Carboxylic Acid & Derivatives-03- Assignments

Chemistry : Carboxylic Acid & Derivatives
ASSIGNMENTS
SECTION - I
SUBJECTIVE QUESTIONS
LEVEL - I
1. Write the final product in the following reactions :
(i) CH3
COOH 4
LiAlH
Ether
 (ii) CH3
COOH 3
2 4
N H
H SO


(iii) CH3
COONa 3
CH COCl
Heat

 (iv) CH3
COONa
Sodalime
Heat


(v) CH3
COOK Electrolysis
 (vi) (CH3
COO)2
Ca Heat


(vii) (CH3
COO)2
Ca 2
(HCOO) Ca
Heat

 (viii) CH3
COONH4
Heat


(ix) NaOH + CO
o
210 C
8 to10 atm

 (x) 0
Glycerol
110 C
COOH
|
COOH


(xi)
3
NH
2
Heat
2
CH COOH
|
CH COOH


(xii) CH2
=CH—CH=CH2
+
HC-COOH
||
HC - COOH


(xiii)
2-
2 7
Cr O
14
3 2 3 Heat
3
O
||
CH CHCH — CCH
|
CH

 (xiv) 3 4
o
H PO
3 3 2 350 C
3
CH —C==CH—CH +CO + H O
|
CH


(xv) HOOC—COOH + HOCH2
—CH2
OH
Heat


(xvi) R C C R
C
O
+ HClO4  (xvii) 3 2
(CH CO) O
2 2
2 2
CH CH COOH
|
CH CH COOH


(xviii) H3CHC
CH2COOH
CH2COOH
3 2
(CH CO) O

 (xix) CH2 C COOH
CH3
3
–
2 2
(i) BH , THF
(ii) H O , OH

(xx) H3C C O
O
+
3
H O
18
2 5
C H (A) + (B)



2. Complete the following equations by writing the missing (A), (B), (C), (D), etc.
(i)
+
2
H O/H
HBr KCN
2 2
Ethylene
CH ==CH (A) (B) (C)

 
 

(ii)
+
5 3
2
PCl NH
H O/H
KCN Heat
2 5
Ethyl alcohol
C H OH (A) (B) (C) (D) (E)

 
 
 
 

(iii) 2 2 4
CO H O LiAlH
3 Ether
Methyl magnesium
bromide
CH MgBr (A) (B) (C)

 
 
(iv) 2 4 2
4
Dil.H SO SOCl
[O]
HgSO
Acetylene
CH CH (A) (B) (C)
   
   

(v) 2 2 7 2 2 7 3
2 4 2 4
Na Cr O Na Cr O NaHCO Sodalime
2 5 H SO H SO
Ethyl alcohol
C H OH (A) (B) (C) (D)

 
 
 

(vi) 2 2
+
Ca(OH) H O
Heat KCN
3 H
Acetic acid
CH COOH (A) (B) (C) (D)

 
 
 

(vii)
+
2 2
Cl H O/H
NaCN
3 (P)
Acetic acid
CH COOH (A) (B) (C)
 
 

(viii)
CH2
CH2
Ethylene
+
2 2
Br H O/H
NaCN
(A) (B) (C)
 
 

(ix) CH3
CHO
+
2 2 7
2
2 4
K Cr O
N O/H
HCN
H SO
(A) (B) (C)

 
 

(x) CH3
COCl 2 3
4 K CO
Pd/BaSO Heat
(A) (B) (C)

  

(xi) CH3
CH2
COOH 2
+
P/Br (i) Alc. KOH (excess)
(ii) H
(A) (B)

 

(xii) 5 4 2 4
PCl LiAlH HBr/H SO Na
3 2 2 3
Ether
(A) (B) (C) (D) CH CH CH CH

  
 

(xiii) 2 4 2
3 2 4
(i) 2NaNH HgSO I /NaOH
(ii) 2CH I H SO
HC CH (A) (B) (C)
   

(xiv) CH3
CH2
MgBr + (A)  CH3
CH2
CH2
OMgBr
+
3
H O

 (B) 4
KMnO
(C)


(xv) CH3
COOH
+
3 2 3
PBr /Br H O
KCN
(A) (B) (C)

 
 

(xvi) CH2
=CHCH=CH2
+
2 3
HBr (i) Mg/Ether
(ii) CO /H O
(A) (B)

 

(xvii) CH3
COOH 2
+ o
3
Red P, Br KOH Glycerol
Excess H O 260 C
(A) (B) (C)

 
 

(xviii) C8
H10
(A) 3
+
3
O
H O

 2C3
H5
COOH (B)

(xix) 2
2
CH COOH
|
CH COOH
3
2
+
3
O
P/Br Alc. KOH
H O
(A) (B) (C)

 
 

(xx) CH3
COOH 2 2 2
4
SOCl H /Pd Ag O
Dil. NaOH
BaSO Heat
(A) (B) (C) (D)

 
 
 

(xxi) C4
H8
O3
(A) 3
CrO Warm
(B)

 
 H3C C CH3
O
+ CO2
(xxii) HC  CH 3
CH MgBr

 CH4
+ (A) 2
CO

 (B)
+
H
 (C) 2 4
4
H SO
HgSO
 (D)
(xxiii) (B) 4
2
HCrO
H O

 (A) 3
CrO
Pyridine

 CH3
CHO
3. Arrange the following in decreasing order of acidic character :
(i) HCOOH, CH3
COOH, C2
H5
COOH, C6
H5
COOH, (CH3
)2
CHCOOH, CH2
ClCOOH
(ii) CH3
CH2
CH2
COOH, 3 2 3 2
CH CH CH COOH, CH CH CH COOH
| |
Cl Cl
, ClCH2
CH2
CH2
COOH
(iii) CH3
COOH, CH2
ClCOOH, CHCl2
COOH, CCl2
—COOH
(iv) CH2
BrCOOH, CH2
ClCOOH; CH2
FCOOH; CH2
ICOOH
(v) CH3
CH2
COOH, 3
CH —CH —COOH
|
Cl
, 3
CH —CH —COOH
|
CN
, 3
2
CH —CH —COOH
|
NO
(vi) OH, CH3
— COOH, COOH
(vii) CH3
—CH2
—COOH, 3 3
, CH
Br
|
CH —CH —COOH —C —COOH
| |
Br Br
4. Complete the following reactions :
(i)
C C 4
3 2
KMnO
or O /H O


(ii)
4
+
3
Conc.KMnO
Δ, H O



(iii)
CH2
2
+
3
CO
HBr Mg/Ether
H O
(A) (B) (C)

 
 

2
+
3
CO
HBr Mg/Ether
Peroxide H O
(D) (E) (F)

 
 

(iv) C
O
OH 3
2
2CH Li
H O
?



(v)
O
C
COOH
O
2 6
2
B H
H O
?


(vi) C
O
Cl + HO
?


5. Complete the following chain of reactions :
CH2
H2C
H2C CH2
O +
2 3
Conc. HI Mg/Ether
Excess CO , H O
(A) (B)

 
4
KMnO
(C) (D)


OH–
6. Identify (A) to (F) in following series of reactions :
3
4
CrO
Alkaline KCN HOH/HCl
KMnO AcOH
(A) (B) (C) (D)

 
 
 
 Red P Δ
HI
(E) (F)

 

7. What are (A) and (B) in following reactions :
(i)
CH2
CH2
HC
HC COOH
HC
HC COOH
+ (A)



(ii)
COOH
COOH
H2C 2 5
P O
2
Δ
(B) +2H O


8. Complete the following reactions :
CH3
OH
2 4
Conc.H SO NBS NaCN HOH/HCl
Δ (N-Bromo Succinimide)
(A) (B) (C) (D)

 

 
 

9. How can you achieve following intercon versions ?
(a) CH2
==CH—CH==CH2
 H2C CH2 COOH
CH
CN CH2 COOH
(b)
COOH
CN
(H2C)2
C
H2C
H2C C
NH
O
O
(c) 3 2
CH CH COOH 

O
O
C
H3
O CH3
O
10. Give the star mark to the hydrogen which is most acidic in following compounds :
(a) 3 2 2 3
O
||
CH —CH —C— CH —CH (b) 3 2
O
| |
CH == CH—CH —C— H
(c) 3 2 3
O
||
CH —C— O—CH —CH (d) 3
O
OH
| |
|
CH —C —C— OH
LEVEL - II
1. An acid (A) reacts with PCl5
to form a compound (B), (A) also reacts with NaOH to form a compound
(C). Both (B) and (C) react together and form acetic anhydride. What are (A), (B) and (C)?
2. An acid (A) reacts with NH3
and forms a compound (B). (B) on heating gives a compound (C). (C) on
treatment with Br2
and NaOH gives ethylamine. Write the names of (A), (B) and (C).

3. An organic compound (A) on treatment with acetic acid in presence of conc. sulphuric acid produces
an ester (B). (A) on mild oxidation gives (C). (C) with 50% KOH followed by acidification with dilute
HCl generates (A) and (D). (D) with PCl5
followed by reaction with ammonia gives (E). (E) on
dehydration produces HCN. Identify the compound (A), (B), (C), (D) and (E).
4. Compound (A), C3
H7
Cl reacts with alcoholic KOH to give (B), C3
H6
, as the major product. Compound
(B) decolourises Br2
.CCl4
solution. Reaction of (A) with Mg in dry ether and subsequent treatment
with CO2
and the dilute acid gives a compound (C), whose molecular formula is C4
H8
O2
. When we
add compound (C) to the aqueous NaHCO3
solution, bubbles are evolved. Give the structural formulae
of (A), (B) and (C) and write equations for all the reactions involved.
5. A liquid (X) having molecular formula C6
H12
O2
is hydrolysed by water in presence of an acid to give a
carboxylic acid (Y) and an alcohol (Z). Oxidation of (Z) with chromic acid gives (Y). What are (X),
(Y) and (Z).
6. An organic compound (A) on treatment of ethyl alcohol gives a carboxylic acid (B) and a compound
(C). (C) on hydrolysis under acidic conditions gives (B) and (D). Oxidation of (D) with KMnO4
also
gives (B). (B) on heating with Ca(OH)2
gives (E). Molecular formula of (E) is C3
H6
O . (E) does not
giveTollen’s test and does not reduce Fehling’s solution but forms 2, 4-dinitrophenyl hydrazone. Identify
(A) to (E).
7. An alkene (A) on ozonolysis yields acetone and an aldehyde. The aldehyde is easily oxidised to an acid
(B). When (B) is treated with phosphorus and bromine, it yields a compound (C) which on hydrolysis
gives a hydroxy acid (D). This can also be obtained from acetone by reaction with HCN followed by
hydrolysis. Identify (A) to (D).
8. A colourless, pungent smelling liquid having chemical equivalent 46 is strongly acidic to litmus. This is
readily oxidised by KMnO4
but reduces mercuric chloride to mercurous chloride. Heating the original
substance with excess of sulphuric acid produces water and carbon monoxide. Give the structural
formula of the compound.
9. A salt (a) of the formula C4
H5
O2
Ag on refluxing with bromine gives (B), C3
H5
Br. Compound (B) on
heating with alcoholic KOH yields (C), C3
H4
, which decolourises Br2
/CCl4
and cold dilute KMnO4
solution, but does not react with ammonical AgNO3
or Cu2
Cl2
. (c) on ozonolysis gives (D), C3
H4
O4
,
which on heating eliminates CO2
to give acetic acid. What are (A) to (D) ?
10. A neutral liquid of formula C7
H14
O2
is hydrolysed to an acid (A), and an alcohol (B). Acid (A) has a
neutralization equivalent of 84. Alcohol (B) is not easily oxidized with an acid solution of Na2
Cr2
O7
.
What is the formula and name of the original compound ?
LEVEL - III
1. An ester of molecular formula C8
H16
O2
on hydrolysis affords an acid (A) and an alcohol (B). Oxidation
of alcohol (B) with Na2
Cr2
O7
gives rise to an acid (C). Sodium salts of acids (A) and (C) on fusion with
solid NaOH yield propane in each case. What is the structural formula of the original ester ?
2. Compound (A), C3
H7
Cl, reacts with alcoholic KOH to form (B), C3
H6
. Compound (B) discharges Br2
/
CCl4
solution. Reaction of (A) with Mg in ether and subsequent treatment with CO2
and dilute acid
gives (C). whose molecular formula is C4
H8
O2
. When we add compound (C) to aqueous NaHCO3
solution, bubbles are evolved. What are (A) to (C) ?
3. Compound (A) has a neutralization equivalent of 116. It forms a semicarbazone or phenyl hydrazone,
and gives positive iodoform test. Compound (A) reacts with SOCl2
to give (B) which on Rosenmund’s
reduction gives (C). Clemmensen reduction of (C) gives n-pentane. What are (A). (B) and (C) ?

4. An organic acid A, C3
H4
O3
is catalytically reduced in presence of ammonia to give B, C3
H7
NO2
. B
reacts with acetyl chloride, hydrochloric acid and alcohols. It can also react with nitrous acid to give
another compound C, C3
H6
O3
, along with the evolution of nitrogen. What areA, B and C. Give reasons.
5. Compound A, C5
H8
O3
, when heated with soda lime gives B which reacts with HCN to give C, C
reacts with PCl5
to give D which reacts with KCN to form E. E, on alkaline hydrolysis gives a salt
which is isolated and heated with soda lime to produce n-butane. A, on careful oxidation with K2
Cr2
O7
gives acetic acid and malonic acid. Give structural formulae of A to E.
6. (a) Can the aromatic ring in benzoic acid stabilize the benzoate anion by -electron delocalization?
Illustrate
(b) Discuss the electronic effect of the p–NO2
group in p–NO2
C6
H4
COO–
7. Two isomeric carboxylic acids H and I, C9
H8
O2
, react with H2
/Pd giving compounds C9
H10
O2
. H
gives a resolvable product and I gives a nonresolvable product. Both isomers can be oxidized to
C6
H5
COOH. Give the structure of H and I.
8. Identify the products (A), (B), (C) and (d) in the following sequence :
4 4
LiAlH KMnO
HCl (i)Mg, ether
15 31 (ii)
C H COOH (A) (B) (C) (D)

   
O
9. A neutral liquid (Y) has the molecular formula C6
H12
O2
. On hydrolysis it yields an acid (A) and an
alcohol (B). Compound (A) has a neutralization equivalent of 60.Alcohol (B) is not oxidized by acidified
KMnO4
, but gives cloudiness immediately with Lucas reagent. What are (Y), (A) and (B)?
10. Esterification does not take place in the presence of ethyl alcohol and excess of concentrated H2
SO4
at 170°C. Explain.

SECTION - II
SINGLE CHOICE QUESTIONS
1. Kolbe electrolysis of potassium succinate gives CO2
and __________ :
(a) C2
H6
and KOH (b) C2
H2
and KOH
(c) C2
H4
, KOH and H2
(d) CH4
, C2
H6
and C2
H4
.
2. In the following reaction identify compounds A, B, C and D :
5 2
PCl SO A B
 
  ;
A + CH3
COOH 
 C + SO2
+ HCl
2C + (CH3
)2
Cd 
 D + CdCl2
(a) SOCl2
, POCl3
, CH3
COCl, CH3
COCH3
(b) SO2
Cl2
, HCl, CH3
Cl, CH3
CHO
(c) SO2
, Cl2
, C2
H5
Cl, CH3
COCH3
(d) None of these.
3. What are A and B in the following sequence of reactions ?
(i) CH3
CH2
COOH
2
P
Br
 A (ii) A
(i) Alc. KOH excess
(ii) H


 B
(a) 3 2
CH —CH COOH, CH CHCOOH
|
Br
 
(b) CH3
CH2
COBr, CH2
=
=CH·COOH
(c) 2 2 2
CH ·CH COOH, CH CH·COOH
|
Br

(d) C
H3 COOH
Br
Br
, H2C C COOH
Br
4. Acetic acid in the vapour state has a molecular weight of 120 because :
(a) its molecule gets solidified
(b) its molecule gets stabilized by resonance
(c) it undergoes intermolecular H-bonding and exists as the dimmer
(d) it forms anhydride in this condition.
5. Carbonation of alkyl magnesium halide followed by acidification gives :
(a) a carboxylic acid (b) an alcohol
(c) an anhydride (d) an aldehyde.

6. Which of the following compound would be expected to decarboxylates when heated
(a) C
H3 OH
O O
(b) C
H3 CH3
O O
(c) C
H3
O O
CH3
O
(d) C
H3
O O
OH
CH2
7.
O
O



 
 OH
CH3
A A is :-
(a)
CH2—CH2
OH COOCH3
(b)
CH2—CH2
OCH3
COOH
(c) both are correct (d) None is correct
8. End product of the following sequence of reaction is
O
C—CH3
O









 

,
H
.
2
,
NaOH
I
.
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, COOH
COOH
9. End product of this conversion
H
CO
CH
CH
CH
C
CH 2
2
2
2
3
||
O




 



 

H
,
O
H
.
2
NaBH
.
1
2
4
is
(a)
=O
CH3
O
(b) =O
CH3
O
(c) =O
O
(d) CH3—CH—CH2CH2CH2CO2H
OH

10. When acetic acid reacts with ketene, product formed
(a) ethyl acetate (b) aceto - acetic ester
(c) acetic anhydride (d) no reaction
11. R—CH2
—CH2
OH can be converted in R—CH2
CH2
COOH. The correct sequence of reagents is
(a) PBr3
, KCN, H+
(b) PBr3
, KCN, H2
(c) KCN, H+
(d) HCN, PBr3
, H+
12. 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
13. 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
)2
C=CH—CH2
COOH
(b) (CH3
)2
CH—COOH
(c) (CH3
)2
C=CH—COOH
(d) (CH3
)2
C=CH—CO—COOH
14. The ease of alkaline hydrolysis is more for
(a)
COOCH3
NO2
(b)
COOCH3
Cl
(c)
COOCH3
(d)
COOCH3
OCH3
15. Which of the following does not undergo Hell - Volhard Zelinsky reaction?
(a) HCOOH (b) CCl3
COOH
(c) C6
H5
COOH (d) All
16. Reaction between solid ice and methyl magnesium bromide gives an addition compound which on
acidification yields :
(a) ethanoic acid (b) propanoic acid
(c) ethanal (d) ethanol.

17. Which reducing agents of the following can be used for the following transformation ?
CH3
—CH=CH.COOH CH3
CH=CH.CH2
OH.
(a) LiAlH4
(b) BH3
, THF
(c) H2
/Ni (d) Na + C2
H5
OH.
18. Which of the following reactions is used to bring about the following conversion ?
(a) Hofmann reaction (b) Curtius reaction
(c) Ritter reaction (d) Schmidt reaction.
19. Which one of the following reagents is used to identify acetic acid ?
(a) NaOH and I2
(b) Ceric ammonium nitrate
(c) neutral FeCl3
solution (d) Tollens reagent.
20. Consider the following reaction scheme :
which of the following would be suitable for converting propanoic acid into the amino acid alanine ?
X Y
(a) Br2
NaNH2
(b) Br2
, P NaOH
(c) Br2
, P NH3
(d) HBr NH3
.

SECTION - III
MULTIPLE CHOICE QUESTIONS
1. Acetic anhydride is prepared industrially by heating sodium acetate with :
(a) PCl5
(b) SOCl2
(c) CH3
COCl (d) Cl2
and SCl2
2. Acetyl chloide is prepared industrially by distilling sodium acetate with :
(a) HCl (b) SO2
Cl2
(c) PCl5
(d) POCl3
3. Urea on heating with ethyl alcohol gives :
(a) urethane (b) semicarbazide
(c) malonyl urea (d) ethyl carbamate
4. Urea may be identified by which of the following tests?
(a) With CHCl3
/KOH, it gives very offensive odour
(b) With nitrous acid, it evolves N2
and CO2
(c) With NaOH and a drop of CuSO4
, it gives violet colour
(d) With NaOH on heating, it gives a smell of NH3
gas
5. Which of the following acids are dicarboxylic acid?
(a) Succinic acid (b) Glutaric acid
(c) Lactic acid (d) Cinnamic acid
6. Formic acid gives the test of :
(a) aldehydic group (b) ketonic group
(c) carboxylic group (d) alcoholic group
7. Optical activity is expected for :
(a) 2-methyl propanoic acid (b) 2-chloropropanoic acid
(c) methyl-2-methylpropanoate (d) methyl-2-chloropropanoic acid
8. Which of the following compounds will give ethyl alcohol on reduction with LiAlH4
?
(a) (CH3
CO)2
O (b) CH3
COCl
(c) CH3
CONH2
(d) CH3
COOC2
H5
9. Which of the following reagents can be used to test carboxylic group?
(a) NaHCO3
(b) FeCl3
(c) Alcohol in presence of conc. H2
SO4
(d) Ceric ammonium nitrate
10. Oxalic acid is used :
(a) for removing ink stains
(b) for the lab preparation of formic acid and allyl alcohol
(c) in making beverages
(d) as a mordant in dyeing and calicoprinting

MISCELLANEOUS QUESTIONS
SECTION - IV
COMPREHENSION TYPE QUESTIONS
Write up - I
Aliphatic carboxylic acids react with bromine or chlorine in presence of phosphorus (or a phosphorus
halide) to give -halo acids, the reaction is known as Hell-Volhard-Zelinski (or HVZ) reaction.
2 2
Cl ,P Cl P
2
Cl
|
RCH COOH RCHCOOH R C COOH
| |
Cl Cl

 

Halogenation occurs specifically at the -carbon.
1. The HVZ reaction is
(a) regiospecific
(b) regioselective
(c) both
(d) none of these
2. During HVZ reaction, halogenation takes place on
(a) the carboxylic acid
(b) the sodium salt of carboxylic acid
(c) the acid halide
(d) a complex compound
3. HVZ reaction involves the formation of
(a) acid halides
(b) enols
(c) both
(d) none of these

Write up - II
The loss of a molecule of carbon dioxide from a carboxylic acids is known as decarboxylation.
2
RCOOH RH CO

 
Decarboxylation of simplecarboxylic acids takes place with great difficulty and is rarely encountered.
However, there are certain groups which if present in -position of a carboxylic acid, decarboxylation
takes place readily. Thus -keto acids decarboxylate readily when they are heated to 100–150°C
(some -keto acids decarboxylate, although slowly, even at room temperature).
100 150
2 3 2
O O O
|| || ||
R —C — CH —C — OH R — C —CH CO

 


 
4. Decarboxylation of keto acids is due to
(a) the presence of ketonic group
(b) the presence of active methylene group
(c) the formation of resonance-stabilized enolate anion
(d) all the three factors
5. Like -Keto acids, --unsaturated carboxylic acids undergo decarboxylation easily because of
(a) formation of resonance-stabilized enolate anion
(b) formation of resonance-stabilized carbanion
(c) the double bond which makes —COOH group unstable
(d) the double bond which makes —COOH group reactive
6. Which of the following undergoes decarboxylation easily?
(a)
COOH
O2N NO2
NO2
(b) C6
H5
CCCOO—
(c) both (a) and (b) (d) C6
H5
CH2
CH2
COOH

MULTIPLE MATCHING TYPE QUESTIONS
7. Match the following :
Colum – A Column – B
(A)
O
O
O 3
CH OH /H

 1. O
COOH
(B) 4
2
(i)NaBH
2 3 (ii)H O/H
O O
|| ||
Ph—C—(CH ) —C—OH 

 2.
O
C
H3
C
H3
(C)
OC2H5
OCH3
COOC2H5
2
H / H O




3. H3
CCOO—(CH2
)2
—COOCH3
(D) 2 5
3
(i) C H MgBr
3 2 2 2 5 (ii) H O
O
O
||
||
CH — C— (CH ) — C— OC H 

 4.
O
O
Ph
(A) (B) (C) (D)
(a) 3 4 1 2
(b) 1 2 3 4
(c) 4 3 2 1
(d) 4 3 1 2
8. Match the following
Column – A Column – B
(A) Aspirin 1. CH3
.CH2
.CH2
.OH
(B) Dehydrogination of isobutyl alcohol 2. 2-methylpropanol
(C) Ethyl carbinol 3. Acetyl salicylic acid
(D) Glycol + lead acetate 4. methanol
(A) (B) (C) (D)
(a) 3 2 1 4
(b) 1 2 3 4
(c) 2 3 4 1
(d) 4 3 2 1

ASSERTION-REASON TYPE QUESTIONS
The question given below consist of an ASSERTION and the REASON. Use the following key for the
appropriate answers
(a) If both Assertion and Reason are correct and Reason is the correct explanation for Assertion
(b) If both Assertion and Reason are correct and Reason is not the correct explanation for
Assertion
(c) If Assertion is correct but Reason is not correct.
(d) If Assertion is incorrect but Reason is correct.
9. Assertion : Only ester that have two -hydrogens undergo the Claisen condensation.
Reason : Enolate carbanion is resonance stabilised.
10. Assertion : When isotopic labelled
18
O of H2O is used in the hydrolysis of 3 3 3
O O
|| ||
CH COCH , CH COH
formed has
18
O (as
18
3
O
||
CH COH)
Reason : CH3 of 3 3
O
||
CH COCH is replaced by H.
11. Assertion : Formic acid is a stronger acid than benzoic acid.
Reason : pKa of formic acid is lower than that of benzoic acid.
12. Assertion : Fluoroacetic acid is stronger than chloroacetic acid.
Reason : Carboxylic acids are weak acids and turn blue litmus red.
13. Assertion : More electropositive element has greater e–
donating effect.
Reason : Me3SiCH2COOH is more acidic than Me3.C.CH2COOH.
14. Assertion : Acetic acid undergoes haloform reaction.
Reason : Acetic acid has no -H5.
15. Assertion : Durin reaction of carboxylic acids with NaHCO3
, the CO2
evolved comes from carboxylic
acid and not from NaHCO3
.
Reason : Carbonic acid is a stronger than a carboxylic acid.

SECTION - V
(PROBLEMS )
A. Only one option is correct (Objective Questions)
1. When benzene sulphonic acid and p-nitrophenol are treated with NaHCO3
, the gases released
respectively are :
(a) SO2
, NO2
(b) SO2
, NO
(c) SO2
, CO2
(d) CO2
, CO2
2. Benzamide on treatment with POCl3
gives :
(a) aniline (b) benzonitrile
(c) chlorobenzene (d) benzyl amine
3. An enantiomerically pure acid is treated with racemic mixture of an alcohol having one chiral carbon.
The ester formed will be :
(a) optically active mixture (b) pure enantiomer
(c) meso compound (d) racemic mixture
4. Ethyl ester 3
CH MgBr
(excess)
P,

 The product ‘P’ will be :
(a)
H3C
H3C OH
CH3
(b)
H3C
H5C2 OH
C2H5
(c)
H5C2
H5C2 OH
C2H5
(d)
H5C2
H7C3 OH
C2H5
5. The product of acid hydrolysis of P and Q can be distinguished by :
CH2
OCOCH3
CH3
, Q =
OCOCH3
C
H3
P =
(a) Lucas reagent (b) 2, 4, -DNP
(c) Fehling’s solution (d) NaHSO3

6.
HOOC
CH
O2N
OH
OH
2
2 moles of NaNH
A


(a)
-
OOC
CH
O2N
O
-
OH
(b) -
OOC
C
-
O2N
OH
(c) HOOC
CH
O2N
O
-
O
-
(d) HOOC
C
-
OH
7. Identify the correct order of boiling points of the following compounds :
3 2 2 2 3 2 2 3 2 2
(1) (2) (3)
CH CH CH CH OH, CH CH CH CHO, CH CH CH COOH
(a) 1 > 2 > 3 (b) 3 > 1 > 2
(c) 1 > 3 > 2 (d) 3 > 2 > 1
8. Benzoyl chloride is prepared from benzoic acid by
(a) Cl2
, hv (b) SO2
Cl2
(c) SOCl2
(d) Cl2
, H2
O

9. When propionic acid is treated with aqueous sodium bicarbonate, CO2
is liberted. The C of CO2
comes
from :
(a) methyl group (b) carboxylic acid group
(c) methylene group (d) bicarbonate
10. Assertion : Acetic acid does not undergo haloform reaction.
Reason : Acetic acid has no alpha hydrogen.
(a) both assertion and reason are correct and reason is the correct explanation of the assertion
(b) both assertion and reason are correct, but reason is not the correct explanation of the assertion
(c) assertion is correct but reason is incorrect
(d) assertion is incorrect but reason is correct
11. Hydrogenation of benzoyl chloride in the presence of Pd on BaSO4
gives :
(a) benzyl alcohol (b) benzaldehyde
(c) benzoic acid (d) phenol
12. Acetamide is treated separately with the following reagents. Which one of the these would give methyl
amine?
(a) PCl5
(b) NaOH + Br2
(c) Sodalime (d) Hot conc. H2
SO4
B. More than one options are correct (Objective Questions)
1. Reaction of 2
O
||
R —C — NH with a mixture of Br2
and KOH gives R—NH2
as the main product. The
intermediates involved in this reaction are :
(a)
O
||
R —C — NHBr (b) R—NHBr
(c) R—N==C==O (d) R C
O
N
Br
Br
C. Comprehension


NH2
O
Cl
NH
O
Cl
Br


N
-
O
Cl
Br


N
C
Cl
O


NH
COO
-
Cl
NH2
Cl
(I) (II) (III) (IV) (V) (VI)



1. For the conversion from I to II, which reagent was used?
(a) NaHCO3
/KBr (b) KBr/NaOH
(c) KBr/NaOCH3
(d) NaOH/Br2
2. Which step is rate determining step?
(a) Formation of II (b) Formation of III
(c) Formation of IV (d) Formation of salt V
3.
NH2
O
15
I
2
NaOH/ Br
?


NH2
O
D
15
II
2
NaOH/Br
?


(a)
NH2
15
NH2
D
(b)
NH2
NH2
D
(c)
NH2
15
NH2
D
(d)
NH2
15
NH2
D
NH2
15
NH2
D
SUBJECTIVEQUESTIONS
1. Complete the following, giving the structures of the principal organic products :
(i)
Me
NO2
+ (COOEt)2 + EtONa  A (2M)
(ii) H3CCOCOC6H5 + NaOH/H3O+  B (1M)

2. Following reaction gives two products. Write the structures of the product.
2
Br /Fe
3 6 5
CH CONHC H 
3. Explain briefly the formation of the products giving the structures of the intermediates :
C
CH2
C
O
OC2H5
O
OC2H5
NaOEt


C
O
CH
Br
C
H3
OC2H5
(i) OH
(ii) H



 C
H3 CH
H2C
C
O
OH
C
O
OH
4. What would be the major product in the following reactions?
N
O
2
Br /Fe (1eq.)


5. Write the structures of the products A and B.
3
18
H O
3 2 5
O
||
CH —C —OC H A B


 
6. Identify X and Y in the following synthetic scheme and write their structure. Explain the formation of
labelled formaldehyde
*
2
(H CO) as one of the products when compound (Z) is treated with HBr and
subsequently ozonolysed. Mark the C* carbon in the entire scheme.
4
3
LiAlH
(i) Mg /ether
2 (ii) X
(iii) H O
CH CH — Br X Z

 
 


7. Five isomeric para-disubstituted aromatic compounds A to E with molecular formula C8H8O2 were
given for identification.
Based on the following observations, give structures of the compounds :
(i) Both A and B form a silver mirror with Tollen’s reagent; also, B gives a positive test with FeCl3
solution.
(ii) C gives positive iodoform test.
(iii) D is readily extracted in aqueous NaHCO3 solution.
(iv) E on acid hydrolysis gives 1, 4 dihydroxy benzene.

8. A racemic mixture of (±) 2-phenyl propanoic acid on esterification with (+) 2-butanol gives two esters.
Mention the stereochemistry of the two esters produced.
9. Convert (in not more than 3 steps)
COOH COOH
F
10. Compound A of molecular formula C9H7O2Cl exists in keto form and predominantly in enolic form B.
On oxidation with KMnO4, A gives m-chlorobenzoic acid. Identify A and B.

ANSWERS
SECTION - I
(Subjective Questions)
Answers are given in the separate booklet (Level – I to Level – III)
SECTION - II
(Single Choice Questions)
1. (c) 2. (a)
3. (a) 4. (c)
5. (a) 6. (a)
7. (a) 8. (c)
9. (a) 10. (c)
11. (a) 12. (d)
13. (c) 14. (a)
15. (d) 16. (a)
17. (a) 18. (d)
19. (c) 20. (c)
SECTION - III
(Multiple Choice Questions)
1. (b, c, d) 2. (b, d)
3. (a, d) 4. (b, c, d)
5. (a, b) 6. (a, c)
7. (b, d) 8. (a, b)
9. (a, b, c) 10. (a, b, d)

SECTION - IV
(Comprehension Type Questions)
1. (b) 2. (c)
3. (c) 4. (c)
5. (b) 6. (c)
(Multiple Matching Type Questions)
7. (a) 8. (a)
(Assertion Reason Type Questions)
9. (b) 10. (c)
11. (c) 12. (b)
13. (c) 14. (d)
15. (d)
SECTION - V
(A. Only one option is correct (Objective Questions)
1. (d) 2. (b)
3. (a) 4. (c)
5. (c) 6. (a)
7. (b) 8. (c)
9. (d) 10. (c)
11. (b) 12. (b)
B. More than one options are correct (Objective Questions)
1. (a, c)
C. Comprehension
1. (d) 2. (d)
3. (b)
SUBJECTIVE
Answers are given in the separate booklet.

Carboxylic Acid & Derivatives-03- Assignments

Carboxylic Acid & Derivatives-03- Assignments

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