Time : 1 hrs Max.

Marks: 87
Single correct [8 × 3=24]
Q.1 Phenol and benzoic acid is separated by
(A) NaHCO3 (B) NaOH (C) Na (D) NaNH2
Q.2 Which of following will form tri-bromo derivative of phenol?
OH
OH OH OH
Br Br
(A) Br
2
 (B) Br
2
 (C) 2  (D) 2 
H 2O H 2O CS2 H 2O

O
|| 18
3O
Q.3 Ph  C  O  CPh 3 H 
Product of this reaction is: 18
O O
|| 18 ||
(A) Ph  C  OH + Ph3C– OH (B) Ph  C  OH + Ph3C–OH

O O
| | 18 18 || 18
(C) Ph  C  OH + Ph3C– OH (D) Ph  C  OH + Ph3C–OH

OH

Q.4 P
.C.C
 (P) HO OH
(Q) (
i ) CH 3MgBr Lucas reagent
  (R)    (S)
( 2 mole ) (1 mole) 
(ii ) H / H 2 O

CH 2OH
The product(s) show white ppt.
(A) Immediate (B) After 5 min.
(C) No ppt. at room temperature (D) No reaction

Q.5 1, 2, 3 butanetriol undergoes oxidative cleavage of HIO4. During this process

(A) 1 equivalent of HIO4 consumed & HCO2H & H 3C  C  CO 2 H are formed

||
O
(B) 2 equivalents of HIO4 consumed & HCO2H, HCH = O & CH3 – CH = O are formed

(C) 3 equivalents of HIO4 consumed & HCO2H (2 eq.) & 1 eq. of CH3CO2H are formed

(D) 2 equivalents of HIO4 consumed & 2 eq. of HCO2H & 1 eq. of CH3CH = O is formed.

Q.6 In which one of the following compounds electron density on phenyl ring is maximum

Page No.1
 (A) (B) (C) (D)

Q.7 Ordinarily the barrier to rotation about a carbon-carbon double bond is quite high but compound A was
observed by NMR to have a rotational barrier of only about 20 K cal / mole

The reason for this is

(A)
(A) double bond having partial triple bond character because of resonance
(B) double bond undergo flipping
(C) double bond having very high single bond character because of aromaticity gained in both 3 & 5
membered ring.
(D) + I effect of nC3H7 groups makes double bond having partial single bond character.
Q.8 What will be the correct IUPAC name of the following compound?
COOH

O
Cl O–C–CH3
(A) 3- Ethanoyl oxy-4-Chloro Cyclopentanoic acid
(B) 3- Chloro-4-Ethanoyloxy Cyclopentanoic acid
(C) 3- Chloro-4-Ethanoyloxy Cyclopentane Carboxylic acid
(D) 3- Ethanoyl oxy-4-Chloro Cyclopentane Carboxylic acid

More than one may be correct [5 × 3 = 15]

Q.9 Which of the following pairs is/are not correctly matched:
(A) Sucrose : reducing sugar (B) Glucose : mutarotation
(C) Fructose : aldose sugar (D) Lactose : monosaccharide
Q.10 Which of following reaction represent major product.

(A) NaBH
4  (B) NaBH
4 

(C) LiAlH
4  (D) LiAlH
4 

O O
|| ||
Q.11 CH 3  C  H and CH 3  C  CH 3 is differentiated by

(A) Tollen's reagent (B) Fehling (C) Iodoform (D) NaHSO3

Page No.2
 conc . NaOH
Q.12 HCHO   

 MeOH + HCOONa
True about the above reaction is / are:
(A) it is cannizaro reaction (B) it is redox reaction
(C) it is a Bimolecular reaction (D) it is a disproportion reaction.

Q.13 Select the incorrect statement(s) from the following:

(A) Rate of sulphonation of C6H6 & C6D6 will be equal

OH
SO3H
(B) On treatment of with Br2 / water (in excess) it results in a dibromo product.

(C) When HCOOEt is treated with MeMgBr in excess followed by hydrolysis it will results in the
formation of tertiary alcohol.

Me Cl
| |
(D) MeCH 2  CH  CH  Me aq
.KOH
 Product. Product is enantiomer of the reactant.

Optically pure SN 2

Comprehension [6 × 3 = 18]
Paragraph for question nos. 14 to 16
Consider the following graph which shows Heat of combustions of isomeric Pentenes and answer the
given.
Heat of combustions

P Q R S T V
Q.14 Which of the following can show Geometrical isomerism ?
(A) V (B) S (C) R (D) T
Q.15 Which of the following pair shows chain isomerism ?
(A) V,P (B) S,R (C) T,Q (D) R,Q
Q.16 Which of the following pair shows positional isomerism ?
(A) Q,T (B) S,T (C) V,S (D) P,R

Paragraph for question nos. 17 to 19

An organic compound A containing C = 62% and H = 10.34% gave the following results:
(i) 0.20 gm of the compound A displaced 77.24 ml of air at 1atm & 273 K.
(ii) On treatment with PCl5 A gave another compound, which contained 46.4% chlorine.

Q.17 IUPAC name of the compound A is:

(A) Propanal (B) Propanone (C) Prop-2-en-1-ol (D) 1,2-epoxypropane
Q.18 An isomer of it B gave compound C containing 62.8% chlorine with PCl5. C gives back B with aq.
KOH correct structure of B is:

Page No.3
 O
||
(A) CH2=CH–O–Me (B) CH 3  C  CH 3 (C) (D) CH2 = CH–CH2–OH

Q.19 An isomer of A & B which gives two organic products with PCl5 is: (Ignore stereoisomers)
O
||
(A) CH2=CH–O–Me (B) CH 3  C  CH 3 (C) (D) CH2 = CH–CH2–OH

Subjective [10 × 3 = 30]

Q.20 Number of cyclic structural isomers of C5H10.
Q.21 Number of  electrons present in styrene (Ph–CH=CH2).

Q.22 Double bond equivalent Ph CHO .

Q.23 Number of 3° carbon atoms present in .

Q.24 How many Hydrogen atoms are replaced by D in the following tautomerization.

O

C —C = C—CH3 D 
D 2O
Long time

Q.25 Number of geometrical isomers for the following compound will be

Cl
2 Total number of monochloro product.
Q.26 2-methoxy propane 
h

Q.27 2-methyl cyclopentanone, total number of enolic tautomers of this compound without counting
mirror images.
Conc.H SO
2
Q.28 1-butanol    4  Total number of alkenes produced.


Conc.H PO
3 4
Q.29      Total number of 1,2-shifts involved during carbocation


rearrangement in this reaction.

Page No.4
 Answers
1. A 2. D 3. A 4. A

5. B 6. A 7. C 8. C

9. A, C, D 10. A, C 11. A, B 12. A, B, C, D

13. A, B, C, D 14. D 15. B 16. C

17. C 18. B 19. A

20. 5 21. 8 22. 9

23. 8 24. 4 25. 2

26. 4 27. 2 28. 3

29. 3