ranjeet shahi

RRRR aaaa nnnn jjjj eeee eeee tttt SSSS hhhh aaaa hhhh iiii CCCC hhhh eeee mmmm iiii ssss tttt rrrr yyyy CCCC llll aaaa ssss ssss eeee ssss

S C O 4 8 , I In d

F l o o r , S e c t o r 2 0 C , C H A N D I G A R H P h : 2 7 2 5 7 4 8 , 3 0 4 0 6 6 0

S C F 7 2 , S e c t o r 1 0 , P a n c h k u l a , P h : 3 9 1 4 8 4 4 T e s t - 4

1

PRACTICE TEST CHEMISTRYPRACTICE TEST CHEMISTRYPRACTICE TEST CHEMISTRYPRACTICE TEST CHEMISTRY

Duration: Two hours

MM: 178


S C O 4 8 , I In d


S C F 7 2 , S e c t o r 1 0 , P a n c h k u l a , P h : 3 9 1 4 8 4 4 T e s t - 4 A

2

ffffor IIT-JEE 2010

Section-A 1. Which of the following compounds has highest enol content?

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

O CHO

O

O O

D

2. Treatment of 1-pentol with excess of 1) BH3 2) NaOH, H2O2 will provide (major product): OH

H

OHOHCHO OH

OH

O

OH

H

OH

OH

H

OH

OHCHO

OH

OH

OOH

I II IIIIV

V VI

1-pentol

(a) I (b) I, II (c) III, IV (d) I, II, V, VI

A

3. C8H10 hydrocarbon is nitrated by HNO3 and sulfuric acid. Two, and only two, C8H9NO2 isomers are obtained. Which of the following fits this evidence? (a) ethylbenzene (b) ortho-xylene (c) meta-xylene (d) para-xylene

B

4. The most reactive and the least reactive arene towards HNO3 +H2SO4 (both concentrated) are respectively:

CH3

NH Cl

NO2

NO2

BrBr

Br

C CH3

O

I II III IV

(a) I&IV (b) I&III (c) II&III (d) II&IV

B

5. What is the major product obtained from the following reaction?

CH3ONa CH

3CH

2Br

H3O+O

O O

CH3OH

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

O OO

OH

OO

OH

O

A

6. Which of the following reaction can’t produce acetamide? (a) (CH3CO)2O + NH3 � (b) CH3CHO + NH3 � (c) CH3COBr + NH3 � (d)CH3COOCH3+NH3�

B

7. Which of the followings compounds will most readily give a cyclic product when treated with a base?

(a) (b) (c)RO OR

O O

RO OR

O O

CH3

CH3

ROOR

O

O

ROOR

O

OCH3

CH3

(d)

C


S C O 4 8 , I In d



3

8. The major product of the following reaction is:

NH2O

2N NaNO

2/HCl

CH3

OH

N NCH3

NO2

(a) (b)

CH3

NO2

(c) N N

OH

CH3

O2N N N

CH3

OHNO2

(d)

0oC

C

9. An equimolar mixture of benzoic acid and benzyl alcohol is dissolved in equal volumes of ether and 5% aqueous NaOH. The resulting mixture separates into two immiscible liquid layers. Which of the following is approximately correct? (a) both organic solutes are largely in the ether layer (b) both organic solutes are largely in the water layer (c) the benzyl alcohol is in the ether layer and the benzoic acid is in the water layer (d) the benzyl alcohol is in the water layer and the benzoic acid is in the ether layer

C

10. Fischer esterification of phenylacetic acid with 1-propanol gave a mixture of 93% of the ester, propyl phenylacetate, contaminated with 7% unreacted acid. Which of the following treatments would be best used to purify the ester? (a) reduce the unwanted acid with LiAlH4 in ether. (b) wash an ether solution of the crude product with concentrated brine (aq. NaCl). (c) wash an ether solution of the crude product with 5% aqueous sulfuric acid. (d) wash an ether solution of the crude product with 5% aqueous sodium carbonate.

D

11. Which of the following is an intermediate in the Fischer esterification of propanoic acid with ethanol? (a) 1-propoxy-1,1-dihydroxyethane (b) 2-propoxy-1,1-dihydroxyethane (c) 1-ethoxy-1,1-dihydroxypropane (d) 2-ethoxy-1,1-dihydroxypropane

C

12. Which statement regarding isotope exchange of 18

OH2 with the oxygen of a carboxyl group is correct? (a) no exchange occurs under any circumstances (b) base-catalyzed exchange is more effective than acid-catalyzed exchange (c) acid-catalyzed exchange is more effective than base-catalyzed exchange (d) acids and bases are equally effective in catalyzing an exchange

D

13. The major organic product of the following reaction is:

O

CHO

NaOH

(CH3)2CuLi

OH2

(a) (b) (c) (d)O

CH3

Ph

OH

Ph

CH3

Ph

CH3

Ph

B

14. Reduction of 4-oxobutyric acid(X), also called succinic semialdehyde, by sodium borohydride followed by aqueous acid gives?

18

OOH

H

O

(i) NaBH4/H

2O

(ii) dil. H2SO

4X

(a) (d)(b) (c)O

O

O

18

OOH

18

OO

18OO

18

C

15. Which sequence of reactions would be best for the conversion of toluene into para-bromophenylacetic acid? (NBS = N-bromosuccinimide ) (a) i) Br2 & FeBr3; ii) KMnO4 & heat; iii) NaCN in ethanol; iv) H3O

(+) & heat

(b) i) Br2 & FeBr3; ii) NBS in CCl4; iii) Mg in ether followed by CO2; iv) H3O(+)

(c) i) Br2 & FeBr3; ii) NBS in CCl4; iii) NaCN in ethanol; iv) H3O

(+) & heat

(d) i) Br2 & FeBr3; ii) KMnO4 & heat; iii) Mg in ether followed by CO2; iv) H3O(+)

C


S C O 4 8 , I In d



4

16. What is the expected product from the reaction sequence drawn below?

O

O

O

AlCl3

HeatC

10H

10O

3

(i) Zn(Hg), HCl

(ii) SOCl2

AlCl3

Heat+ ?

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

O O

O

O

C

17. A mixture is comprised of the three compounds shown below: This mixture is dissolved in diethyl ether, an organic solvent. The organic solution is extracted with dilute aqueous HCl. After separation of the aq. layer from the organic layer(A), the aq. solution is set aside. The organic solution(A) is then extracted with dilute aqueous NaOH. Once again, after separation of the organic layer(B), the aq. solution is set aside. Which compound or compounds remain dissolved in the diethyl ether solution A and B? (a) A-I and II; B-I (b) A-I and III; B-I (c) A-II and III; B-II (d) A-III; B-None

CH3

NO2

NH2

CH3

OH

CH3

(I) (II) (III)

B

18. Predict major product of the following reaction:

O

COOH

COOH

(i) Heat

(ii)CH2N

2(1.0 equivalent)

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

O

COOCH3 COOH

OO

COOCH3

COOH

O

B

19. Which of the following is true regarding role of –NO in nitrosobenzene when it is subjected to aromatic electrophilic substitution reaction: (a) meta directing and deactivating (b) ortho/para directing and deactivating (c) meta directing and activating (d) ortho/para directing and activating

B

20. Which of the following compounds undergoes nucleophilic substitution most readily?

Cl

COCH3

(a) (b)

Cl

(c)

Cl

CH3

(d)

Cl

O2N

D

21. One of the completions A to D is incorrect. Choose the letter corresponding to the incorrect completion. In the nitration of benzene by concentrated sulphuric and concentrated nitric acid (a) the reaction is irreversible. (b) the rate determining step is the removal of H

+ from the intermediate.

(c) the attacking electrophile is NO2+. (d) the 2

nd nitro group enters the benzene ring meta to the first nitro group

B

22. Choose the statement that is correct concerning the following reaction: Phenol + CH3I/NaOH � Major product

(a) This reaction results in methylation of oxygen in phenol. It is utilized frequently because the hydroxide group is often highly activated. This reaction can be reversed with HI.

(b) This reaction results in methylation of oxygen in phenol. The resulting product is activated approximately the same amount as in phenol. The reaction can be reversed with HI.

(c) This reaction results in methylation of oxygen in phenol. The resulting product is more highly activated than phenol. This reaction can be reversed with HI.

(d) This reaction results in an SN-2 reaction between methyl iodide and NaOH. The resulting iodide ion substitutes at ortho and para positions of phenol. Treatment of this product with Mg will give Grignard reagent.

A


S C O 4 8 , I In d



5

23. Rank the following compounds in decreasing order of reactivity in electrophilic aromatic substitution reaction:

O

O

NH

O

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

(a) IV > I > III > II (b) III > I > IV > II (c) I > III > IV > II (d) III > II > I > IV

B

24. Select the best reaction sequence to accomplish the following transformation: NH

2

HNO3

H2SO

4

Cl

O

AlCl3

Zn(Hg), HCl

excess

(a) (b)HNO

3

H2SO

4

Cl

AlCl3

Zn(Hg), HCl

excess

(c)HNO

3

H2SO

4

Cl

O

AlCl3

Zn(Hg), HCl

excess

Zn(Hg)

ClH

HNO3

H2SO

4

Cl

O

AlCl3

Zn(Hg), HCl

excess

(d)

D

25. Two equivalents of the Wittig reagent (CH3)2C=CH-CH=P(C6H5)3 were allowed to react with a C4H4O2 compound. The chief product was 2,11-dimethyl-2,4,6,8,10-dodecapentaene, (CH3)2C=CH(CH=CH)3CH=C(CH3)2. What was the C4H4O2 compound used in this reaction? (a) 2-butyne-1,4-diol (b) 1,2-cyclobutanedione (c) 1,3-butadien-2,3-diol (d) 2-butenedial

D

26. You have two C6H10O ketones, I and II. Both are optically active, but I is racemized by treatment with base and II is not. Wolff-Kishner reduction of both ketones gives the same achiral hydrocarbon, formula C6H12. What reasonable structures may be assigned to I and II? (a) I is 3-methyl-4-penten-2-one; II is 4-methyl-1-penten-3-one (b) I is 2-methylcyclopentanone; II is 3-methylcyclopentanone (c) I is 3-methylcyclopentanone; II is 2-methylcyclopentanone (d) I is 2-ethylcyclobutanone; II is 3-ethylcyclobutanone

B

27. Which of the following reaction sequences would be best for preparing 2,2-dimethyl-3-hexanone from butanal? (a) (i) addition of tert-butylmagnesium bromide in ether; (ii) hydrolysis workup; (iii) PCC in CH2Cl2 (b) (i) NaBH4; (ii) PBr3; (iii) Mg in ether; (iv) 2,2-dimethylpropanal, followed by hydrolysis (c) (i) Wittig reaction with (C6H5)3P=C(CH3)2; (ii) BH3 in THF; (iii) H2O2 & base; (iv) PCC in CH2Cl2 (d) (i) Wittig reaction with (C6H5)3P=CHC(CH3)3; (ii) BH3 in THF; (iii) H2O2 & base; (iv) PCC in CH2Cl2

A

28. Which of the following procedures would not be suitable for preparing 3-methyl-1-phenyl-1-butanone, C6H5COCH2CH(CH3)2? (a) (i) C6H5COCH=CHCH3 + (CH3)2CuLi in ether; (ii) H3O

+ workup

(b) (i) benzene + (CH3)2CHCH2COCl & AlCl3 (ii) H3O+ workup

(c) (i) C6H5MgBr + (CH3)2CHCH2CHO in ether; (ii) H3O+ workup; (iii) PCC in CH2Cl2

(d) (i) (CH3)2CHMgBr + C6H5COCH3 in ether; (ii) H3O+ workup; (iii) PCC in CH2Cl2

D

29. Reduction of 4-oxobutyric acid, also called succinic semialdehyde, by sodium borohydride followed by aqueous acid gives a C4H6O2 product.This product is which of the following compounds? O

OO

O

O

OH

O

O

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

D

30. A C7H9N base reacts with sodium nitrite and hydrochloric acid at 0 ºC, giving a clear solution. On heating with KCN and Cu2(CN)2 a gas evolves, and continued heating with conc. HCl yields a C8H8O2 crystalline acid. Heating this acid with aqueous KMnO4 produces a C8H6O4 product, which dehydrates on strong heating to give a crystalline C8H4O3 compound. What is the C7H9N base? (a) benzylamine (b) N-methylaniline (c) para-aminotoluene (d) ortho- aminotoluene

D


S C O 4 8 , I In d



6

Section-B Following Five Questions may have more than one correct answer.

31. Which of the following will produce more than one stereomers of aldol in aldol condensation reaction?

(a) CH3CHO (b) Acetone (c) Cyclopentanone (d) C6H5CHO

A

C

32. Which of the following are more reactive than unsubstituted Benzaldehyde in a Perkin reaction?

(a) p-chloro Benzaldehyde (b) p-aminobenzaldehyde

(c) p-methoxy Benzaldehyde (d) benzene-1,4-dicarbaldehyde

A

D

33. Which of the following will be reduced in Cannizzaro reaction with C6H5CHO?

(a) p-methoxy Benzaldehyde (b) p-methyl Benzaldehyde

(c) m-chloro Benzaldehyde (d) p-aceto Benzaldehyde

C

D

34. Which of the following have meta-directing, deactivated aromatic ring?

(a)

CF3

(b)

CONH2

(c)

OCOCH3

(d)

A

B

35. Which of the following compounds is(are) more reactive than chlorobenzene in reaction with NaCN(aq)?

(a)

CF3

Cl

(b)

Cl

Cl

(c)

Cl

NH2

(d)

Cl

A

B

Section-C

Following Five questions consist of a assertion followed by the reason:

In each question, choose the correct description and reason from the list below: (a) The statement and reason are both factually true, and reason is the correct explanation of statement. (b) The statement and reason are both factually true, but the reason is not correct explanation of statement. (c) The statement is true but the reason is false. (d) The statement is false but reason is true.

36. Assertion: A 2o-amide does not undergo Hoffmann’s bromamide degradation to amine on treatment with alkaline bromine

solution.

Reason: 2o-amide can not form isocynate, a key intermediate in the reaction.

A

37. Assertion: Phenol is brominated with Br2-H2O, even in absence of Lewis acid catalyst.

Reason: The HO-group in phenol is a strong activating group in electrophilic substitution reaction.

B

38. Assertion: Aliphatic amines do not forms diazonium salt as a stable product like aniline.

Reason: Benzene diazonium salt is stabilized by resonance.

A

39. Assertion: During Friedel Craft acylation of benzene using(CH3)3C-COCl/AlCl3, Some tertiary butyl benzene is also formed.

Reason: The acylium ion formed initially, decomposes partially in case where tertiary carbocation is formed.

A

40. Assertion: The equilibrium constant of the following process is greater than one.

O O O OH

Reason: The enol is more stable than keto form due to conjugation and intramolecular H-bonding.

A


S C O 4 8 , I In d



7

Section-D Comprehension Section

Comprehension-1:

Consider the following synthetic scheme to answer the next three questions:

CH3

OC2H

5

O

CH3

O

C2H

5ONa

O

MeO

Aheat

B

NaBH4/H

2O

CH

+

heatD

HO–/H2O

41. The structure of A and B respectively:

(a)

O

COOC2H

5

OMe

and

O

OMe

(b)

OMe

O

COOCH3

OMe

O

and

(c)

OMe

O

COOC2H

5

O

and

OMe

O O

(d)

O

CH3

O

C COOC2H

5C

CH3

O

CH3

O

C CH3

CH

and

C

42. If C is treated with excess of CH3COCl, what would be formed?

(a) (b)

(c) (d)

OCOCH3

OMe

OCOCH3

OMe

OCOCH3

OCOCH3

OMe OCOCH3

OCOCH3

C


S C O 4 8 , I In d



8

43. Which of the following is the most likely structure of product D?

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

OMe OMe OMe OMe

B

Passage-2 Consider the following cross aldol condensation reaction and the possible products:

O

O

X

Y

NaOH

O O

O O

Possible Enolates

OH

O O

OH

O

OH

O

OH

O

OH OH

O O

OH

O

OH

A

B C D

E F G H

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

+H2O

+ + +

Aldol Products

Answer the following questions based on the above information.

44. Which is the most stable enolate? (a) I (b) II (c) III (d) IV

B

45. Which of the above enolate is formed most rapidly? (a) I (b) II (c) III (d) IV

C

46. Nucleophilic addition of enolate on carbonyl compound gives A-H. Which of the following combination of enolate-carbonyl compound and the resulting product is correctly matched? (a) I + X � A; II + X � C and III + X � D (b) II + X � C; III + Y � D and III + X � E (c) IV + Y � F; III + Y � H and IV + X � G (d) I + Y � E; II + Y � D and III + X �G

B


S C O 4 8 , I In d



9

Section-E

Single Integer Answer Type

47. If ethanedial (HOC—COH) is treated with excess of HCN(aq) followed by hydrolysis of product results in diacids. How many

different diacids would be formed?

3

48. An organic compound(X) has molecular formula C7H6O2 and it does not effervesces with NaH. A on treatment with excess of

HBr(aq) gives Y(C6H6O2) and CH2Br2. Y forms a violet coloured solution with FeCl3. If X is treated with Br2/Fe, how many

different monobromination product would result?

2

49. An organic acid (X) has molecular formula C8H16O2. X on heating with NH3 forms Y which on treatment with alkaline Br2

forms Z. Z on treatment with HNO2 followed by heating with H2SO4 gives 2,4-dimethyl-2-pentene. How many different acids

(X) can give the indicated final product?

4

50. If CH2D–CHO is treated with dilute alkaline solution, how many different aldols (excluding stereo-isomers) are expected? 4


S C O 4 8 , I In d



10

Answer Sheet

Name: _______________________________________________________________________

Batch: _______________________________________________________________________

1. A B C D

18. A B C D

35. A B C D

2. A B C D

19. A B C D

36. A B C D

3. A B C D

20. A B C D

37. A B C D

4. A B C D

21. A B C D

38. A B C D

5. A B C D

22. A B C D

39. A B C D

6. A B C D

23. A B C D

40. A B C D

7. A B C D

24. A B C D

41. A B C D

8. A B C D

25. A B C D

42. A B C D

9. A B C D

26. A B C D

43. A B C D

10. A B C D

27. A B C D

44. A B C D

11. A B C D

28. A B C D

45. A B C D

12. A B C D

29. A B C D

46. A B C D

13. A B C D

30. A B C D

14. A B C D

31. A B C D

15. A B C D

32. A B C D

16. A B C D

33. A B C D

17. A B C D

34. A B C D

50. 47.

48.

49.

50.


S C O 4 8 , I In d



11

Answer Test Series 4[+2] IIT-JEE 2010 Set AAAA B CCCC Set A B C Set

1. D D B 21. B D B 41. C

2. A C D 22. A C C 42. C

3. B A B 23. B B B 43. B

4. B C D 24. D D C 44. B

5. A B A 25. D A B 45. C

6. B B A 26. B A B 46. B

7. C C D 27. A D C 47. 3

8. C B B 28. D B A 48. 2

9. C C C 29. D D C 49. 4

10. D B D 30. D B D 50. 4

11. C C D 31. A C

12. D D D 32. A D

13. B D B 33. C D

14. C B B 34. A B

15. C C A 35. A B

16. C A C 36. A

17. B B B 37. B

18. B B D 38. A

19. B D D 39. A

20. D D C 40. A

Documents

ranjeet shahi