Paragraph Types Questions

1. An organic compound (A) on treatment with ethyl alcohol and sulphuric acid produces
water and compound (B). Compound (B) on hydrolysis under acidic conditions gives
ethyl alcohol and (A). On heating (A) with Ca(OH)2 gives (C) (C3H6O). (C) does not
reduce Tollen’s reagent or Fehling solution but form a
2, 4-nitro phenyl hydrazine with 2, 4-DNP reagent. Reduction of compound (A) gives
(D) on reaction with LiAlH4.
(i) Identify the compounds (A) to (D).
(ii) Name the reaction for the formation of compound (C) from compound (A).

2. An aromatic compound ‘A’ with molecular formula C 7H8 on oxidation with CrO2Cl2
in gives (B) which gives positive Tollen’s test. The compound (B) on further oxidation
gave (C) which gives further effervescence with NaHCO 3.
(C) on distillation with soda lime gives a hydrocarbon (D). Identify (A), (B), (C) and
(D) compounds.

3. C7H6O is the organic compound (A) which on treatment with NaOH followed by acid
hydrolysis gives two products (B) and (C). (B) on oxidation gives (A) which on further
oxidation gives (C). Chloro derivative of (C) is formed when (C) reacts with PCl 5. The
compound (C) on treating with ammonia gives (D) which with Br2 and KOH gives
aniline.
(i) What are (A), (B), (C) and (D)?
(ii) Acetic acid is less acidic strength than formic acid. Why?

4. Ethyl alcohol when reacts with PCl5 gives a compound (A). When compound (A) is
treated with alc. KOH, compound (B) is formed along with KCl and H2O.

5. An organic compound A has the molecular formula of C 7H6O. When A is treated with
NaOH followed by acid hydrolysis, it gives two products, B and C. When B oxidized,
it gives A. Chloro derivatives of (C) formed when C react with PCl5. The compound
on treatment with ammonia gives (D) which with Br2 and KOH gives aniline. Identify
A to D.

6. An organic compound (A) on treatment with aq. KCN produces compound (B).
Compound (B) on reduction with Na/C2H5OH gives compound (C) with molecular
formula C2H7N. Compound (C) reacts with NaNO2 and HCl to form compound (D).
Compound (D) on treatment with acetic acid in presence of conc. H2SO4 produces a
sweet smelling compound (E).
(i) Identify the compounds (A) to (E).
(ii) Name the reaction for the formation of compound (E) from compound (D).

7. An organic compound (A) having molecular formula C6H6O gives a characteristic

colour with aqueous FeCl3 solution. (A) on treatment with CO2 and NaOH at 400K
 under pressure gives [B] which on acidification gives compound (C). (C) reacts with
acetyl chloride to give (D) which is a popular pain killer.
Identify the compounds (A), (B), (C) and (D).

8. An organic compound with the molecular formula C7H6O gets oxidised by Tollens'
reagent. It does not respond to Fehling test but can undergo the Cannizzaro reaction.
Identify the compound. Show how you used the above information to identify the
compound.

9. An organic compound (A) which has characteristic odour, on treatment with NaOH
forms two compounds (B) and (C). Compound (B) has molecular formula C7H8O
which on oxidation gives
back (A). The compound (C) is a sodium salt of an acid. When (C) is treated with soda
lime, it yields an aromatic hydrocarbon D.
(i) Deduce the structures of (A), (B), (C) and (D). Write the sequence of reactions
involved.
(ii) How will you convert the compound (D) to benzoic acid?

10. An organic compound (A) with molecular formula C4H8O2 was hydrolysed with dil.
H2SO4 to give a carboxylic acid (B) and an alcohol (C). (C) on dehydration gives
ethene and (C) also on oxidation gives back (B). Identify (A), (B) and (C) and write
the chemical equations for the reactions involved.

11. An organic compound (A) with molecular formula C 5H10O does addition compound
with NaHSO3 and gives positive iodoform test on heating with NaOH in the presence
of I2. On vigorous oxidation, it gives ethanoic and propanoic acid. Write
(i) The possible structure of the compound.
(ii) The IUPAC name of the compound.
(iii) The reaction of (A) with NaHSO3.

12. Primary alkyl halide (A), C4H9Br reacted with alcoholic KOH to give compound (B).
Compound (B) when reacted with HBr gives (C) which is an isomer of (A). When (A)
was reacted with sodium metal it gave a compound (D), C8H18 that was different
from the compound obtained when n-butyl bromide was reacted with sodium metal.
Give the structures of (A), (B), (C) and (D).

13. A Compound (A) with molecular formula C4H10O on oxidation forms a compound (B)
with molecular formula C4H8O2 which gives a positive iodoform test. The reaction of
(B) with CH3MgBr followed by acidic hydrolysis gives a compound with molecular
formula C5H12O. Identify (A), (B) and (C) and write the reactions.

14. A compound (A) with molecular formula C5H12O, on oxidation forms compound B
with molecular formula C5H10O. The compound (B) gives iodoform test, but does not
reduce ammonical silver nitrate (Tollen’s reagent). (B) on reduction with amalgamated
 Zn and HCl gives compound (C) with molecular formula C5H12. Identify (A) ,(B) and
(C). Write down the chemical reactions involved.

15. A and B are two functional isomers of compound C 3H6O. On heating with NaOH and
I2 isomer (A) forms yellow precipitate of iodoform whereas isomer B does not form
any precipitate. Write the formulae of A and B.

16. An aromatic compound (A) on heating with ammonia and cuprous oxide at high
pressure gave (B). (B) on treatment with ice cold water solution nitrite and HCl gas
(C). (C) heated with copper powder and HCl gas gave (A) gain. Identify the compound
(A), (B) and (C).

17. When bromobenzene is monochlorinated, two isomeric compounds (A) and (B) are
obtained. Monobromination of (A) gives several isomeric products of molecular
formula C6H3Br2Cl, while monobromination of (B) yields only two isomers (C) and
(D). Compound (C) is identical to one of the compounds obtained from the
bromination of (A). However, (D) is totally different from any of the isomeric
compounds obtained from the bromination of (A). Give the structures of (A), (B), (C)
and (D), and also the structures of the four isomeric monobrominated products of (A).

18. An aromatic compound (A) on treatment with CHCl3 and KOH gives (B) and (C).
Both B and C give the same product (D) when distilled with Zinc dust. Oxidation of D
gives E having molecular formula C7H6O2. The salt of (E) on heating with soda lime
gives F which may be obtained by distilling (A) with zinc dust. Identify A to F.

19. A hydrocarbon (A) on heating with conc. H2SO4 gives a sulphonic acid (B). Sodium
salt of (B) on fusion with NaOH followed by hydrolysis with dil. H2SO4 gave (C). (C)
is soluble in caustic alkali but insoluble in Na2CO3. Identify (A), (B) and (C).

20. A ketone (A) (C4H8O), which undergoes haloform reaction, gives compound (B) on
reduction. (B) on heating with sulphuric acid gives compounds (C) , which forms
mono-ozonide (D). (D) on hydrolysis in the presence of zinc dust gives only
acetaldehyde (E). Identify A, B, C, D and E. Write down the reaction involved.

21. An organic compound (A) of the formula C2H6O on heating with conc. H2SO4 at 413
K gives a neutral compound (B), C4H10O. The compound on treatment with KCN yield
a compound (C), C3H5N.The compound (C) on hydrolysis gives an acid C 3H6O2. What
are the compounds?