10.

21 Primary alkyl halide C4H9Br (a) reacted with alcoholic KOH to give compound
(b). Compound (b) is reacted with HBr to give (c) which is an isomer of (a). When
(a)
a) is reacted with sodium metal it gives compound (d) H which is different
8 18

from the compound formed when n-butyl bromide is reacted with sodium.
Give the structural formula of (a) and write the equations for all the reactions.

12.10 An organic compound with the molecular formula C9H10O forms 2,4-DNP derivative,
reduces Tollens’ reagent and undergoes Cannizzaro reaction. On vigorous oxidation,
it gives 1,2-benzenedicarboxylic acid. Identify the compound.
12.11 An organic compound (A) (molecular formula C8H16O2) was hydrolysed with
dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation
of (C) with chromic acid produced (B). (C) on dehydration gives but-1-ene.
Write equations for the reactions involved.
12.19 An organic compound contains 69.77% carbon, 11.63% hydrogen and rest oxygen.
The molecular mass of the compound is 86. It does not reduce Tollens’ reagent
but forms an addition compound with sodium hydrogensulphite and give positive
iodoform test. On vigorous oxidation it gives ethanoic and propanoic acid. Write
the possible structure of the compound.
13.10 An aromatic compound ‘A’ on treatment with aqueous ammonia and heating
forms compound ‘B’ which on heating with Br2 and KOH forms a compound ‘C’
of molecular formula C6H7N. Write the structures and IUPAC names of compounds
A, B and C.

29. Compound ‘A’ was prepared by oxidation of compound ‘B’ with alkaline KMnO4. Compound ‘A’ on reduction with
lithium aluminium hydride gets converted back to compound ‘B’. When compound ‘A’ is heated with compound B in the
presence of H2SO4 it produces fruity smell of compound C to which family the compounds ‘A’, ‘B’ and ‘C’ belong to?

47. An alkene ‘A’ (Mol. formula C5H10) on ozonolysis gives a mixture of two
compounds ‘B’ and ‘C’. Compound ‘B’ gives positive Fehling’s test and also
forms iodoform on treatment with I2 and NaOH. Compound ‘C’ does not give
Fehling’s test but forms iodoform. Identify the compounds A, B and C. Write
the reaction for ozonolysis and formation of iodoform from B and C.
48. An aromatic compound ‘A’ (Molecular formula C8H 8O) gives positive
2, 4-DNP test. It gives a yellow precipitate of compound ‘B’ on treatment with
iodine and sodium hydroxide solution. Compound ‘A’ does not give Tollen’s
or Fehling’s test. On drastic oxidation with potassium permanganate it forms
a carboxylic acid ‘C’ (Molecular formula C7H6O2), which is also formed along
with the yellow compound in the above reaction. Identify A, B and C and
write all the reactions involved.
49. Write down functional isomers of a carbonyl compound with molecular
formula C3H6O. Which isomer will react faster with HCN and why? Explain
the mechanism of the reaction also. Will the reaction lead to the completion
with the conversion of whole reactant into product at reaction conditions? If a
strong acid is added to the reaction mixture what will be the effect on
concentration of the product and why?
50. When liquid ‘A’ is treated with a freshly prepared ammoniacal silver nitrate
solution, it gives bright silver mirror. The liquid forms a white crystalline solid
on treatment with sodium hydrogensulphite. Liquid ‘B’ also forms a white
crystalline solid with sodium hydrogensulphite but it does not give test with
ammoniacal silver nitrate. Which of the two liquids is aldehyde? Write the
chemical equations of these reactions also.
75. A hydrocarbon ‘A’, (C4H8) on reaction with HCl gives a compound ‘B’, (C4H9Cl),
which on reaction with 1 mol of NH3 gives compound ‘C’, (C4H11N). On reacting
with NaNO2 and HCl followed by treatment with water, compound ‘C’ yields
an optically active alcohol, ‘D’. Ozonolysis of ‘A’ gives 2 mols of acetaldehyde.
Identify compounds ‘A’ to ‘D’. Explain the reactions involved.
76. A colourless substance ‘A’ (C6H7N) is sparingly soluble in water and gives a
water soluble compound ‘B’ on treating with mineral acid. On reacting with
CHCl3 and alcoholic potash ‘A’ produces an obnoxious smell due to the
formation of compound ‘C’. Reaction of ‘A’ with benzenesulphonyl chloride
gives compound ‘D’ which is soluble in alkali. With NaNO2 and HCl, ‘A’ forms
compound ‘E’ which reacts with phenol in alkaline medium to give an orange
dye ‘F’. Identify compounds ‘A’ to ‘F’.
77. Predict the reagent or the product in the following reaction sequence.

55. Compound ‘A’ with molecular formula C4H9Br is treated with aq. KOH solution. The rate of this reaction
depends upon the concentration of the compound ‘A’ only. When another optically active isomer ‘B’ of this
compound was treated with aq. KOH solution, the rate of reaction was found to be dependent on concentration of
compound and KOH both.
(i) Write down the structural formula of both compounds ‘A’ and ‘B’.
(ii) Out of these two compounds, which one will be converted to the product with inverted configuration

An organic compound 'A' on treatment with ethyl alcohol gives carboxylic acid 'B' compound 'C'.
Hydrolysis of 'C' under acidic condition gives 'B' and 'D'. oxidation of 'D' with KMnO4 also gives 'B'.
'B' on heating with Ca(OH)2 gives 'E' with molecular formula C3H6O. 'E' does not give Tollen's or
Fehling test but forms 2,4 - dinitrophenyl hydrazine. Identify A, B, C, D and E.
(iii)
(iv)
(v) An organic compound [A] having molecular formula C2H7N on treatment with nitrous acid gives a
compound [B] having molecular formula C2H6O. [B] on treatment with an organic compound [C]
gives a carboxylic acid [D] and a sweet smelling compound [E]. Oxidation of [B] with acidified
potassium dichromate also gives [D]
(vi) Identify [A],[B],[C],[D] and [E]
(vii) An organic compound A with molecular formula C2H7N on reaction with nitrous acid gives a
compound B. B on controlled gives compound C. C reduces Tollen's reagent to given silver mirror
and D. B reacts with D in the presence of concentrated sulphuric acid to give sweet smelling
compound E. Identify A,B,C,D and E. Give the reaction of C with ammonia?
(viii) An organic compound A (molecular formula C2H4O2) reacts with Na metal to form a compound B
and evolves a gas which burns with a pop sound. Compound A on treatment with an alcohol C in the
presence of a little of concentrated sulphuric acid forms a sweet-smelling compound D (molecular
formula C3H6O2). Compound D on treatment with NaOH solution gives back B and C. Identify A,
B, C and D.
(ix) .