CHEMISTRY for IIT-JEE

ON

&

Kakadeo Kanpur
Contact Number : 9889655556
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 [Section - A]

01. In the given reaction sequence.

CH3
K2Cr2O 7 , H2SO4 SOCl2
CH3 — C — CH2CH2OH (A) (B)
H 2O
CH3
(CH3)2NH 1. LiAlH4
(C) (D)
2. H3O+
Identify the given compounds.

Et
(A) Compound (B) is Me2C – COCl

(B) Compound (A) is (CH3)3CCH2CHO

(C) Compound (C) is (CH3)3CCH2CONHCH3

(D) Compound (D) is (CH3)3CCH2CH2N(CH3)2

02. Which of the following amines will react with cyclohexanone to give enamine?

(A) CH3NH2 (B) (CH3)2NH (C) (D)

03. on reaction with diethyl oxalate forms :

(A) (B)

(C) (D)

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 04.

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

05. Match the following :

Column I Column II

(a) CH3 – NH2 p. Formation of Schiff base

(b) CH3 – NH – CH3 q. Carbylamine reaction

(c) r. Reaction With R – MgX

(d) s. More basic than NH3

t. Less basic than NH3

u. Gives N2 gas with NaNO2/HCl at 0° – 5°C

(A) A—p,q,r,s,u ; B—r,s ; C—t ; D—p,q,r,t

(B) A—p,q,r, ; B—r,s,u ; C—t ; D—p,q,r,t

(C) A—p,q,r,s,u ; B—r,s,u ; C—p,t ; D—q,r,t

(D) A—p,q,r,u ; B—r,s ; C—t,u ; D—p,q,t

06.

The major product of the reaction would be :

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 (A) (B)

(C) (D)

07.M Which of the following amine can be synthesized using Gabriel phthalimide syn-
thesis?

(A) CH3CH2NH2 (B) CH3 — CH — CH2 CH2NH 2

CH3

(C) CH3 – CH = CH – NH2 (D) CH2 NH2

08.M Which of the following reactions represent major products ?

(A)

(B)

(C)

(D) Br2 + NaOH

CHBr3 + COONa

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 09.M

Products A and B are :

(A) Ph — NH2 (B) Ph – CH2 (C) Ph — CH2 — NH2 (D) Ph —

10.M Optically active amine having molecular formula C5H13N on reaction with

NaNO2 + HCl produces, 3° optically inactive alcohol. Find out structures of

amines :

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

11.M Consider the structures :

Which of the following statements are correct ?

(A) The base strength of II is more than that of I.

(B) The base strength of II is less than that of I.

(C) The base strength of IV is more than that of III.

(D) The base strength of IV is less than that of III.

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 Comprehension #

An organic compound ‘A’ has molecular formula C9H13NO and it can be resolved
into enantiomers. A does not decolourise bromine water solution. A on refluxing
with dilute H2SO4 yields another resolvable compound B (C9H14O3) which gives
effervescence with NaHCO3. B on treatment with NaBH4 yields C (C9H16O3) which
on heating with concentrated H2SO4 yields ester D (C9H14O2).

Compound A on reduction with LiAlH4, followed by treatment of H2SO4 yields

following compound :

12. Find out structure of compound ‘A’ :

(A) (B)

(C) (D)

13. The sweet smelling neutral compound D is :

O O
(A) (B)
O
O

(C) (D) O

14. Due to reduction of optically pure ‘B’ with NaBH4 two isomeric products are
formed. These products are

(A) Enatiomers

(B) Diastereomers

(C) Position isomers

(D) Functional isomers

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 Integer Type #

15. Of the following amines, how many gives black precipitate in Hoffmann’s mustard
oil reaction ?

(A) 4

16. CH3 – NH2 reacts with Ph – SO2 – Cl to give a compound, say ‘P’. Number of ‘H’
atoms(s) which can be removed from P using NaOH is :

(A) 1

17. Number of -bonds in the product of the given reaction is :

(A) 5

18. An amine with molecular formula C4H11N may have different isomers. The number
of isomers from above formula which can give alcohol on action of HNO2 is equal
to :

[Section-B]

01. Benzamide (PhCONH2) on treatment with LiAlH4 gives :

NH2

(a) Aniline (b) Isomer of p—toluidine

Me

(c) Ph CH(OH) NH2 (d) N-phenylformamide

02. n—butyric acid (Et CH2COOH) on treatment with LiAlH4 gives :

(a) Primary alcohol (b) n—pentane (c) propane (d) n—butane

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 03. When the vapours of propionic acid (CH3 CH2 COOH) are passed over heated MnO, the

product obtained is :

(a) 2–pentanone (b) 3–pentanone (c) butanone (d) propane

04. Et COOH can be converted to Et CHO by :

(a) H2—Ni (b) Li AlH4 (c) DIBALH (d) SBH

05. In Hell Volhard Zelinsky reaction the product formed is :

(a) –hydroxy acid (b) –hydroxy ester (c) –halo acid (d) –keto acid
06. CO2 gas is produced in :

(a) HOOC(CH2)2COOH + heat 

(b) HOOC(CH2)3COOH + Na HCO3 
(c) MeCOCH2CH2COOH + heat 
COOH
O
(d) + heat 

07. Propionic acid on reaction with HN3 gives :

(a) Et COO NH4 (b) Et CO NH2 (c) Et NH2 (d) Me2 NH

08. Salicylic acid on reaction with acetic anhydride gives :

OCOCH3
(a) (b) Aspirin (c) Paracetamol (d) Benzilic acid
COOCH3

09. The no. of  bonds in one molecule of Cinnamic acid are :

(a) 4 (b) 5 (c) 6 (d) 7

10. HOOC (CH2)5 COOH on heating gives (A) which on reaction with HN3 gives :

(a) —lactam (b) —lactam (c) —lactam (d) Nylon– 6 , 6

11. Adipic acid on reduction with LiAl H4 followed by reaction with PhMgBr gives :

(a) PhCOCH3 (b) PhH

(c) Ph(CH2)4Ph (d) Ph2C(OH)(CH2)4C(OH)Ph2

12. Ethanamide when treated with Br2/ KOH gives :

(a) EtNH2 (b) MeBr (c) MeNH2 (d) EtBr

13. PhNHCOCH3 on treatment with LiAlH4 gives :

(a) PhNH2 + CH3CH2OH (b) PhNHEt

(c) PhNH CH CH3 (d) p-ethyl aniline

OH
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 14. Most reactive towards hydrolysis is :

(a) MeCOOEt (b) EtCOOMe (c) MeCOCl (d) EtCOCl

15. Primary alcohol is obtained in :

(a) MeCOOCHMe2 + DIBAH  (b) MeCH2COCl + H2/Pd—BaSO4 

(c) Me2CHCOOCMe3 + LiAlH4  (d) EtCHO + Zn-Hg , conc. HCl 
16. Ethyl cyanide on Stephen’s reduction followed by treatment with methyl amine gives :

(a) Et CH2 N Me2 (b) Et CH2 NH2 (c) Et CH = N Me (d) EtCH2NHMe

17. n—butyl amine on reaction with CHCl3/KOH gives :

(a) EtCH2CH2Cl (b) EtCH2CH2NC (c) EtCH2CHCl2 (d) EtCH2CH2CN

18. Ethyl benzene on treatment with hot acidic KMnO4 followed by reaction with HN3 gives:

(a) aniline (b) benzyl amine

(c) benzamide (d) benzenediazonium salt

19. The no. of moles of CH3 Mg Br consumed when 3 moles of Cl CO (CH2)20 COCl reacts

with 25 moles of CH3 Mg Br :

(a) 12 (b) 18 (c) 15 (d) 21

20. Ph CH Me2 on reaction with O2/ h followed by treatment with conc. H2SO4 gives :

(a) PhCH2OH (b) acetone

(c) Me2CH— —OH (d) Cyclihexanol

21. Me2 C (OH) C (OH) Me2 on treatment with HIO4 gives :

(a) Pinacol (b) Pinacolone (c) acetone (d) acetic acid

22. Butanone on reaction with Me2 NH in presence of glacial acetic acid gives mainly :

(a) N (b) N

(c) (d)
N N

23. Me COOEt undergoes Claisen condensation to give (A) which on reaction with Na BH4

gives :

(a) Me CH (OH) CH2 COOEt (b) Me CH2 CH2 COO Et

(c) Me CH2 CH (OH) COOEt (d) Me CH (OH) CH2 CHO

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 O
+
24. i)
NaOH ii) H
 Product is :
O
COOH
COOH
(a) (b) OH
OH

(c) (d) O

25. Ph (CH2)3 COOH on treatment with H3PO4 gives :

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

O
26. Benzene on reaction with acetyl chloride in presence of anhyd. Al Cl3 followed by reac-
tion with HN3 mainly gives :
Ac NHMe
(a) Ph NH Ac (b) Ph CO NH Me (c) (d)
NH2 CHO
27. In Gattermann Koch aldehyde synthesis the gas involved is :

(a) NH3 (b) CO (c) CO2 (d) O2

[Section-C]
01. Primary amine + CHCl3 + KOH  product, here product will be :
(a) Cyanide (b) Isocyanide (c) Amine (d) Alcohol
02. The compound formed in the positive test for nitrogen with the Lassaigne solution of
an organic compound is :
(a) Fe 4[Fe(CN) 6] 3 (b) Na3[Fe(CN)6] (c) Fe(CN)3 (d) Na4[Fe(CN)5)NOS]
03. Which one of the following methods is neither meant for the synthesis nor for sepa-
ration of amines :
(a) Hofmann method (b) Hinsberg method (c) Curtius reaction (d) Wurtz reaction
04. In the chemical reaction, CH3CH2NH2 + CHCl3 + 3KOH  (A) + (B) + 3H2O, the
compounds (A) and (B) are respectively :
(a) C2H5CN & 3KCl (b) CH3CH2CONH2 & 3KCl
(c) C2H5NC & K2CO3 (d) C2H5NC & 3KCl
05. In the chemical reactions ,

(i) HBF4
A B , the compounds 'A' and 'B' respectively are :-
(ii) Heat
(a) Nitrobenzene and chlorobenzene (b) Nitrobenzene and fluorobenzene
(c) Phenol and benzene
(d) Benzene diazonium chloride and fluorobenzene
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 06. In the chemical reactions :

A B , the compounds A and B respectively are :

(a) Fluorobenzene and phenol (b) Benzene diazonium chloride and benzonitrile
(c) Nitrobenzene and chlorobenzene (d) Phenol and bromobenzene
07. Compound (A), C8H9Br , gives a white precipitate when warmed with alcoholic AgNO3.
Oxidation of (A) gives an acid (B), C8H6O4. (B) easily forms anhydride on heating.
Identify the compound (A) :

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

08. An organic compound A upon reacting with NH3 gives B. On heating, B gives C. C in
presence of KOH reacts with Br2 to give CH3CH2NH2. A is :

(a) CH3COOH (b) CH3CH2CH2COOH (c) Me2CHCOOH (d) CH3CH2COOH

09. On heating an aliphatic primary amine with chloroform & ethanolic potassium
hydroxide the organic compound formed is :

(a) An alkyl cyanide (b) An alkyl isocyanide (c) an alkanol (d) an alkanediol

10. In the reaction CH3COOH 

LiAlH4 A 
PCl5
 B 
alc. KOH
 C ‘C’ is :
(a) Ethylene (b) Acetyl chloride (c) Acetaldehyde (d) Acetylene
11. In presence of small amount of P4 , Carboxylic acids react with Cl2 or Br2 to yield a com-
pound in which -hydrogen has been replaced by halogen. This reaction is known as :
(a) Etard reaction (b) Hell - Volhard - Zelinsky reaction
(c) Wolff - Kischner reaction (d) Rosenmund reaction
12. In the Hofmann bromamide degradation reaction, the number of moles of NaOH and
Br2 used per mole of amine produced are :
(a) 4 moles of NaOH & 1 mole of Br2 (b) 1 mole of NaOH & 1 mole of Br2
(c) 4 moles of NaOH & 2 moles of Br2 (d) 2 moles of NaOH & 2 moles of Br2
13. The major product expected from the following reaction is :

HCl /CCl

(g) 4


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

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 14. The increasing order of basicity of the following compounds is :

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

(a) (B) < (A) < (C) < (D) (b) (B) < (A) < (D) < (C)

(c) (D) < (B) < (A) < (C) (d) (A) < (B) < (C) < (D)

15. Major product of the following reaction is :

(a) (b)

(c) (d)

16. The major product obtained in the following reaction is :

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

17. The major product of the following reaction is :

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

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 18. Which dicarboxylic acid in presence of a dehydrating agent is least reactive to give
an anhydride :

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

19. The decreasing order of ease of alkaline hydrolysis for the following esters is :

(a) IV > II > III > I (b) III > II > I > IV (c) III > II > IV > I (d) II > III > I > IV
20. The major product formed in the reaction given below will be :

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

21. An aromatic compound 'A' having molecular formula C7H6O2 on treating with aque-
ous ammonia and heating forms compound 'B'. The compound 'B' on reaction with
molecular bromine and potassium hydroxide provides compound 'C' having molecu-
lar formula C6H7N. The structure of 'A' is :

(a) (b)

(c) (d)

22. A compound 'X' on treatment with Br2/NaOH, provided C3H9N, which gives positive
carbylamine test. Compound 'X' is :
(a) CH3COCH2NHCH3 (b) CH3CH2COCH2NH 2
(c) CH3CH 2CH 2CONH 2 (d) CH3CON(CH3) 2

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 23. The increasing order of reactivity of the following compounds towards reaction with
alkyl halides directly is :

(a) (B) < (A) < (D) < (C) (b) (B) < (A) < (C) < (D)
(c) (A) < (C) < (D) < (B) (d) (A) < (B) < (C) < (D
24. The major product of the following reaction is :

(i) NaNO2 H+
(ii) CrO3 H+
(iii) H2SO 4 (conc.) 

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

25. Which of the following amines can be prepared by Gabriel phthalimide reaction ?

(a) Neo-pentylamine (b) n-butylamine (c) triethylamine (d) t-butylamine

26. The major product obtained in the following reaction is :

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

27. The major product of the following reaction is :

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

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 28. Hinsberg's reagent is :

(a) C6H5SO 2Cl (b) C6H5COCl (c) SOCl2 (d) (COCl)2

29. The major product of the following reaction is :

(a) (b) CH3CH = CH – CH2NH2

(c) (d)

30. Ethylamine (C2H5NH2) can be obtained from N-ethylphthalimide on treatment with :

(a) NaBH4 (b) CaH2 (c) H2O (d) NH2NH2

31. The major product 'Y' in the following reaction is :

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

32. In the given reactions sequence, the major product ‘C’ is :

(a) (b)

(c) (d)

33. The conversion of propan-1-ol to n-butylamine involves the sequential addition of

reagents. The correct sequential order of reagents is.
(a) (i) SOCl2 (ii) KCN (iii) H2/Ni,Na(Hg)/C2H5OH
(b) (i) HCl (ii) H2/Ni, Na(Hg)/C2H5OH
(c) (i) SOCl2 (ii) KCN (iii) CH3NH2
(d) (i) HCl (ii) CH3NH2

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 34. The reaction of amide with bromine and KOH gives RNH2 as the end product. Which
one of the following is the intermediate product formed in this reaction ?
(a) R–O–C–NHBr (b) R–NH–Br (c) R–N=C=O (d) R–C–NBr2
O O
35. During halogen test, sodium fusion extract is boiled with concentrated HNO3 to :
(a) remove unreacted sodium (b) decompose cyanide or sulphide of sodium
(c) extract halogen from organic compound (d) maintain the pH of extract
36. Which of the following ketone will NOT give enamine on treatment with secondary
amines ? [where t-Bu is –C(CH3)3]
O O O O

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

H5C2 C2H5 C2H 5 CH3 t-Bu t-Bu
37. Which statement is NOT correct for p-toluenesulphonyl chloride?
(a) It is known as Hinsberg’s reagent.
(b) It is used to distinguish primary and secondary amines.
(c) On treatment with secondary amine, it leads to a product, that is soluble in al-
kali.
(d) It doesn’t react with tertiary amines.
38. The final product ‘C’ in the following series of reactions :

(a) (b)

(c) (d)

39. Statements-I : In Hofmann degradation reaction, the migration of only an alkyl group
takes place from carbonyl carbon of the amide to the nitrogen atom.
Statement-II : The group is migrated in Hofmann degradation reaction to electron
deficient atom. choose the most appropriate answer from the options given below :
(a) Both Statement-I and Statement-II are correct.
(b) Both Statement-I and Statement-II are incorrect.
(c) Statement-I is correct but Statement-II is incorrect.
(d) Statement-I is incorrect but Statement-II is correct.
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 40. Identify the major product formed in the following sequence of reactions :
NH 2 (i) Br2–H2O
(ii) NaNO2/HCl
(iii) H3PO2
NH–NH 2 OH
Br Br Br Br Br
(a) (b) (c) (d)

Br Br Br
41. A primary aliphatic amine on reaction with nitrous acid in cold (273 K) and there after
raising temperature of reaction mixture to room temperature (298 K). Gives a/an :
(a) nitrile (b) alcohol (c) diazonium salt (d) secondary amine
42. With respect to the following reaction, consider the given statements :
NH 2
HNO 3
Products
H2SO4 . 288 K
(A) o-Nitroaniline & p-nitroaniline are the major products
(B) p-Nitroaniline & m-nitroaniline are the major products
(C) HNO3 acts as an acid (D) H2SO4 acts as an acid
(a) (A) and (C) are correct statements (b) (A) and (D) are correct statements
(c) (B) and (D) are correct statements (d) (B) and (C) are correct statements
Comprehension :

43. NaOH layer (C) contains :

(a) sodium salt of 1O amine N—alkyl benzenesulphonamide (c) both (a) and (b)
(b) sodium salt of 2 amine N, N—dialkyl benzenesulphonamide (d) None of these
O

44. Ethereal layer contains :

(a) 2O amine & 3O amine (b) 3O amine & N, N—dialkyl benzene sulphonamide
(c) 1O amine, 2O amine (d) only 3O amine
45. Distillation of ethereal layer gives :
(a) A (N, N—dialkyl benzene sulphonamide) and B (3O amine)
(b) A (sodium salt of N—alkyl benzene sulphonamide) and B (3O amine)
(c) A (2O amine) and B (3O amine) (d) None of these
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