TIFR PYQs Organic Chemistry

CHEMACADEMY 1
TIFR PREVIOUS YEAR QUESTIONS WITH SOLUTION

(2014 TO 2019)
ORGANIC CHEMISTRY
BIOCHEMISTRY / POLYMER
Q.1 Many times enantiomers give rise to different odors For example (–) Carvone (I) has sweetish minty smell
and (+)-Carvone(II) has a spicy aroma, like Persian cumin seeds. Similarly, (+)-Limonene (III) is found in
oranges and (–). Limonene (III) is found in lemons. What would be the stereochemical descriptors of their
absolute configurations?
O O
(-) Carvose (+) Carvose (-) Limonene (+) Lim onene

(f ound in gardes mist) (f ound in Persian cumin) (f ound in Lemon) (found in Oranges)
I II III IV
CHEM ACADEMY
(a) (I)-S, (II)-R, (III)-R, (IV)-S
(c) (I)-R, (II)-S, (III)-S, (IV)-R
(b) (I)-R, (II)-S, (III)-R, (IV)-S
(d) (I)-S, (II)-R, (III)-S, (IV)-R
Sol. (c)
O O
(3)
3 2 (2) 3 S 2 3
(2) R R
H H 1 H H
(1) S (1) (1)
(I) (II) (III)
Q.2 A dilute solution of the peptide shown is treated with excess 10% formaldehyde in methanol. Predict the
product formed.
O O O O O
H H2 H
H 2N CH C NH C C HN C C HN C C HN CH C OH
CH2 CH CH3 CH 2 CH 2
CH 3 CH 2
CH2
H 2C
NH2 OH
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CHEM ACADEMY 2
O O O O O
H H H
(a) N CH C NH C C HN C C HN C C HN CH C OH
CH2 CH CH3 CH 2 CH 2
CH 3 CH 2
CH2
H 2C
HN OH
O O O O O
H H H
(b) H 2N CH C NH C C HN C C HN C C HN CH C OH
CH2 CH CH3 H 2C CH 2 CH 2
CH 3 CH 2
CH2
H 2C
CHEM ACADEMY
O O O O
HN OH
O
H H H
(c) N CH C NH C C HN C C HN C C HN CH C OH
CH2 CH CH3 CH2 CH 2 CH 2
CH 3 CH 2
CH2
CH2
OH
NH2
O O O O O
H H H
(d) N CH C NH C C HN C C HN C C HN CH C OH
CH2 CH CH3 CH2 CH 2 CH 2
CH 3 CH 2
CH2
CH2
OH
N
CHEMACADEMY 3
Soln. (a)
O O O O COOH
H H H H H H
NH 2 C C N C C N C C N C C N CH
(dil. solution H H CH 2
of given peptide)
H2C CH 2
Me Me Ph
O
NH2
amine f ormation H C H (excess) OH
O
H O H H O H H O H
CH2 N C C N C C N C C N NH
CH2 COOH
Ph Ph
N=CH 2
Aromatic E OH
Since OH is EDG
substitution
CHEM ACADEMY Mannich Type Macrocydization
CH 2 O O O O
H H H H H H H COOH
N C C N C C N C C N CH C N CH
CH 2
Ph Ph
N
H OH
Q.3 Compound I (1 mg) was added to anti-cavity fluoride toothpaste (25 mg). The toothpaste turned blue.
What did compound I get converted to ?
Me2N S NMe2
O O
Compound-1 Si
O
CHEM ACADEMY 4
(a) Me2N S NMe2 (b) Me2N S NMe2
N N
F
O F
(c) Me2N S NMe2 (d) Me2N S NMe2
N N
O OH
Sol.3 (c)
NMe2 S NMe2
Anti cavity
N Fluoride Reagent Tends to break
F - Toothpaste O – Si bond of silyl ether
Compound (I) O O (25 mg)
(1 mg)
CHEM ACADEMY
t
Bu
Ph
Si
O
Ph
NMe2 S NMe2
N
COOH
Neutralization
NMe2 S NMe2
NMe2 S NMe2 Since
O is a very strong N
N EDG. Hence Tend to Cleavage
C – O bond O O
O O
O
Q.4 Which of the following natural amino acids is not hydrophobic?
(a) Valine (b) Arginine (c) Leucine (d) Isoleucine
Soln. (?)
CHEMACADEMY 5
Q.5 Which of the following equations measuringfully represents the change of concentration of a non-ribosonal
protein (P) inside a cell. Here  is rate at which proteins are synthesized by the ribosomes from constitutent
amino acids and  is the rate of degradetion dilution of the protein due to proteases and cell growth
P P
(a)  P  P (b)  t   P
t t
P P
(c)  P   (d)    P
t t
Soln. (?)
Q.6 Predict the feasible product/products of the following bio-conjugation reaction.
O
pH 7.4
N R 1 SH
R HEPES Buff er
O
CHEM ACADEMY
O
N
O
N R
(1) R 1 R (2) H
S
O CO2H
O O
R
N R N
(3) R1 H (4) R 1 S
S CO2H
O
(a) 1, 2 and 3 (b) 1 only

(c) 2, 3 and 4 (d) 1 and 2
Ans. (a)
Sol.
O O
R
N pH = 7.4
+ R 1 — SH O S OH
HEPES =
Buff er N
N
O (aq.)
HO
CHEM ACADEMY 6
Since pH = 7.4 Basic mu

R 1— SH
aq. HEPES
R 1 — S (Increased nu)
H —OH
OH
Possible product / Products?
Possibility (1)
O O
R
N Michael N
+ R1— S H O H
add b/c
-c is E S
O O
O
R
N
CHEM ACADEMY O
N
R
Since
R1 — S
O
OH is present
R1 — S COOH Hence Basic (Product (1))
Hydrolysis is also possible
Acid-Base
Reaction then
Neutrals -3 atoms
O
R
N
H
R1 — S COOH
Product - (3)
Possibility (2)
CHEMACADEMY 7
O O
R R 1— S R
N N
Since carbonyl (C) S — R1
is also E
O Hence Here Nu O
Substitution will occur OH
with ring opening Basic
Hydrolysis
O
R
N
OH
O as e
R c i d-B henn
O
A n T
N o
c tio iz ati
H R ea ut r a l
COOH Ne
Q.7 The restriction enzyme EcoRI recognize and cuts a six basepair long DNA sequence (GAATTC). You are
given a bacterial genome which is 5 × 106 base pairs of unknown sequence. Estimate the number of
EcorRI cut sites that you would expect
(a) 1220
Sol.7 (a) CHEM ACADEMY (b) 10037 (c) 124 (d) 102874
The frequency of cutting ina random DNA sequence for a given restriction enzyme is once per energyi.e.,
4n
* where n is the number of basis in the restriction enzymes recognition sequence
* The ‘4” derives from the flat that there are four different possible nucleotides that may be
inserted at any one position (h, A, T or C)
* ECO RI have a six base recognition site so they will cut once per energy
 4 6  4096 base
Bacterial genome = 5 × 106 base pair
5 10 6
Number of ECO RI cut sites =  1220
4096
Q.8 Based on the behaviour of the metalioenzymes, consider the following statements
(i) In the enzymes, Zinc activates O2 to form peroxide species
(ii) In the enzymes, Zinc activates H2O and provides a Zinc-bound hydroxide
(iii) In the oxidases, Iron activates O2 to break the bonding between the two oxygen atoms
(iv) Zinc ion acts as a nucleophile and attaccks at the peptide carbonyl
Which combination of statements is the correct one
(a) (i) and (ii) (b) (ii) and (iii) (c) (iii) and (iv) (d) None of the above
Soln. (c)
CHEM ACADEMY 8
Q.9 The following bio-conjugation reaction is known as native chemical ligation (NCL) and is used to stitch to
peptides together. The intermediate for this reaction has been shown. Predict the product of the following
NCL reaction.
HS
S
H2N
O O
= amino acid in a peptide chain
H 2N
CHEM ACADEMY O
Interm ediate
O
(a)
N N
H H
SH
O
(b)
N
H O
(c) HS
N
H O
O
(d)
S S
N
O H
CHEMACADEMY 9
Sol.9 (b)
good UG (more Nu)

SH
S — Ph +
O NH 2
(Less Nu)
S – Nu
is more Hence Tedn
to attack 1st
good UG
Intermediate O
NH 2
O
CHEM ACADEMY
NCL (native chemical Ligation) – Reaction to
make peptide in stiching manner
(Peptide Bond)
O SH
NH
O
Q.10 You want to purify a DNA binding protein (pI ~ 9.0) from other cellular proteins (pI ~ 5.5) by ion
exchange chromatography. You have the choice of choosing high pH (9.0) or low pH (5.5) buffers and
anion and cation exchange columns. Anion exchange columns are positively charged and cation exchange
columns are negatively charged. To purify the protein you will use
(a) Anion exchange column with a low pH (5.5) buffer
(b) Anion exchange column with a high pH (9.0) buffer
(c) Cation exchange column with a low pH (5.5) buffer
(d) Cation exchange column with a high pH (9.0) buffer
Sol.10 (d)
Protein is positively charged. Hence will use cation exchanger. Since pH of protein is 9.0 we will use pH
9.0 buffer to elute it as at this pH, the protein will no longer be changed and elute out of the chamber.
CHEM ACADEMY 10
Q.11 Where on a given protein are you mere likely to find a Leuctine residue whose structure is given below
NH 2
O
OH
(a) In the interior part of the system
(b) In the exterior part
(c) Equally likely in the exterior or the interior parts
(d) Depends on whether the protein is water-soluble or is a membrane protein
Soln. (?)
Q.12 What is the role of reagent A in the macrocyclization reaction based on the nucleophilic attack of 2 and 1?
1
O O
N
S O O S
N
O O water/toluene NH
CHEM ACADEMY
O O
LiOH
N
NH
S S C16H 33P+(C4H 9)3

NH HN O
O (reagent A)
N 80°C, 6h
2
(a) Reagent A is transferred to the toulene layer and pulls hydroxyl ions to toluene to
deprotonate 2
(b) Reagent A acts as a catalyst for the macrocyclization reaction by forming coordinate covalent
bonds with 1 and 2
(c) Reagent A is transferred to water and hydroxyl ions are transferred to toluene to
deprotonate 2
(d) Reagent A reacts with LiOH to form a lithiated intermediate that catalyzes the reaction
CHEMACADEMY 11
Sol.12 (a) Me
O O Me
N
M S O 1° 1°
O S M Ms N
O Ms O OMs
O
Mesyl group (Soluble in both medium)
= Ms = Methyl sulphonyl
Phase Transf er
Catalyse
LiOH H 1C16H 33P(C 4H9)3Cl
H 1C16H 33P(C 4H9)3Cl
cross the boundary
O H H O
S N N S Me OH P (C 16H3)
CHEM ACADEMY
O N
H
O
Base
Base
(C 4H9) 3
O O
H
S N
HN S Me OH P (C 16H3)
N (C4H 9)3
O
O
Me Base
Deprotonation will occur
Me
1°
OMs OMs
N
1°
O
N N S Me
N
O
Me
CHEM ACADEMY 12
Since Reagent (A) is transfered to H2O and OH are transfered to Toluene where (2) and (1) is
present. Hence deprotants (2) to  rate of SN 2
O Me
O
S N
Me
N N S Me
O
OH O
OH Desulphonation occur by basic
hydrolysis then nuetralization
Since Reagent (A) is tranferred to H2O and OH are transferred to toluene where (2) and (1) is present.
Hence deprotants (2) to  rate of SN 2
O Me
O
CHEM ACADEMY S N
Me
N N S Me
O
OH N O
M OH Desulphonation occur by basic
hydrolysis then nuetralization
NH
N (1)
NH
(2) NH
N
Me
Q.13 All natural amino acids, except one, react with cold nitrous acid and produce nitrogen gas. Which one of
the following is that odd amino acid?
(a) Tryptophan (b) Glycine (c) Proline (d) Histidine
Sol.13 (c) Proline

R – NH 2  HNO 2  R   N2 
 R  N 2 
HNO 2
OH not gives N2 gas due to 2° – amine
N
H O
CHEMACADEMY 13
Q.14 NMR spectroscopy can be used to assay for drug binding to certain protein targets. One of the primary
objectives of any binding assay is the quantification of the free and the bound forms of a drug molecule at
a certain concentration of the protein target. Let us assume that the fully bound drug exhibits a 1H chemical
shift of  A while that of the free form resonates at  B for the same proton (as shown in figure). If the
exchange timescale (i.e., proportional to kOFF as kON is diffusion limited) between the free form of the drug
and its bound form is in microseconds, which of the following statements cannot be true assuming that the
drug is only 50% bound with its protein target?
(a) The NMR linewidth of the observed transition(s) will be different from the free form of the drug
(b) There will be two resonances obtained in the NMR spectrum of the Protein-Drug complex: one of the
free form while other for the bound form
CHEM ACADEMY
(c) We will see a single resonance at a position  eff which is in between  A and  B
(d) Varying the concentration of the drug molecule while observing the NMR signatures will provide an
estimate of the binding constant
Ans. (b)
Sol. Since the process is in equilibrium
So, at room temperature will observe only one peak for 1H NMR
So, option (b) is not true.
Correct option is (b)
Q.15 A bio-conjugation reaction can be used to modify a specific residue on a protein to attach therapeutics and
diagnostic agents. Predict the major product of the following bio-conjugation reaction with Fluorescein.
H
N
NH
S
NH
C-terminal
COOH
O pH 7.9
SH HO O OH
N-terminal
H2 N
Protein
CHEM ACADEMY 14
NH 2 HS NH2
O
C
NH
S O
NH
(a) O
HO O OH
NH 2
S NH2
NH
S HOOC
NH
CHEM ACADEMY
O
(b)
HO O OH
CO2H
NH 2
SH
N
NH H
S
NH
O
(c) HO O OH
CHEMACADEMY 15
HO 2C
(d) CO 2H
NH 2 S S NH2
HN HN
HN
NH S
S HN
NH
O
O
O
O
HO O OH
HO O OH
Ans. (b)
Sol.15
CHEM ACADEMY NH
N
COOH O
+
N-Terminus NH2 SH
HO O OH
pH = 7.9
(Basic Medium)
COOH
NH 2 S
(more Nu )
SN 2 type Bioconjugation reaction
to give ring opening of Aziridine
CHEM ACADEMY 16
NH2
S
NH 2
NH
S
O HOOC
NH
O
HO O OH
Q.16 Predict the products X and Y of the following peptide ligation reaction.
SH
PPh2
H O H
N N
S X
O O
H
N
1. N 3 O
CHEM ACADEMY 2. H2O
O
O
H
N
N
H O
H
N Y
X Y
O SH O
H
(a) N PPh2
S
O PPh2
H O
SH N
S
O PPh2
O PPh2
H N
(b) N N
S
O O O NH
CHEMACADEMY 17
SH SH
SH O
PPh2 PPh2
(c) O PPh2
N N
S
O O
H O
N
S
(d) O PPh2
Ans. (a)
SH O
O H
H H PPh2
N NH
N N S
S
Sol.
O
CHEM ACADEMY O O
S H
PPh2
O
N H O N N
N O
N
S
N
H O N O PPh2
H
N H N
S N N N
O PPh2
O
H O H O
N N
S S
O PPh2 O PPh2
N N

 

HN HN
O O O
H H
CHEM ACADEMY 18
H 2O
O
H O
N H
S H O
O N
O Ph2P H S
N O PPh2
O N

 

HN O
O NH H
H
O H O
HS N
+ N N
PPh2 H H
O O
Q.17 Predict the product for the following sugar functionalization reaction
OR
NaN 3, DMF
RO O
CHEM ACADEMY H3OC
O
SPh
OR = O S CH3
O
N3 N3
(a) N3 O (b) N3 O
SPh SPh
N3 H 3CO
N3 N3
(c) N3 O N (d) RO O SPh
N3 3
N3
Ans. (b)
OR
b
Sol. O
RO SPh
MeO a
CHEMACADEMY 19
Here O will show NGP or

Intramolecular SN2 at Ca
O as well as at Cb
–OR = –OMs = O S Me = Methyl sulphonyl
Mesylate  –OMs O
N 3 Attack at Ca and Cb hence N3
stereo of N 3 will be same as
stereo of leaving group. O
N3 SPh
NGP-Intermediate MeO
Q.18 Thiols are important molecular species present in cells and can mediate cell signaling processes. Aprocedure
for detecting thiols has been recently reported based on the following reaction. Predict the structures of
reaction products.
O N
O pH 7.6
CHEM ACADEMY
O S O
O
SH
(a) O N
S
O
O S O
N
O
O O O
(b) O S
S
CHEM ACADEMY 20
–
O O N
(c) O S
O
N
S O
(d) O S O O O
S
Soln. (a)
O S
O CHEM ACADEMY O
O
N
+ SH
PH = 7.6
Basic medium
S
Nu
Me
Me Me O
S O N
S–Nu
O S + O
Substitution O
S O N
O S + + O CH2
O
CHEMACADEMY 21
Q.19 A common characteristic of conducting polymers, such as polypyrrole and polythiophene, which make
them conduct electricity is
(a) The presence of stereogenic centers of the same configuration
(b) A monodisperse distribution in molecular weight
(c) Conjugation throughout the polymer chain
(d) A very long glass transition temperature
Soln. (c)
Q.20 Which of the following monomers do you expect to find in a RNA molecule?
NH 2
O O–
N
NH 3+ N
(i) HO O (ii) O
O N
N
O P O
O– O
O
O HO
CHEM ACADEMY NH 2 (iv) R O

(iii) C CH 2
N N
O O CH3
N N R O C H O
C CH 3
O P O N+
O H 2C P CH 2
O O O CH 2
O CH3
O O
(a) (i) (b) (ii) (c) (iii) (d) (iv)

Sol. (b)
Nucleotide
Sugar Base Phosphate

(-D-Ribose) groups
RNA is a polymer of nucleotide so three molecules will present will RNA
(i)   D Ribose
(ii) Nitrogen containing base
(iii) Phosphate groups
CHEM ACADEMY 22
Q.21 The number of peptide bonds in a protein consisting of a linear chain of 128 amino acids is
(a) 127 (b) 128 (c) 129 (d) None of the above
Sol. (a)
Number of peptide bond – 127 in a protein consisting of a linear chain of 128 amino acids.
Q.22 The restriction enzyme Alu1 recognizes four DNA base pairs and cuts right in the middle as shown below

5 AGCT 3
3 TCGA5

What fragments of DNA do you expect to recover from the reaction mixture if the following DNA sequence
5 CGACTAGCTACTGAGCTAAA 3
3 GCTGATCGATGACTCGATTT5
is partially digested with Alu1. Partially digested means that the reaction is not allowed to proceed to
completion, say only to 50%.
(i) 5 CGACTAG 3 5 CTACTGAGCTAAA 3

and

3 GCTGATC 5  3 GATGACTCGATTT 5
(ii)
CHEM ACADEMY
5 CGACTAGCTACTGAG 3
3 GCTGATCGATGACTC 5
and
5 CTAAA 3
3 GATTT 5
5 CGACTAG 3 5 CTACTGAG 3 5 CTAAA 3

(iii) 3 GCTGATC 5 and 3 GATGACTC5 and 3 GATTT 5
(iv) 5 CGACTAGCTACTGAGCTAAA 3
3 GCTGATCGATGACTCGATTT 5
(a) Only (i) and (ii) (b) Only (i) and (iii)
(c) Only (iii) and iv (d) (i), (ii), (iii) and (iv)
Sol. (d)
C G A C T A G C T A C T G A G C T AAA
a+b b+c
C C TGATC GATGAC TC GATTT
a b c
Ans a+b b+c
5 C G A C T A G C T A C T G A G C T A A A 3
3 C C T G A T C G A T G A C T C G A T T T 5
a b c
CHEMACADEMY 23
a+b  b+c – Be3 partially digested

CGACTAGCTACTGAG
GCTGATCGATGACTC
a+b
CTACTGAGCTAAA
CATGACTCGATTT
b+c
C G A C TA G
(a)
C C TGATC
C T A A A (c)
GATTT
Ans. 4 It has all the possible combination. If it had been completely digested, you would have got only a,
b and c and not combinations.
Q.23 Molecular knots have been observed in DNA and proteins. Although synthetically challenging, a few
purely organic molecular knots have been reported in the literature. One such elusive knot is the trefoil
knot. An organic trefoil knot. An organic trefoil knot was prepared by reacting two structurally distinct
components X and Y. The reaction mixture contained four products as shown in the figure below
Y Y Y X
CHEM ACADEMY
X X X X
X X Y Y
X X X X
Y Y Y Y Y Y Y Y
(C) (D) (E) (F)
Which spectra will afford distinguish spectral features for (1) C and D? and (2) E and F?
(a) Circular Dichrosim Spectra for C and D; 1H-NMR for E and F
(b) 1H-NMR and 13-C-NMR Spectra for C and D; Circular Dichroism for E and F
(c) Absorbance and Emission spectra for C and D; Circular Dichrosim for E and F
(d) Infra-Red spectra for C and D; Circular Dichrosim for E and F
Soln. (a)
NAME REACTION / REACTION MECHANISM / REAGENTS
Q.24 Predict the reaction condition for the following synthetic transformation?
H
?
N N
COOEt
H COOEt
(a) Acid (b) Heat (c) Base (d) Light
Ans. (b)
CHEM ACADEMY 24
H
H

Soln. heat
H N N
H
EtO 2C CO2Et
4   2  Photo  Con
4  2  heat  dis
# Direction of both hydrogen is opposite.
Dis
Opposite
ODC
ODC
Q.25 Product of the following reaction is

O
Ph Zn
Br THF
N Ph
BoC
CHEM ACADEMY Ph Ph Ph Ph
(a) OH (b) OH (c) OH (d) OH

N N N N
Ph Ph Ph Ph
Boc Boc Boc Boc
Ans. (c)
Ph O
Ph Zn  Zn +2 + 2e –
+
Br THF
N Ph
BOC
Ph
Sol.
OH
N Ph
Br
CHEMACADEMY 25
Q.26 What is the main product of below reaction?
OH (i) LiAlH 4, MeONa, THF
?
(ii) I2–
(a) (b) OH
I OH I
I
(c) OH (d)
OH
I
Ans. (?)
OH
I
OH Hydride attack at Ca I–I
Sol.
b a OH
H
Q.27 Predict the product obtained in the following reaction
O O
CHEM ACADEMY OCH 3
NaBH 4, CeCl 3
EtOH, H 2O
–15°C
CHO
O
(a) all of these (b) OH
CHO
OH O O O
(c) OCH3 (d) OCH 3
CHO OH
Ans. (c)
O O OH O
NaBH 4, CeCl3
OCH 3 EtOH, H 2O OMe
Sol. –15°C
CHO CHO
Chemoselective
reduction of Ketone
CHEM ACADEMY 26
Q.28 Phosphite esters undergo nucleophilic substitution with alkyl halides. Predict the final stable product of the
following reaction
O I
P
O O
O I
O I
(a) P (b) P
O O O O
O I I
O
(c)
CHEM ACADEMY
O
P
O
I (d)
O
P
O
OH
Ans. (b)
O I
O
P P +
O I O O
Sol. O
P I O
O O
O I
P
O O
CHEMACADEMY 27
Q.29 Identify the products A and B in the following reaction scheme
CHO
1. PPh 3
2. NaH OH
Br I P
Br NaH
P= C
(a) I = Br Ph3P
PPh3
(b) I = Ph3P P=
OH
OH
PPh3
(c) I = Ph3P P=
OH
OH
CHEM ACADEMY
(d) I = Br Ph3P P=
O
Ans. (d)
Soln.
Now, stablized phosphorous ylide forms Z-alkene from aldehyde.
Correct option is (d)
CHEM ACADEMY 28
Q.30 Predict the major product of the following hydroboration reaction

R heat
BH CH 3CH = C(CH 3)2
R=
R
R R
B
(a) R (b)
B
R
R
(c) R (d) B
B R
R
Ans. (c)
R CH3 CH3 CH3
Sol. B H + CH3 CH C CH CH
CH3 R2B CH3
R
Q.31 What major products are obtained in the following Mitsunobu reaction?
CHEM ACADEMY
OH
O
Ph 3P
X + Y
H EtO 2C N N CO2Et
H
CO 2Me PhCO2H
CO2Ph
and Ph3P = O
(a)
O
H H CO2Me
CO2Ph
and Ph3P = O
(b) O
H H CO2Me
OH
and Ph3P = O
(c)
O
H H CO2Ph
CO2Ph
and Ph3P = O
(d)
O
H H CO2Ph
Ans. (b)
CHEMACADEMY 29
H–CO2Ph
EtO2C
EtO2C  N  N  CO 2 Et N N
Sol.
Ph3P CO2Et
: PPh3
OH
EtO2C H Ph3P O
EtO2C H
O
H H
N N CO2Me N N + O
Ph3P CO2Et H CO Et H H CO Me
2
CO2Ph
PhCOOH + Ph3P = O
 O
H H CO Me
2
Q.32 What is the product of the following reaction?

CHEM ACADEMY
N N + 1/n (HCHO)n + Me3SiCl
Ethyl Acetate
70°C
Dip Dip
Dip = 2, 6-diisopropylphenyl
N N Cl N N Me3Si
(a) Dip Dip (b) Dip Dip
C C
SiMe 3 Cl
N N Cl
(c) Dip Dip (d) None of the above
C
H
CHEM ACADEMY 30
Soln. (c)
O
||
Dip N N Dip HCH Dip N N Dip 
ClSiMe3

Sol. H
O H
Dip N N Dip 3 CH COO Dip N N Dip Dip N N Dip



H C 

C H OSiMe
Me SiO H Me SiO H
Dip N N Dip
C + SiMe3O   CH 3COOH  
Cl  SiMe3OH  CH 3COO
H
Q.33
CHEM ACADEMY
Predict the products of the following reaction
AgBF4
PhCl
O
Cl
O
+ AgCl
(a) + CO2 (b)
Cl F2B
O
+ BF3
O Cl
+ HF
(c) (d)
Ans. (a)
Sol. Correct answer is (a)
CHEMACADEMY 31
Q.34 What is the product of the following reaction?
DCM
Ph2P PPh2 + PBr3 +
P
(a) Ph2P PPh2
Br3
Br
P
(b) Ph2P PPh2
Br Br
Br
P
(c) Ph2P PPh2
Br3 Br
(d) None of the above

Ans. (b)
CHEM ACADEMY
Br Ph2 Ph2 Ph2
PPh2 P P P
P Br Br
P Br P Br P Br + Br2
Sol.
PPh2 Br P P P
Ph2 Ph2 Ph2
Br E Br
addition Br
Br E Br
DCM
(solvent) Br
Q.35 What would be the likely ratio of products X and Y for the following reaction on
2-methyl-cyclohexanone if we consider that torsional effects play a significant role in the reaction outcome?
O–
H
LiAlH4 LiAlH 4
O
H
O¯
H H
H
X Y
(a) X:Y = 80:20 (b) X:Y = 50:50 (c) X:Y = 20:80 (d) X:Y = 1:99
Soln. (a)
CHEM ACADEMY 32
Q.36 Degenerate C-C coupling reactions are very important for synthesizing supramolecular organic structures.
Name the reagents X, Y and Z that would be necessary to make the C3 symmetric product?
N
Br
Y
+ X
Z
Br Br
N N
H H
B
(a) X= Y = Pd(PPh3)3 Z = Na2CO3

N
H H
B
(b) X = Y = NiCl2(PPh3)2 Z = Na2CO 3
CHEM ACADEMY
HO
N
B
OH
(c) X= Y = Pd(PPh3)4 Z = Na2CO 3

N
HO OH
B
(d) X = Y = Pd(PPh3)4 Z = HCl

N
Sol.36 (a)
N
Br
Y
+ X
Z
Br Br O
In this Suzuki coupling takes place, this reaction takes place in basic medium and
boric acid are used in this reaction
CHEMACADEMY 33
H H
B
Pd(PPh3)4 Na 2(CO)3
N
(X) (Y) (Z)
INTERMEDIATES / GOC
Q.37 Which of the following is INCORRECT
Ph
(a) is more acidic than
(b) Acidity of following oxy-acids in water HIO < HIO2 < HIO3 < HIO4
(c) [Fe(H2O)6]3+ is less acidic than [Fe(H2O)6]2+ in water
(d)
CHEM ACADEMY and are tautomers
O
HO
Sol. (a)
H Ph
H
–H+ –H +
Ph
(I) (II)
I is more acidic than II due to annelation effect.
7 5 3 1
(b) HIO  HIO  HIO  HIO
4 3 2
HIO4 is more acidic due to A.S.  O.S
A.S  Acidic strength
O.S  Oxidation state
CHEM ACADEMY 34
3 2
(c) A.S.   Fe  H 2O      Fe  H 2O  6 
A.S.  O.S
taut
(d)
HO O
Both are tautomers
Hence answer (c)
Q.38 Cyclooctatetrane is
(a) Aromatic, because it is planar and it follows Huckel’s rule
(b) Antiaromatic, because it is not plannar and it does not follow Huckel’s rule
(c) Antiaromatic, because it is planar and it does not follow Huckel’s rule
(d) Nonaromatic, because it is not planar and it does not follow Huckel’s rule
Sol.38 (d)
Q.39
CHEM ACADEMY
It does not follow Huckel’s Rule.
Predict the products of the following reactions between cis-2 butene and singlet and triplet methylenes.
C
H H
Singlet
C
H H
Triplet
Singlet Triplet
(a)
Singlet Triplet
(b)
CHEMACADEMY 35
Singlet Triplet
(c)
Singlet Triplet
(d)
Ans. (a)
C
Sol. + H H
singlet
singlet carbene is stereospecific in nature.
H H
C H H
C
CHEM ACADEMY
concerted Mechanism Only cis product
C
H H
singlet
Triplet carbene is non stereospecific in nature.
H
H H H
Bond rotation
C H H
then spin
C
inversion
H
H
only spin
inversion
Both cis and trans product formed.
CHEM ACADEMY 36
STEREOCHEMISTRY
Q.40 Which among the following molecules is chiral?
H OH
O O
OH
COOH
OH H
O
(I) (II) (III)
(a) I (b) II (c) III (d) None of the above
Soln. (d)
H OH O
(I) (II) O
COOH COOH
POS achiral NOS POS
NOC COS
Chiral
CHEM ACADEMY
HO
OH
H H
POS achiral
COS
SPECTROSCOPY (NMR / UV / IR / 13C NMR / MASS)
Q.41 In the broadband decoupled 13C NMR spectrum, the number of signals appearing for the two pyrenediols.
A and B
OH
OH
OH OH
(A) (B)
(a) five and eight (b) eight and eight
(c) eight and seven (d) five and ten
Ans. (d)
CHEMACADEMY 37
POS POS OH
2 POS
4
OH 5 3 1
6
3 7 8 4
2 9
5
1 10
Soln. HO OH
(A) 5 signals (B) 10 signals
Q.42 If the peak in the mass spectrum of C2F6 at mass number 138 is 100 units tall, what will be the heights of
the peaks at mass numbers 139 and 140. Isot opic abundances: 12 C, 98.89%,
13C, 1.11%, 19F, 100%
(a) 2.24 and 0.0126 (b) 50 and 25
(c) 2.24 and 0.025 (d) 1.12 and 0.0126
Soln. (a)
CHEM ACADEMY
Mass spectrum of C2F6  138

Intensity of isotopic signal  m : m  1 : m  2
138 139 140
Intensity of m+ 100%
Intensity of (m + 1) = (Relative abundance × number of atom) + .....
(m + 1) 100%  1.1 × 2 = 2.2
Intensity of (m + 2) = 0.006 × 2 = 0.01 2
m+1:m+2
2.22 : 0.012
Q.43 Identify the compound whose molecular ion appears as a pair of equal intensity peaks at
m/z = 122 and m/z = 124. Large fragment ions are seen at m/z = 43 (base peak).
(a) 1-bromopropane (b) 2-bromopropane
(c) Both A and B (d) None of them
CHEM ACADEMY 38
Soln. (c)
Relative intensity of one Bromine
 m+ .......... m + 2
79Br : 81Br
100 : 97.5
1 : 1
e– Br
Br
(a)
-Cleavage
+ + Br
Br e– Br +
(b)
CHEM ACADEMY Both (a) and (b)

Bromine molecular ion appears as a pair of equal intensity.
Q.44 Identify the organic molecule which contains 66.6% carbon, 11.1% hydrogen. In infra-red spectrum of
the molecule, bands are observed at 2941-2857, 1715 and 1640 cm–1. In proton NMR, three signals
appeared at : (i) 7.52 (q, 2H), (ii) 7.88 (s, 3H), (iii) 8.93 (t, 3H) in ppm scale.
(a) Ethylmethylketone (b) 2-Butanol
(c) 1-Butanaldehyde (d) None of them
Ans. (d)
Soln. since signals chemical shift are not matching any of given option, hence correct option is (d) None of them.
Q.45 For electronic transitions in organic molecules, the expected energy ordering of the transition is:
(a)  to *  n to *   to *  n to *
(b)  to *  n to *  n to *   to *
(c) n to *   to *  n to *  to *
* * * *
(d) n to    to   n to    to 
Ans. (c)
CHEMACADEMY 39
*

*
n
Soln.   to *  n to *   to *  n to *

Correct option (c)
Q.46 An organic compound (C9H10O3) exhibited the following spectral data : 1R: 3400, 1680 cm–1; 1H-NMR
: 7.8 (1H, doublet, J = 8 Hz), 7.0 (1 H, doublet , J = 8 Hz), 6.5 (1 H, singlet), 5.8 (1H, singlet, D2O
exchangeable), 3.9 (3 H, singlet), 2.3 (3 H, singlet). The compound is,
O
(a) HO (b) HO
OMe
Me
O
Me OMe
(c) CHEM ACADEMY

MeO
O
H
(d) HO
O
OMe
OMe Me
Ans. (d)
Sol. (d) C9H10O3
5.8 (1H, singlet, D2O exchangeable)  shows there is a acidic proton (O – H).
6.5
7.8
HO
O
7.0
OMe Me
Q.47 Predict the multiplicities for hydrogens on C1, C3 and C4 of butanone associated with the spin-sping
coupling in its 1H NMR spectrum.
(a) H’s on C1: Singlet; H’s on C3: Doublet; H’s on C4: Triplet
(b) H’s on C1: Singlet; H’s on C3: Triplet; H’s on C4: Quartet
(c) H’s on C1: Singlet; H’s on C3: Quartet; H’s on C4: Triplet
(d) H’s on C1: Triplet; H’s on C3: Doublet; H’s on C4: Triplet
Ans. (c)
CHEM ACADEMY 40
O
Sol.
CH3 CH2 C CH3
4 3 2 1
Triplet quartet (S)
Q.48 An organic compound has the following spectroscopic properties: Mass Spectrometry: m/z 102 (very
small), 87 and 43 are the largest ions; 1H NMR:  1.4 & 3.9 ppm (both singlets, intensity ratio 3:2); 13C
NMR:  108, 64 & 25 ppm; Infrared spectroscopy: several strong absorptions in the 1000 to 1300 cm–1
region. Which of the following is the most likely formula of this compound?
O O
(a) (b) O
O
O O
(c) O (d)
O
Ans.
Sol.
(a)
CHEM ACADEMY
m/2  102 means molecular ion peak therefore molecular mass of a compound is 102 unit.
1
H NMR    1.4 ppm 3.9 ppm
3 2
(Singlet) (Singlet)
(there two should be connected to deshielding atom)

1000 – 1300 cm–1 region represents then C–O stretching in 13CNMR
O
C 110–120 ppm
O
O CH2 60–700 ppm
CH3 15–30 ppm
64ppm 108ppm
H H H
4H O 1.4ppm
H H
3.9ppm H H 25ppm
O
H
H H
all are equivalent don’t split.
CHEMACADEMY 41
Q.49 A compound with molecular formula C5 H12 O2 , has strong infrared absorption at 3300 to
3400 cm–1. The 1H HMR spectrum showed three singlets at  0.90,  3.45 and  3.20 ppm; with relatives
areas 3 : 2 : 1. Addition of D 2 O to the sample eliminates the lower field signal. The
13C NMR spectrum shows three signals all higher than
 100 ppm . Which of the following compounds
best fits this data?
(a) 1, 5-pentanediol (b) 1, 3-dimethyl-1, 3-propane
(c) 2, 2-dimethyl-1,3-propanediol (d) 2, 4-pentanediol
Ans. (c)
12
Sol. C5 H12 O 2 DBE  5  1  0
2
3300  3400 cm 1  means  O  H bond
 0.9 3.45 3.2

relative area 3 2 1
number of hydrogen 6H 4H 2H
CHEM ACADEMY
HO H2C C CH2 OH
CH3
CH3
(Answer can be predicted on the basis of intensity comparision).
Q.50 Neopentyl chloride, (CH3)3CCH2Cl, reacts with a strong base (sodium amide) to produce a new
compound. This compound has two 1H NMR singlets at  0.20 pmm and  1.05 ppm (intensity ratio =
2:3). What is the most probable structure of this compound?
(a) 2-methyl-2-butene (b) 1, 1-dimethylcyclopropane
(c) methylcyclobutane (d) cyclopentane
Soln. (b)
H 3C H3C
H2   H 3C H 0.20 ppm
H 3C C C Cl N a N H2
H2
  H 3C C C Cl H 3C H
Sol. H CH2 H
5 ppm H 2C H
1.0
Q.51 Which of the following statements is the best definition of the base peak in a mass spectrum?
(a) The molecular ion peak (b) The lowest m/z peak
(c) The highest mass rearrangement ion (d) The ion peak of greatest intensity
Ans. (d)
CHEM ACADEMY 42
Sol. Base peak in most spectrum is the ion peak of greatest intensity.
this is base peak

Q.52 A C5H12O2 compound has strong infrared absorption at 3300 to 3400 cm–1. The 1H NMR spectrum has
three singlets at  0.9,  3.45 and  3.2 ppm with relative areas 3 : 2 : 1. Addition of D2O to the sample
eliminates the lower field signal. The 13C NMR spectrum shows three signals all at higher field than
 100 ppm . Which of the following compounds best fits this data?
(a) 1, 5-pentanediol (b) 1, 3-dimethoxypropane
(c) 2, 2-dimethyl-1, 3-propanediol (d) 2, 4-pentanediol
Ans. (c)
12
Sol. C5 H12O 2 DBE  6  5  1 
 66  0
2
IR  3300 to 3400 cm–1 means –O–H group.

intensity
CHEM ACADEMY
0.9
3
3.45
2
3.2 ppm
1
6H 4H 2H
CH3 (3.2ppm) CH3

|  |
D2O shake
HO  H 2C  C  CH 2  OH (3.45ppm)   DO  CH 2  C  CH 2  OD
| |
CH3 (0.9ppm) CH 3
After addition of D2O it starts to convert into deturition product.
Q.53 A compound of formula C5H12 gives one signal in the 1H NMR and two signals in the 13C NMR spectra.
The compounds is
(a) pentane (b) 2-methylbutane
(c) 2, 2-dimethylpropane (d) cannot tell without more information
Ans. (c)
Sol. C5 H12
CH3
H3C C CH3 1H NMR one singlet
CH3
In 13C NMR number of signals = no. of different type of carbon. Here two type of carbon hence two
peaks.
CHEMACADEMY 43
Q.54 The 1H NMR of 1, 1-dibromoethane consists of two well-separated signals, one large and another one
small. Which one of the following statements is correct?
(a) The large signal is a quater and the small signal is a doublet
(b) The large signal is a triplet and the small signal is a singlet
(c) The large signal is a singlet and the small signal is a triplet
(d) The large signal is a doublet and the small signal is a quartet
Ans. (d)
Br
Sol. H3C CH
d q
Br
large signal is doublet of 3H
small signal is quartet of 1H
Q.55 A magnetic resonance spectrum, recorded using a radiation of frequency 100 MHz, is shown below.
What can you say about the nature of this spectrum?
CHEM ACADEMY
Signal
Magnetic field
(a) It is a continuous-wave NMR spectrum
(b) It is a Fourier transform NMR spectrum
(c) It is an ESR spectrum
(d) None of the above
Soln. (c)
Q.56 If the peak in the mass spectrum of C2F6 at mass number 138 is 100 units tall, what will be the heights of
the peaks at mass numbers 139 and 140. (Isotopic abundances: 12 C, 98.89%,
13C, 98.88%; 13C, 1.11%; 19F, 100%)
(a) 2.24 and 0.0126 (b) 1.12 and 0.0126

(c) 50 and 25 (d) 2.24 and 0.025
Soln. (a)
CHEM ACADEMY 44
PERICYCLIC REACTION
Q.57 Predict the product of the following reaction
Me
O
210°C, 8h
SO2
Me O Me O
H H
(a) H (b) H
H H
Me O Me O
H H
(c)
CHEM ACADEMY
H
H
(d) H
H
Ans. (c)
Me O
Me O
210°C
H
8h
SO2
(4 + 2) cyclo addition
above
Sol. O Me O
Me H
H
H
H
H
below
CHEMACADEMY 45
Q.58 Predict the final product of the following reaction:
Me 1. Heat
?
2. Maleic anhydride, AlCl 3
Me
H H
Me Me
H H
Me Me O
(a) (b) O
O
O O O
H
H
Me
Me Me
H Me
H O
(c)
CHEM ACADEMY O
O
(d) O
O O
Ans. (a)
O
(1) 
+ O
electric cyclization
ODC O
4h + 2  heat  dis ODC
(4 + 2) cyclo addition
H
H CH 3
CH 3
Soln.
H
H
O
O
O
due to secondary interaction
CHEM ACADEMY 46
Q.59 What are X and Y in the following reaction?

O
SiMe3 CsF
X Y
OS(O)2CF3
O
(a) (b) O
X Y X Y
(c) O (d) O
X Y X Y
Ans. (c)
Me
Si
CHEM ACADEMY
Me
Me CsF
O 
Sol.
O S CF
3 X
O
+ O O
Y
BASIC MATHEMATICS
Q.60 The equation y = exp(ikx) where i = sqrt(–1) has a purely oscillatory solution if an only if
(a) When k is imaginary (b) When k is complex
(c) When k is real and negative (d) When k is real and non-zero
Soln. (?)
Q.61 A bag contains 20 coins each labeled with one-letter code for amino acids. A coin is drawn at random the
letter on the coin is noted down the coin it kept back in the bag before the next draw. If the process is
continued for five times, then what is the probability that the letters on the drawn coins make the word
‘DRAWN’, in that sequence?
CHEMACADEMY 47
(a) 1.0 × 10–10
(b) 0.05
(c) Not possible as the word ‘DRAWN’ has letters which are not codes for amino acids
(d) 3.125 × 10–7
Ans. (d)
D R A W N 1 1
 5 5 
 0.03125  105  3.125 10 7
Soln. 1 1 1 1  20 2  10
20 20 20 20 20
Q.62 Which of these represents f(x) = sin|x|?
1
0.8
0.6 1
0.4 0.8
0.2 0.6
f(x)
0 0.4
–0.2 0.2
(a) (b)
f(x)
–0.4 0
–0.6 –0.2
–0.8 –0.4
CHEM ACADEMY
–1 –0.6
10 –5 0 5 10
x –0.8
–1
1 1 10 –5 0 5 10
0.8 0.8 x
0.6 0.6
0.4 0.4
0.2 0.2
f(x)
f(x)
(c) 0 (d) 0
–0.2 –0.2
–0.4 –0.4
–0.6 –0.6
–0.8 –0.8
–1 –1
10 –5 0 10 –5 10 10 –5 0 5 10
x x
Ans. (a)
Graph of sin x Graph of sin | x |
Soln.
Q.63 You are measuring the weight of a sample using a balance. After 7 measurements, the measured weight is
10  1gm. To get the standard error to  0.5gm, approximately how many measurements will you have
to do?
(a) 14 (b) 100 (c) 49 (d) 28
CHEM ACADEMY 48
Soln. (?)
  
Q.64 The volume of a parallel piped formed by three polar vectors : A  1iˆ  2ˆj, B  4kˆ and C  2iˆ  4ˆj is
(a) 20 cubic units (b) 40 cubic units
(c) 12 cubic units (d) 0 cubic units
Ans. (d)
a1 a 2 a3 1 2 0
b b2 b3 0 0 4
Sol. volume of parallelopiped = [a b c] = 1 = =0
c1 c2 c3 2 4 0

a  a1i  a 2 j  a 3 k

b  b1i  b 2 j  b3 k

c  c1i  c 2 j  c3 k
Q.65 The position of a particle in space has a Gaussian probability distribution function. This implies that the
CHEM ACADEMY
underlying potential energy surface for the particle
(a) Is flat in space
(b) Has a linear dependence on spatial coordinates
(c) Has a quadratic dependence on spatial coordinates
(d) Has a cubic dependence on spatial coordinates
Soln. (?)
Q.66 Mr. Bhatt has two children; the older child is a boy. Mrs. Ghose also has two children; at least one of them
is a girl. Let PB be the probability that both children of Mr. Bhatt are boys, and PG be the probability that
both children of Mrs. Ghose are girls. Assume the following (1) Birth of boys and girls are independent; (2)
no identical t wins are born; (3) neither parent followed
sex-selective birth of their offsprings, and (4) none of the children was transgender. What would be values
PB and PG?
(a) PB = PG (b) PB < PG
(c) PB > PG (d) PB = PG = 1/2
Ans. (c)
CHEMACADEMY 49
Mr. Bhatt Mrs. Ghose
(Two Children) (Two Children)
Boy PB atleast one girl PG

(Elder) (GG)
(BG)
(GB)
Both Boys
Both Girls
Soln.
PB = 1 / 2
PG = 1 / 3
1 / 2 > 1/3
PB > PG
Q.67 If R and r are the radii of outer and inner circles, respectively, then what is R/r? [Hint: the triangle is
equilateral]
CHEM ACADEMY
(a) 0.5 (b) 2 (c) 2 3 (d) 4
Ans. (d)
r R
• r 2
R
R 30º
Soln. 2
30º
3R
2
R
rr R
2
R
r
4
R R
ratio =  4
r R/4
CHEM ACADEMY 50
Q.68 In an experiment measuring the weight of the object, 100 repeats were performed by one student. He
found the mean weight of 332 grams with standard error of the mean as 5 grams. A lazier student only
performs 10 measurements on the same object. Which of the following values will her result be closest to?
(a) 330  50 grams (b) 400  15 grams
(c) 330  15 grams (d) 330  5 grams

Soln. (c)
Q.69 If the outer circle radius is ‘Z’, in the diagram given below, then what is the line segment AB? The ratio of
inner circles’ diameters is 2.
A B
4 2
(a)
3
CHEM ACADEMY
Z (b) Close to 2Z
5 2 5
(c) Z (d) Z
2 3
Ans. (a)
R
Soln. 2
r
R  2r
2z  2r  2R
2z  2r  2(2r)
2z  2r  4r
2z  6r
z
r
3
2z
R
3
2 2z 2 2z 4 2z
 
3 3 3
CHEMACADEMY 51
Q.70 What is the value of continued fraction given below?
2000
1
2000
2
2000
2
2 
(a) 1999 (b) 2000
(c) 2001 (d) None of them

Soln. (c)
Q.71 What is the value of i log10 i2, where i  1 ?

(a) Real and positive number (b) Real and negtive number
(c) Complex number (d) Purely imaginary
Ans. (b)
Soln. i log10 i 2  2i log10 i

i = 1
2   log10 
Negative
CHEM ACADEMY
1
Im aginary

1  Re a l Negative
Im aginary
Negative
For e.g. 2i×3i = -6
Q.72 A carpenter claims to have made a rectangular parallelepiped (cuboid), the length of whose three face
diagonals are 33, 56 and 65 metres. You are required to determine the length the main diagonal joining a
pair of opposite corners of this parallelpiped.
(a) 65 2 meters
65
(b) meters
2
(c) 65 meters
(d) It is not possible to make a rectangular parallelpiped with the claimed dimensions of three faces
Ans. (d)
Soln. Length of main diagonal is greater than other 3 diagonal of three faces of parallelepiped`
d12  d 22  d 33
Length of main diagonal =
3
332  562  65 2
 65
2
hence, It is not possible to make a rectangular parallelepiped with the claimed dimensions of the three
faces.
CHEM ACADEMY 52
a
Q.73 The integral  cos(x) sin(x) dx
a
(a) Equals to zero for any value of a, and cos(x) is symmetric in the range of the integral
(b) Is not equal to zero except for certain values of a, and sin(x) is antisymmetric in the range of the
integral
(c) Is not equal to zero except for certain values of a, and cos(x) is symmetric in the range of the integral
(d) Has a non-zero value depending on a

Ans. (a)
2 cos  x  sin  x  dx sin 2x

Soln. 
2 2
sin 2x
a
a dx this is odd function, hence its integration is 0
2
  
CHEM
 
ACADEMY
Q. 74 A set of N vectors X1 , X 2 ,.....X N satisfy the eigenvalue equation for an operator A with scalar eigenvalues

 
1,  2 ,..... N i.e., AX k   x X k . The linear combination vector X 
N  
C X
k 1 k k , where

Ck ’s are non-
zero scalar coefficients
(a) is not an eigen vector of A
(b) is an eigen vector of A only if the  k 's are all distinct (no two eigen values are equal)
(c) is an eigen vector of only if the  k 's are all equal

(d) is an eigen vector of only if Ck’s are equal
Soln. (c)
Q. 75 ABCD is a rectangle of area 50 m2. The mid-points AB, BC and AD are E, F and G, respectively. When
EF is extended, it meets extended DC at H. Similarly, when EG is extended CD at J. What is the area of
triangle EHJ?
(a) 50 m2
(b) 100 m2
(c) 200 m2
(d) The area cannot be determined without knowing the length and breadth of the rectangle
Ans. (a)
CHEMACADEMY 53
E
A B
G F
J D C H
Soln.
there is 8 equal
sections so 50 = 25 
8 4
is area of each section
hence area of Triangle EHJ = 50 mtr sq.
Q. 76 What is the value of i(i+2), where i  1
(a) Real number (b) Complex number
(c) Cannot be calculated (d) None of the above
Ans. (a)
i
i2
Soln.  i i  i 2  i i
CHEM ACADEMY
i  0  i cos  is in
2

2

i
ie 2
ei  cos   i sin 
Taking power iota both side
i
 i 
i
i    e 2 
 
 
 i2  
i
i    e 2 
 
 
  
i
i    e 2 
 
 
x x 2 x3
Since e  1  x   .........
2 3
2 3
i  1   1
i  1        ..........
2 2 2  2 3
CHEM ACADEMY 54
cos A  sin A  1
Q. 77 Consider the trigonometric function . It can be simplified as
cos A  sin A  1
1  sec A  tan A
(a) (b) cosecA + cot A
1  sec A  tan A
(c) 1/(cosec A – cot A) (d) All of the above
Soln. (d)
(A)
divide by cos on num. and den.
1  tan A  sec A
1  tan A  sec A
(B)
divide by sin on num. and den.
CHEM ACADEMY
cos ecA  cot A  1
 cos escA  1  cot A
cosec A + cot A
1
(C) cosec A + cot A =
cosec A – cot A
(D) All of the above
Q. 78 Which of the following is the curve x = y2.

30 30
20 20
10 10
Y 0 Y 0
–10 –10
–20 –20
i ii
–30 –30
–10 –5 0 5 10 –10 –5 0 5 10
X X
CHEMACADEMY 55
–10 –10
–5
–5
Y 0 Y 0
5 5
iii iv
10 10
–30 –20 –10 0 10 20 30 –30 –20 –10 0 10 20 30
X X
(a) (i) (b) (ii) (c) (iii) (d) (iv)

Ans. (c)
Soln.
CHEM ACADEMY
x = y2
x
Shape is parabola
××××

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CHEMACADEMY 1

TIFR PREVIOUS YEAR QUESTIONS WITH SOLUTION

(-) Carvose (+) Carvose (-) Limonene (+) Lim onene

CHEM ACADEMY Mannich Type Macrocydization

(a) Me2N S NMe2 (b) Me2N S NMe2

(c) Me2N S NMe2 (d) Me2N S NMe2

(a) 1, 2 and 3 (b) 1 only

Since pH = 7.4 Basic mu

= amino acid in a peptide chain

good UG (more Nu)

S S C16H 33P+(C4H 9)3

LiOH H 1C16H 33P(C 4H9)3Cl

H 1C16H 33P(C 4H9)3Cl

cross the boundary

Deprotonation will occur

Here O will show NGP or

CHEM ACADEMY NH 2 (iv) R O

(a) (i) (b) (ii) (c) (iii) (d) (iv)

Sugar Base Phosphate

(i) 5 CGACTAG 3 5 CTACTGAGCTAAA 3

5 CGACTAG 3 5 CTACTGAG 3 5 CTAAA 3

Ans a+b b+c

a+b  b+c – Be3 partially digested

(C) (D) (E) (F)

Q.25 Product of the following reaction is

(a) OH (b) OH (c) OH (d) OH

(a) all of these (b) OH

(c) OCH3 (d) OCH 3

Now, stablized phosphorous ylide forms Z-alkene from aldehyde.

Correct option is (d)

Q.30 Predict the major product of the following hydroboration reaction

Q.32 What is the product of the following reaction?

Dip N N Dip 3 CH COO Dip N N Dip Dip N N Dip

(d) None of the above

(a) X= Y = Pd(PPh3)3 Z = Na2CO3

(b) X = Y = NiCl2(PPh3)2 Z = Na2CO 3

(c) X= Y = Pd(PPh3)4 Z = Na2CO 3

(d) X = Y = Pd(PPh3)4 Z = HCl

(a) is more acidic than

Both cis and trans product formed.

(A) 5 signals (B) 10 signals

CHEM ACADEMY Both (a) and (b)

(c) CHEM ACADEMY

(there two should be connected to deshielding atom)

 0.9 3.45 3.2

this is base peak

CH3 (3.2ppm) CH3

(a) 2.24 and 0.0126 (b) 1.12 and 0.0126

Q.59 What are X and Y in the following reaction?

Graph of sin x Graph of sin | x |

Boy PB atleast one girl PG

(c) 330  15 grams (d) 330  5 grams

(a) 1999 (b) 2000

(c) 2001 (d) None of them

Q.71 What is the value of i log10 i2, where i  1 ?

Soln. i log10 i 2  2i log10 i

(d) Has a non-zero value depending on a

2 cos  x  sin  x  dx sin 2x

(c) is an eigen vector of only if the  k 's are all equal

Q. 78 Which of the following is the curve x = y2.

(a) (i) (b) (ii) (c) (iii) (d) (iv)

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