Carboxylic Acids Amines

CHEMISTRY
Daily Practice Problems

EXERCISE-I
1. In the given reaction, [X] will be::
[X] + Acetic anhydride  Aspirin
(A) Benzoic acid (B) o-methoxybenzoic acid
(C) o-Hydroxybenzoic acid (D) p-Hydroxybenzoic acid
2. In the reaction sequence, (B) will be :
CH MgBr (i ) CO
CH3–CC–H 3  CH4+ (A)  
2  (B)

( ii ) H 2O / H
(A) CH3–CC–CH3 (B) CH3–CC–MgBr (C) CH3–CC–COOH (D) CH3–CH=CH–COOH
3. Consider the given reaction, which one of the following acid will give maximum yield of R–Br in the
above reaction?
Br / 
RCOOAg 2  R–Br
(A) CH 3  CH  COOH (B) CH3–CH2–CH2–COOH

|
CH 3
CH 3
|
(C) CH 3  C  COOH (D) All will give same yield
|
CH 3
4. In the given reaction, [X] will be:
CH3–CH2–COOH   [X]

(i)AgOH
(ii) Br2 /
(A) Ethyl bromide (B) Propyl bromide (C) Propyl propanoate (D) All of these
5. Benzoic acid on treatment with hydrazoic acid (N3H) in the presence of concentrated sulphuric acid
gives:
(A) Benzamide (B) Sodium benzoate (C) Aniline (D) C6H5CON3
6. In the given reaction, [X] will be :

O
||
 CHBr3 + [X]
( i ) Br2 / KOH
C6 H 5  C  CH 3  
( ii ) H 
(A) C6H5–CHO (B) C6H5COOH (C) C6H5–CH2OH (D) CH3COOH
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CHEMISTRY
7. In the given reaction, [X] will be :
O O
|| ||
C  CH 3  CH 3  C  OC 2 H 5 C
2 H 5ONa
 [X]
C2 H5OH
OH O O
| || ||
C  CH 2  C  CH 3 HC  CH  C  CH 3
(A) (B)
|
H
O O O
|| || ||
(C) CH 3  C  CH 2  C (D) CH 3  C  CH 2  COOH
8. Number of cross products in the given reaction:

C 2H5ONa
CH3COOC2H5 + C6H5–CH2–COOC2H5  
C2 H5OH
(A) One (B) Three (C) Two (D) four

9. In the reaction sequence, total lactides obtained are :
O
|| H O / H
CH 3  C  H HCN 
 (A)
2  Product
OH 
(A) 4 (B) 3 (C) 2 (D) 1

10. In the given reaction, major product on reaction with hinsberg reagent gives :
O
|| LiAlH 4
C6 H5 CNH CH 3   
(A) Base soluble primary sulphonamide (B) Base insoluble Tertiary sulphonamide
(C) Base insoluble secondary sulphonamide (D) Base soluble secondary sulphonamide
11. Which one of the following compounds gives carboxylic acid with HNO2?
(A) C6H5CH2NH2 (B) C6H5CONH2 (C) CH3CH2OH (D) PhNH2
12. Arrange following compounds in decreasing order of reactivity for hydrolysis reaction :
(I) C6H5COCl (II) NO2 COCl
O
||
(III) CH3 COCl (IV) OHC C  Cl
(A) II > IV > I > III (B) II > IV > III > I
(C) I > II > III > IV (D) IV > III > II > I
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CHEMISTRY
13. Arrange these esters in decreasing order of ease of esterfication with CH3OH/H :
(I) CH 3  CH  COOH (II) CH 3  CH  CH 2  COOH
| |
CH 3 CH 3
CH 3
|
(III) CH 3  C  COOH (IV) (CH3–CH2)3C–COOH
|
CH 3
(A) II > I > III > IV (B) I > II > III > IV (C) III >IV > II > I (D) IV > III > II > I
14. In the given reaction sequence (C) will be :

( i ) KMnO / O H /  (i ) SOCl Br / KOH
CH3–CH2–OH   4    (A)  2  (B) 2  (C)
( ii ) H  (ii ) NH3 / 
(A) Methylamine (B) Eltylamine (C) Propylamine (D) Acetamide

15. Sodium bicarbocate reacts with salicylic acid to form:
(A) C6H5ONa (B) (C) (D)
16. Which one of the following on heating gives unsaturated acid:

(A) -Hydroxy acid (B) -Hydroxy acid (C) -Hyroxy acid (D) -Hydroxy acid
17. Which will form lactone on treatment with NaOH ?
(A) -Bromo acid (B) -Bromo acid (C) -Hydroxy acid (D) -Bromo acid
18. Which of the following will undergoes decarboxylation on heating?
(A) Succinic acid (B) Phthalic acid (C) Malonic acid (D) Glutaric acid
19. In the given reaction, major product will be:
(i ) Br2 / red P
CH3–COOH   
( ii ) NaCN
( iii ) H 2O / H  / 
(A) CH3COOH (B) COOH–CH2–CH2–COOH

(C) Succinic anhydride (D) Malonic anhydride
O
||
CH 3  CH  C  CH 2  CH 3 CF COOOH
3  
|
CH 3
O O
|| ||
(A) CH 3  CH 2  C  O  CH  CH 3 (B) CH 3  CH  C  O  CH 2  CH 3
| |
CH 3 CH 3
O
||
(C) CH 3  C  OC(CH 3 )3 (D) (CH3)3COOCH3
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CHEMISTRY
21. Which one of the following reactions can be used for the preparation of -hydroxy ester:
(A) Perkin reaction (B) Reformatsky reaction
(C) Aldol condensation (D) Claisen condensation
22. Which acid can be oxidised by Fehling solution:
(A) Malonic acid (B) Acetic acid (C) Oxalic acid (D) formic acid
23. Reducing property of formic acid is due to the presenceOof :
O
|| ||
(A) – OH (B)  C  H (C)  C  OH (D) All of these
24. In the given reaction sequence major product B will be :
CH 2  COOH
 CH  CH NH / 
|  (A) 3 2 2  (B)
CH 2  COOH
O O
|| ||
(A) CH 2  C  NH  C 2 H 5 (B) CH 2  C
| |
CH 2  C  NH  C 2 H 5 CH 2  C
|| ||
O O
O
||
CH 2  COOH CH 2  C  NH  C 2 H 5
(C) | (D) |
CH 2  COOH CH 2  COOH
25. In the given reaction sequence major product B will be :
( i ) NaCN / HCl
CH3CHO     (A) Fenton
  (B)
(ii ) H 2O / H /  reagent
(A) Acetic acid (B) Oxalic acid (C) Pyruvic acid (D) Citric acid
26. In which reaction major product is hydrocarbon?
(A) RCOOK Electrolys
 is
 2 /
(B) RCOOAg I
CH 3
Cl / hv
| C 2 H 5OH
(C) CH3–CH3 2 
 (D) CH 3  C  Cl  
|
CH 3
27. Which of the following compound gives carbondioxide with NaHCO3?
(A) Acetic acid (B) Hexanol (C) Phenol (D) Acetylene
28. Which one of the following esters cannot undergo self Claisen condensation?
(A) CH3–CH2–CH2–COOC2H5 (B) C6H5COOC2H5
(C) C6H11–CH2–COOC2H5 (D) C6H5–CH2COOC2H5
29. The treatment of an open chain ester with LiAlH4 followed by acid hydrolysis produces :
(A) Two aldehyde (B) One carboxylic acid and one alcohol
(C) Two alcohols (D) Two acids
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CHEMISTRY
30. N-Ethyl pthalimide on hydrolysis gives:
(A) Methyl alcohol (B) Ethyl amine (C) Dimethyl amine (D) Diethyl amine
31. Which gas will be evolved out when [CH3CH2NH2 + (CH3)2CHNH2] is treated with sodium nitrite and
HCl:
(A) Chlorine (B) Ammonia (C) Nitrogen (D) NO2
32. Which of the following diazonium salt is relatively stable at 0-5°C:

(A) CH3–NN}Cl– (B) CH3C(CH3)–NN}Cl–
(C) C6H5–NN}Cl– (D) (CH3)3C–NN}Cl–
33. Which of the following can be detected by carbylamine reaction:

(A) Urea (B) CH3CONH2 (C) C2H5NH2 (D) (CH3)2NH
34. Hydrolysis of alkyl isocyanide yields:

(A) Primary amine (B) Tert. amine (C) Alcohol (D) Aldehyde
35. Which of the following compound gives the smell of mustard oil:
(A) Alkyl isocyanate (B) Alkyl isothiocyanate(C) Alkyl isocyanide (D) Alkyl isonitrile
36. The compound obtained by the reaction between primary amine and aldehyde is:
(A) An amide (B) Imine (C) Nitrite (D) Enamine
37. In the given reaction sequence major product X and Y will be respectively :
( i ) NH , 
Y   
3 ( i ) ND , 
( ii ) KOD ,Br 
COOH  3 X
2 ( ii ) KOH ,Br2
(A) X is NH2;Y is ND2(B) X is ND2; Y is NH2
(C) both ND2 (D) both NH2
38. Major end product of the following sequence of reaction is:

Ca ( OH ) ,Cl HNO
CH3CH2CH2CONH2   
2
2  X 2  Z

(A) CH3CH2CH2NH2 (B) CH3CH2CH2OH
(C) CH 3CHCH 3 (D) CH3CH2COOH

|
OH
39. Name the products in the acid-base reaction:

(a) CH3CH2NH2+ HI , (b) (CH3)3N + HBr
(A) (a) Trimethyl ammonium iodide (b) Trimethyl ammonium bromide
(B) (a) Ethyl ammonium iodide (b) Methyl ammonium bromide
(C) (a) Ethyl ammonium iodide (b) Trimethyl ammonium bromide
(D) All of these
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CHEMISTRY
40. Reductive amination of A forms:

A:
(A) (B) (C) (D)
41. Which of the following(s) will liberate CO2 on reaction with NaHCO3 :
CH OH
(A) OH (B) CH3COOH (C) Ascorbic acid (D) | 2
CH 2OH
42. Which of the following will form acetyl chloride with PCl5?
(A) MeCOOH (B) MeCOOMe (C) MeCOOCOMe (D) Me–CONH2
43. Sodium salt of which monobasic acids on electrolysis does not give hydrocarbon:
(A) C6H5COOH (B) HCOOH
(C) Me3C–COOH (D) COOH–CH=CH–COOH
44. Which one of the following compounds is least reactive with water?
O O O O
|| || || ||
(A) CH 3  C  Cl (B) C 6 H 5  C  NH 2 (C) CH 3  C  NH 2 (D) C 6 H 5  C  Cl
45. Following reaction is known as :

(i)SOCl 2
RCOOH 
(ii) NaN3
(iii)H 2 O,

(A) Hoffman rearrangement (B) Curtius rearrangement

(C) Lossen rearrangement (D) Schmidt rearrangement
46. Which of the following amine reacts with Hinsberg reagent to give base soluble product
(A) Neopentyl amine (B) secpropyl amine (C) diethyl amine (D) Ethyl methyl amine
47. Major product of following reaction is :
COOH

COOH + (CH3CO)2O
O
COOCOCH3
(A) O (B)
O CH2COOCOCH3
COOCOCH3 COOH
(C) (D)
CH2COOH CH2COOCOCH3
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CHEMISTRY
48. X and Y in following reaction is :
Formic acid 
Conc.H 2SO 4
X+Y
(A) CO2 & CO (B) CO & SO2 (C) H2O & CO (D) (COOH)2 & CO
49. Which of the following can released CO2 with NaHCO3.

Picric acid Malic acid Pyruvic acid
(i) (ii) (iii)
(A) (i), (ii) & (iii) (B) (i) & (ii) (C) (ii) & (iii) (D) (i) & (ii)
50. An alcohol, an aldehyde and a carboxylic acid of comparable mass will have their boiling points in the
order:
(A) alcohol < carboxylic acid < aldehyde (B) aldehyde < alcohol < carboxylic acid
(C) alcohol < aldehyde < carboxylic acid (D) carboxylic acid < aldehyde < alcohol
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CHEMISTRY
EXERCISE-II O
1. Which of the following set of reaction can prepare R–C–OH as the final product :
dry ether (i) SnCl 2 + HCl
(A) R–MgX + O=C=O (B) R–CN (ii) H2O / H+
CH2CH2CH3
KMnO 4, OH CrO3
(C) 
(D) CH3(CH2)8CH2OH H2SO4
2. Which of the following order(s) is/are correct for acidic strength :

(A) Maleic acid > Fumeric acid (B) Malonic acid > Succinic acid
(C) Salicylic acid > Benzoic acid (D) Formic acid > Benzoic acid
O
Ph–C–Cl + O NH
morpholine
O O O O
O
(A) Ph–C– N O (B) Ph–C– O N (C) Ph–C– N (D) Ph–C– NH2
4. Find out major product of following reaction :

H3CO
NaOCH3
O O
+
H
O
O
(A) O (B)
O O
COOCH3 O
OCH3
H3CO O
(C) (D) O
O O
O
CO2CH3
5. Which of the following is/are present in mixture of product :
O
C–O–CH2–CH3


HOH/ H

18
C–O–Ph
O
O OH
O OH C
C
18
(A) CH3CH2OH (B) (C) Ph  O H (D)
18 C–OH
C–OH
O
O
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CHEMISTRY
6. RCOOR' can be prepared by:

(A) Reaction of RCOOH with ROH, H+
(B) Reaction of RCOOH of CH2N2
(C) Baeyer-Villiger oxidation of RCOR' with peroxy acid
(D) Reaction of RCOCl with R'OH in presence of pyridine
7. Among the following, which statement is/are correct ?

(A) Acetic acid will not respond to haloform test
(B) Schiff's regent and Schiff's base are different compounds
(C) Fehling's solution is a good reagent to detect aromatic aldehydes
(D) Both aldehyde and ketone can react with braddy's reagent
8. If T can evolve effervescence of CO2 with aq. NaHCO3, then correct statement(s) is/are :
NaOH CH3–CH2 –I H3O+

O P R S+T
N–H
O NaOH Q + Na2CO3
Br2
(A) S & Q can be distinguished by dye azo test

(B) T is most acidic among all isomeric benzenoid dicarboxylic acid
(C) Q & S can be distinguished by mustered oil test
(D) P, Q & T all are soluble in aq. NaHCO3
9. Correct options for given sequence is/are :

COOH
(P) C8H6O2 

(i) NaOH
(ii) H O
 (Q) 
KMnO 4

3
OH
O
H CH OH
C C
(A) ‘P’ is C (B) ‘Q’ is
O O
CHO COOH
(C) ‘P’ is (D) ‘Q’ is
CHO CH2OH
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CHEMISTRY
10. Which of the following carboxylic acids undergoes decarboxylation on gentle heating ?
O
(A) Cl3C–C– OH (B) PhCH2COOH
(C) (D) 2-oxocyclohexane carboxylic acid

O COOH
11. For the following compounds, choose the correct option (s)
CH3 – NH2 Ph–NH2
(P) (Q)
(A) (P) is more basic than (Q)
(B) Both (P) & (Q) will give foul smelling compound with CHCl3, KOH
(C) Both (P) & (Q) will form base soluble sulphonamide with Hinsberg reagent
(D) Both (P) & (Q) can be obtained by gabriel phthalimide synthesis
12. Which of oxidation reactions in which organic reactant gets oxidised & one of the major product is
carboxylic acid/salt :
O
C CH2OH
CH3 NaOI H5IO6
(A) (B) H OH
CHO
CHO NC
(C) Fehling solution (D) H3O
13. Which of the following compound evolve 2 mole of CO2 on gentle heating :
COOH
COOH COOH
O COOH
(A) (B) O (C) (D) COOH
COOH
O O
COOH COOH
14. Choose the incorrect option(s) for given reaction if X is aromatic in nature?
O

H3C – C– O – C = CH2   X +Y
H 3O
Ph
(A) Both X and Y are soluble in hot aq. NaOH
(B) Y will evolve CO2 gas with aq. NaHCO3
(C) X has higher rate of nucleophilic addition than 4-methyl benzaldehyde
(D) X will give yellow ppt. with alkaline solution of bromine
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CHEMISTRY
15. Which of the following compounds react with HNO2 :
(A) NO2 (B) NO2 (C) NO2 (D) NH2
16. In which of the following rearrangements migration at electron deficient nitrogen take place :
(A) Hoffman rearrangement (B) Curtius rearrangement
(C) Lossen rearrangement (D) Schmidt rearrangement
COOH
14 
HOOC
COOH 14 COOH
14
(A) (B) (C) (D)

14
18. A compound undergoes the following sequence of reactions and gives the product (C8H4O3).
(i) reaction with dilute aq. NaOH (ii) acidification
(iii) treatment with acidic Na2Cr2O7 (iv) heating.
Hence, the compound is
(A) (B) (C) (D)
19. Consider the following reactions, major product M and Y respectively are :
M 
CH3 I
 L 
LDA
273K
 
NaH
 X 
CH3 I
 Y (LDA = lithiumdiisopropyl amide)
298K
O O OLi O
(A) and (B) and
O O O O
(C) and (D) and
20. Ethyl propanoate has a pineapple like odour and is used as a flavoring agent in fruit syrups. It is prepared
as follows :
C2H5OH (aq) + C2H5COOH (aq)  C2H5COOC2H5 (aq) + H2O()
In an experiment, 306 grams of ethyl propanoate was obtained from 230 grams of ethanol, with propanoic
acid in excess. The percentage yield of the above reaction is :
(A) 40 (B) 60 (C) 54 (D) 85
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CHEMISTRY
21. In this reaction the product (E) is :
COOH

 (A)   (B)   (C) 
Br2  KOH
 (D)  (E)
NH 3 NaOH HCl
H 2O
COOH
(A) o-nitrobenzoic acid (B) Salicylic acid (C) Anthranilic acid (D) Crotonic acid
22. Compare the percentage enol content of following reaction products :
(1) C2H5ONa
(P) O + H–C–OC2H5
(2) H
O
(1) C2H5ONa
(Q) O + CH3–C–OC2H5
(2) H
O
(1) C H5ONa
(R) O + C2H5–O–C–OC2H5 (2) H2
O
(A) P > Q > R (B) R > Q > P (C) Q > R > P (D) R > P > Q
23. In the given reaction sequence, major product (y) will be :
(1) OH
(x) NH2–NH2/OH (y)
(2) C6H5CHO/
O
(A) CH–C6H5 (B)
CH–C6H5
(C) CH2–C6H5 (D)
CH2–Ph
24. Compound (X) C9H10O gives yellow coloured ppt with 2,4 DNP but does not give red coloured ppt
with Fehling’s solution. (X) on treatment with NH2OH/H+ gives compound (Y) C9H11NO. (Y) when
treated with PCl5 gives isomeric compound (Z). (Z) on hydrolysis gives propanoic acid and aniline.
What will be the correct structure of (X), (Y) and (Z) ?
(X) (Y) (Z)
(A) C6H5–C–C2H5 ; C6H5–C–C2H5 ; C6H5–C–NH–C2H5
O OH—N O
C6H5–C–C2H5 C6H5–C–C2H5 C2H5–C–NH–C6H5

(B) ; ;
O N–OH O
(C) C6H5–CH2–C–CH3 ; C6H5–CH2–C–CH3 ; CH3–C–CH2–NH–C6H5

O N–OH O
(D) C6H5–C–C2H5 ; C6H5–C–C2H5 ; C6H5–C–NH–C2H5

O N–OH O
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CHEMISTRY
25. Which of the following methods would serve to prepare 1-phenylpropan-2-ol.
(A) Addition of benzyl grignard reagent to ethanal.
(B) Addition of phenyllithium to methyloxirane
(C) Addition of methyl grignard reagent to phenyl acetaldehyde.
(D) Addition of phenyl Magnesium bromide with ethanal.
26. Which of the following reactions will give -hydroxy acid as major product:
( i ) NaCN / HCl
(A) CH3–CHO     (B) CH3CHO + Br–CH2–COOC2H5 (
i ) Zn
 
(ii ) H 2O / H /  (ii ) NH 4Cl / HOH
(iii ) HOH / H  / 
X
|
(D) CH3COOH  
(i) Red P/Br2
(C) CH 2  CH 2  COOH NaOH
 /HOH
 (ii) NaOH
27. In the given reaction major product and mechanism used is :

Ph Ph
18 
O 
H O H/ H

O
18
OH OH
| 18 |
(A) HOOC–CH2–CH2– CH (Ph)2, AAC1 (B) HOOC –CH2–CH2– CH (Ph)2, AAC2
18
OH OH
| |
(C) HOOC–CH2–CH2– CH (Ph)2, AAC1 (D) HOOC–CH2–CH2– CH (Ph)2, AAl1
COOC2 H 5
+ | 
Pyridine
COOC2 H 5
H H
N O N OC2H5
(A) Barbituric acid (B) (C) (D) Veronal
N O N OC2H5
H H
29. An optically active compound 'X' has molecular formula C4H8O3. It evolves CO2 with aq. NaHCO3.
'X' reacts with LiAlH4 to give an achiral compound. 'X' is :
(A) CH 3CH 2CHCOOH (B) (CH3)2CH(OH)COOH
|
OH
(C) CH 3CHCOOH (D) CH 3CHCH 2COOH

| |
CH 2OH OH
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CHEMISTRY
30. For the given reaction, X is a tertiary alcohol then choose correct option(s) about reactant amine :
C4H11N + HNO2  X (C4H10O)
(A) It will give positive carbyl amine and Hofmann mustard oil test
(B) It will give liquid product with diethyl oxalate
(C) Total two amines are possible for reaction
(D) It will give base insoluble product with Hinsburg reagent
31. Mixture of 1°, 2° and 3° amines can be separated by:
(A) Hinsberg's method (B) Hofmann's isocyanide test
(C) fractional distillation (D) NaNO2 / HCl
32. Which is/are correct reaction(s):

(A) Cl + NH3  + NH4Cl
(B) Cl + 2NH3 ,   NH2+ NH4Cl
(C) Cl + NH3 ,   + NH4Cl
0C OH
(D) NH2 + HNO2 
33. Which of the following compounds will give acetic acid with KMnO4/H/:
(A) CH3–CHO (B) CH3–CH=CH–CH3
(C) CH3–CC–CH3 (D) CH3CH2OH
34. Acetic acid can be used for the preparation of :
(A) Ethane (B) Methane (C) Acetone (D) ethanol
35. Consider the following reaction & true about the below reaction is/are :
O  O
|| H ||
CH 3  C  OH  CH 3  OH CH 3  C  O  CH 3  HOH
(A) Product is having smell like fruits

(B) Nucleophilic addition followed by elimination reaction
(C) It follows AAC2 mechanism
(D) It is irriversible reaction
36. Which one of the following acids undergoes decarboxylation on strong heating:
(A) Adipic acid (B) 3-butenoic acid (C) Formic acid (D) Salicylic acid
37. Acetic anhydride is used as:

(A) Solvent (B) Dehydrating agent
(C) Acetylating agent (D) Anticeptic
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CHEMISTRY
38. In the given reaction [X] can be:
O O
|| [X]
||
R  C  OH  R  C  O  CH 3
(A) CH2N2 (B) CH3OH/H (C) MeOTs/Benzene (D) Me2SO4/NaOH
39. Which of the following gives silver mirror test?

(A) HCOOH (B) CH3COCH2OH (C) PhNHOH (D) D Glucose
40. Hofmann degradation is given by:
(A) NBS (B) Benzamide (C) CH3CONHBr (D) Phthalimide
41. Metahemipinic acid J, (C10H10O6) on heating with CaO, gives veratrole. J forms an anhydride on heating
and forms only one monoester on esterification. Structure of metahemipinic acid is
COOH
COOH MeO COOH
MeO COOH iii)
(A) (B)
MeO OMe
COOH
MeO
MeO COOH
(C) (D)
COOH COOH
MeO
OMe
42. On hydrolysis, if given ester racemises slowly then mechanism can be
Ph
O CH3
(A) AAC1 (B) BAl1 (C) AAl1 (D) BAC2
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CHEMISTRY
Paragraph for Q.No. 43 to 45
Observe the esterification mechanisms for primary and tertiary alcohols.
O
Type.1 CH3–COOH + CH3–CH2–CH2–OH  CH3–C–O–Pr Conc. H2SO4
Propyl=Pr
Mechanism
.. OH
O OH OH O O
H  Pr H
CH3–C   CH3–C–OH 
Step 3
 CH3–C–O–Pr
Step 1. CH3–C CH3–C Step 2
OH OH O

–H
OH –H2O
Pr H
O CH3 CH3
Conc.H 2 SO 4
Type. 2 CH3–C + CH3–C–OH  CH3–C–O–C–CH3
OH CH3 CH O 3
..
O–H
CH3 CH3 CH3–C CH3

H
CH3–C–OH   CH3–C + H2O O CH3–C–O–C–CH3
Mechanism Step 1.
CH3 CH3 CH3 O
18
43. Conc. H2SO4
CH3–COOH + C2H5OH   (P)
18
Conc. H2SO4
CH3–COOH + (CH3)3C–OH   (Q)
In the above reaction (P) and (Q) are respectively :
O O CH3 O O CH3
18 18
(A) CH3–C–O–C2H5 , CH3–C–O–C–CH3 (B) CH3–C–O–C2H5 , CH3–C–O–C–CH3
CH3 CH3
O O CH3 O O CH3
18 18 18
(C) C2H5–C–O–CH3 , CH3–C–O–C–CH3 (D) CH3–C–O–C2H5 , CH3–C–O–C–CH3
CH3 CH3
H
Conc.H 2 SO 4
44. CH3COOH + D OH   (X)
CH3
CH3
Conc.H 2 SO 4
CH3–COOH + Ph–C–OH   (Y)
C2H5
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CHEMISTRY
(A) (X) is optically active while (Y) is optically inactive.
(B) Both (X) and (Y) are optically active.
(C) Both (X) and (Y) are optically inactive.
(D) (X) is optically inactive while (Y) is optically active.
45. (+) Octan-2-ol esterifies with Acetic acid to give optically inactive racemised product. It must have gone
by
(A) Type I mechanism (B) Type II mechanism
(C) Mix type I and type II mechanism (D) More by type I and less by type II mechanism

Observe the following sequence of reaction and answer the questions based on it
z  w
Gentle heat
Phenylacetylene x y  CO2
46. Which of the following are soluble in aqueous NaOH :

(A) x (B) y (C) z (D) w
47. Which of the following statement is/are correct

(A) y decolourises Br2 /H2O solution (B) z with aq. NaHCO3 liberates CO2 gas
(C) w on reaction with NaOI gives yellow ppt (D) x with HgSO4/H2SO4 give w
48. Which of the following compound give benzoic acid on KMnO4 oxidation
(A) w (B) y (C) z (D) x
Ester having -hydrogen on treatment with a strong base eg. C2H5ONa undergoes self condensation to
produce -keto esters.This is called claisen condensation.
C2H5O– + H – CH2COOC2H5 C2H5OH +
O O–
–.. –
CH3 – C + CH2 – COOC2H5 CH3 – C – CH2 – C – OEt CH3–C–CH2–C–OEt + C2H5O
OEt OEt O O O
O
EtONa
CO2Et
O O O
CO2Et
(A) (B) (C) CO2Et (D)
CO2Et
50. Correct statement(s) regarding major product P is/are :
O
EtO – C – OEt + Ph – CH2 – C – OC2H5 
(i) EtONa
(ii)Slight H 
P 
H 2O

 Phenyl acetic acid
O
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CHEMISTRY
(A) Total number of stereoisomer are 2
(B) It can't show stereoisomerism
(C) On oxidation it gives benzoic acid
(D) Can be obtained by sodium salt of diethyl malonate and PhCl
51. Major product can oxidise with :
CH3 – C – CH2 – C – OEt (1) C2 H 5ONa H 3O 
(2) CH3  I
  

O O
(A) NaOI (B) Aq. NaHSO3 (C) Br2/CH3COOH (D) 2,4-DNP
O3 Conc. KOH
A B+C Benzyl alcohol + salt of benzoic acid
O
dil. KOH
CH3–CH–CH2–C–H
OH HCN

H3O
D E
52. Which of the following can show stereoisomerism :
(A) B (B) E (C) A (D) D
53. Which of the following pairs are correctly matched with method of differentiation
(A) A & B  Br2 / H2O (B) B & C  Fehling solution
(C) A & C  Tollen’s reagent (D) A & B  2,4-DNP
54. Structure of E is :
OH OH Me
OH
(A) (B) (C) (D)
HO O O O O O O O O
For the following sequence if P has 'R' absolute configuration :
(i) CH3CH2CH2COOH Red P
Br2
P+ Q
(ii) P NH3 R
NaNO2
S
(2 eq.) HCl
(iii) Q Aq. T
KOH
55. Choose the correct option(s) ?

(A) S & T are non superimposable mirror images
(B) Absolute configuration of Q & T are same
(C) All P,Q,R,S,T are soluble in aq. NaHCO3
(D) R is a chiral amino acid having 'S' absolute configuration
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CHEMISTRY
56. Which of the followings products formation involves neighbouring group participation ?
(A) R (B) P (C) S (D) T
For the given reactions:
CH2COOH CH2OH
NH3 Br2 / NaOH CrO3 N3H
(P) 
(Q) H2SO4 H2SO4
COOH SOCl2 (i) CH2N2 CH2CN

98% LiAlH4
(R) (ii) Ag2O, (S)
(iii) H2O H2SO4 Et2O
57. Which of the following reactions involves carbon chain upgradation

(A) P (B) Q (C) R (D) S
58. In which reaction major product is homologous of phenylmethyl amine?
(A) P (B) Q (C) R (D) S
59. Which of the following reactions involves migration towards electron deficient nitrogen
(A) P (B) Q (C) R (D) S
60. Column I Column II
(organic compounds oxidised by HIO4) (products of HIO4 oxidation)
(A) CH3COCHO (P) PhCH = O + HCOOH
(B) 1,2-cyclohexane dione (Q) CH3CH2CHO + HOOCCH3
(C) PhCH (OH) CHO (R) HOOC (CH2)4COOH
(D) CH3CH2CH (OH) COCH3 (S) CH3COOH + HCOOH
(Reagents reacting with PhCH2COOH) (Product formed)
(A) CH3MgBr (P) PhCH2COCl
(B) PCl5 (Q) PhCH2COOCH3
(C) NH3, followed by heating (R) CH4
(D) CH3OH in the presence of conc. H2SO4 (S) PhCH2CONH2
62. Column I (Reactions) Column II (Products)
(A) 2CH3NH2 + (P) N = CH
(B) (CH3)2NH + C6H5COCl (Q) CH3 – NH—
O
||
(C) + (R) (CH3)2N– C
O O
|| ||
(D) CH3NH2 + SO2Cl (S) CH 3 NH  C  CH 2 CH 2  C  O Na
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CHEMISTRY
NaNO  HCl
(A) R'NH2  2 
 (P) RR'N–N= O
NaNO  HCl
(B) PhNH2  2 
 (Q) Ph–N+  NCl–
NaNO  HCl
(C) PhN(CH3)2  2 
 (R) (CH3)2N N=O
NaNO  HCl
(D) RR'NH  2 
 (S) R'OH + N2
(A) PhCONH2  PhCH2NH2 (P) B2H6 , AcOH, H2O
(B)  HO–CH2–(CH2)2–CH(OH)–C6H5 (Q) LiAlH4
(C) C6H5CH = CH– COOH C6H5 – CH = CH2OH (R) H2 ,Pt/
(D) CH3COCl  CH3–CHO (S) DIBAL-H
(T) H2 , Pd/BaSO4
(A) RCN reduction

  (P) 1° Amine
( i ) CH MgBr
(B) RCN  3  (Q) Alcohol
( ii ) H 2O
(C) RNC hydrolysis

  (R) Ketone
(D) RNH2 HNO

2  (S) Acid
(T) Aldehyde
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CHEMISTRY
66. Match the following question :
Column - I (Reaction) Column-II (Products)
CH3
(A) HOOC  (P) Diastereomers
COOH  
H D
C2H5
CH3

(B) HOOC COOH   (Q) Racemic mixture
C2H5
HOOC COOH

(C)   (R) Meso compound
CH3
COOH

(D)   (S) CO2 gas will evolve
COOH
(T) Geometrical Isomers
67. Match the following question :
Column I Column II
(Reaction) (Correct about product)
H3O 
(A) R – CN  (P) Yellow oily liquid

CHCl
(B) R – NH2 
KOH
3
(Q) Gives red colour with CAN
NaNO
(C) R – NH2 
HCl
2
 (R) Gives fruity smell with CH3OH
NaNO
(D) R2NH 
HCl
2
 (S) Foul smelling compound
68. Find out number of reactions which involve electron dificient nitrogen during reaction mechanism.
O
H3 C Dilute.H SO
(a) C N 2 4
(b) H3C C Ph PhCO H 3
Ph OH
O O
(1) SOCl2
Br 2+ KOH (2) CH 2N2
(c) CH3 C NH2 (d) CH3 C OH (3) Ag2O/H2O
O O
N3H.Dilute H2SO4
(e) Ph C OH (f) NaN3
CH3 C Cl H2O, 
O H
O
CHCl3 + KOH
(g) NH3 (h) H / H 2O
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CHEMISTRY
69. P = number of compounds which gives (+ve) dye azo test on treatment with HNO2 followed by -napthol
Q = number of compounds which gives (+ve) isocynide test
Then find value of (P + Q) ?
CH2–NH2 NH–CH3 NH2
NH2
NH
NH2 NH2
O
N
NH2
N
H CH3
70. How many of following esters show AAl1 hydrolysis mechanism :
O CH3 O C6H3 O
CH3–C–O–C–CH3 , CH3–C–O–C–C6 H5 , C–O–CH3
CH3 C6H3
Ph Ph
H3C O
O
H3C C–O–CH3 , CH3CO2Et ,
CH3 O
71. Examine the structure of following compounds, and find out number of compounds that will undergo
decarboxylation on moderate heat.
O
O O
O
O O OH OH OH
, , ,
OH O
O
O
COOH HOOC
OH COOH
COOH
, , ,
O COOH COOH
COOH O
O
C OEt
NaOC2H 2
72. Br ( )n Br + CH2  Cyclic product,
C2 H 2OH
C OEt
O
At what value of 'n' the formation of six membered ring take place.
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CHEMISTRY
73. In all reactions the sum of organic product are :

(1) CH3CH2–CH–COOH (2) CH3CH2–CH–COOH 
NH2 OH
(3) CH3CH–CH2–COOH  (4) CH2CH2–CH2–COOH 

OH OH
74. Total number of compounds which are soluble in hot aq. NaOH are :
(i) Salicyclic acid (ii) Aspirine (iii) Carbolic acid (iv) Acetic acid
(v) Succinic anhydride (vi) Cyclohexanone (vii) Benzene sulphonamide
(viii) Cyclohexene (ix) Benzaldehyde
75. If x is number of moles of Br2 and y is number of moles of NaOH required in bromoform reaction to
produce 1 mole of bromoform while p is number of moles of Br2 and q is number of moles of NaOH
x p
required to produce 1 mole of amine in Hoffman degradation reaction. Then find value of   
y q
where [· ] represent greatest integer function.
23
CHEMISTRY
EXERCISE - III
Complete the following equation by writting the missing A, B, C, D..................etc.

PCl
1. Ester (A) 5  B + C aq
.KOH

 (CH3)2CHCH2OH
(D) LiAlH
 4  (CH3)2CHCH2OH
ND HCl
2. 3  (A) Br
R–COOH  ,KOH
2  (B) NaNO
 2 (C)
 
3. Acid (A) SOCl

2  C
 MeNH
 A   B  
PCl5
4. O 
H
MeOH
2  C

5.  A+B
6. CH3(CH2)14CH2CH2COOH Br / PBr

2 3  (A) 
(i) Alc.KOH
 (B) (
C)


(ii) H
(i ) Ag  ( ii ) Br
CH3(CH2)14COOH    2  (D)
7.  
LiAlH
4  (A) HCl
 (B) (
C)
 BaO
 (D) + CO2+H2O

H / Pd
8. HCCH (
i ) 2 Na
 (A) 2 
 (B)
( ii ) 2CO 2 BaSO4

9. Phthalic acid + NH3  D  E
10. MeCH(CH2COOH)2 (

CH3CO ) 2 O
  F

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CHEMISTRY
Account for following:
11. Fluoro acetic acid is stronger than chloro acetic acid.
12. C–O bond length in formic acid are 1.23 Å and 1.36 Å but in sodium formate both carbon and oxygen
bonds have same value i.e. 1.27 Å.
13. Acetic acid can be halogenated in presence of phosphorous and chlorine but formic acid cannot be
halogenated in the same way.
14. The C–G bond in acid derivative is expected to be shorter and stronger than alkyl derivative.
15. An acyl chloride undergoes nucleophilic attack more rapidly than does an alkyl halide.
16. Primary and secondary amide exist as dimer in solid and pure liquid state.
17. Acetic acid is stronger acid than carbonic acid.
18. Amphoteric nature of Amide.
19. An Aq solution of formic acid can not be fractionated to get anhydrous acid.
20. How will you bring about the following transformation:

(i) Propanoic acid into lactic acid.
(ii) Nitroethane to acetic acid.
(iii) Benzoic acid to benzamide.
(iv) Ethyl benzene to 2-phenyl propionic acid.
(v) Acetamide from acetone.
(vi) Tartartic acid from ethylene.
(vii) Lactic acid from acetic acid.
(viii) Pyruvic acid from ethyl bromide.
(ix) -hydroxy propionic acid from ethylene oxide.
(x) Butanoic acid into butanamine
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CHEMISTRY
Q.13 The correct sequence of reagents for the following conversion will be [JEE(Main)-2017]
O OH
CHO
OH
(1) [Ag(NH3)2]+ OH–, H+/CH3OH, CH3MgBr

(2) CH3MgBr, H+/CH3OH, [Ag(NH3)2]+ OH–
(3) CH3MgBr, [Ag(NH3)2]+ OH–, H+/CH3OH
(4) [Ag(NH3)2]+ OH–, CH3MgBr, H+/CH3OH
Q.14 The major product of thee following reaction is : [JEE MAIN-2019]

O
C
NH2  
(i) Br2 /hv
(ii) KOH (dil)
CH2CH3
O O
NH NH NH
(1) (2)) (3) (4)) NH
CH3
CH3
Q.15 The major product formeed in the reaction given below will is : [JEE MAIN-2019]
NH2
 
NaNO 2
Aq HCl,05ºC

NO2 OH
NO2 (3) OH
(1) (22) (4
4)
Q.16 An aromatic compound ‘A’ having molecular formula C7H6O2 on treating with aqueous ammonia and
heating forms compound ‘B’. The compound ‘B’ on reaction with molecular bromine and potassium
hydroxide provides compound ‘C’ having molecular formula C6H7N. The structure of ‘A’ is:
[JEE MAIN-2019]
COOH
(1) O (2)
CH–CH–CHO
CHO OHC
(3) (4)
OH OH
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CHEMISTRY
Q.17 The decreasing order of ease of alkaline hydrolysis for the following esters is : [JEE MAIN-2019]
I II
III IV
(1) IV > II > III > I (2) II > III > I > IV (3) III > II > I > IV (4) III > II > IV > I
Q.18 Which dicarboxylic acid in presence of a dehydrating agent is least reactive to give an anhydride ?
[JEE MAIN-2019]
O
C COOH COOH CH2
CH2 OH CH2 COOH
(1) (2)) (3) (4))
CH2 OH CH2 COOH
C COOH COOH CH2
O
Q.19 The major product obtain

ned in the following reaction is : [JEE MAIN-2019]
CO2Et
Na / 
OEt 
O
O
O O
(1) (2) CO2Et
CO2Et
O O
(3) (4) CO2Et
CO2Et
Q.20 The increasing order of reactivity of the following compounds towards reaction with alkyl halides directly
is : [JEE MAIN-2019]
(A) (B)
(C) (D)
(1) (B) < (A) < (D) < (C) (2) (A) < (C) < (D) < (B)
(3) (B) < (A) < (C) < (D) (4) (A) < (B) < (C) < (D)
29
CHEMISTRY
Q.21 The major product of the following reaction is:
OH
ethyl formate (1 equiv.)
CH 3CHCH2 CH2 NH2 triethylamine
OH
(1) CH 3 – CH – CH = CH 2 (2) CH3CH = CH – CH2NH2
OH O H
(3) CH 3CHCH2 CH2 NHCHO (4) CH 3CHCH2 CH2 NH2
Q.22 Ethylamine (C2H5NH2) can be obtained from N-ethylphthalimide on treatment with:

[JEE MAIN-2019]
(1) NH2NH2 (2) NaBH4 (3) CaH2 (4) H2O
Q.23 Which of the following is NOT a correct method of the preparation of benzylamine from cyanobenzene
? [JEE MAIN-2019]
(1) H2/Ni (2) (i) HCl/H2O (ii) NaBH4
(3) (i) LiAlH4 (ii) H3O+ (4) (i) SnCl2 + HCl(gas) (ii)
NaBH4
Q.24 Which of the following amines can be prepared by Gabriel phthalimide reaction?[JEE MAIN-2019]
(1) neo-pentylamine (2) n-butylamine (3) triethylamine (4) t-butylamine
Q.25 Hinsberg’s reagent is : [JEE MAIN-2019]

(1) SOCl2 (2) (COCl)2 (3) C6H5COCl (4) C6H5SO2Cl
30
CHEMISTRY
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CHEMISTRY
PARAGRAPH Q.20 to Q.21

An organic acid P (C11H12O2) can easily be oxidized to a dibasic acid which reacts with
ethyleneglycol to produce a polymer dacron. Upon ozonolysis, P gives an aliphatic ketone as one of the
products. P undergoes the following reaction sequences to furnish R via Q. The compound P also
undergoes another set of reactions to produce S. [IIT 2018]
1) H 2 /Pd C
2) NH3 /  1) H 2 /Pd C 1) HCl
3) Br2 / NaOH 2)SOCl2 2) Mg/Et 2O
S  
4)CHCl3 ,KOH, 
P 
3) MeMgBr,CdCl 2
 Q 
3)CO 2 (dryice)

5) H 2 /Pd C 4) NaBH 4 4) H3 O
Q.20 The compound R is

HO 2C
(A) CO 2H (B)
CO 2H CO 2H
(C) (D)
Q.21 The compound S is
H
(A) (B) (C) (D) N
NH2
NH2 HN
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CHEMISTRY
Q.22 Total number of hydroxyl groups present in molecule of the major product P is ____ [IIT 2019]
(i) H 2, Pd-BaSO4, quinoline

P
(ii) dil. KMnO 4 (excess), 273K
Answer the following by appropriately matching the lists based on the information given in the
paragraph
List-I includes starting material and reagents of selected chemical reactions. List-II gives structures of
compounds that may be formed as intermediate products and / or final products from the reactions of
List-I. [IIT 2019]
List-I List-II
i) DIBAL-H CHO
CN
(I) O
ii) dil. HCl (P)
iii) NaBH 4 CO2 H
O iv) conc. H2SO 4
i) O3 OH
(II) ii) Zn, H2O (Q)
OH
CO2H iii) NaBH 4
iv) conc. H 2SO4
i) KCN
Cl
(III) ii) H3O+,  (R)
O
CO 2CH 3 iii) LiAlH4
iv) conc. H 2SO4
CO2Me OH
(IV) i) LiAlH 4 (S)
CO2 Me ii) conc. H2SO4 CO2 H
CO2H
(T)
CO2 H
(U) O
Q.23 Which of the following options has correct combination considering List-IOand List-II?
(A) (II), (P), (S), (T) (B) (I), (S), (Q), (R) (C) (II), (P), (S), (U) (D) (I), (Q), (T), (U)
Q.24 Which of the following options has correct combination considering List-I and List-II?
(A) (III), (T), (U) (B) (III), (S), (R) (C) (IV), (Q), (R) (D) (IV), (Q), (U)
37
CHEMISTRY
EXERCISE - V
Q.1 Compound (A) (C6H12O2) on reduction with LiAlH4 yielded two compounds (B) and (C). The compound
(B) on oxidation gave (D) which on treatment with aqueous alkali and subsequent heating furnished (E).
The latter on catalytic hydrogenation gave (C). The compound (D) was oxidised further to give (F)
which was found to be monobasic acid (molecular mass = 60.0). Deduce the structure of (A), (B), (C),
(D) and (E). [IIT 1990]
Q.2 In the following reactions, identify the compounds (A), (B), (C) and (D) [IIT 1994]
PCl5 + SO2  (A) + (B)
(A) + CH3COOH  (C) + SO2 + HCl
2(C) +b (CH3)2Cd  2(D) + CdCl2
Q.3 Complete the following equations by writing the missing A and B [IIT 1995]
(i) CH3CH2COOH P
/ Br2
 (A) (
i ) Alc.KOH( excess)
    (B)
( ii ) H 
O
CrO 3
||
(ii) C4H8O3(A)  (B) Warm
 CH 3  C  CH 3  CO 2
Q.4 A mixture of an acid anhydride (A) and a monobasic acid (B) on heating produces another monobasic
acid (C) of equivalent weight 74 and an anhydride (D). The acids and anhydrides remain in equilibrium.
The anhydride (D) contains two identical fluoro-alkyl groups. The acid (B) contains a trifluoromethyl
group and has an equivalent weight of 128. Give structures of (A) to (D) with proper reasoning. (Atomic
weight of fluorine = 19). [IIT 1998]
Q.5 Identify A and B in the following equations: [IIT 1999]
O
||
(i ) OH  H C  CH  C  OH
CH2   (A)
NaOEt (B)    3

( ii ) H  |
CH 2  C  OH
||
O
Q.6 Write the structure of product A & B: [IIT 2000]
O
|| H3O
CH3  C  O18C 2 H 5   A + B
Q.7 Identify X, Y and Z in the following synthetic scheme and write their structure. Explain the formation of
labelled formaldehyde (H2C*O) as one of the products when compound Z is treated with HBr and
followed by ozonolysis.
BaC*O3 + H2SO4  X (gas) [C* denotes C14] [IIT 2001]
(i ) Mg / ether LiAlH
CH 2  CH  Br    Y   4  Z
( ii ) X
( iii ) H3O 
Q.8 Mention two esters produced when a racemic mixture of 2-phenyl propanoic acid is treated with (+)
2-butanol. What is the stereochemical relationship between these esters? [IIT 2003]
38
CHEMISTRY
ANSWER KEY
EXERCISE # I
1. C 2. C 3. B 4. A 5. C
6. B 7. C 8. B 9. B 10. B
11. B 12. A 13. A 14. A 15. B
16. B 17. D 18. C 19. A 20. A
21. B 22. D 23. B 24. B 25. C
26. A 27. A 28. B 29. C 30. B
31. C 32. C 33. C 34. A 35. B
36. B 37. A 38. C 39. C 40. C
41. BC 42. ABC 43. BC 44. B 45. B
46. AB 47. A 48. C 49. A 50. B
EXERCISE # II
1. ACD 2. ABCD 3. A 4. A 5. ACD

6. ABCD 7. ABD 8. ABD 9. AB 10. ABD
11. ABC 12. AB 13. D 14. AC 15. BCD
16. ABCD 17. D 18. C 19. C 20. B
21. C 22. A 23. A 24. B 25. ABC
26. AD 27. D 28. B 29. C 30. AC
31. AC 32. ACD 33. ABCD 34. ABCD 35. ABC
36. ABCD 37. ABC 38. ABCD 39. ABCD 40. ABCD
41. C 42. C 43. B 44. A 45. B
46. ABC 47. ABCD 48. ABCD 49. D 50. BC

51. AC 52. BCD 53. ABCD 54. C 55. ABC
56. ACD 57. C 58. BD 59. AB
60. (A)S; (B)R; (C)P; (D)Q; 61. (A) R; (B)P; (C)S; (D)Q;
62. (A)S; (B)R; (C) P; (D)Q; 63. (A) S; (B)Q; (C)R; (D)P;
64. (A)PQR; (B)PQR; (C)P; (D)ST; 65. (A) T; (B)R; (C)P,S; (D)Q;
66. (A)PS; (B)QS; (C)PST; (D)R 67. (A) R; (B)S; (C)Q; (D)P;
68. 4 69. 7 70. 3 71. 5 72. 3
73. 9 74. 7 75. 1
EXERCISE # III
Q.1 (A) (CH3)2CHCOOCH2CH(CH3)2 ; (B) (CH3)2CHCOCl; (C) (CH3)2CHCH2Cl
Q.2 (A) RCOND2; (B) RNH2; (C) ROH
Q.3 (A) R–COOH; (B) R–COONa; (C) R–COCl; (E) (R–CO)2O
Q.4 (A) HOOCCH2CH2COOMe; (B) ClOCCH2CH2COOMe; (C) MeNHOCCH2CH2COOMe
39
CHEMISTRY
Q.5 (A) (B)
Q.6 (A) CH3(CH2)14CH2CHBrCOOH; (B) CH3(CH2)14CH=CHCOOH; (C) KMnO4;

(D) CH3(CH2)14Br
Q.7 (A) ; (B) ; (C) CN–/H3O+ ; (D)
Q.8 (A) C COOH ; (B) H  C  COOH ;

| || ||
C COOH H  C  COOH
Q.9 (D) ; (E) 10. (F)
EXERCISE # IV (A) (JEE-MAIN)

Q.1 2 Q.2 1 Q.3 4 Q.4 4 Q.5 4
Q.6 2 Q.7 4 Q.8 4 Q.9 2 Q.10 1
Q.11 2 Q.12 1 Q.13 1 Q.14 4 Q.15 Bonus
Q.16. 2 Q.17 3 Q.18 4 Q.19 1 Q.20 3
Q.21 3 Q.22 1 Q.23 2 Q.24 2 Q.25 4
EXERCISE # IV (B) (JEE ADVANCED)

Q.1 (B) Q.2 (A) Q.3 (B) Q.4 (D) Q.5 (C)
Q.6 (C) Q.7 (A) Q.8 (A) Q.9 (C)
Q.10 (A)R, S ; (B)P, Q ; (C)P, Q, R ; (D)P,S
Q.11 (A)P, Q, S, T ; (B)P, S, T ; (C)P ; (D)R
Q.12 (A) Q.13 (ACD) Q.14 (BD) Q.15 (2) Q.16 (A)
Q.17 (A) Q.18 (C) Q.19 (B) Q.20 (A) Q.21 (B)
Q.22. (6.00) Q.23. (C) Q.24. (C)
EXERCISE # V
Q.1 (A) CH3CH2CH2COOCH2CH3; (B) CH3CH2OH ; (C) CH3CH2CH2CH2OH; (D) CH3CHO;

(E) CH3CH= CHCHO
Q.2 (A) SOCl2; (B) POCl3; (C) CH3COCl; (D) CH3COCH3

Q.3 (i) (A) CH3CHBrCOOH; (B) CH2 = CHCOOH;
(ii) (A) CH3CH(OH)CH2COOH; (B) CH3COCH2COOH
40
CHEMISTRY
Q.4 (A) CH3CH2COOCOCH2CF3 ; (B) CF3CH2COOH; (C) CH3CH2COOH; (D) (CF3CH2CO)2O
HC  (COOC2 H 5 ) 2
|
Q.5 (A) NaCH(COC2H5)2; (B) CH 3  HC  COOC2 H 5
Q.6 (A) CH3COOH; (B) C2H5O18H
Q.7 BaC*O3 + H2SO4  C*O2(X) + BaSO4

(i ) Mg ,( ii ) C*O
CH2=CH–Br    2 
(iii ) H 3O 
CH2=CH–C*OOH(Y) LiAlH
 4 

CH2=CHC*H2OH(Z) H
CH2=H–C* H 2 C* H 2 CH=C*H2
 Br–  Br–
CH2=CH–C*H2 Br BrCH2 – CH=C*H2
O3ZnH2O  O3ZnH2O Br–C*H2CHO + HCHO Br–CH2CHO + HC*HO
H
|
Ph H (  ) CH 3CH 2 COH
| | |
CH 3
Q.8 CH 3  C  COOH + CH 3  C  COOH     
| | conc.H 2SO 4 , 
H Ph
(racemic mixture)
Ph H H H
| | | |
CH 3  C  C  O  C  CH 2 CH 3 + CH 3  C  C  O  C  CH 2 CH 3
| || | | || |
H O CH 3 Ph O CH 3
during esterification reaction only –COOH and –OH partcipates. There is no effect on structure or
configuration of carbon adjacent to these groups. So when(±) acid reacts with pure (+) alcohol two
esters are produced which are diastereoisomers of each other.
41

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CHEMISTRY

Daily Practice Problems

2. In the reaction sequence, (B) will be :

(A) CH3–CC–CH3 (B) CH3–CC–MgBr (C) CH3–CC–COOH (D) CH3–CH=CH–COOH

(A) CH 3  CH  COOH (B) CH3–CH2–CH2–COOH

4. In the given reaction, [X] will be:

CH3–CH2–COOH   [X]

6. In the given reaction, [X] will be :

(A) C6H5–CHO (B) C6H5COOH (C) C6H5–CH2OH (D) CH3COOH

8. Number of cross products in the given reaction:

(A) One (B) Three (C) Two (D) four

(A) 4 (B) 3 (C) 2 (D) 1

(I) C6H5COCl (II) NO2 COCl

(A) Methylamine (B) Eltylamine (C) Propylamine (D) Acetamide

(A) C6H5ONa (B) (C) (D)

16. Which one of the following on heating gives unsaturated acid:

(A) CH3COOH (B) COOH–CH2–CH2–COOH

32. Which of the following diazonium salt is relatively stable at 0-5°C:

33. Which of the following can be detected by carbylamine reaction:

34. Hydrolysis of alkyl isocyanide yields:

(A) X is NH2;Y is ND2(B) X is ND2; Y is NH2

(C) both ND2 (D) both NH2

38. Major end product of the following sequence of reaction is:

(A) CH3CH2CH2NH2 (B) CH3CH2CH2OH

(C) CH 3CHCH 3 (D) CH3CH2COOH

39. Name the products in the acid-base reaction:

40. Reductive amination of A forms:

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

45. Following reaction is known as :

(A) Hoffman rearrangement (B) Curtius rearrangement

49. Which of the following can released CO2 with NaHCO3.

2. Which of the following order(s) is/are correct for acidic strength :

4. Find out major product of following reaction :

6. RCOOR' can be prepared by:

7. Among the following, which statement is/are correct ?

NaOH CH3–CH2 –I H3O+

(A) S & Q can be distinguished by dye azo test

9. Correct options for given sequence is/are :

(P) C8H6O2 

(C) (D) 2-oxocyclohexane carboxylic acid

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

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

(A) and (B) and

(C) and (D) and

(A) CH–C6H5 (B)

(C) CH2–C6H5 (D)

C6H5–C–C2H5 C6H5–C–C2H5 C2H5–C–NH–C6H5

(C) C6H5–CH2–C–CH3 ; C6H5–CH2–C–CH3 ; CH3–C–CH2–NH–C6H5

(D) C6H5–C–C2H5 ; C6H5–C–C2H5 ; C6H5–C–NH–C2H5

27. In the given reaction major product and mechanism used is :

(C) CH 3CHCOOH (D) CH 3CHCH 2COOH

(B) Cl + 2NH3 ,   NH2+ NH4Cl

(C) Cl + NH3 ,   + NH4Cl

(A) Product is having smell like fruits

37. Acetic anhydride is used as:

(A) CH2N2 (B) CH3OH/H (C) MeOTs/Benzene (D) Me2SO4/NaOH

39. Which of the following gives silver mirror test?

42. On hydrolysis, if given ester racemises slowly then mechanism can be

(A) AAC1 (B) BAl1 (C) AAl1 (D) BAC2

Q.7 BaCO3 + H2SO4  CO2(X) + BaSO4