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COMPULSORY PROBLEMS
18. CARBONYL COMPOUNDS {Q.No.70 (c)}
1. Compound (A) of molecular formula C2H4O reduce Tollens reagents.(A) on
treatment with HCN gives compound (B).Compound (B) on hydrolysis with acid
compound (C) with molecular formula C3H6O3 which an optically active
compound. Compound (A) on reduction with N2H4/C2H5ONa gives a
hydrocarbon (D) of molecular formula C2H6.Identify A,B,C, and D. Explain the
reaction. [Mar-2013]
ANSWER:
CH3CHO + HCN CH3CH(OH)CN
(A)
(B)
RESULT:
S.No Compound
1
A
2
B
3
C
4
D
CH3CHO
(A )
H+/H2O
N2H4/C2H5ONa
4(H)
Formula
CH3CHO
CH3CH(OH)CN
CH3CH(OH)COOH
CH3CH3
CH3CH(OH)COOH
(C)
CH3CH3 + N2 + H2O
(D)
Name
Acetaldehyde
Acetaldehyde cyanohydrin
Lactic acid
Ethane
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CH3CH(OH)COOH
(B)
(O)
RESULT:
S.No Compound
Formula
1
A
CH3CHO
2
B
CH3CH(OH)COOH
3
C
CH3COCOOH
H+/H2O
CH3CH(OH)COOH
(B)
CH3COCOOH
(C)
Name
Acetaldehyde
Lactic acid
Pyruvic acid
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3. Compound (A) (C2H4O) reduce Tollens reagent .(A) on treatment with Zinc
amalgam and con.HCl gives compound (B) .In the presence of con.H2SO4 (A)
forms cyclic compound (C) which is used as hypnotic .Identify A,B and C.
Explain the reaction. [Jun-2011]
ANSWER:
CH3CHO
(A)
RESULT:
S.No Compound
1
A
2
B
3
Zn / Hg conc.HCl
4(H)
CH3CH3 + H2O
(B)
(C)
Formula
CH3CHO
CH3CH3
Name
Acetaldehyde
Ethane
Paraldehyde
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4. An organic compound (A) (C2H4O) with HCN gives (B) (C3H5ON). Compound (B)
on hydrolysis compound (C) (C3H6O3) which is an optically active
compound.(C) also undergoes iodoform test. Identify A, B and C. Explain the
reaction. [Oct-2011]
ANSWER:
CH3CHO + HCN CH3CH(OH)CN
(A)
(B)
H+/H2O
CH3CH(OH)COOH
(C)
RESULT:
S.No Compound
1
A
2
B
3
C
Formula
CH3CHO
CH3CH(OH)CN
CH3CH(OH)COOH
Name
Acetaldehyde
Acetaldehyde cyanohydrin
Lactic acid
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H+/H2O
CH3CH(OH)COOH
(C)
(O)
RESULT:
S.No Compound
Formula
1
A
CH3CHO
2
B
CH3CH(OH)CN
3
C
CH3CH(OH)COOH
4
D
CH3COCOOH
CH3CH(OH)COOH
(C)
CH3COCOOH
(D)
Name
Acetaldehyde
Acetaldehyde cyanohydrin
Lactic acid
Pyruvic acid
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6. An organic compound (A) C2H3OCl on treatment with Pd and BaSO4 gives (B)
C2H4O which answers iodoform test .(B) when treated with conc.H2SO4
undergoes polymerization to give (C) a cyclic compound. Identify A,B and C.
Explain the reaction. [Oct-2009]
ANSWER:
CH3COCl + H2
(A)
RESULT:
S.No Compound
1
A
2
B
3
C
Pd / BaSO4
CH3CHO + HCl
(B)
Formula
CH3COCl
CH3CHO
(CH3CHO)3
Name
Acetyl chloride
Aceytaldehyde
Paraldehyde
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7. An organic compound (A) C2H3N on reduction with SnCl2 / HCl gives (B) C2H4O
which reduce Tollens reagent. Compound (B) on reduction with N2H4/C2H5ONa
gives (C) C2H6. Identify the compounds A,B and C. Explain the reactions.[Oct-12]
ANSWER:
CH3CHO
(B)
RESULT:
S.No Compound
1
A
2
B
3
C
N2H4/C2H5ONa
4(H)
Formula
CH3CN
CH3CHO
CH3CH3
(B)
CH3CH3 + H2O
(C)
Name
Methyl cyanide
Aceytaldehyde
Ethane
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CH3CH2OH
(A)
H+/
K2Cr2O7
CH3CHO + H2O
(B)
(C)
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RESULT:
S.No Compound
1
A
2
B
3
C
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Formula
CH3CH2OH
CH3CHO
(CH3CHO)3
Name
Ethanol
Aceytaldehyde
Paraldehyde
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RESULT:
S.No Compound
Formula
1
A
CH3COCH3
2
B
(CH3)2C=CHCOCH3
3
C
(CH3)2C=CHCOCH=C(CH3)2
Name
Acetone
Mesityl oxide
Phorone
10. An organic compound (A) C3H8O answers Lucas Test within 5-10 mins and
oxidation form (B) C3H6O. (B) On further oxidation forms (C) C2H4O2 which
gives effervescence with NaHCO3. (B) Also undergoes iodoform test. Identify
A,B and C. Explain the reaction. [Jun-2009]
ANSWER:
(O)
(O)
(CH3)2CHOH
CH3COCH3
CH3COOH
+
+
(A)
H / K2Cr2O7
(B)
H / K2Cr2O7
(C)
RESULT:
S.No Compound
Formula
Name
1
A
(CH3)2CHOH
2-Propanol
2
B
CH3COCH3
Acetone
3
C
CH3COOH
Acetic acid
K N SUBRAMANI .M.Sc.B.Ed., PGT in Chemistry, VVMHSS, Karamadai Cbe 641 104
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11. Compound (A) of molecular formula C3H6O does not reduce Tollens reagent
and Fehlings solution. Compound (A) undergoes Clemmensen reduction to
give compound (B) of molecular formula C3H8. Compound (A) in the presence
of con.H2SO4 condenses to give an aromatic compound (C) of molecular
formula C9H12.Identify A,B and C. Explain the reaction.
[Mar-2012]
ANSWER:
RESULT:
S.No Compound
1
A
2
B
3
C
CH3COCH3
(A)
Zn/Hg conc.HCl
4(H)
CH3CH2CH3 + H2O
(B)
(C)
Formula
CH3COCH3
CH3CH2CH3
C6H3(CH3)3
Name
Acetone
Propane
Mesitylene
12. Compound (A) C3H6O does not reduce Tollens reagent, but under goes halo
form reaction. Compound (A) under goes dehydration in the presence of dry
HCl to give compound (B) C6H10O.Three molecules of compound (A) under
goes condensation reaction in the presence of conc. H2SO4 to give a cyclic
compound (C).Identify the compounds A,B and C. Explain the reaction [Jun-12]
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ANSWER:
(CH3 )2C=O + H2CHCOCH3
(A)
RESULT:
S.No Compound
1
A
2
B
3
C
Dry HCl
(CH3)2CHCOCH3
(B)
H2O
Formula
CH3COCH3
(CH3)2C=CHCOCH3
C6H3(CH3)3
(C)
Name
Acetone
Mesityl oxide
Mesitylene
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CH3COCH3
(A)
2(H)
(CH3)2 CHOH
(B)
Alc.KOH
Formula
CH3COCH3
(CH3)2 CHOH
(CH3)2 CHCl
CH3C=CH2
Name
Acetone
2-Propanol
Isopropyl chloride
Propene
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14. Compound A of molecular formula C7H6O reduce Tollens reagents and also
gives Cannizzaro reaction. (A) on oxidation gives compound (B) with
molecular formula C7H6O2. Calcium salt of (B) on dry distillation gives
compound (C) with molecular formula C13H10O Identify A,B, and C. Explain the
reaction.
[Mar-2008]
ANSWER:
(O)
C6H5CHO
C6H5COOH
(A)
alkaline KMnO4
(B)
(A)
RESULT:
S.No Compound
1
A
2
B
3
C
(B)
Formula
C6H5CHO
C6H5COOH
C6H5COC6H5
Name
Benzaldehyde
Benzoic acid
Benzo phenone
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15.An aromatic aldehyde (A) of molecular formula C7H6O which has the smell of
bitter almonds on treatment with (CH3CO)2O and CH3COONa to give compound
(B) which is an aromatic unsaturated acid. (A) also react with (A) in the
presence of alc. KCN to give dimer (C).Identify A,B, and C. Explain the reactions.
[Oct-2007]
ANSWER:
CH3COONa
C6H5CH=O + CH3COOCOCH3
(A)
C6H5CH=O + H- C- C6H5
||
(A)
O
RESULT:
S.No Compound
1
A
2
B
3
C
alc.KCN
Formula
C6H5CHO
C6H5CH=CHCOOH
C6H5CH(OH)COC6H5
C6H5CH=CHCOOH + CH3COOH
(B)
C6H5CH(OH)- C- C6H5
||
O
(C)
Name
Benzaldehyde
Cinnamic acid
Benzoin
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16. An organic compound (A) (C7H6O) form a bisulphate .(A) when treated with
alcoholic KCN forms (B) (C14H12O2) and (A) on refluxing with sodium acetate
and acetic anhydride forms an acid (C) (C9H8O2).Identify A,B and C. Explain the
reaction.[Jun-07]
ANSWER:
C6H5CH=O + H- C- C6H5
||
(A)
O
C6H5CH=O + CH3COOCOCH3
(A)
RESULT:
S.No Compound
1
A
2
B
3
C
alc.KCN
CH3COONa
Formula
C6H5CHO
C6H5CH(OH)COC6H5
C6H5CH=CHCOOH
C6H5CH(OH)- C- C6H5
||
O
(B)
C6H5CH=CHCOOH + CH3COOH
(C)
Name
Benzaldehyde
Benzoin
Cinnamic acid
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CaO /NaOH
NaOH
C6H5COOH + C6H5CH2 OH
(B)
(C)
C6H6 + CO2
Formula
C6H5CHO
C6H5COOH
C6H5CH2OH
Name
Benzaldehyde
Benzoic acid
Benzyl alcohol
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ANSWER:
C6H5CH=O + C6H5NH2
(A)
OH
|
[- H2O]
C6H5CHNHC6H5
C6H5CH=NC6H5
(B)
(C)
RESULT:
S.No Compound
1
A
2
B
3
Formula
C6H5CHO
C6H5CH=NC6H5
Name
Benzaldehyde
Schiffs base
m- chloro benzaldehyde
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19. An aromatic compound (A) with molecular formula C7H6O has the smell of
bitter almonds.(A) react with Cl2 in the absence of catalyst to gives (B) and in
the presence of catalyst to fives compound (C). Identify the compounds A,B
and C. Explain the reactions. [Mar-2009, Oct - 2014]
ANSWER:
C6H5CHO + Cl2
(A)
C6H5COCl + HCl
(B)
(C)
RESULT:
S.No Compound
1
A
2
B
3
Formula
C6H5CHO
C6H5COCl
Name
Benzaldehyde
Benzoyl chloride
m- chloro benzaldehyde
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20. An organic compound (A) C7H8,on oxidation at 773K in the presence of V2O5
gives compound (B) of molecular formula C7H6O.(B) reduce Tollens
reagent.(B) on heating with sodium acetate in the presence of acetic anhydride
gives compound (C) of molecular formula C9H8O2.identify A,B and C. Explain
the reaction. [Mar-11, Jun- 13,Oct-13]
ANSWER:
C6H5CH3
(A)
(O)
air/ V2O5 773K
C6H5CHO + H2O
(B)
CH3COONa
C6H5CH=O + CH3COOCOCH3
(A)
RESULT:
S.No Compound
Formula
1
A
C6H5CH3
2
B
C6H5CHO
3
C
C6H5CH=CHCOOH
C6H5CH=CHCOOH + CH3COOH
(C)
Name
Toluene
Benzaldehyde
Cinnamic acid
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21. An organic compound (A) C7H8, on oxidation at 773K in the presence of V2O5
gives compound (B) of molecular formula C7H6O, which has smell of bitter
almonds. Alkaline KMnO4 oxidise compound (B) to (C) of molecular formula
C7H6O2. Compound (B) treatment with N2H4/KOH give back compound (A).
Identify A,B and C. Explain the reaction. [Jun-2010]
ANSWER:
C6H5CH3
(A)
C6H5CHO
(B)
C6H5CHO
(B)
RESULT:
S.No Compound
1
A
2
B
3
C
(O)
C6H5CHO + H2O
(B)
(O)
alkaline KMnO4
N2H4 / KOH
C6H5COOH
(C)
C6H5CH3 + H2O
(A)
4(H)
Formula
C6H5CH3
C6H5CHO
C6H5COOH
Name
Toluene
Benzaldehyde
Benzoic acid
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C6H5CH=O + C6H5NH2
(A)
C6H5CHO + Cl2
(A)
RESULT:
S.No Compound
1
A
2
B
3
C
OH
|
[- H2O]
C6H5CHNHC6H5
C6H5CH=NC6H5
(B)
C6H5COCl +
(C)
Formula
C6H5CHO
C6H5CH=NC6H5
C6H5COCl
HCl
Name
Benzaldehyde
Schiffs base
Benzoyl chloride
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23. An organic compound (A) C7H8, on oxidation at 773K in the presence of V2O5
gives compound (B) of molecular formula C7H6O. (B) on reduction with
lithium aluminium hydride to form (C) of molecular formula C7H8O. Identify
(A), (B), and (C) and explain the reactions. [Mar 2015]
ANSWER:
C6H5CH3
(A)
C6H5CHO
(A)
RESULT:
S.No Compound
1
A
2
B
3
C
(O)
C6H5CHO + H2O
(B)
C6H5CH2OH
(C)
[ H ]
Formula
C6H5CH3
C6H5CHO
C6H5CH2OH
Name
Toluene
Benzaldehyde
Benzyl alcohol
24. Compound A of molecular formula C7H6O is called oil of bitter almonds. (A)
on oxidation gives compound (B) with molecular formula C7H6O2 , which gives
brisk effervescence with NaHCO3 solution ,then, (A) is refluxed with alcoholic
KCN compound (C) is formed. Identify A,B and C. Explain the reaction.[Jun-14]
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ANSWER:
C6H5CHO
(A)
(O)
alkaline KMnO4
C6H5CH=O + H- C- C6H5
(A)
||
O
RESULT:
S.No Compound
1
A
2
B
3
C
C6H5COOH
(B)
alc.KCN
Formula
C6H5CHO
C6H5COOH
C6H5CH(OH)COC6H5
C6H5CH(OH)- C- C6H5
||
O
(C)
Name
Benzaldehyde
Benzoic acid
Benzoin
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RESULT:
S.No Compound
1
A
2
B
3
C
4
D
Name
Benzaldehyde
Hydrobenzamide
Benzoin
Triphenyl methane dye
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ANSWER:
C6H5CH=O + CH3COOCOCH3
(A)
CH3COONa
NaOH
C6H5CHO + CH3COCH3
(A)
RESULT:
S.No Compound
Formula
1
A
C6H5CHO
2
B
C6H5CH=CHCOOH
3
C
C6H5CH=CHCOCH3
3. An organic compound A (C8H8O) undergoes iodo form test. When reduced with
Zinc amalgam and HCl it gives B (C8H10). A with Br2 in ether at 273K gives C
(C8H7OBr). Identify A, B, and C explain the reactions.
ANSWER:
C6H5COCH3
Zn / Hg conc.HCl
(A)
4(H)
C6H5CH2CH3 + H2O
(B)
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C6H5COCH2H + BrBr
(B)
Ether
C6H5COCH2Br
(C)
HBr
RESULT:
S.No Compound
Formula
Name
1
A
C6H5COCH3
Acetophenone
2
B
C6H5CH2CH3
Ethyl benzene
3
C
C6H5COCH2Br
Phenaceyl bromide
4. An organic compound A (C5H10O) does not reduce Tollens reagent. It is a
linear compound and undergoes iodoform test. On oxidation A gives B
(C2H4O2) and C (C3H6O2) as the major product. Identify A, B, and C explain the
reactions.
ANSWER:
(O)
CH3COCH2CH2CH3
CH3COOH +
(A)
(B)
RESULT:
S.No Compound
Formula
1
A
CH3COCH2CH2CH3
2
B
CH3COOH
3
C
CH3CH2COOH
CH3CH2COOH
(C)
Name
2-Pentanone
Acetic acid
Propionic acid
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6. 0.04 N solution of a weak acid has a specific conductance 4.23 x10-4 mho.cm-1.
The degree of dissociation of acid at this dilution is 0.0612. Calculate the
equivalent conductance of weak acid at infinite solution. (Oct-2009)
Solution :[Specific conductance k = 4.23 x10-4 mho.cm-1 ; = 0.0612]
c = (k x 1000) /C = (4.23 x10-4) / 0.04 = (4.23 x10-4) /(4 x 10-2)
c= (4.23/4) x 10-2 = 1.0575 x 10-2 mho.cm2.eq-1.
c = 105.75 mho.cm2.eq-1.
= c/
Log 10.575 = 1.0242
Log 0.0612 = 2.7868 (-)
= c / = 10. 575 / 0.0612
2.2374
2
-1
= 172.8 mho.cm .gm.equiv.
Ant.log of 2.2374 = 1.728 x 102
K N SUBRAMANI .M.Sc.B.Ed., PGT in Chemistry, VVMHSS, Karamadai Cbe 641 104
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7. Equivalent conductivity of acetic acid at infinite dilution is 390.7 and for 0.1 M
acetic acid the equivalent conductance is 5.2 mho.cm2.gm.equiv.-1. Calculate
degree of dissociation, H+ ion concentration and dissociation constant of the
acid.
(Jun-2007)
Solution :
= c/ = 5.2 / 390.7 = 0.01333 = 1.33%
Log 5.2 = 0.7160
CH3COOH CH3COO +
H+
Log 390.7 = 2.5918 (-)
C (1 )
C
C
2.1242
[H+] = C= 0.1 x0.0133 = 0.00133 M
Ant.log of 2.1242=1.331 x 10-2
K =2C /(1- )
= (0.01332 x 0.1) /(1- 0.0133)
= (0.0001769 x 0.1)/0.9867 =
0.0000179
K= 1.79 x 10-5 M
8. Ionic conductances at infinite dilution of Al3+ and SO42are 189 ohm1 cm2
gm.equiv.-1 and 160 ohm-1 cm2 gm.equiv.-1. Calculate equivalent and molar
conductance of the electrolyte at infinite dilution.(Mar-2010,13)
Solution:
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9. Calculate the pH of 0.1 M CH3COOH solution.Dissociation constant of acetic acid
is 1.8 x10-5 M.(Jun-2009,Mar-2011)
Solution:
For weak acids,
[H+] = KaxC
Log1.34 = 0.1271
-5
-6
= 1.8x10 x 0.1 = 1.8x10
[H+] = 1.34 x 103 M
pH = log [H+] = -log (1.34 x103 )
=-log1.34 - log10-3 = -log1.34- (-3log10)
pH = -0.13 +3 = 2.87
10. Calculate the pH of 0.02 m Ba(OH)2aqueous solution assuming Ba(OH)2 as a
strong electrolyte.
Solution:
Ba(OH)2 Ba2+ + 2OH
[OH] = 2 [Ba(OH)2] = 2 x0.02 = 0.04 M
Log4 = 0.6020
-2
= 4 x 10
K N SUBRAMANI .M.Sc.B.Ed., PGT in Chemistry, VVMHSS, Karamadai Cbe 641 104
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&
pH = 5.0457 }