ORGANIC CHEMISTRY Adv Revision # 01

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 + nCO2
CO2Et

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

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

This section contains 4 multiple choice questions. Each question has four choices (A), (B), (C) and
(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

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
(C) is 'Q' product

O
CH–Ph
(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
(A) (B)
O Ph O

O O
(C) (D)
O O Ph

Paragraph for Q.No. 13 to 14

O O
NH2 H
+
+ +
H3O H
R P –gas Q R S
–H2O Dimerise
COOH –2H2O

Se
T

13. Identify 'T' product is above sequence ?

N N
(A) (B)
N

N NH 2
(C) (D)
N NH 2
14. Identify 'R' product in above sequence ?
O
NH2 H–C COOH
(A) (B)
O H2N O

HOOC
(C) (D)
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 ?
(i) Ph–CH=O (ii) HCHO
OH
O
(iii) (iv) Me–CCH

(v) HCOOH (vi) MeCOOH

OH

(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

(i) CH 2–CH–CH2 (ii) HO

OH OH OH
OH
COOH
HO H
(iii) (iv) HOOC–CH–CH3
HO H
COOH OH

OH NH2
COOH
(v) (vi)
HO OH

OH
COOH

(vii) CH2–—C–CH 2 (viii)

COOH OH COOH HO OH

NH2
OH

(ix) (x)
HO H 2NCH 2 CH2OH
OH
 ORGANIC CHEMISTRY Adv Revision # 02
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)
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–CH2–C (D) All correct
H H H H H CH3

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
NO2
(A) (B)

SO3H NO2

NH2 NH2
OH NO2
(C) (D)

NO2

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

This section contains 6 multiple choice questions. Each question has four choices (A), (B), (C) and
(D) out of which ONE or MORE are correct. 4(–1)
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) H N + Me–C–NH
(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) (B)
OH

(C) (D)

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 (C5H10 O) 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

SECTION–I(iii) : Paragraph Type

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)
Paragraph for Q.No. 13 to 14
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
OH OH OH O

–
(C) Ph–C–CH2OH (D) Ph–CH–CO2
O OH

14. Compound C is :

Ph O OH
(A) PhCH=CH–CH=O (B)
HO O Ph

–
(C) Ph–C–CH=O (D) Ph–CH–CO2
O OH
 Matching List Type
This Section contains 2 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. 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 FeSO4 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

This section contains 4 questions. The answer to each question is a single digit Integer, ranging from
0 to 9 (both inclusive) 4(–1)
1. Identify reactions correctly matched with their major product ?

O O
–
O Hot
O
(a)
Aqueous NaOH
OH
Me Me
LAH
(e)
C N C–OH
O

N=N–Ph
OH OH
1. Ph–N2Cl
(b)
T < 5ºC
(aq. NaOH)
+
2. H

+ – Aq. NaOH
(f) N C NH2
+
H–COOH
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'
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) :