ORGANIC CHEMISTRY

Master Practice Problems

Target IIT JEE-2020
RAPID CRASH COURSE

MPP-1

Single correct :

Q.1 Arrange the following in increasing order of acid strength.

(f) (a)
H OH (b)
O COOH
(e)
HO3S (d) (c)
H—CH2 CH2–H
(A) c < f < d < a < b < e (B) f < d < c < b < e < a
(C) f < c < d < b < e < a (D) c < d < f < a < b < e

Q.2 Four isomeric alcohols are possible for molecular formula C4H10O.

OH OH OH
OH
(a) (b) (c) (d)
Which of the following statement is true for given compounds?
(A) Correct boiling point order is a >b>c>d (B) Boiling point of b > a
(C) Boiling point of c > a (D) Solubility of c > d.

Q.3 Which order is not correct for stability of resonating structures..


CH2 CH2

(A)
C
< C (B) <
O H O H 
OCH3 O–CH3


 
(C) H 3C  C  N  CH 3 > H 3C  C  N  CH 3 (D) < 

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Comprehension :
Paragraph for question nos. 4 to 6
CHO CHO CHO CHO
H OH H OH H OH HO H
H OH H OH HO H HO H
H OH HO CH2OH HO H H CH 2OH
CH2OH H CH2OH OH

(I) (II) (III) (IV)

Q.4 Which of the above compounds are enantiomers?

(A) I and III (B) II and III (C) II and IV (D) I and IV

Q.5 Which of the above compounds are identical?

(A) III and IV (B) II and III (C) I and II (D) I and III

Q.6 Which of the above compound(s) have L-configuration ?

(A) I and III (B) III only (C) III and IV (D) II and IV

Paragraph for question nos. 7 & 8

d
OH

O2 N NO2
e c
H2 N COOH

NO2
f b
CH3 – HN SO3H
a
HO
NH–C–CH3
g
O
Q.7 How many moles of NaHCO3 will consume on reaction with 1 mole of this compound?
(A) 2 (B) 3 (C) 4 (D) 1

Q.8 What is the correct order of basic strength of the following?

(A) e > f > g (B) f > e > g (C) g > e > f (D) e > g > f

More than one correct :

Q.9 Select true statement :
(A) Gauche form of 3-hydroxy propanol is more stable than it's anti form
(B) Anti form of n-butane (across C2 – C3) is more stable than it's Gauche form.
(C) At room temperature mole fraction of eclipsed form is almost zero.
(D) Dipole moment of 1,2-dichloro ethane decreases on heating.

2
 O
Q.10 Tautomers of the compound CH3—C is / are

O
OH O
CH3–C CH3–C
(A) (B)
O OH
O OH
(C) CH3—C (D) CH2=C

HO O

Q.11 Which of the following option is not correct ?

COOH COOH
H OH H OH
(A) & are diastereomer
H OH
H OH
COOH
COOH

H H H CHO
(B) C=C=C & C=C=C are enantiomer

OHC CHO OHC H

(C) E-3-Bromohex-3-ene & Trans-3-bromo but-3-ene are identical compound

CH3 CH3
Br H H Br
(D) & are identical compound.
H Br Br H
CH3 CH3

Q.12 Which of the following reaction will form stable ion.

(A) 
+ aq. AgNO3  (B) 
+ 2K  

(C) + HBr  (D) HBF4 

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Q.13 Which of the following is / are aromatic species.

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


N O
H

Match the column :

Q.14 Match the column :
Column I Column II

(A) (P) Planar

(B) (Q) Non-planar

N

(C) (R) (4n + 2)  electron

(D) (S) (4n)  electron

Q.15 Column I Column II

(Pair of compounds) (Relationship)

(A) O O (P) Enantiomer

Cl Cl
Br Br

COOH OH
H OH H CH3
(B) H2 N H H2 N H (Q) Diastereomer
CH3 COOH

COOH COOH NH2

H OH H
H NH2 H
(C) (R) Positional isomer
OH
CH3
CH3
(S) Chain isomer

4
Subjective :
Cl

Q.16 Cl
2  number of theoritically possible dichloro derivatives
h

Q.17 How many total isomers are possible from C3H6O and also find out the number of optically active
isomers?

Br
Br
Q.18 How many stereoisomers are possible for ?
Br Br

Q.19 Find the number of molecules which are soluble in NaOH.

OH COOH OH

CH3 –CCH CH3 – CH = CH2

OH OH
O 2N NO2
SO3H
CH3CH2OH
NO2 NO2

Q.20 Consider following compounds.

COOH OH SO3H

O
COOH
OH
O2 N NO2
C CH NH2

NO2 OH
(a) Number of compounds which are aromatic (x).
(b) Number of compounds which can evolve H2 gas on reaction with Na metal (y).
#(c) Number of compounds which can evolve CO2 gas on reaction with NaHCO3 (z).
[If answer is x,y & z respectively, then fill 0xyz in OMR sheet]

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 ANSWER AND SOLUTION
Single correct :
Q.1 (D)
(a)
Hf OH (b)
C(1)
O COOH e > b > a > f > d > c
SO3H    Resonance

Sol. (e) 3eqRS

COOH O C C with Benzen
]
2eqRS Resonance
HO3S (d) (c) with O
–C–
H—CH2 CH2–H
Q.2 (A)

Q.3 (C)

Q.4 (D)

Q.5 (C)

Q.6 (C)

Q.7 (A)
Sol. Those acids which are stronger than H2CO3 will react with NaHCO3.

Q.8 (B)
Sol. Aliphatic bases are stronger than aromatic bases. Greater the availability of lone pair greater the basic
strength.

More than one correct :

Q.9 (A, B, C)

O
CH2
O
Sol. (A) due to intramolecular H-bonding in Gauche form

Repulsion
CH3 CH3
CH3

(B)

CH3
(Anti) (Gauche)
(C) Stability of eclipsed form is less than staggered at room temperature.

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 Cl Cl
Cl

(D)
Cl
=0 0
On heating rate of interconversion from anti-Gauche increases therefore µ increases.

Q.10 (A, B, C, D)
O
Sol. All are tautomeric structures of CH3—C 


O
Q.11 (C)

COOH
H OH
Sol. (A) The fisher projection of the newmann projection is
HO H , so both are diastereomers.

COOH

(B) Interchange at only one gemiral carbon will result enantiomers in chiral allenes.
(C) They are not isomers
(D) Both have COS so both are identical.

Q.12 (A, B, D)

Ph Ph
 
Sol. (A) + aq. AgNO3  Aromatic

Ph Ph

(B) 
+ 2K  Aromatic

OH

(C) + HBr  Antiaromatic

OH

 OH
(D) HBF4  Aromatic

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Q.13 (A, B, C)
Sol. D is non aromatic due to tub shaped structure.

Match the column :

Q.14 (A) P, R (B) P, R (C) Q,R (D) Q,S

Q.15 (A) P (B) R (C) Q

Subjective :
Q.16 9
Cl Cl Cl
Cl
Sol.  (1)  (3) [2 op-active + 1 meso]

Cl
Cl

 (3) [2 op-active + 1 meso]  (2) [cis & trans] both inactive]

Cl Cl

Q.17 11, 2
CH3 CH3 OH CH 3  C  CH 2
H CH 2  CH  CH 2
Sol. (i) C=C (ii) C=C (iii) | (iv) |
H H OH OH
H OH
(v) CH 3  CH 2  C  H (vi) CH 3  C  CH 3 (vii) CH2 = CH – OCH3
|| ||
O O

(viii) (ix) (x) (xi) O ]

OH O
H CH3
Optically active

Q.18 8
Sol. This symmetrical so the total number of stereoisomers is 23 = 8.

Q.19 5
Sol. Those molecules whose conjugate base are less basic than NaOH are soluble in NaOH.

Q.20 0684
Sol. x = 6 y=8 z=4