1.

Phenol on reaction with Br2 in non - polar aprotic solvent

(A) 2, 4, 6 - Tribromophenol (B) p-Bromophenol
(C) ortho & para-bromophenol (D) m-Bromophenol

2. Phenol is heated with Phthalic anhydride in presence of concentration H 2SO4. The product
gives pink colour with alkali. The product is
(A) Phenolphthalein (B) Bakelite (C) Salicylic acid (D) Fluorescein

3. Product C in the reaction

C2H5Br ⎯⎯⎯→ A ⎯⎯→ ⎯ B ⎯⎯⎯→ C will be
NaoH Na CH3l
( aqueous )
(A) Propane (B) Ethyl iodide (C) Ethane (D) Ethyl methyl ether

4. Tert- Butyl methyl ether on heating with HI of one molar concentration gives
(A) CH3OH + (CH3)2Cl (B) CH3l + (CH 3)3COH (C) CH3l + (CH3)3Cl (D) None of these

5. Which one of the statements about HOH 2CCH(OH)CHO is not correct ? It

(A) is an isomer of 1, 3–dihydroxypropanone (B) contains a tertiary alcoholic group
(C) has the same empirical formula as glucose (D) can show optical isomerism.

6. The end product in the following sequence of reaction is

HC CH ⎯⎯⎯⎯⎯
1% HgSO4
→ A ⎯⎯⎯⎯
20% H2SO4
CH3MgX
→ B ⎯⎯⎯[O]
→
H2O

(A) Acetic acid (B) Isopropyl alcohol (C) Acetone (D) Ethanol

7. The major product of the reaction will be

+
⎯⎯⎯
H3 O
→

OH

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

8. 14
CH2
O
H3C CH3
⎯⎯ → A ⎯⎯⎯ → ⎯⎯⎯⎯ →
KOH 3 O
  Zn / H O 2

The products of ozonolysis are,

OH

OH H3C CH3
14
H3C CH3 + CO2
(A) + H3C
(B)
O
O
OH OH
H3C CH3
H3C CH3
14
+ H3C and CO2
(C) (D)
O
O
14
O H

9. Cl
−
* ⎯⎯⎯→ The product is
OEt
O
 Cl
Cl
(A) * (B) *
HO OEt
EtO OH
EtO *
OEt
(C) * (D )
O O

10. Ph

CH3 ⎯⎯ ⎯→?
RMgX
H O+
O 3

Ph
Ph
CH3
(A) HO (B) CH3
HO
R
OH
Ph

(C) CH3 (D ) None of these

R
OH

11.
CH2
O
+
⎯⎯ ⎯→ A, A is
H3 O

CH3
HO OH (C OH (D) H3C
)

(A) (B)
CH3
CH3
CH3 OH
CH3
OH OH

12. H3C CH3

OH
+
⎯⎯⎯
H
→ P. The product P is:

H3C CH3 CH3 ( H3C CH3 (D CH3

C ) CH3
(B CH3
(A) ) OH
)

13. OH

OH
H3C
⎯⎯⎯
HIO 4
→ P + 2Q + R

HO OH

O
 O
(A) H3C CHO, HCOOH and HCHO (B) H3C , HCHO, HCOOH
COOH
OH
(C HCHO, CH3CHO and (D CH 3CHO, HCOOH and HOOC
) OH ) OH
O

14. In which of the following case configuration about chiral carbon is retained
Me Me
OH OH
(A) ⎯⎯→
⎯ ⎯⎯ ⎯
Na
⎯→
CH3Br
(B) ⎯⎯⎯→ ⎯⎯
TsCl
⎯⎯→
CH3 ONa

Ph Ph
Et Et
Me
OH
(C) ⎯⎯⎯→ ⎯⎯
PCl5
⎯⎯→
CH3ONa (D) None
Ph
Et

15. Predict the product

H
O

+
⎯⎯⎯
Ni
H2 ,
→ A ⎯⎯⎯⎯
K 2Cr2O7
H 2SO4
→ B ⎯⎯⎯
NH 2OH
⎯→ C ⎯⎯→
H
D

16.

The main product is :

(A) (B)

(C) (D)

17. An organic compound A (Molecular formula C 6H12O) does not change the colour of acidic
dichromate solution. Compound A on treatment with H2SO4 produces alkene, which on
oxidative ozonolysis gives a molecule (C 6H10O3) which gives positive iodoform test. Find out
structure of ‘A’.

18. The relative rate of acid catalysed dehydration of following alcohols would be :
 (A) R > P > S > Q (B) R > S > P > Q (C) P > R > S > Q (D) R > S > Q > P

19.

The final product is

(A) (B)

(C) (D)

20. The order of solubility of

in water is:
(A) 1 > 2 > 3 > 4 (B) 1 > 3 > 2 > 4 (C) 4 > 3 > 2 > 1 (D) 4 > 3 > 1 > 2

21.

(A) (B)

(C) (D)

22.
 (A) (B) (C) (D) None of these

23. An organic compound having molecular formula C 3H6O does not react with 2, 4–dinitrophenyl
hydrazine and does not react with Na metal. The compound is expected to be :
(A) CH3CH2CHO (B) CH3COCH3 (C) CH2=CH–CH2–OH (D) CH2=CH–O–CH3

24. When 2–chloroethanol is warmed slightly with dilute NaOH, the major product formed is :
(A) Cl − CH2 − CH2 − O − CH2 − CH2 − Cl (B) HO − CH2 − CH2 − CH2 − CH2 − OH

(C) HO − CH2 − CH2 − OH (D) O

25. Which of the following ethers is the most uncreative to cleavage with conc. HBr ?

(A) Ph–CH2–O–CH3 (B) Ph–O–Ph (C) (D)

26.

Reagent A used in this change is

(A) B2H6 (B) LiAlH4 (C) Sn/HCl (D) NaBH4

27.

28. Which of the following can give purple colour with neutral FeCl3 ?

(A) (ii) and (iv) (B) (i) and (iii) (C) (ii) and (iii) (D) (iii) and (iv)

29. Which combination of reagents will bring about the following conversion ?

(A) MeMgBr / H( ) ,H2SO 4 / ,HBr / H2O2 (B) MeMgBr / H( ) ,H2SO 4 / ,HBr

+ +

(C) MeMgBr / H( ) ,HBr / CCl (D) HBr / H O ,MeMgBr / H( )

+ +
4 2 2
30. Which of the following reactions are correctly matched ?

(B
(A)
)

(C (D
) )
 ANSWERS

1. C 2. A 3. D 4. B
5. B 6. C 7. C
8.B,Claisen rearrangement, followed by elimination

9.D 10.A ,Base catalyzed ring opening of epoxides less lindered ‘C’ is attacked.

11. C 12. B 13. A

14. A, In only (A) chiral carbon–oxygen bond is not cleaved.

16. C 17. D 18. A 19. B

20. C 21. A 22. A 23. D
24. D 25. B 26. B

27.C ,B–keto acids undergo decarboxylation readily

28.A 29.A 30. A, B, C