOH
(A) But-2-ene (P) Evolve CO2 on heating
(iv) CrO3 , H2SO4
+
HO H
(B) CH3 –CH=O + (Q) Cyclic gemdiether
HO
(i) KCN/HCl
(C) CH3CHO + (R) Give cyclic ester product on heating
(ii) H3O
(i) O3
(D) (S) Evolve CO2 with aq. NaHCO3
(ii) H2O2
(T) Can give diol on reduction with LiAlH4

ENTHUSIAST COURSE
ENTHUSIAST COURSE

5
OH
O
+
3 H
OH Product
1. MeOH
HO OH
4 1
OH
2
Correct option regarding product
(A) The product gives +ve test with tollens reagent
5
(B) Only O H group will be methylated
(C) This reaction involves carbanion mechanism
(D) Product when reacts with HIO4, a new product having multifunctional group is formed.
The groups in new product are aldehyde, alcohol and ether.
2. How many reaction give aromatic products ?
(NH 4)2CO 3
Na2 CO3
(I) (II)
O O O O
(i) Br2/CCl4 red hot

(III) (ii) Alc. KOH / (IV) CH3 – C CH
Fe tube
conc.
(V) CH3 – C CH 3
H2SO4
O
(A) 2 (B) 3 (C) 4 (D) None
(1) NaNH 2
3. major product is?
(2) Et-I
(3) Na, liq. NH 3
(4) Br2, CCl4
Et Et
Br Br
H Br
(A) (B) (C) H Br (D)
Br H
Br Br H Br
Et Et
(1) Cl2/AlCl3
4. major product is?
(2) HNO3 + H2SO4
(3) NaOEt / EtOH
(4) Cl2 + AlCl3
OEt OEt OEt
Cl Cl
OEt Cl
(A) (B) (C) (D)
Cl Cl
NO2 NO2 NO2
NO2

SO3
X (Major product)
Low temperature
5. SO3
High temperature
Y (Major product)
X and Y are respectively
SO3H SO3H
SO3H
(A) SO3H (B) ;
;
SO3H SO3H
SO3H SO3H
(C) ; (D) ;
(ii) One or more options correct Type

6. In the given reaction identify the unknowns :
HBr / CCl4
[A]
Br2 / CCl4
[B]
[C]
CH3CH2CH3
Br
(A) Compound [B] is Br (B) Compound [A] is
(C) Compound [B] is Br Br (D) Compound [C] is LAH
7. Among the following reactions, identify the INCORRECT ones.
NH2
(1) NaNO2 / HCl
COOH
(0 5 C)
(A) CO 2H O 2N N N
(2)
NO2 (Major)
Ac 2O
(B) H2N OH H2N OAc
(Major)
D D
(C) (1) TsCl, pyridine

OH (2) NaCN H CH2NH2
H (3) LiAlH4
CH3 (4 ) H2O CH3
(Major)
Ph Ph H
H NMe3
OH
(D) + NMe3 + H2O
H CH3
Ph Ph CH3
CH3CH2MgBr
8. (X) CH3 – CH3 + Other products
(X) can be?
OH
H3C
Br
(A) (B) (C) CH3 – CHO (D)
H3C CH3
9. Which of the following statement(s) is/are correct ?

(A) Deoxyribose is present as aldose sugar in nucleic acids.
(B) First member of aldose sugar is aldotriose.
(C) is more acidic than CH2 = CH – CH2 –CH = CH2
H
Me Br
(D) Major alkene product formed by reaction of and alcoholic KOH/ is trans.
H H
Et
10. Consider the reaction given below
OH
conc.H 3PO4
?
H
Select the correct option(s)
(A) Three products are obtained
(B) The major product is
(C) Two products are obtained

(D) Two minor products are enantiomers.

(iii) Paragraph Type

This section contains 01 paragraph1 each describing theory, experiment, data etc. Each question of
a paragraph has only one correct answer among the four choices (A), (B), (C) and (D).
Paragraph for Q. No. 11 to 12
O O
CO + HCl O / MeCOO
(C) (D)
AlCl3 MeCOOH /
(1) HNO3 + H2 SO4
(1) HNO3 + H 2SO4
(2) NH2 – NH2 /OH /
(2) Fe, HCl
(3) Ni / H2
(A) (E)
O
(1)
Cl / Py
(2) HNO3 + H2 SO4
(3) H 3O +
(4) NaNO 2 + HCl
H
(B) (F)
T < 5°C
11. Identify (F) product?
(A) O2N N=N NH2 (B) N=N NH2
CH3 NO2 CH3

NO 2 NO2
N=N NH2 N=N NH2

(C) (D)
CH3 Me
(1) Ni / H 2
12. 'D' product (2) SOCl2 major product is?
(3) AlCl3
(A) O (B) (C) (D)
O O

(iv) Matching List Type

13. Match the List.
List – I List – II
(Reaction) (Oxidising reagents)
CH2
Oxidi sing
(P) Reagent 2 organic product (1) OsO 4
CH2
Oxidi sing
(Q) Reagent 3 organic product (2) Bayers reagent
Oxidi sing
(R) Reagent 3 organic product (3) (i) O3, (ii) H2O
Oxidi sing
(S) Reagent 1 organic product (4) (i) PhCO3H, (ii) H3O
Codes :
P Q R S
(A) (1,3) (3) (4) (3)
(B) (1,2) (4) (4) (1,2,3)
(C) (3) (1,3) (3,4) (2,3)
(D) (4) (2) (1,2,3,4) (1,2,3,4)
14. Match the List.
List – I List - II
H2O Cu2Cl 2
(P) Mg 2C3 A NH4OH
? (1) Purple colour
Al2O3 Cr2O3 Oleum

(Q) Hexane B C
neutral
( i)NaOH FeCl3
D ? (2) Yellow colour
(ii) H
Et2SO4 air FeSO4

(R) Ethanol E h
F KCNS
? (3) Red colour
Na Br2
(S) Ethylpropandioate G H
NK
O H3O Ninhydrin
I J ? (4) No colour

Codes :
P Q R S
(A) (1) (2) (3) (4)
(B) (3) (1) (3) (1)
(C) (1) (3) (4) (2)
(D) (4) (4) (1) (3)
H 3C – C = O
1.
CH = CH – CH2 – Cl
How many reactions are possible for the above compound?
(i) Nucleophilic substitution (ii) Free radical substituion
(iii) Electrophilic addition (iv) Nucleophilic addition
(v) Aldol condensation (vi) Electrophilic substitution
2. Find the total number of substrates more reactive than CH 3CH 2CH 2CH 2Cl with KI in acetone.
CH 3Cl, CH 3 2
CH Cl,CH 2 CH CH 2Cl, P h CH 2Cl,CH 3OCH 2Cl, P h CO CH 2 Cl, CH 3 3
CCl,C 6 H 5Cl
3. Find the total number of optically active compounds
O
,
O
CH 3 CH C CH CH 3 ,
NO 2 Br
O
, ,
SO 3H NO
2
fac Co gly 3
, P t gly 2
4. How many transition states are formed during the formation of product (major)
+
Conc.H , Product
OH
5. Total number of functional groups in following compound which can be reduced using NaBH4
HOOC H O
N C–O–CH3
O 2N
O Ph
O
ENTHUSIAST COURSE
ENTHUSIAST COURSE

1. The relative acidity of the indicated H in each of the following is
O O O
(i) C (ii) C CH3 (iii) C
H3C H H 3C O H3C OH
(A) i > ii > iii (B) ii > iii > i (C) i > iii > ii (D) iii > i > ii
CH3
2. CH3 – CH – CH2 – CH 3 (X)
when X undergoes monochlorination and then the products fromed undergo fractional
distillation, the number of fractions obtained is :
(A) 1 (B) 2 (C) 3 (D) 4
3. + CH2Cl2 + AlCl3 X
(excess)
X + NBS Y
Hydrolysis
Y Z
Correct option regarding X, Y, Z.
(A) Z when reacts with lucas reagent, white turbidity is formed within 5-10 minutes.
(B) Maximum number of benzonoid structures X can have is two.
(C) Z when reacts with PCC, benzophenone is formed as product.
(D) Y when reacts with silver nitrate, white precipitate is formed instant.
O O
(i) NaOCH2CH3, Ethanol KOH.H2O H3O
4. CH3—C—CH2—C—OCH2CH3 Heat
(ii) CH2Cl
Which of the following is the final product of the series of reactions shwon above :
O O O
(A) CH2—C—CH2—C—CH3 (B) CH2—O—C—CH2—CH3
O O O
(C) CH2—CH2—C—CH3 (D) CH3—C—CH—C—OH
5. Which of the following is natural condensation Co–polymer ?

(A) Natural rubber (B) Starch (C) Insulin (D) Dacron


6. Diethyl ether does not react with
(A) Na (B) NaNH2 (C) Aqueous HCl (D) Aqueous NaOH
7. Consider the reaction given below :
OH O OH
KOH
Ph Ph
Select the correct statement(s)
O
(A) having E, E configuration about double bonds is produced as

Ph Ph
the major product
(B) The reaction involves E1CB mechanism
(C) Since the intermediate anion is planar, the stereochemistry of the starting compound is
irrelevant and the less hindered product is formed
(D) Aldol condensation takes place forming major product
8. Which one of the following is an oxidation product of a primary amines ?
(A) A hydroxylamine (B) A nitroproduct
(C) A nitroso product (D) A alkyl hydrazine
9. Predict correct orders among the following ?
(A) > > > (resonance energy).

S N O
H
(B) -D-glucopyranose > –D–glycopyranose > open chain form of D-glucose (stability).
Cl Cl Cl Cl
NO2
> > >
(C) (Aromatic Nucleophilic substitution).
NO2
NO2 NO2
(D) CF3 > CH3 (% p character in orbital having unpaired electron).

10. Which of the following compounds give(s) iodoform test ?
(A) CH 2 CH CH O (B) CH 3COCH 3
(C) CH 3COCH 2COOC 2H 5 (D) CH 3 CH OH CH 2 CH OH CH 3


This section contains 01 paragraph each describing theory, experiment, data etc. two questions relate
to one paragraph with two questions on each paragraph. Each question of a paragraph has one or
more than one correct answer among the four choices (A), (B), (C) and (D).
Paragraph for Questions 11 and 12
Consider the scheme of reactions given below :
O O2N
OH
(I) +
DMSO
80o C
Major product
Br
OH
excessof CH3I
(II) KOH major product
HO OH
11. Select the correct statement(s) regarding reaction (I)
O O NO2
(A) The major product is
(B) It involves nuclophilic substition

(C) DMSO acts as base
(D) It involves electrophilic aromatic substitution
12. Select the correct statement(s) regarding reaction (II)
(A) The formation of major product involves nucleophic substitution
(B) It involves acid-base reaction
(C) The major product has six methyl groups
(D) The major product is triketo compound
13. List-I List-II

(compounds) (tests)
(P) CH 3 CH 2 CH 2 Cl (1) Br2 /H2 O
O
(Q) R – C – CH 3 (2) Baker-mulliken test
OH
(R) (3) Iodoform test
NO2
(S) (4) Beilstein test
Codes :
(P) (Q) (R) (S)
(A) 4 3 1 2
(B) 2 3 1 4
(C) 3 2 1 4
(D) 2 4 1 3
1. All the compounds which gives positive test with Bredy's reagent (2,4–DNP) and are having
molecular mass 100 are treated separately with NaBH4. Product of how many of these can be
used effectively to separate racemic mixture of 2-methylbutanoic acid.
2. Consider the reaction given below
OH
excess of
?
D3O in D2O
How many hydrogen atoms are replaced by deuterium atoms in the major product ?
3. Find the difference between the number of optically active and optically inactive isomers of
4. Find all possible Lactones with six membered ring having molecular formula (C6H10O2),
which when reacts with (1) LiAlH4 (2) H2O gives meso diol.
1) LiAlH4
Lacton Meso diol.
2) H2O
O
O
9 1 2 Br2 / FeBr3
5. 8 3 products.
7 6 5 4
major organic product will have Bromine at position.

SECTION–IV : Matrix-Match Type

This Section contains 01 question. Question has four statements (A, B, C and D) given in Column
I and five statements (P, Q, R, S and T) in Column II. Any given statement in Column I can have correct
matching with ONE or MORE statement(s) given in Column II. For example, if for a given question,
statement B matches with the statements given in Q and R, then for the particular question, against
statement B, darken the bubbles corresponding to Q and R in the ORS. 8(0)
1. Column-I Column-II
(A) CH3 Cl NaOH CH3OH NaCl (P) Rate of reaction increases in
polar protic solvent
(B) CH3 Cl NH3 CH3 NH2 HCl (Q)Rate of reaction increases in
polar aprotic solvent
Me
(C) S + NH3 Me NH2 Me2S (R) SN2 mechanism

Me Me
Cl OMe OMe
(D) + MeOH + (S) SN1 mechanism

(T) TS has positive charge

ENTHUSIAST COURSE
ENTHUSIAST COURSE

1. The correct statement for the given reaction is
CH3
Br H
NaI CF3CO3H
Br H Acetone
X Y
CH3
(A) Y is optically inactive due to external compensation
(B) Y is optically inactive due to internal compensation
(C) X is predominantly cis-alkene
(D) Y does not have chiral centres
O
H / H2O
2. (X)
CH2
H3C CH3
The product (X) is :
OH CH2OH CH2OH
OH
OH
(A) (B) (C) (D)

CH2
OH OH
H3C CH3 H3C CH3

H3C CH3 H3C CH3
3. An organic compound on reaction with 2,4 – dinitrophenyl hydrazene (2,4 –DNP) gives a
yellow ppt. It also gives silver mirror with ammonical AgNO3. It gives an alcohol and sodium
salt of carboxylic acid on reaction with concentrated NaOH. It yields benzene – 1,2 – dicar-
boxylic acid on heating with alkaline KMnO 4. The structure of the compound among the
following is :
(A) (B) (C) (D)

C C H
CHO COOEt
O O

4. The major product formed in the following reaction is :
O
Br
NaOMe
O O O
COOMe
(A) (B) (C) (D)
5. Which of the following statements is correct ?

(A) Lysine is example of basic & nonessential amino acid
(B) The IUPAC name of isoprene is 2-chloro-1,3-butadiene
(C) Lactose is example of disacchride which is formed by combination of C1 of -D-galactose
& C4 of -D-glucose followed by elimination of H2O
(D) Glucose gives +ve test with Tollen's ; Fehling ; schiff reagent & NaHSO3 solution
6. Consider following sequence of reactions
OMe
Solid N 2O 5 Sn/HCl NaNO2/HCl KCN (1)H3O+
P Q R S T
MeCN 0–5ºC CuCN (2)
Which of the following statement(s) is/are correct ?

(A) Formation of product P involves electrophilic aromatic substitution.
(B) Product T may be O
(C) Compound R is unstable at temperature > 25ºC

(D) Compound Q can give positive carbyl amine Test.
HI (excess)
7. A Product
Identify compound A for which more than 4 moles of HI will be consumed
OPh OCH3 OCH3

OPh CH2 OH OCH3 OCH3
|
(A) (B) CH OH (C) (D)
|
OPh CH2OH OCH3 OCH3
(i) RMg X
8. Cyclopentadiene (ii) FeCl2 X
correct statements regarding X
(A) X is organometallic compound (B) X has centre of symmetry
(C) X has plane of symmetry (D) X has C2 axis of symmetry
9. Which of the polymers are example of condensation polymer with ester linkage?
(A) Dacron (B) Nylon 6, 6 (C) Bakelite (D) Glyptal
10. Identify reactions corrctly match with their major products?
COOH
(1) Cl2 + AlCl3
(2) Br2 + AlBr3
(A) (3) KMnO4 / NaOH/
(4) HNO3 + H2SO4 Cl NO2
(5) Cl2 + AlCl3 Br
(1) Cl
Cl + 2eq. AlCl3 Br
(B) (2) Br2 + AlBr3
O 2N
(3) HNO3 + H2SO4
CH3 COOH
CrO2 Cl2
(C)
O
C–H N
NH2 – NH2
(D) H+/ N
C–H
O
This section contains 01 paragraph each describing theory, experiment, data etc. Each question of
Stereoisomers can be divided into two categories : Enantiomers & Diastereoisomers.
Stereomers which are non – super imposable mirror images of each other are know as
enantiomers and stereoisomers which are not mirror images each other are known as
diastereomers. On basis of this information give answer of following questions.
11. Select correct statement.
(A) Optically inactive compound can also show enantiomers.
(B) All diastereomers are geometrical isomers.
(C) All geometrical isomers are diastereomers.
(D) Both optically active & inactive compounds can show diastereomers.
12. Select correct statement for following compound.
O O
(A) It can show G.I. & O.I. (B) It has 5 optically inactive stereoisomers.
(C) It has 2 enantiomeric compound. (D) It has 2 diastereomers.

13. List-I List-II
(Reaction) (Reagent)
(P) (CH3)3C – CH = CH2 (H3C)2C – CH(CH3)2 (1) B2H6/H 2O2/OH –
OH
(Q) (CH3)3C – CH = CH2 (CH3)3C – CH – CH 3 (2) H2O/H+/Cu/300°C
OH
(R) H5C6 – CH = CH2 C6H5 – CO – CH3 (3) Hg(OAc)2/H2O/NaBH4
(S) C6H5 – C CH C6H5 – CH2 – CHO (4) H2O/H +
Codes :
(P) (Q) (R) (S)
(A) 1 2 3 4
(B) 2 3 1 4
(C) 4 3 2 1
(D) 3 2 4 1
1. Find the total number of compounds which do not give Fehling’s test.
Fructose, Sucrose, Glyoxal, HCHO, glyoxalic acid, CH 3CH O 3 ,
N 2H 4 , benzaldehyde, H COOH
2. Given sequence of reaction is :
O
( i) aq.NaOH CHCl
A NaOH3 B PhNH2 C D
(ii ) H3O
O
How many of the following statement(s) are true regarding above reaction sequence and
products.
(i) Compound A is used for the formation of Aspirin.
(ii) C and D are geometrical isomers.
(iii) B on treatment with conc.NaOH followed by acidification forms an acid which is more
acidic than o–toluic acid.
(iv) B can reduce fehling solution.
(v) Compound A when treated with Ph–N2 /NaOH then it forms yellow dye.
(vi) Compound C or D is more basic than aniline.
SiMe3
3. HCl
(A) + (B)
2 mole
Unsaturated Saturated
2 Mole compound compound
AlCl3 CH2Cl2
(C)
The degree of unsaturation of compound (C) is :

4. How many will give positive Lessagnai test for N :
NH2 NH2
(a) CH3–NH2 (b) (c) (d)

O N S
NH2 O
(e) (f) NH2–C–NH–NH 2 (g) Brady's reagent (h) NH2–NH2
N
H
5. Count number of reactions in which new "Carbon-Carbon" bond is formed :
OH OH
Cl O
CHCl3 CO2 Na
Conc.
(i) (ii) (iii) Dry ether (iv) Ph–C–H NaOH
NaOH + NaOH
O O O
– O
OH O
(v) (vi) Ph–C–H –
MeCOO /
SECTION–IV : Matrix-Match Type

This Section contains 01 question. Question has four statements (A, B, C and D) given in Column
I and five statements (P, Q, R, S and T) in Column II. Any given statement in Column I can have correct
matching with ONE or MORE statement(s) given in Column II. For example, if for a given question,
statement B matches with the statements given in Q and R, then for the particular question, against
statement B, darken the bubbles corresponding to Q and R in the ORS. 8(0)
(Transformation) (Name of process involved during
this transformation)
(A) -D-Glucopyranose -D-Glucopyranose (P) Anomerisation
(B) Glucose Mannose (Q) Mutarotation
(C) Fructose Glucose (R) Tautomerisation
H O CH2OH
C
C=O
H OH
(D) HO H HO H (S) Epimerisation
CH 2–OH CH2–OH
(T) Isomerisation

ENTHUSIAST COURSE
ENTHUSIAST COURSE
ORGANIC CHEMISTRY GR # 07 SCORE-ADVANCE

1. The principle functional group in following compound for IUPAC naming :
O
N H
OH O
(A) Aldehyde (B) Ketone (C) Amine (D) Amide
2. Which of the following represent aromatic compound :
O O O
(A) (B) (C) (D)

O
+
O
NO2
(i )CH3I,K 2CO3
3. HO (ii) H2SO4 ,HNO3 Major product of the reaction is :
NO2 NO2
H3C
(A) HO (B) MeO
NO2 NO2
NO2 NO2
O2N O2N
(C) HO (D) MeO
CH3

4. In the following reaction the major product [X] is :

O
Me (i )SeO2 / HOAc
[X]
(ii )NaOH
(iii )H3O
O HOOC OH COOH
COOH Me COOH
Me OH (C) Me
(A) (B) (D)
5. Major product 'Y' in following reaction sequence is :

–
O3 OH
O Zn X Y
C–H O O
C–H O
(A) (B) (C) (D)

6. Identify correct reaction set(s) ?
Cl O -
O + O
+ Br N Br
N -
O HS S
(A) + Base
Cl Cl
Cl
(B) MeOH MeO
O O
H3C CO2H H3C CO2H

(C) OH-,Ag+
Br OH
O
O
(D) Base
Cl
O O

7. To prepare 2° amine (as major product) which of the following reactions can be used up :
CH3
+ – LiAlH4 + CH3 –
(A) N C (B) N OH
CH3
(C) NH3 / (D) O + 1. MeNH2

Cl 2. H2(Pd)
8. Select correct statement(s) out of following?
O NH
(A) is more reactive than towards reaction with PhMgBr
Cl
Cl2 (aq)
(B) O O (major product)
h
Conc. H 2SO 4
(C) 2 (Major)
(Catalytic)
PhNHNH 2
(D) D-glucose + D-mannose + D-fructose only one osazone
9. Select correct statement(s) out of following for compound given below :

Br(x)
O Br(y)
Br(z)
(A) Br(y) is the most reactive Br towards SN2 reaction in this compound.
(B) Br(z) is the most reaction Br towards SN1 reaction in this compound.
(C) 16 stereoisomers are theoretically possible for this compound.
(D) This compound is capable of showing geometrical isomerism
10. Identify reactions give naturally occuring amino acids?
(1)H–CN (1) Red 'P' + X 2
(A) NH (B) Me – CH2 – COOH
(2)H3O (2) NH3
O Cl O O
(1) CH – C C
C CH3
Me OEt
N Na (1) NaOI
(C) (2) H3O (D)
C (2) H
Cl (3) NH3
O


N 2H4 OH
C6H10O
(A)
(1) CH3MgBr Conc. H2SO4 (1) O3

(B) (C) (D) OH ,
(E)
(2) H2O , -H2O (2) Zn, H2O Intra Molecular
Aldol condensation
(dicarbonyl
compound)
(1) Li (CH3)2Cu
(2) H2O
Zn - Hg
(F)
HCl
# Compound (A) has (S) - configuration at the chiral center.

# All organic products are major in above reaction scheme
11. Select the correct statement ?
(A) Formation of Compound (F) involves 1, 2-Addition.
(B) Compound (C) on reaction with HBr or HBr, R2O2 gives same organic product.
(C) Compound (A) on reaction with NaCN / HCN followed by H2O gives enantiomers pair as
a product.
Br
(D) Compound (C) can also be obtained as major product when heated with
O K
12. Select the correct one
O
(A) Compound (F) = (B) Compound (C) = CHO
O OH
CH3
(C) Compound (A) = (D) Compound (B) =
H


13. Match the following question :
List - I List-II
(Reaction) (Products)
CH3
(P) HOOC COOH (1) Diastereomers
H D
C 2H 5
CH3
(Q) HOOC COOH (2) Racemic mixture
Ph
HOOC COOH
(R) (3) Meso compound
CH3
COOH
(S) (4) CO2 gas will evolve
COOH
Select CORRECT code for your answer :
(A) (P) 1, 4 ; (Q) 2, 4 ; (R) 1, 4 ; (S) 3 (B) (P) 1, 4 ; (Q) 2, 4 ; (R) 1, 4 ; (S) 3,4
(C) (P) 1, 4 ; (Q) 2,3,4 ; (R) 1, 4 ; (S) 3 (D) (P) 1, 4 ; (Q) 2, 4 ; (R) 1, 3 ; (S) 3
14. Mark the correct option assuming monobromination in all reactions (include stereo isomers
wherever possible)
List I List II
Br2
(P) hv
(1) Even number of optically active products
Br2
(Q) hv
(2) Odd number of total products obtained
after fractional distillation
Br2
(R) hv
(3) Even number of total products
Br2
(S) hv
(4) Even number of optically inactive products
(A) P 1,2,4 ; Q 2,3,4 ; R 1,3,4 ; S 1,3,4

(B) P 1,3,4 ; Q 1,2,3 ; R 2,3,4 ; S 2,3,4
(C) P 1,3,4 ; Q 2,3,4 ; R 2,3,4 ; S 1,3,4
(D) P 2,3,4 ; Q 1,2,4 ; R 1,3,4 ; S 2,3,4


1. Electrodes are immersed in a solution of pH ‘X’ which is prepared by using 0.1 M formic acid
(Ka = 10–4) and 0.1 M sodiumformate in equal volume. To this solution amino acid, assorbic
pKa = 4 pKb = 4
NH2
acid, a naturally occurring amino. acid HO—C—CH2—CH is added.
O C O
OH
pKa = 2
Assorbic acid pKa values
Then, if net migration of amino acid is towards anode, then your answer is (X + 1). If migra-
tion is towards is cathode, then your answer is (X + 2) . If migration is neither towards anode
nor towards cathode then your answer is X.
O
2.
Ph—CH=CH—C—CH=CH—Ph
CH2(COOEt)2 (1 mole)
NaOEt
(A)
(Six membered ring)
How many oxygen atoms are present in (A) ?

3. How many equivalents of base are consumed in the following reaction ?
Br2 / OH /
CH3CHO HCBr3 HCOO
(1equivalent)
4. In the given reaction sequence, find number of possible 5 and 6 membered Lactone(s) having
different boiling points :
(i) LiAlH4
'X' (Lactone)
(ii) H2O
Molecular
formula = C6H10O2 (iii) Red P / HI

5. How many of the following compound will give silver mirror with Tollen's reagent ?
CH2OH
H OH
(a) Me–CHO (b) Ph–CHO (c) H (d) Ph–NH–OH
OH H
HO OD
H OH
CH 2OH
HO OH
H
H HO H
H O CH2OH COOH
H O OH
OH H HO H H OH
(e) O
(f) Me–C CH (g) OH H (h)
OH H H OH
H HO CH 3
H OH H H COOH
(i) HCOOH (j) Me–COOH

6. How many theoretically possible dipeptides can be produced if we have only Glycine and
Alanine ?

JEE (MAIN
JEE (Main + ADVANCED)
+ Advanced) 20222020
GUIDED REVISION LEADER + ENTHUSIAST COURSE
ENTHUSIAST COURSE
Only one correct :

1. Select the incorrect statement about Nylon 2-nylon-6 :
(A) It is a copolymer
(B) It is biodegradable
(C) It is an alternating polyamide

(D) It is made up of CH 3 CH COOH and H2N(CH2)5COOH
|
NH 2
2. When N and S both present the Lassaignes test is sometimes incomplete due to formation of
(A) Na(CNS) (B) Na(NCS) (C) NaCN (D) Na2S
3. Which of the vitamins given below is water soluble?
(A) Vitamin E (B) Vitamin K (C) Vitamin C (D) Vitamin D
OCOCH3
COOH
4. is used as :
(A) Insecticide (B) Antacid (C) Antihistamine (D) Analgesic

5. Which of the following is an anionic detergent ?
(A) Glyceryl oleate (B) Sodium stearate
(C) Sodium lauryl sulphate (D) Cetyltrimethyl ammonium bromide
HCO 3H H3O Pthalic Anhydride
6. Acetophenone A B+C Indicator (D) ; C & D are :
H
(A) CH3OH & (B) PhOH &
(C) PhOH & (D) CH3OH &

7. ? Product is:
(A) (B)
(C) (D) No reaction
8. A solution of (+) -1-chloro-1-phenylethane in toluene racemises slowly in the presence of small amount
of SbCl5, due to the formation of:
(A) Carbanion (B) Carbene (C) Free-radical (D) Carbocation
9. Identify the set of reagents / reaction conditions 'X' and 'Y' in the following set of transformation:
X Y
CH3 – CH2 – CH2Br Product CH 3 CH CH 3
|
Br
(A) X = dilute aqueous NaOH, 20°C; Y = HBr / acetic acid, 20°C
(B) X = concentrated alcoholic NaOH, 80°C; Y = HBr/ acetic acid 20°C
(C) X = dilute aqueous NaOH, 20°C; Y = Br2 / CHCl3, 0°C
(D) X = concentrated alcoholic NaOH, 80°C; Y = Br2/CHCl3, 0°C
+
H / KMnO 4
10. A B Pthlic Anhydride ; A is :
Me Me
Me
(A) (B) (C) (D)
Me Me Me
Me
11. 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

12. Cellulose upon acetylation with excess acetic anhydride / H2SO4 (catalytic) gives cellulose triacetate
whose structure is :
AcO
AcO
H O O–
H O O– H
H AcO
AcO OH H
OAc H H O O H
H O O H H
H AcO
AcO OH H H OH
OAc H H OAc O O
O O H H H
H H H
OH H H OH
OAc H H OAc
(A) –O
(B) –O H
H
H OH
H OAc
AcO AcO AcO AcO AcO
O H H O H AcO
H H
H
H O O–
H H O H H O H H
H O O–
(C) OAc H OAc H OAc H
(D) H H
H
H
H
–O O O H H H
H –O O O
H H
OAc H OAc H OAc OAc OAc OAc OAc OAc OAc
13. The reactivity of compound Z with different halogens under appropriate conditions is given
below :
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
Matrix Match Type :
14. Match the column-
Column-I Column-II
COOEt (1) EtONa
(A) Ph–CHO + CH2 (2)H3O / (P) Perkin’s reaction.
COOEt
(1) Zn
(B) Ph–CHO + CH2–COOCH3 (2) H3O /
(Q) Reformatskii reaction.
Br
(C) Ph–CHO + CH3COOCOCH3 (1)CH3COONa /

(R) Product is a carboxylic acid with aromatic ring
(2)H3O /
O O within the same molecule.
(D) Ph–C–C–Ph + NaOH (2) H

(S) Double bond equivalent of the product formed
is less than or equal to 8.
(T) The major product cannot show optical isomerism

15. Match the column

Column I Column II
(Component of mixture) (Reagent)
(A) Crystalline Na2CO3 + (P) Fehling solution
Sodium citrate + CuSO4(aq. sol.)
(B) CuSO4 + Rochelle Salt + NaOH(Aq. sol.) (Q) Nesseler's Reagent
(C) 10% - naphthol in alcohol (R) Bennedict's solution
(D) HgCl + KI + KOH (aq. sol.) (S) Molisch's Reagent

JEE (Main + Advanced) 2022
ENTHUSIAST COURSE
Me Na Me – I
(A)
Dry Ether
1. H OH Ether
Et SOCl2 NaOMe
(B)
Low Temp.
Identify relationship between produts ?

(A) Diastereo Isomers (B) Enantiomers (C) Functional Isomers(D) Geometrical Isomers
O
(1) Mg–Hg Conc.
2. (2) H2O H2SO4
Major product
O O O O
(A) (B) (C) (D)

O
3. The correct sequence of reagents for the following conversion is
(A)
(B)
(C)
(D)
4. 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

5. Which of the following is/are the proper sequence of reagents for the conversion
(A)
(B)
(C)
(D)
6. Acetone (CH3COCH3) is the major product in :
I CH2 = C = CH2 II CH3C CH IIICH3C CH
(A) I, II (B) I, III (C) II, III (D) I, II, III

7. Observe the following two set/s of reactions (I and II). Select the true and false statements about the ratio
of their rate constants (K).
+ -
NO2 + C2H5O
C6H6 C6H5NO2 + H CH3 CH2 Br CH2 = CH2
Set - I Set - II
+ -
NO2 + C2H5O
C6 D6 C6D5NO2 + D CD3CH2Br CD2 = CH2
K ( C6H6 ) K( CH
3 CH2 Br )
(1) In set - I ~ 6.0 (2) In set - II K ( CD ~ 1.0
K( C6D6 ) 3 CH2 Br )
(3) In both the cases the ratio of rate constants is less than one.
(A) FFF (B) TFF (C) FTF (D) FTT
Multiple Correct Type :
Me HOCl aq.AgNO 3 H2SO 4 /
8. Ph (W)
(P)
‘W’ is also obtained by
–
BH3 – THF H2 O2/OH CrO3
(A) P
(1) (2) (3)
HBr / R 2O 2 KOH / DMSO Pyridinium Chloro Chromate

(B) P
(1) ( 2) (3 )
(C) Ph – CH2 – C – OEt + CH3MgBr

O
(D) Ph – CH2MgBr + Et – O – C – CH3
O

9.
out of the followings which one is/ are correct
(A) 1, (B) 2, (C) 3 , (D) 4,
10. Product
In the above reaction which of the following is observed

(A) Dehydration (B) A rSE2 (C) Acid-base reaction (D) Aromatisation
Passage Q. No. (11 to 13)
Observe the following reactions.
H2SO4 /
H2SO4 (i) MeMgBr (1eq.) (Z) LiAlH4 (80°)
(X) (Y) (W)
(1) (ii) H+ (2) C6H12O2 (3) (4) – H2O O
Me Me
(M.F.)
11. The compound 'X' is
HO O
COOH COOH
(A) (B)
Me Me
O COOH HO COOH
(C) (D)
Me Me
12. Compound Y is :
O COOH
(A) (B) (C) Me COOH (D)
Me O O Me O O Me
13. The corrrect statement about 'Z' and 'W' is

(A) Both give positive Tollen's test (B) Both give positive iodoform test
(C) Both give positive test with 2, 4-DNP (D) W on CrO 3 / H oxidation gives Z.

Matrix Match Type :

(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–CH2–C–Cl Aldehyde (R) NaOBr, / Mild H+

O
(D) CH2=CH–C–CH 3 Saturated alcohol (S) H 2/Ni,
O
(T) Diisobutylauminium hydride (DIBAL–H)
Integer Type :
15. Give stability order in the following pairs.
I II I II
(a) (b)
(c) CH2 = N H2 C H2 –NH2 (d)

JEE (Main
JEE (Main + Advanced)
+ Advanced) 2022
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ENTHUSIAST COURSE
1. The end product of following reaction is :

(1) O3 (3) LiAlH4 (5 ) PBr3 ( excess ) Mg / ether 1 eq. HCOOEt
( 2) Me2S,H2O ( 4) H (6) H (7 )
(A) (B) (C) (D)
2. The structure of the starting material X is :
3, 4 Dimethyl 3 hexanol
(3,4 MkbZesfFky 3 gsDlkukWy½
(A) (B) (C) (D)
3. The major products of following reaction sequence are :
(I) (II) (III)
(A) I = (B) I = (C) III = (D) III =
H
4. Catalyst
Product
OH
(A) (B) (C) (D)
HO
D
NaSMe
5. Br Cl DMSO
Major product
D D
(A) Br (B) Br
SMe SMe
D D
(C) MeS (D) MeS
SMe SMe

6. In which of the following reaction the product will also be optically active
(A) (B)
(C) (D)
HI( Cold)
7. A+B
conc.
A, B are
(A) (B) C2H5 I (C) CH3 I (D)

8. Which of the given compounds can be the main products of following reaction
CH3 – CH = CH2 Br2 / aq. NaCl NaI NaNO 3
(A) (B)
(C) (D)
9. Compound 'X' (C8H8) rapidly decolourises cold aqueous KMnO4 solution. It reacts with Br2 / CCl4 to
yield C8H8Br8. The structure of 'X' cannot be :
(A) (B) (C) (D)
10. In which of the following cyclic transition state is formed.

500 C
(A) CH3 COOCH CH2 CH3 CH2 = CH – CH 2CH3 + AcOH
|
CH3
(i) B 2D6 / THF
(B) CH3 – CH = CH – CH3 (ii ) H2O2 / OD ¯
CH3 CH CH CH3
| |
D OH
(C) CH2N2 / h
HgSO4
(D) CH 3 – C C – Ph CH3 CH2 C Ph
H2SO4 / H2O ||
O

Comprehension (Q.No. 11 to 13)

Observe the following experiment
11. If the reactant ‘P’ is ethyl chloride then the product R can be :
(A) (B) CH3CH2 – O – CH2CH3
(C) (D)
12. If the liquid Q is H C OC 2H5 then the product R can be (P can be any other halide)
||
O
(A) (B) (C) (D)
13. If R is then P and Q can be respectively.
(A) , CH3 – – OC2H5 (B) CH3 – Cl,
(C) CH3 – – CH3, (D) , CH3Cl

Matrix Match Type :

14. Match the rearranged C+ of column II with initially formed carbocation in column I :
Integer Type :
15. For the conformational isomers, the net dipole moment is obs = ixi where obs = obsereved dipole
moment of the compound i = dipole moment of the stable conformational isomers xi = mole fraction of
stable conformers for the compound Cl – CH2 – CH2 – Cl, if Xanti = 0.7 and obs = 2D, then find gauche.

JEE (MAIN
JEE (Main + ADVANCED)
+ Advanced) 2022
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ENTHUSIAST COURSE

1. Which one is correct for the products of the given reaction
(A) only X and Z are formed (B) Z > Y (amount)

(C) X > Y (amount) (D) Y > X (amount)
2. Which one will undergo hydrolysis (solvolysis) more rapidly amongst the given pairs of compounds
I II III IV
(A) x>y y>x x>y x>y
(B) y>x y>x x>y x>y

(C) x>y x>y y>x y>x
(D) y>x y>x x>y y>x
3. The correct order of SN2 / E2 ratio for the % yield of product of the following halide is –
(P) (Q) (R) CH3 – CH2 – I (S)
(A) R > S > Q > P (B) R > Q > S > P (C) P > R > S > Q (D) Q > P > R > S

(i) Grignard reagent (excess)

4. Phenyl ester 'P', 'P' can be
(ii) H+
Ph Me Ph Ar Ph Me
(A) (B) (C) (D)
H OH Me OH Et OH
5. The slowest chain propagation step of the following reaction is

R 2O 2
CH4 + SO2Cl2 CH3Cl + SO2 + HCl
(A) RO + CH4 ROH + CH3 (B) CH3 + SO2Cl2 CH3Cl + SO2 Cl
(C) SO2 Cl SO2 + Cl (D) Cl + CH4 HCl + CH3
6. Observe the following diagram for relative boiling points of different alkanes. Identify the
hydrocarbons X, Y, Z, W, R.
Z
W
X
R
Y
B.P.
Alkanes
(X) (Y) (Z) (W) (R)
(A)
(B)
(C)
(D)
7. The end product of following reaction is :
O O +
CH3MgBr PhMgBr H
(1) (2) (3)
O
(A) -diketone (B) -Hydroxy acid (C) 1, 2-Diol (D) -Hydroxy ketone

H – C C Na NaNH 2 I (CH2 )7 Cl NaCN H3 O H2 / Pd / CaCO3 / Quinoline

8. E (3 ) (5 ) (6 )
(1) (2) ( 4)
Identify the compound 'E'.

(A) 1-Fluorodecane (B) 1-Bromo-8-Fluorooctane
(C) 1-Bromo-7-Fluoroheptane (D) 1-Bromo -11-Fluoroundec -2-yne
9. The compound 'X' can be synthesized by using the reagents.
(I) + CH3MgBr (II) +
(III) + (IV) +
(A) I and III (B) I, II, III (C) All (D) I, II only
10. An aromatic chiral compound G (C8H8Br2) on treatment with NaOH/DMSO gives H (C8H9BrO). On
heating ‘G’ with potassium tert-butoxide I (C8H7Br) is formed. With one equivalent of methyl magne-
sium bromide in ether p-bromoisopropylbenzene is formed which observations is/are correct about these
reactions.
(A) (I) is an optically inactive aromatic alkene (B) H is an optically active alcohol
(C) G =
(D) Benzylic halide gives nucleophilic substitution with faster rate than aryl halide
Passage for (Q.No. 11 to 13)
Observe the following reactions and given answers

11. Which of the following structure represents the transition state of slow step of reaction I.
(A) (B)
(C) (D)
12. Which of the reaction (I – IV) involves rearrangement of reaction intermediate.
(A) I only (B) I, III (C) II, III, IV (D) I, II, III
13. Planar reactive intermediates are formed in reactions :
(A) I, III (B) II, III (C) I, II (D) I, III, IV

Matrix Match type :
14. Compare the properties of two isomeric products x and y formed in the following reaction.
1. CCl4 / KOH/ , 2. H
Reimer Tiemann Reaction
Match the following :
Integer Type :
15. Calculate molecular weight of the lowest alkane containing a sequence of 10, 20, 30 and 40 carbon atoms.

ENTHUSIAST COURSE
ENTHUSIAST COURSE
1. The correct energy level diagram for the following reaction is

Ar – H NO 2 Ar – NO 2 H
P.E. P.E.
(A) (B) +
ArH + NO+2 ArNO2 + H+ ArH + NO+2 ArNO2 + H
Reaction coordinate Reaction coordinate
P.E. P.E.
(C) +
(D) +
ArH + NO+2 ArNO2 + H ArH + NO+2 ArNO2 + H
Reaction coordinate Reaction coordinate
2. Which common factor is responsible for the regioselective nature of the following reactions.
HCl Cl2 / FeCl3

(I) CH2 = CH – Cl CH3 – CHCl2 (II) +
HBr
(III) H – C C – Br CH2 = CBr2 (IV)
(A) – I effect of halogens (B) + I effect of halogens

(C) + M effect of halogens (D) – M effect of halogens
HF
3. In the following reaction the product obtained is C6H6 + CH2 = CH – CH = CH2
(A) C 6H5CH2CH CHCH2 C6H5 (B)

| |
C 6H5 C 6H5
(C) CH3 CH CH CH2 (D) C6H5 – CH2 – CH = CH – CH3
|
C6H5
Br2 Fu min g HNO 3

4. Y water X,
X and Y are respectively :

(A) Picric acid, 2, 4, 6-tribromophenol (B) 4-Nitro salicylic acid, 4-Bromo salicylic acid
(C) o-Nitro phenol, o-Bromo phenol (D) none of the above is correct

5. The intermediate product ‘X’ of following synthesis is identified as :

Cl2 / FeCl3 conc. H2SO4 Fu min g HNO3 NH3 / Cu2O / dil. H2SO4 ,
’X’ 120 C 100 C
2, 6-Dinitroaniline
(A) (B) (C) (D)
6. Which is not the correct reaction ?
(A) Ph + Base Ph – N =
(B) + Base
(C) + Butter yellow
Base
(D) +
7. The end product ‘W’ is :
(W)
(A) (B) (C) (D)
8. The reagents are :
OH
( a) (b ) (c ) ( d) ( e)
NO2
Cl2 / Fe HNO3 H2SO4 , NH4HS NaNO2 / HCl KCN
(A) (a) (b ) (c ) ( d) H2O / (e )
HNO3 H2SO4 , NH4HS NaNO2 / HCl / boil Sn / HCl CO2 / NaOH/

(B) (a) (b) (c ) ( d) ( e)
HNO3 H2SO4 (i) Cl2 / Fe Sn / HCl Cl2 / Fe KCN

(C) (a ) (ii ) NaOH / (c ) ( d) ( e ) H3O
(b )
(D) Both B and C are correct

9. In which of the following reaction of p-nitrobenzene diazonium sulphate a colourless odourless gas is
evolved out.
(A) with p-Cresol (B) with o-Toluidine
(C) with C2H5OH (D) with H2 / Ni
10. For the given reaction consider the statement 1,2 and 3 :
+
G: N N G:
+
(I) (II)
N
(1) Presence of –NO2 group in aromatic ring I will increase the rate of reaction.
(2) Presence of –NO2 group in aromatic ring II will increase the rate of reaction.
(3) In this reaction a Wheland intermediate ( complex) is formed.
(A) TTT (B) FFF (C) FTT (D) FTF
11. The end product V (major) of the following reaction sequence is :
(I) (II)
(V) (IV) (III)
(A) (B)
(C) (D)

Comprehension Q. No. (12 to 14)

4-Isomeric alkenes P ,Q, R, S with molecular formula C4H8 has following heat of combution data
Heat of Combution
S
Q
R
P
12. Identify alkene give meso product on reaction with Br2 / CCl4?
(A) P (B) Q (C) R (D) S
13. Identify alkene give fastest reaction with HBr / CCl4?
(A) P (B) Q (C) R (D) S
14. Identify alkene give racimic mixture on reaction with Br2 / CCl4 ?
(A) Q (B) R (C) P (D) All of these
Matrix Match Type :
15. Match the mechanism/s mentioned in List-2 with reactions of List-1. More than one options of List-2
can match with one reaction of List-1.

ENTHUSIAST COURSE
ENTHUSIAST COURSE

Single Correct Type :
1. Compound ‘X’ on ozonolysis followed by iodoform reaction produces 4 moles of CHI3 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. In compound A (C30H60O) following tests are observed negatively, A can be
(A) an unsaturated ether (B) an epoxide

(C) a cycloalkanol (D) can't predict
3. An aromatic compound ‘X’ (C9H8O3) turns blue litmus to red. It gives yellow precipitate with
I2 / NaOH and forms Y (C8H6O4). Y forms three mononitro isomers. Identify X :
(A) (B) (C) (D) none of these
4. A set of reagents (1 to 7) are successively reacted with the following compound
1. NaHCO3 2. 2, 4, DNP 3. Na metal 4. AgNO3 + NH4OH

5. Fehling’s solution 6. Cu2Cl2 + NH4OH 7. Br2 / H2O
The reagents which give positive test with the given compound are :
(A) 1, 2, 3, 4, 5 (B) 3, 4, 5, 6, 7 (C) 1, 2, 3, 4, 7 (D) 1,2,3,4,6,7
5. The total number of optically active alkynes having molecular formula C3FClBrI is
(A) 2 (B) 4 (C) 6 (D) 8

6. Give the correct order of initials T or F for following statements. Use T if statement is true and F if it is
false.
X (molecular formula, C7H6O2) is an aromatic white solid which liberates colourless, odourless gas on
reacting with .
S1 : Only three of the five functional isomers of X (including ‘X’ itself) will give positive 2, 4-DNP test.
S2 : The liberated colourless, odourless gas will contaning radioactive 14C.
S3 : Except ‘X’, no other functional isomer will liberate colourless odourless gas with .
S4 : The DU of higher homolog of ‘X’ will be four.
(A) TTTF (B) FTTF (C) FTTT (D) TTFF
7. Which of the following resonating structure is not possible for 2, 4, 6 – trinitroiodo benzene
.. .. ..
:I: .. :I+ :I+
:I+
ON NO2 + O- ON
2 NO2 O2N NO2
2
O2N N
-
O ..-
+ +
N+ -
N -
N -
- NO2 O O O O
O O (II)
(A) I (B) II (C) III (D) IV

8. Na /(Dry ether )
Products obtained in above Wurtz reaction is :
(A) (B)
(C) (D)
9. In which of the following reaction a racemic mixture will be formed.

.. ..
N N
(A) H3C | CH2CH3 DCl (B) H3C | CH2CH3 HCl
H H
.. ..
N N
(C) H3C | CH2CH3 DCl (D) H3C | CH2CH3 HCl
D D

10. Select the correct informations about products in reactions I and II.
I II
H CH3 H CH3 H CH3
(A) +
H I H F F H
H I I H H F
(B)
H3C H H3C H H3C H
I CH3 F H F CH3
(C) +
H H H CH3 H H
(D) SN
2
SN
1
11. Which of the following can be the product/s of following reaction
NaOH
(A) (B) (C) (D)
Passage (Q.No. 12 to 13 )
A flask contains “mixture” of unknown Alkenes obtained by treatment of 2-chlorobutane with alc.
KOH. When the “mixture” is boiled, the fraction that comes out firstly is A.
12. A on Hydrogenation followed by Treatment with Cl2/h gives how many monochloro products.(only
structural isomers)
(A) 1 (B) 2 (C) 3 (D) 4
13. The remaining Alkene mixture is ozonolysed carefully in presence of Zinc and Products are treated with
mixture of NH2OH. How many oximes obtained.
(A) 2 (B) 3 (C) 4 (D) 5

Matrix Match Type :

14. Match the following compound with their IUPAC name :
Compound IUPAC Name
COOH
(P) (W) 3-[2-(2-Oxoethyl)phenyl]propanoic
acid
CHO
CH2 – COOH (X) 2-[2-(3-Oxopropyl)phenyl]ethanoic

(Q) acid
CHO
CH2CH2COOH
(R) (Y) 2-(2-Formylphenyl)ethanoic acid
CH2CHO
CH2 – COOH
(Z) 2-Formylbenzenecarboxylic acid
(S)
CH2CH2CHO
Integer Type :
15. What is the lowest molecular weight of a saturated cyclic hydrocarbon which has all its carbon atoms
different.

ENTHUSIAST COURSE
ENTHUSIAST COURSE
1. One mole of was treated with NaOH / I2 and then acidified. The product after acidification
has isolated and then heated with 3 equivalents of NaOH to give a new ionic species. The ionic species
formed will be :
(A) (B) (C) (D)
2. The reactvity order of benzen ring for the given reaction is (benzene ring with highest electron
density will be most reactive)
(A) x > w > y > z (B) z > y > w > x (C) x > z > y > w (D) y > z > w > x
3. Identify major product of reaction ?
Br2 Alco. NBS
product
hv. KOH /
Br
(A) (B) Br (C) Br (D)
4. Which nitrogen is LSD (Lysergic acid diethylamide) is most basic ?
(1) O
H–N || (3)
(2) C – N(C2H5)2
N
|
CH3
(A) 1 (B) 2 (C) 3 (D) all are equally basic

5. Which of the following looses their optically activity after the reaction.
D 2O
(A)
OD
D 2O(excess)
(B)
OD
D 2O
(C)
OD
D 2O
(D)
OD
6. The end product of the following reaction is :

+
CH2 rearrangement +
–H
14
(1) (2)
OH
CH3
14 14
(A) OH (B) O (C) 14 O (D) 14 O
7. The correct nucleophilicity order is :
(A) 1 > 2 > 3 > 4 (B) 3 > 2 > 1 > 4 (C) 3 > 2 > 4 > 1 (D) 2 > 1 > 3 > 4
8. The correct statement/s about the following reaction is / are
NaI / Acetone ‘Y’
(A) The product is achiral compound

(B) The product does not have isotopic iodine
(C) It is an allylic bimolecular nucleophilic substitution reaction
(D) Ozonolysis product of ‘Y’ give positive iodoform test

9. In which reaction D-exchange in compound is observed.

Ph Ph
(A) NaOEt / EtOD (B) NaOEt / EtOD

O Br O OH
(C) NaOEt / EtOD (D) N
Passage (Q.10 to Q.14)

Observe the following compound 'P' and give answer
(1)
H I
(4)
O (6)
D
H
D (5)
(3)
(2) D
Br
(P)
10. The enol form of 'P' is formed by ionization at position :

(A) 1 (B) 2 (C) 3 (D) 4
11. A stable carbocation is formed by ionisation at position :
(A) 3 (B) 1 (C) 4 (D) 2
12. The ozonolysis product of P, (by using reductive ozonolysis) gives negative test with
(A) 2, 4-Dinitrophenyl hydrazine (B) Ammonical silver nitrate
-
(C) I2 / OH (Iodoform test) (D) Ammonical cuprous chloride
-
13. The carbocation of 'P' obtained by ionisation of X (halide ion), can be observed at position/s :
(A) 3, 5 (B) 3, 6 (C) 5, 6 (D) 4, 5
14. The total number of chiral centres in 'P' is
(A) 1 (B) 2 (C) 3 (D) 4
Matrix Match Type :
15. Match the relationship between the compounds of column-I with column-II.
Column-I Column-II
(A) Pentanetetraene and Penta-1,4-diyne (P) Chain isomer
(B) Benzene and Toluene (Q) Functional isomer
(C) Cyclohexane and 1,2,3-Trimethylcylopropane (R) Metamer
(D) Methylpropanoate and Ethylethanoate (S) Homologues

ENTHUSIAST COURSE
ENTHUSIAST COURSE

1. Longest bond length (C=O) among the following :
O O O O O
(A) (B) O (C) NH (D)
OH
NH2
NaNO2
2. HCl
(X)
Major
t-Bu
Product ‘X’ is
OH O
CHO
NH2 OH
(A) (B) (C) (D)
3. Which of the following reaction is incorrect ?

I
Fe FeX 3
(A) + Cl2 (B) + I—Cl
N N Cl
H
NO H NO
Cl
FeBr3 BF3
(C) + Br2 (D) + Cl2
N N
Br
4. The relative yield of the following alkenes produced by the reaction of 1-chloro-(Z)-1, 2-
dimethylcyclohexane with KOH/heat is
(i) (ii) (iii)
(A) i > ii > iii (B) ii > iii > i (C) i > iii > ii (D) iii > i > ii

5. Major product in following reaction is :

O O
O –
MeCOO /
O
C–H
O in MeCOOH solvent
O O
(A) CH=CH–C–OH (B)
C–H
O O
O
O
O
(C) C–H (D)
O O O
+

6. CH3 – CH2 – C CH CH3 – C C – CH3
(A) (B)
Which option is correct regarding this interconversion ?
(A) To carry out forward reaction alcoholic KOH / is required
(B) To carry out backward reaction alcoholic KOH / is required.
(C) A is more acidic than B
(D) In the intermediate (CH2 = C = CH – CH3) formed during this interconversion, maximum
number of atoms present in same plane are 5.
7. H 2N – C NH2 product (P). Correct statements regarding product P is
O
(A) P is example of tridentate ligand
(B) P is detected on addition of NaOH / CuSO4 by observing violet colour.
(C) P has glycosidic linkage
(D) P is example of bidentate ligand
8. Consider the reaction given below :-
O
NaOH
OTs ? (Major product (X))
Select the correct statement(s)

(A) The major product gives effervescence with NaHCO3 solution
(B) (X) decolourises Br2 – water
(C) Formation of major product involves nucleophilic attack
(D) The given reaction involves nucleophilic substitution.

9. Ph C C CH CH COOH conc
H 2SO 4
? (Major product)
Select the correct option(s)
O O Ph
(A) is the major product
(B) Sulphonation takes place in the aromatic ring forming major product
(C) Benzoic acid is the major product
(D) Anchimeric assistance provided by –COOH group facilitates preferential elelectrophilic
addition to acetylenic linkage
10. Which of the following reactions is / are correct with respect to the major product given ?
(A) aqueous THF I

KI
Br
OH Cl
(B) SOCl2 NEt 3
Br
CH3 CH3
(C) CH 2 C C N HBr
Br CH 2 CH CN (D) Py Br2

For the following sequence of reactions.
Conc.
O H SO P
2 4
HCCl3 AC2O
P NaOH
(Q) (R)
ACO /
11. Major product Q will be
OH
OH OH OH
CHO CH2Cl
(A) (B) (C) (D)
O
CHO
H
12. Q R reaction is?
(A) Perkin (B) Cannizaro
(C) Friedal craft alkylation (D) Friedal craft acylation

(iv) Matching List

This section contains SIX questions of matching type.
This section contains Two tables (each having 3 columns and 4 rows)
Based on each table, there are THREE questions
Each question has FOUR options (A), (B), (C) and (D). ONLY ONE of these four options
is correct
For each question, darken the bubble corresponding to the correct option in the ORS.
For each question, marks will be awarded in one of the following categories :
Full Marks : +3 If only the bubble corresponding to the correct option is darkened.
Zero Marks : 0 If none of the bubbles is darkened.
Negative Marks : –1 In all other cases
Answer Q.13, Q.14 and Q.15 by appropriately matching the information given in the
three columns of the following table.
Column-I Column-II Column-III
Compound Formed by the reaction Properties of compound
(A) Crotonic acid (P) When phenol reacts (i) It does not have –CO2H
with concentrated HNO3 but it gives effervescence
of CO2 with NaHCO3
(B) Picric acid (Q) When glucose reacts (ii) It decolorises bromine
with dilute HNO3 water
(C) Valeric acid (R) When acetaldehyde (iii) It has two –CO2H group
reacts with CH2(CO2Et)2
in pressence of NaOEt
followed by hydrolysis
and heating
(D) Glucaric acid (S) When pentane nitrile (iv) Carboxylic acid with
undergoes hydrolysis hydrophobic alkyl group
13. Which is correct option?
(A) A, S, iv (B) B, Q, iii (C) C, S, iv (D) A, R, iii
(A) B, S, i (B) B, P, i (C) D, S, iv (D) C, Q, ii
(A) D, Q, iii (B) C, R, i (C) A, Q, iv (D) None of these

Answer Q.16, Q.17 and Q.18 by appropriately matching the information given in the
three columns of the following table.
Column I Column II Column III

Me
MeCH2CH2CH2Cl
(I) (A) Only one organic (P) Carbocation is formed
AlCl3
product is formed as intermediate

NO2
(1) NaOH
(2) H
(II) (B) Product is optically (Q) Carbanion is formed
F
active as intermediate
Red P (limited)
(III) CH3CH2COOH (C) This process involves (R) Free radical is
Br2 (leq.)
nucleophite substitution formed as
reaction at one of the intermediate
carbon
COOH
NaNO2 + HCl
(IV) CH3 NH2 (D) This process involves (S) Nitrene is formed as
H
electrophle substitioun intermediate
reaction at one of the
carbon
16. Which of the following option is correctly matched :
(A) (I),(D),(P) (B) (II), (D), (Q) (C) (III), (A), (R) (D) (IV), (B), (S)
17. Select incorrect match :
(A) (I), (D), (P) (B) (II), (A), (Q) (C) (III), (B), (R) (D) None of these
18. Product of (III) can be converted into product of (IV) by :
(A) NaNO2 + HCl (B) aq. KOH followed by H
(C) NH3 (D) AgNO2


1. The structural formula of sativene is shown below. How many stereogenic centers are there
in this molecule ?
O3 / H2O
2. Product (A) + B (gas)
The number of moles of gas [B] per mole of given compound.

NH2
3. Find the total number of compounds which are less basic than
NH2 CH3 NH2
NH2 -
O +
(i) (ii) (iii) N
O
H
NH
N
(iv) (v) CH3 – CN (vi)
NH2
N
NH
COCH3
(vii) (viii)
N
NH NH
CH3
(ix) (x)
CH3
NH2
(xi)
CH3

4. Consider following sequence of reactions
O O
H3O +
A + B
O O (cyclic)
sodalime D
C
OH/
B
B E
E
Total sum of degree of unsaturations of product D & E will be

5. How many of the following will give aldol as well as iodoform reaction with suitable reagents
O
O
(a) MeCHO (b) Me–CH2–CHO (c) Me–C–Me (d)
O
O O
(e) Ph–CH2–C–CH3 (f) Me–CH=CH– C–Ph (g) Ph–C–Me (D)
O O

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JEE (MAIN + ADVANCED) 2022

GUIDED REVISION JEE (Main + Advanced) 2022

ORGANIC CHEMISTRY GR # 01 SCORE-1

SECTION–I : (i) Only One option correct Type

2. Select reaction which does not involve formation of free radical.

(A) 1 (B) 2 (C) 3 (D) 4

ORGANIC CHEMISTRY / GR # 01 (Set-3) E-1/5

Identify reagent sequence for above conversion :

(A) (i) Cl2 / hv ; (ii) Na / Et2O

7. Identify major product formed are correctly matched in following reactions ?

E-2/4 Physics / GR # 000

Identify correct statement for above reaction sequence ?

(A) 'Z' product is sweet smelling substance

(D) 'Z' product is resolvable

SECTION–I(iii) : Paragraph Type

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

12. (T) on reaction with HCHO in acidic medium produces :

ORGANIC CHEMISTRY / GR # 01 (Set-3) E-3/5

Paragraph for Q.No. 13 to 14

13. Identify 'T' product is above sequence ?

(R) (3) It can show geometrical isomerism , optical isomerism

E-4/4 Physics / GR # 000

(v) HCOOH (vi) MeCOOH (vii) O (viii) HC CH

(v) (vi) (vii) CH2–—C–CH 2 (viii)

ORGANIC CHEMISTRY GR # 02 SCORE-1

(A) Alanine (B) Valine (C) Glycine (D) Leucine

NO2 OCH3 CH3 OCH3

(i) HNO3/H2SO4 CH3COCl (i) conc. H2SO4 (i) dil. H2SO4 ,

NH2 NH2 NH2 NH2

SO3H NO2 NO2

SECTION-I(ii) : One or More than one

(i) Me2CuLi, Et2O

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

(A) Nucleophilic substitution (B) Elimination

ORGANIC CHEMISTRY / GR # 02 (Set-3) E-2/6

(A) (2) (C) (D)

11. Choose the correct option ?

ORGANIC CHEMISTRY / GR # 02 (Set-3) E-3/6

SECTION–I(iii) : Paragraph Type

(i) R' (i) KOH

16. List-I List-II

2. How many of reagents can carry out following transformation :

(e) Jones reagent (f) KMnO4, NaOH, (g) Al(OCMe3)3 , O O

3. Consider all possible carbonyl compounds including stereoisomers of molecular formula

give a racemic product(s) is/are :

ORGANIC CHEMISTRY / GR # 02 (Set-3) E-6/6

ORGANIC CHEMISTRY GR # 03 SCORE-1

SECTION–I : (i) Only One option correct Type

N–OH N–OH OH N–OH

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

Correct statement about compound-I & compound-II is :

ORGANIC CHEMISTRY / GR # 03 (Set-3) E-1/6

Above conversion is carried out with the help of :

Br2 NH3 N3H (i) HNO2

(B) (R) on reaction with NaNO2, HCl produces (X)

(C) Major product (P) & (S) are identical

(C) (i) H2 / Pd , BaSO4 ; (ii) HBr / H2O2 ; (iii) Na / Et2O

(B) CH3–CHO + 3Br2 + 4NaOH HCOONa + CHBr3 + 3NaBr + 3H2O

SECTION–I(iii) : Paragraph Type

ORGANIC CHEMISTRY / GR # 03 (Set-3) E-3/6