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Time : 1 hrs Max.

Marks: 75
Single correct [6 × 3=18]

Q.1 Cinnamic acid (Ph–CH=CH–COOH) is nitrated preferably at________ and it is ________ then nitration
of benzene.
(A) m-position, faster (B) o & p-positions, faster
(C) m-position, slower (D) o & p-position, slower

Q.2 Which of the following isomeric sugars is most stable?

(A) (B)

(C) (D)

2 4 aq. H SO
Q.3 MeCH (CN) CO Me    P

(A) P giving +ve iodoform test & –ve test with Fehling solution.
(B) P giving –ve iodoform test & +ve test with NaHCO3 solution.
(C) P gives +ve Lucas test & –ve test with NaHSO3 solution
(D) P gives +ve test with NaHSO3 & cerric ammonium nitrate solution.
Q.4 Compound A (C7H8O) is insoluble in water, dilute HCl & aqueous NaHCO3, it dissolves in dilute
NaOH. When A is treated with Br2 water it is converted into a compound C7H5OBr3 rapidly. The
structure of A is

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

O
|| 
Q.5 Me  C  O  CH 2  CH 2  N H 3 NaOH
 Q
Q is:
O O
|| ||
(A) Me  C  O  CH 2  CH 2  NH 2 (B) Me  C  NH  CH 2  CH 2  OH

(C) (D) MeCOONa + HOCH2CH2NH2

Page No.1
Q.6 Nylon-6 is prepared by linear condensation homopolymerization reaction of:
(A) caprolactum (B) hexamethylene diamine and adipic acid
(C) 6-aminohexanoic acid (D) acrylonitrile

Comprehension [6 × 3 = 18]

Paragraph for question nos. 7 to 9

O3 KOH N 2H 4 CrO 3
P1 P2 P4
Zn/H 2O EtONa
P3
KOH H2/Pd HBr NH3
 P5 excess
P6 excess P7
Q.7 Which of the following statement is correct about P4?
(A) It will not give yellow/orange or red colour with 2, 4-DNP.
(B) It will give red colour with Cerric Ammonia Nitrate
(C) It will not give Fehling test.
(D) It will give Bielstien test
Q.8 Which of the following statement is correct about P7?
(A) It will not give mustard oil reaction.
(B) It will not give carbylamine test or isocyanide test
(C) It will decolourize bromine water.
(D) It will give base soluble product with Hinsburg reagent
Q.9 Which of the following reaction will be useful for conversion of P3 into P4.
(A) Clemmenson's reduction
(B) Oppenauer oxidation
(C) Meerwin Pondorff Verely reduction
(D) Tischenko reaction

Paragraph for question nos. 10 to 12


(F) (G)
Br2 h NBS 
Monobromination

(C) + (D) + (E) (Alkene)


Major
Disproportionate
Products.
Na Et2O

NaOH (i)AgOH
(J) C–OH (A) + (B)
O (ii)Br2, CCl4,  Major Minor
(X)
Kolbe
Electrolysis Na, EtOH, liq NH3

Na, liq NH3


(K) + (L) (H)
Major Minor EtOH
FeSO4 H2O2

(I)
On the basis of reactions involved in above interconversions answer the given questions.

Page No.2
Q.10 Find out the incorrect statement?
(A) Product G is a racemic mixture
(B) Product F is 3° halide
(C) Product A, C, F, H, I are optically inactive.
(D) No product ( A to L) can show the geometrical isomerism.

Q.11 Reaction which does not involve free radical mechanism in above reactions is:
(A) X to A, B (B) H to I (C) A to C, D, E (D) X to J

Q.12 Which name reaction is not involved in above interconversion.


(A) Acyloin condensation (B) Pinacol formation
(C) Hundsdiecker reaction (D) Wurtz reaction

More than one may be correct [3 × 4 = 12]


Q.13 Select incorrect statement(s).
(A) Methoxy ethane give iodoethane with one equivalent anhydrous HI
(B) Order of basicity in aqueous medium MeNH2 < Me2NH < Me3N
(C) Optically active alkanol will show total retaintion of configuration during its reaction with SOCl2.
(D) S-2-bromobutane gives R-2-methyl butane nitrile with AgCN as major product.

Q.14 Select the correct statement(s).


O
||
(A) HOOC  CH 2  NH  C  CH  NH 2 is a dipeptide of Glycine & Alanine, whose abbreviated
|
CH 3
name is GLY-ALA

OH
(B) shows Keto-enol tautomerism.

O
(C) Phenol & benzoic acid can be distinguished by NaHCO3.
O O
O
(D) and can be distinguished by iodoform test.
O

Q.15 Which of the following are chiral object.


(A) Screw (B) Fan (C) Kids tricycle (D) Hockey stick

Match the column [12]


Q.16 Column I Column II
(Polymer) (Monomer)
(A) Orlon (P) 1.3-butadiene
(B) Buna-N (Q) Terephthalic acid
(C) Buna-S (R) Ethylene glycol
(D) Terylene (S) Vinyl cyanide
(T) Styrene
Page No.3
Subjective [3 × 5 = 15]
Q.17 A polyhydroxy alcohol having molecular weight = 168, on acetylation the molecular weight increases to
294, the number of –OH groups present in the alcohol is X?

Q.18 Reaction 1— 5HIO


 4 

Reaction 2— 5HIO
 4 

Ratio of moles of formaldehyde obtained in the reaction (1) and reaction (2)

(1) Ac O, AcONa , 
Q.19 Reaction 1—  2    (A)

( 2 ) H3O , 

O
|| Al ( OCHMe 2 )3
Reaction 2— Ph – CH  CH – C  CH 3      (B)
CH 3  CH OH
|
CH 3

OH
| (1) NaOI
Reaction 3— Ph – CH  CH  CH  CH 3    (C)

( 2) H
Degree of unsaturation present in compound (A + B + C) is?

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

5. B 6. C 7. C 8. D

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

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

16. (A) S ; (B) PS ; (C) P, T ; (D) Q, R

17. 3 18. 2 19. 17

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