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1 Carboxylic Acid MCQs With Solutions By Arvind Arora
Q.1.
O
O ⎯⎯⎯⎯ →⎯
OHCH3 A A is :-
(A) CH2—CH2
OH COOCH3
(B) CH2—CH2
OCH3COOH
(C)
both are correct
(D)
None is correct
Q.2. End product of the following sequence of reaction is
O
C—CH3
O
++⎯⎯⎯⎯⎯⎯ →⎯
,H .2
,NaOHI .1 2
(A) Yellow ppt. of CHI3,
O
COOH
(B) Yellow ppt. of CHI3,
O
CHO
(C) Yellow ppt. of CHI3,
O
(D) Yellow ppt. of CHI3, COOHCOOH
Q.3. End product of this conversion HCOCHCHCHCCH 22223
||O
−−−−−+
⎯⎯⎯⎯ →⎯H,OH.2
NaBH.1
2
4 is
(A)
(a) =O
CH3
O
(B)
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(b) =O
CH3
O (C)
(c) =OO
(D)
CH3—CH—CH2CH2CH2CO2H
OH
Q.4. When acetic acid reacts with ketene, product formed
(A) ethyl acetate
(B) aceto - acetic ester
(C) acetic anhydride
(D) no reaction
Q.5. R—CH2—CH2OH can be converted in R—CH2CH2COOH. The correct sequence of reagents is
(A) PBr3, KCN, H+
(B) PBr3, KCN, H2
(C) KCN, H+
(D) HCN, PBr3, H+
Q.6. The pKa of acetylsalicylic acid (aspirin) is 3.5 . The pH of gastric juice in human stomach is about 2-3 and
pH in the small intestine is about 8. Aspirin will be.
(A) Unionized in the small intestine and in the stomach
(B) Completely ionized in the stomach and almost unionized in the small intestine.
(C) Ionized in the stomach and almost unionized in the small intestine
(D) Ionised in the small intestine and almost unionised in the stomach
Q.7. On subjecting mesityl oxide to the iodoform reaction, one of the products is the sodium salt of an organic acid. Which
acid is obtained?
(A) (CH3)2C=CH—CH2COOH
(B) (CH3)2CH—COOH
(C) (CH3)2C=CH—COOH
(D) (CH3)2C=CH—CO—COOH
Q.8. The ease of alkaline hydrolysis is more for
(A)
COOCH3
NO2
(B)
COOCH3
Cl
(C)
COOCH3
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(D)
COOCH3
OCH3
Q.9. Which of the following does not undergo Hell - Volhard Zelinsky reaction?
(A) HCOOH
(B) CCl3COOH
(C) C6H5COOH
(D) All
Q.10. Consider the following sequence of reactions :
X
(C11H14O2)
OH–
Y + CH3CH2COO–
1. KMnO4/OH–
2. H3O+
COOH
COOH The compound ‘X’ is -
(A)
O
O
(B)
O
O
(C)
O
O
(D)
O
O
Q.11.
SO3H
OH
⎯⎯⎯⎯ →⎯COONaCH3 products, the
products are -
(A)
SO3H
ONa
+ CH3COOH
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(B)
SO3Na
ONa
+ CH3COOH
(C)
SO3Na
OH
+ CH3COOH
(D) No reaction
Q.12. CH2 – COOK |
CH2 – COOK | CH2
Electrolysis P (Predominant)
P can be ?
(A) CH3 – CH2 – CH3
(B)
(C)
(D) none of these
Q.13. An ester (A) with mol. formula C9H10O2 was treated with excess of CH3–Mg Br and
the complex. So formed was treated with H2SO4 to give on olefin (B). Ozonolysis of (B) gave
a ketone with molecular formula C8H8O which shows the iodoform test the structure of (a) is
-
(A) C6H5 COOC2H5
(B) CH3COCH2COC6H5
(C) P CH3O–C6H4–COCH3
(D) C6H5COOC6H5
Q.14. In the following sequence of reaction, what is D ?
CH3
[O] A
SOCl2 B
NaN3 C
Heat D
(A) Primary amine
(B) An amide
(C) phenyl isocynate
(D) A chain lengthened hydrocarbon
Q.15. Arrange the following in order of increasing reactivity towards nucleophilic substitution
reaction -
CH3–C–OCH2CH3
O
(1)
CH3–C–Cl
O
(2)
CH3–C–NH–CH3
O
(3) (A) 1 < 2 < 3
(B) 3 < 1 < 2
(C) 1 < 3 < 2
(D) 2 < 1 < 3
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Q.16.
O
OMe +
OH Con.HCl
O
O
+
MeOH
Above reaction is an example of -
(A) Esterification
(B) Saponification
(C) Hydrolysis
(D) Trans Esterification
Q.17. Acrylic acid react with HBr to give -
(A) Br–CH2–CH–COOH
Br (B) Br–CH2–CH2–COOH
(C) CH2=CH–COBr
(D) CH3–CH–COOH
Br Q.18. An optically active compound 'X' has molecular formula C4H8O3. It evolves CO2 with
NaHCO3. 'X' reacts with LiAlH4 to give an Achiral compound 'X' is -
(A) CH3–CH2–CH–COOH
OH (B) CH3–CH–COOH
Me (C) CH3–CH–COOH
CH2OH
(D) CH3–CH–CH2–COOH
OH Q.19. What is compound Z ?
CH3–CH2–CH2–Br NaCN
X H3O
Y
CH3–CH2–OH H
Z
(A)
CH3–CH=CHCOH
O
(B) CH3–CH2–CH2CH=NOCH2CH3
(C) CH3–CH2–CH2CH(OCH2CH3)2
(D) CH3–CH2–CH2–
C–OCH2CH3
O
Q.20. End product of the following sequence of reaction is -
CHCH
CH3–Mg–Br CHC–Mg–Br (i) CO2(ii) H3O
HgSO4–H2SO4
Ag2O
(A)
CH3–C–COOH
O
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(B)
CH2
COOH
COOH
(C)
CH3–C–CHO
O
(D)
H–C–CH2–COOH
O
Q.21. On vigorous oxidation by permanganate solution (CH3)2C = CH–CH2–CH3 gives
(A)
CH3–C––CH–CH2–Cl3
OH
CH3
OH
(B)
CH–CO2H+CH3–CH2–COOH CH3
CH3
(C)
CHOH+CH3–CH2–CH2–OH CH3
CH3
(D)
C=O+CH3–CH2–COOH CH3
CH3 Q.22. Formic acid is obtained when -
(A) Calcium acetate is heated with conc. H2SO4
(B) Calcium formate is heated with calcium
acetate
(C) Glycerol is heated with oxalic acid at 373 K
(D) Acetaldehyde is oxidised with K2Cr2O7 and
H2SO4
Q.23. Which of the following carboxylic acid undergoes decarboxylation easily ?
(A) C6H5–CO–CH2–COOH
(B) C6H5–CO–COOH
(C) C6H5– CH
OH
–COOH
(D) C6H5– CH–COOH
NH2 Q.24. The strongest acid among the following is -
(A) CF3COOH
(B) CCl3COOH
(C) CBr3COOH
(D) CH3COOH
Q.25. Which of the following does not give benzoic acid salt on oxidation with hot alkaline
KMnO4.
(A) Ph–CH3
(B) Ph–CH=CH–CH3
(C) Ph–CC–CH3
(D) Ph–C(CH3)3
Q.26. The acid D obtained through the following sequence of reactions is
C2H5Br ⎯⎯⎯ →⎯ KOH.AlcA
4
2
CCI
Br⎯→⎯ B)excess(
KCN⎯⎯ →⎯ C ⎯⎯ →⎯+OH2 D
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(A) Succinic acid
(B) Malonic acid
(C) Maleic acid
(D) Oxalic acid
Q.27. Formic acid can be distinguish from acetic acid because formic acid :
(A) Release H2 with sodium
(B) Gives ester with alcohol
(C) Reduces AgNO3
(D) Turns red litmus to blue
Q.28. Which of the following methods is not used for the conversion of carboxylic acids into
acid halides ?
(A) RCOOH + SOCl2 ⎯→⎯
(B) RCOOH + PCl5 ⎯→⎯
(C) RCOOH + Cl2 ⎯→⎯
(D) RCOOH + PCl3 ⎯→⎯
Q.29. Which of the following will not undergo Hell-Volhard Zelinsky (HVZ) reaction ?
(A) HCOOH
(B) CH3 COOH
(C) CH3 CH2 COOH
(D) CH3 CHBrCOOH.
Q.30. CH3–CH2–CH2–COOH ⎯⎯⎯ →⎯ + 2BrPdRe
Br
COOHHCCHCH|
23 −−− This reaction is
called
(A) Cannizzaro reaction
(B) Schmit reaction
(C) Hell Volhard Zelinsky reaction
(D) Reimer tiemann reaction
Q.31. The decreasing order of reactivity towards nucleophilic acyl substitution is
(A) CH3COCl (B) CH3COOC2H5,
(C) CH3CONH2 (D) (CH3CO)2O
(A) (i) > (iv) > (iii) > (ii)
(B) (i) > (iv) > (ii) > (iii)
(C) (iv) > (iii) > (i) > (ii)
(D) (iii) > (i) > (iv) > (ii)
Q.32. Acetic anhydride is prepared in the laboratory by heating sodium acetate with
(A) Ethyl chloride
(B) Acetyl chloride
(C) Conc. H2SO4
(D) Zinc dust
Q.33. Synthesis of an ester involves the reaction of alcohols with
(A) A ketone
(B) An amide
(C) CH3MgBr
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(D) RCOCl
Q.34. Benzoyl chloride on treatment with ammonia gives
(A) Benzamide
(B) Acetamide
(C) Benzylamine
(D) Benzoic acid
Q.35. The reaction, RCOOR + ROH (excess) ⎯⎯⎯ →⎯−+ OHorH
RCOOR + R OH is called.
(A) Esterification
(B) Trans-esterification
(C) Saponification
(D) Hydrolysis
Q.36. 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
Q.37. ⎯⎯ →⎯ 3NaN
X−
⎯⎯ →⎯
OH)2(
)1(Product.
Product is/are
(A) only
(B) , HCOO–
(C)
(D)
Q.38. Consider the following statements for hydrolysis reaction :
(I) is more reactive than C6H5COOC2H5
(II) , is more reactive than
(III) is more reactive than
Of these the correct statements are
(A) I and II
(B) I, II and III
(C) II and III
O
Cl
CONH2
– C – OH + NH4
O+
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(D) I and III
Q.39. An organic compound X (C4H8O2) gives positive test with NaOH and phenopthalein.
Structure of X will be :
(A)
O
OHCCHCHCH| |
223 −−−−
(B)
O
CHC
O
CCH 3| || |
3 −−−
(C)
O
HCOCCH 52| |
3 −−−
(D)
O
OCHCCH 3| |
3 −−
Q.40. Which one of the following esters is the most reactive for saponification ?
(A)
(B) 3
3
|
| |
3 CHH
CH
CO
O
CCH −−−−
(C) 3
3
3|
|
| |
3 CH
CH
CH
CO
O
CCH −−−−
(D)
Q.41. A compound with molecular formula C4H10O4 on acylation with acetic anhydride
gives a compound with molecular formula C12H18O8. How many hydroxyl groups are
present in the compound ?
(A) One
(B) Two
(C) Three
(D) Four
Q.42. CH3CH2CH2CONH2 is boiled with aqueous NaOH, then the reaction mixture is
acidified with HCl. The products obtained are
(A) CH3CH2CH2COO– + NH3
(B) CH3CH2CH2COONa + NH3
(C) CH3CH2CH2COOH + NH4Cl
(D) CH3CH2CH2COO– + NH4Cl.
Q.43. When excess of chlorine is passed through acetic acid in presence of red phosphorus, it
forms
(A) Acetic anhydride
(B) Chloral
(C) Trichloroacetic acid
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(D) Methyl chloride.
Q.44. SAcetamide and ethyl acetate can be distinguished by reacting with
(A) Aqueous HCl and heat
(B) Aqueous NaOH and heat
(C) Acidified KMnO4
(D) Bromine water.
Q.45. + 3 NaOH ⎯→⎯ (Q) + salt of fatty acid.
Product (Q) of the reaction is
(A) Ethylene glycol
(B) Glycerol
(C) Glyceryl tri nitrate (explosive)
(D) Cumene hydrogen peroxides
Q.46. Starting from propanoic acid, the following reactions were carried out
Propanoic acid ⎯⎯ →⎯ 2SOCI
X ⎯⎯ →⎯ 3NH
Y ⎯⎯⎯ →⎯ +KOHBr2 Z
What is the compound Z
(A) CH3–CH2–Br
(B) CH3–CH2–NH2
(C)
(D) CH3–CH2–CH2–NH2
Q.47. Identify the final product in the following sequence of reaction.
⎯⎯ →⎯ 2SICI ⎯⎯ →⎯ 3NH⎯⎯ →⎯ 52OP
(A)
(B)
(C)
(D)
Q.48. Which of the following acids remains unaffected on heating
(A) Malonic acid
(B) Malic acid
(C) Fumaric acid
(D) Succinic acid
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Q.49. Identify the final product in the following sequence of reaction.
⎯⎯ →⎯ hv/Br2A
⎯⎯⎯ →⎯OH)2(
KCN)1(
3
(A)
(B)
(C)
(D)
Q.50. Esterification of the acid (P) with the alcohol (Q) will gives
+
(R– configuration) (±)
(A) Only one enantiomer
(B) A mixture of diastereomer
(C) A mixture of enantiomer
(D) Only one fraction on fractional distillation
Answers with Solution for these mcqs
Ans. 1. [A]
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O
OThis bond breaks hence intermediate is
O–
O
CH3OH+
O
OCH3
OH Ans. 2. [C]
Intermediate is
O
COOH
Which loses CO2 on heating (-keto acid)
Ans. 3. [A]
NaBH4 reduces reactant to
CH3—CH—CH2—CH2—CH2—CO2H which forms ester
OH Ans. 4. [C]
)Ketene(23 OCCHCOOHCH ==+ ⎯⎯→ acetc anhydride
Ans. 5. [A]
RCH2CH2OH ⎯⎯⎯ →⎯ 3PBr RCH2CH2Br ⎯⎯⎯ →⎯
KCN RCH2CH2CN ⎯⎯⎯⎯ →⎯
+H/OH2 RCH2CH2COOH
Ans. 6. [D]
More ionized in basic medium and less ionized in acidic medium, common ion effect
Ans. 7. [C]
CH3
C=CH—C—CH3 ⎯⎯⎯⎯ →⎯ 2I/NaOHCH3
O
C=CH—C—OH + CHI3CH3
CH3
O
mesityl oxide
Ans. 8. [A]
COOCH3
NO2
Then is more electron deficiency oncarbonyl carbon.
Ans. 9. [D]
None of these contain alpha H atom
Ans. 10. [B]
O
O
OH–
(C11H14O2)
CH3
OH
CH3
KMnO4/OH–
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COOH
COOH
Ans. 11. [C]
SO3H is most acidic
Ans. 12. [C] CH2
CH2
CH2
Ans. 13. [A]
C6H5 COOC2H5 (i) 2CH3–Mg–Br
(ii) H/H2O
C6H5 C OH
CH3
CH3
–H2O H2SO4
A MF. C9H10
HCHO + C6H5COCH3 O3/Zn
C6H5–C=CH2
CH3
MFC8H8O Ans. 14. [C] CH3
[O] SOCl2
–SO2–HCl
COOH
(A)
COCl
(B)
NaN3 –NaCl
CO–N–NN
. .
. .
Benzoylazide (C)
CO–N
. .
. . N=C=O
(Benzoyl nitrene) (Phenyl isocynate)
(D) Ans. 15. [B]
Leaving group tendency
(–Cl > – OEt > – NH–CH3)
Ans. 16. [D]
Trans esterification – reaction in which ester convert into another ester.
Ans. 17. [B]
1, 4 Addition occurs to , unsaturated carbonyl compound.
CH = CH–C=O + HBr
OH
+ – 1,4–Addition
Br–CH2–CH = C–OH
OH Tautomerises
Br–CH2–CH2–COOH Ans. 18. [A]
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CH3–CH–COOH
CH2–OH
LiAlH4 CH3–CH–CH2–OH
CH2–OH
(X)
NaHCO3
*
CH3–CH–COO
CH2–OH + CO2
*
Ans. 19. [D]
X = CH3–CH2–CH2–CN
Y = CH3–CH2–CH2–CO2H
Z = CH3–CH2–Cl2–
C–OEt
O
Y ⎯→ Z is esterificatin reaction
Ans. 20. [B] CHCH
CH3–Mg–Br CHC–Mg–Br
CO2
HCC–COOMgBr
H3O
CHC–COOH HgSO4+H2SO4
Addition of H2O H–C=CH–COOH
OH
Tauetomerise H–O–CH2–COOH
O Ag2O
HO–C–CH2–C–OH
O O
Ans. 21. [D]
C=CH–CH2–CH3
CH3
CH3 KMnO4/H
+
C=O+OCH–CH2–CH3
CH3
CH3 Ans. 22. [C]
(COOH)2 373K/Glycerol
H– COOH
Ans. 23. [A]
–keto Acid on heating easily undergo decarboxylation via a six-membered. Cyclic transition
state.
C
CH2
C
C6H5
O
H
O
O
–CO2
C6H5 C
OH
CH2
Tauto
merises
C6H5–C–CH3
O
Ans. 24. [A]
+ CF3 COOH –I +
CCl3 COOH –I +
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CBr3 COOH – CH3 COOH +I
Ans. 25. [D]
Ph–CH3 ⎯⎯⎯⎯⎯⎯ →⎯ 4KMnOAlkalineHot
Ph–COO– Ph–CH=CH–CH3⎯⎯⎯⎯⎯⎯ →⎯ 4KMnOAlkalineHot
Ph–COO– Ph–
CC–CH3 ⎯⎯⎯⎯⎯⎯ →⎯ 4KMnOAlkalineHotPh–COO–
Ans. 26. [A]
C2H5Br ⎯⎯⎯ →⎯ KOH,AlcCH2=CH2
4
2
CCI
Br⎯→⎯
Br
Br
HCHC 2
|
2|
−)excess(
KCN⎯⎯ →⎯
CN
CN
HCHC 2
|
2|
− ⎯⎯ →⎯+OH3
COOH
COOHCHHC 22|
−−
Ans. 27. [C]
HCOOH ⎯⎯⎯⎯⎯ →⎯+ OHNHAgNO 43 CO2 + H2O + Ag
Ans. 28. [C]
RCOOH + SOCl2 ⎯→⎯ RCOCl + SO2+ HCl
RCOOH + PCl5⎯→⎯
RCOCl + POCl3
RCOOH + PCl3 ⎯→⎯ RCOCl + H3PO3
Ans. 29. [A]
-halogenation reaction [-H must present].
Ans. 30. [C]
It is Hell Volhard Zelinsky reaction.
Ans. 31. [B]
Reactivity Partial positive charge on C=O carbon.
Ans. 32. [B]
CH3COONa + CH3COCl ⎯→⎯ CH3–COO–COCH3
Ans. 33. [D]
R–CH2OH + RCOCl ⎯→⎯ R–CH2–O–CO–R
Ans. 34. [A]
Ph–COCl ⎯⎯ →⎯ 3NHPh–CONH2 + HCl
Ans. 35. [B]
When an ester converts into another ester, it is called trans esterification.
Ans. 36. [C]
CH3–COOH + C2H5OH ⎯→⎯H
CH3COOC2H5 (ester)
Ans. 37. [B]
⎯⎯ →⎯ 3NaN⎯⎯ →⎯ − 2N
Ph – N = C = O ⎯⎯ →⎯−OH
+
HCOO–
O
Cl
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Ans. 38. [A]
Electron withdrawing groups increase the rate of SN2Th reaction.
Ans. 39. [C]
Ester gives positive test with NaOH and phenopthalein.
Ans. 40. [A]
Saponification is a base catalysed hydrolysis (SN2Th) reaction which is a sterically
controlled reaction too. The least crowded ester around acyl carbon will be most reactive
towards this reaction.
Ans. 41. [D]
C4H10O4 ⎯⎯ →⎯ OAc2 C12H18O8
Ans. 42. [C]
CH3CH2CH2CONH2⎯⎯ →⎯NaOH
CH3CH2CH2COO– ⎯⎯→⎯HCICH3CH2CH2COOH + NH4Cl
Ans. 43. [C]
HVZ reaction.
Ans. 44. [B]
CH3CONH2 ⎯⎯ →⎯NaOH
NH3 + CH3COO–
52
| |
3 HOC
O
CCH −−⎯⎯ →⎯NaOH
HO
O
CCH| |
3 −− + C2H5OH
Ans. 45. [B]
+ 3 NaOH ⎯→⎯ + RCOOH\
Ans. 46. [B]
CH3CH2COOH ⎯⎯ →⎯ 2SOCICH3CH2COCl ⎯⎯ →⎯ 3NH
CH3CH2CONH2 ⎯⎯⎯ →⎯ +KOHBr2
CH3CH2NH2
Ans. 47. [C]
⎯⎯ →⎯ 2SOCI⎯⎯ →⎯
••
3HN ⎯⎯ →⎯ 52OP
Ans. 48. [C]
In fumaric acid both COOH groups are present on opposite side so it is unaffected on heating.
Ans. 49. [D]
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⎯⎯ →⎯ hv/Br2
⎯⎯⎯ →⎯OH)2(
KCN)1(
3 Ans. 50. [B]
+ ⎯→⎯ (Diastereomers)
+ ⎯→⎯