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4 - Carboxylic Acids and Its Derivatives (Booklet-1)
4 - Carboxylic Acids and Its Derivatives (Booklet-1)
H2O / H
7. H3C O CH3 A (an acid) B ; Where A and B are, respectively,
18
CH3
O O
18
(A) H3C and Me3C OH (B) H3C and Me3C OH
OH OH
18
O O
18
(C) H3C and Me3C OH (D) H3C and Me3C OH
18 18
OH OH
8. The acid D obtained through the following sequence of reactions is
+
Alc.KOH Br2 H3 O
C2 H5Br A B
KCN
C D
CCl 4 (excess)
(A) Succinic acid (B) Malonic acid (C) Maleic acid (D) Oxalic acid
9. In which of the following reaction the final product is neither an acid nor an acid salt.
-
Tollen's reagent KMnO4 /OH
(A) Ph–CHO (B) CH 3 –CH 2 – OH
Fehling solution K Cr O /H+
(C) Ph–CHO (D) Ph–CH2– OH
2 2 7
10. Formic acid can be distinguish from acetic acid because formic acid :
(A) release H2 with sodium (B) gives ester with alcohol
(C) reduces AgNO 3 /NH3 (D) turns red litmus to blue
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11. Which of the following best describes the nucleophilic addition step in the acid-catalyzed hydrolysis of
acetonitrile (CH3CN)?
12.
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20. Which of the following reagent/solution can be used to distinguish between methanoic acid and
ethanoic acid?
(A) Tollens reagent (B) FeCl3 solution
(C) NaOH solution (D) Na2CO3 solution
21. Which of the following reducing agents can be used to reduce RCOOH to RCH2OH?
(A) NaBH4 (B) Na/EtOH (C) LiAlH4 (D)H2/Catalyst
22. Sodium bicarbonate reacts with salicylic acid to form:
23. Which optically active compound on reduction with LiAlH4 will give optically inactive compound?
(A) CH3 CH COOH (B) CH 3 CH 2 CH COOH
| |
OCH3 OH
H+or OH–
24. The reaction, RCOOR + ROH (excess) RCOOR + R OH is called.
(A) Esterification (B) Trans-esterification (C) Saponification (D) Hydrolysis
25. Ethanol on heating with acetic acid in the presence of a few drops of sulphuric acid gives the smell of
(A) Oil of wintergreen (B) Oil of mustard
(C) Fruity smell (D) Oil of bitter almonds
26. Given three acids
; ;
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29. Which of the following is the correct order of decarboxylation of keto carboxylate anion?
(A) a > b > c > d (B) c > d > a > b (C) c > d > b > a (D) d > c > a > b
30. Which of the following acid on heating gives geometrical isomers as a product?
(A) (B)
(C) (D)
H3 O
33. X and Y in the reaction sequence R C N X
Diazomethane
Y are given by the set:
(A) Carboxamide, Carbonitrile (B) Carboxylic acid, Carbonitrile
(C) RCOOH, RCOOCH3 (D) RCONH2 , RCOCH3
34. Which of the following organic acid decolourises bromine water as well as forms anhydride?
(A) HOOC COOH (B) HOOC CH2 COOH
H C COOH H C COOH
|| ||
(C) (D)
H C COOH HOOC C H
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36. The correct sequence of reagents for the following conversion is:
2 61.B H
37. Pr oduct :
2.H2O2,OH
3.H3O
(A) (B)
(C) (D)
Br
39. The product formed in the reaction is
CH 3 C CH 2 C OC 2H5 D+
Product
O O
(A) CH 3 C CD 2 C OC 2H 5 (B) CH 3 C CH C OC 2H5
O O OH O
(C) CD 3 C CH C OC 2H5
(D) CD3 C CH2 C OC2H5
O OH || ||
O O
CCl4 ,Reflux
40. The reaction : RCOOAg + Br2 R–Br +AgBr + CO2 is called
(A) Wurtz reaction (B) Hunsdiecker reaction
(C) Friedel-Crafts reaction (D) Kolbe's reaction
41. Identify the correct order of boiling point of the following compounds:
CH3CH2CH2CH2OH CH3CH2CH2CHO CH3CH2CH2COOH
1 2 3
(A) 1 > 2 > 3 (B) 3 > 1 > 2 (C) 1 > 3 > 2 (D) 3 > 2 >1
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45. Benzoyl chloride on heating with ammonia gives
(A) Benzamide (B) Acetamide (C) Benzylamine (D) Benzoic acid
46. Arrange following compounds in decreasing order of reactivity for hydrolysis reaction:
(A) II > IV > I > III (B) II > IV > III > I (C) I > II > III > IV (D) IV>III> II > I
47. In order to prepare acetone from CH3COCl in one step, which of the reagent is best?
(A) H2 /Pd – BaSO4 (B) HI (C) CH3 MgCl (D) (CH3 )2 Cd
48. Which of the following orders of reactivity of acid derivatives towards a nucleophile is correct?
(A) acid chloride anhydride ester (B) acid chloride anhydride ester
(C) acid chloride ester anhydride (D) anhydride acid chloride ester
49. Which of the following orders regarding the base strength of a leaving group in a reaction of an acid
derivative with a nucleophile is correct?
(A) Cl– RCOO– RO– (B) Cl– RO– RCOO–
(C) RO– RCOO– Cl– (D) RO– Cl– RCOO–
50. The correct sequence of decreasing order of reactivity of hydrolysis of acid chlorides is
(A) PhCOCl p-O2NC6H4COCl p-CH3OC6H4COCl
(B) PhCOCl p-CH3OC6H4COCl p-O2NC6H4CoCl
(C) p-O2NC6H4COCl PhCOCl p-CH3OC6H4COCl
(D) p-O2NC6H4COCl p-CH3OC6H4Cl PhCOCl
51. The treatment of an ester with LiAlH4 followed by acid hydrolysis produces
(A) two alcohols
(B) two acids
(C) two aldehydes
(D) one molecule of alcohol and another of carboxylic acid
52. The correct sequence regarding their reactivity of the given acid derivative is
(A) RCOCl RCON3 (RCO)2O (B) RCOCl (RCO)2O RCON3
(C) RCON3 RCOCl (RCO)2O (D) RCON3 (RCO)2O RCOCl
53. Choose the best sequence of reactions for transformation given. Semicolons indicate separate reaction
steps to be used in the order shown.
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56. The product of acid hydrolysis of P and Q can be distinguished by
OCOCH3 H3C
P = CH2 Q=
CH3 ,
OCOCH3
(A) Lucas Reagent (B) 2, 4-DNP (C)Fehling’s Solution (D) NaHSO3
CH3 MgBr
57. Ethyl ester
excess
P . The product P will be
H3C OH H5 C2 OH
H5 C2 C2 H 5 H5 C2 C2 H 5
(C) (D)
H5 C2 OH H7 C3 OH
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5. Which of the following will liberate CO2 on reaction with NaHCO3:
(B) O2N OH
(A) OH
NO 2
6. Which of the following are correct methods for the preparation of propanoic acid?
Mg CO2
(A) H3 C CH CH2 HBr
Ether
H O
3
O3
(D) H 3 C CH C CH 3
Ag 2 O
|
CH3
7. Choose the incorrect rate of decarboxylation in the mentioned conditions.
O O
|| ||
(A) H3C CH CH CH2 C OH H3C CH2 CH CH C OH (decarboxylation on heating)
O
||
(B) F3C COOH Cl3C C OH (decarboxylation on heating with sodalime)
(D)
9.
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1.Mg 2 3 2 SOCl CH NH
10.
X Y Z
2.CO2
O
3.H3
11. Which of the following reactions are used in the preparation of alcohols?
H2 O
(C) (D) CH3CH2 Cl
O O
|| ||
(1) H2 O/H
(C) CH3 C CH2 CH2 C OC 2 H5
(2) NaOH(cao)
O O
|| ||
(D) CH3 CH2 C CH C OH
|
CH3
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PARAGRAPH BASED QUESTIONS
PARAGRAPH FOR NEXT FOUR QUESTIONS
Amides undergo hydrolysis to yield carboxylic acid plus amine on heating in either aqueous acid or
aqueous base. The conditions required for amide hydrolysis are more severe than those required for the
hydrolysis of esters, anhydrides or acid chlorides, but the mechanism is similar (nucleophilic acyl
substitution). Nucleophilic acyl substitutions involve a tetrahedral intermediate, hence these are
quite different from alkyl substitution (RCH2 Br
NaCN
RCH2 CN) which involves a pentavalent
intermediate or transition state.
One of the important reactions of esters is their reaction with two equivalent of Grignard reagent to give
tertiary alcohols.
1. The mechanism involved during the hydrolysis of acid derivatives is:
(A) elimination-addition (B) addition-elimination
(C) nucleophilic addition elimination (D) electrophilic addition elimination
2. Which of the following constitutes the best substrate during the acidic hydrolysis of amides?
O O OH O
|| || || ||
(A) R C NH2 (B) R C NH3 (C) R C NH 2 (D) R C NH3
3. For which functional derivative of carboxylic acids, acidic hydrolysis is the fastest?
(A) Acid chlorides (B) Acid amides (C) Acid anhydrides (D) Esters
O
4. When O is treated with two equivalent of methyl magnesium iodide and the product acidified
(A) OH (B) OH
OH
OH
HO
(C) OH (D) OH
OH OH
Cl
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MATRIX MATCH QUESTIONS
1. Match the following column I & column II:
Column I Column II
Undergoes decarboxylation
3. Find the total number of different products obtained when
CH3
HOOC COOH
H D
CH3
is heated strongly.
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4. How many mole of NaOH would be required for complete neutralization of following compounds:
5. How many moles of CO2 will released when following compound treated with heat.
6. Examine the structural formulas of following compounds and find out how many compounds can
show Claisen condensation reaction.
JEE MAIN
1. In the Hofmann bromamide degradation reaction, the number of moles of NaOH and Br2 used per
mole of amine produced are: [2016]
(A) Four moles of NaOH and one mole of Br2 . (B) One mole of NaOH and one mole of Br2 .
(C) Four moles of NaOH and two moles of Br2 . (D) Two moles of NaOH and two moles of Br2 .
KMnO4 SOCl 2 H2 /Pd
2. In the following sequence of reactions Toluene A B
BaSO 4
C, the product C
is: [2015]
(A) C2 H5CHO (B) C6 H5COOH (C) C6 H5 CH3 (D) C6 H5CH2 OH
LiAlH4 PCl 5
3. In the reaction, CH3COOH A B
Alc.KOH
C , the product C is [2014]
(A) Ethylene (B) Acetyl chloride (C) Acetaldehyde (D) Acetylene
4. 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).
CH2Br [2013]
CH2Br C2H5 CH2Br
(A) (B) (C) (D)
Br CH3
CH3 CH3
5. Sodium ethoxide has reacted with ethanoyl chloride. The compound that is produced in the above
reaction is: [2011]
(A) Diethyl ether (B) 2-Butanone
(C) Ethyl chloride (D) Ethyl ethanoate
6. A liquid was mixed with ethanol and a drop of concentrated H2 SO4 was added. A compound with a
fruity smell was formed. The liquid was: [2009]
(A) HCHO (B) CH3COCH3 (C) CH3COOH (D) CH3OH
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JEE ADVANCED
1. The major product of the reaction is [2015]
3. The compound that undergoes decarboxylation most readily under mild condition is [2012]
4. With reference to the scheme given, which of the given statement(s) about T, U, V and W is (are)
correct? [2012]
excess
(A) T is soluble in hot aqueous NaOH
(B) U is optically active
(C) Molecular formula of W is C10H18O4
(D) V gives effervescence on treatment with aqueous NaHCO3
5. Identify the binary mixture(s) that can be separated into individual compounds, by differential
extraction, as shown in the given scheme. [2012]
NaOH(aq)
Compound 1 Compound 2
Binary mixture containing
Compound 1 and Compound 2
Compound 1 Compound 2
NaHCO3 (aq)
(A) C6 H5 OH and C6 H5COOH (B) C6 H5 COOH and C6 H5 CH2 OH
(C) C6 H5 CH2 OH and C 6 H5 OH (D) C6 H5 CH2 OH and C 6 H5CH2 COOH
6. This question contains Statement - 1 (Assertion) and Statement - 2 (Reason) and has 4 choices (A), (B),
(C) and (D) out of which ONLY ONE is correct. [2007]
Statement - 1 : p-Hydroxybenzoic acid has a lower boiling point than o-hydroxybenzoic acid.
because
Statement - 2: o-Hydroxybenzoic acid has intramolecular hydrogen bonding.
(A) Statement- 1 is True, Statement - 2 is True; Statement - 2 is a correct explanation for Statement - 1.
(B) Statement - 1 is True, Statement - 2 is True; Statement - 2 is NOT a correct explanation for Statement - 1
(C) Statement - 1 is True, Statement - 2 is False
(D) Statement - 1 is False, Statement - 2 is True.
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ANSWER KEY
MATRIX-MATCH ANSWERS
1. A PRS; B PQS; C PRS; D PRS 2. A PRS; B PRS; C QS; D QS
JEE MAIN
1. A 2. A 3. A 4. D 5. D 6. C
JEE ADVANCED
1. C 2. * 3. B 4. ACD 5. AD 6. D
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