ORGANIC
1. Compound X(C6 H10) gave 2 - methalypenate when treated with H2 and Pd. When treated with acid solution of
mercury sulphate, it yielded C6H12O. Compound X did not react when ammoniacal CuCl or metallic sodium suggest
the structure of X.
2. An organic compound A with molecular formula C5H8 when treated with sodium in liquid ammonia followed by
treatment with n – propyl iodide yields C8H14(B). When treated with dilute sulphuric acid containing mercuric sulphate,
A gives the ketone C(C5H10O). On oxidation with alkanline potassium permanganate B gives two isomeric acids
C4H8O2(D and E). Identify the compounds A to E giving the reactions involved.
3. 0.218 g of thee acetyl derivative of a polydric alcohol (molar mass of alcohol is 92 g mol–1) requires 0.168 g KOH for
hydrolysis. Calculate the number of hydroxyl groups in the alcohol.
4. On careful reduction, A(C2H2) gives B(C2H4) which reacts with hydriodic acid to give C(C2H5I). A form a di-
Grignard derivative which reacts with compound C to give mainly D(C6H10). With dilute sulphuric acid containing
mercuric sulphate D gives E(C6H12O) which reacts with the Grignard derivative of C to give F(C8H18O). On oxidation
D gives G(C3H6O2) which gives an acid chloride H. The latter reacts with one molecule of the Grignard reagent from
C to give I (C5H10O). With two molecules of the same Grignard reagent from C to give J (C7H16O). Identify the
compounds A to J giving the reactions involved.
5. An organic compound A which is a neutral liquid is found to have molar mass of 216 g mol –1. Hydrolysis of the
compound A gives an acid B with equivalent mass of 80 g eq–1. B loses carbon dioxide wen heated and yields another
acid C with equivalent mass of 116 g eq–1. Decarboxylation of C by heating with sodalime yields a hydrocarbon
which is identified as n-pentane. Give the possible structures for A and B.
6. With bromine and caustic potash thee straight chain compound C4H9ON (A) gives C3H9N(B). With caustic soda, A
gives C4H7O2Na(C) and with phosphorus pentoxide, C4H7N(D). With hydrochloric acid, D gives C4H8O2(E) of
which C is the sodium salt. B may be converted to an alcohol (F) then to a halide. The Grignard reagent from the latter
reacts with carbon dioxide to give E. On oxidation F gives successively C3H6O(G) and C3H6O2(H). Identify the
compounds A to H.
7. 0.4 g of a sample of impure urea on treatment with alkaline sodium hypobromite gave 112.0 cm3 of nitrogen at STP.
Calculate the per cent purity of the sample off urea.
8. An organic compound A(C3H6Cl2) gives with alkali B(C3H6O) or C(C3H4). The compound B gives D (C5H12O) with
ethyl magnesium iodide. The compound D forms an iodide E. Thee compound C reacts with dilute sulphuric acid
containing mercuric sulphate to give F(C3H6O) which gives the salt G(C2H4O2) with bromine in alkali. The Grignard
reagent from E reacts with F to give H(C8H18O). Identify the compounds A to H giving the reactions involved.
9. An organic compound X contains 68.97% carbon, 14.94% hydrogen, the remaining being nitrogen. It reacts with
nitrous acid, producing a substance Y which does not contain nitrogen. Y on oxidation yields an acid Z whose ethyl
ester has the vapour density 65. X, Y and Z are optically active. Deduce the structures of X, Y and Z with adequate
interpretation.
10. An organic compound A of the formula C2H6O on treatment with concentrated H2SO4 gives a neutral compound B
(C4H10O). The latter on treatment with PCl5 gives a product which on subsequent treatment with KCN yields a
compound C(C3H5N). The compound C on hydrolysis gives an acid (C3H6O2) and on reduction with sodium amalgam
gives a base C3H9N. What are the compounds A, B and C? Also give the reactions involved.
11. The compound C8H9Cl(A) on treatment with KCN followed by hydrolysis gives C9H10O2(B). Ammonium slat of B
on dry distillation yields C which reacts with alkaline solution of bromine to give C8H11 N(D). Another compound
E(C8H10O)is obtained by the action of nitrous acid on D or by the action of aqueous potash on A. E on oxidation
gives F(C8H6O4) which gives the inner anhydride G on heating. Deduce the structures of A to G giving the reactions
involved.
12. An organic compound A(C7H6O2) forms a crystalline derivative with sodium bisulphite. When A is treated with cold
sodium hydroxide solution, two substances, the sodium salt of an acid B and C, a primary alcohol, are obtained, B
contains 60.9% carbon and 4.35% hydrogen and may also be obtained by oxidation of A. B when distilled with soda
lime gives phenol. C contains 67.75% carbon and 6.45% hydrogen and may be obtained by reducing A. Deduce the
structures A, B and C giving involved reactions.
13. A substance A shows the following composition : 70.6% carbon, 5.87% hydrogen and 23.5% oxygen. Its vapour
density is 68. A when treated with PCl5 and subsequently with NH3 gives a substance B. When reacted with Br2 and
KOH, B forms a base C which on diazotization and boiling with water gives o-cresol. What are A, B and C?
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1. Compound X(C6 H10) gave 2 - methalypenate when treated with H2 and Pd. When treated with acid solution of
mercury sulphate, it yielded C6H12O. Compound X did not react when ammoniacal CuCl or metallic sodium suggest
the structure of X.
2. An organic compound A with molecular formula C5H8 when treated with sodium in liquid ammonia followed by
treatment with n – propyl iodide yields C8H14(B). When treated with dilute sulphuric acid containing mercuric sulphate,
A gives the ketone C(C5H10O). On oxidation with alkanline potassium permanganate B gives two isomeric acids
C4H8O2(D and E). Identify the compounds A to E giving the reactions involved.
3. 0.218 g of thee acetyl derivative of a polydric alcohol (molar mass of alcohol is 92 g mol–1) requires 0.168 g KOH for
hydrolysis. Calculate the number of hydroxyl groups in the alcohol.
4. On careful reduction, A(C2H2) gives B(C2H4) which reacts with hydriodic acid to give C(C2H5I). A form a di-
Grignard derivative which reacts with compound C to give mainly D(C6H10). With dilute sulphuric acid containing
mercuric sulphate D gives E(C6H12O) which reacts with the Grignard derivative of C to give F(C8H18O). On oxidation
D gives G(C3H6O2) which gives an acid chloride H. The latter reacts with one molecule of the Grignard reagent from
C to give I (C5H10O). With two molecules of the same Grignard reagent from C to give J (C7H16O). Identify the
compounds A to J giving the reactions involved.
5. An organic compound A which is a neutral liquid is found to have molar mass of 216 g mol –1. Hydrolysis of the
compound A gives an acid B with equivalent mass of 80 g eq–1. B loses carbon dioxide wen heated and yields another
acid C with equivalent mass of 116 g eq–1. Decarboxylation of C by heating with sodalime yields a hydrocarbon
which is identified as n-pentane. Give the possible structures for A and B.
6. With bromine and caustic potash thee straight chain compound C4H9ON (A) gives C3H9N(B). With caustic soda, A
gives C4H7O2Na(C) and with phosphorus pentoxide, C4H7N(D). With hydrochloric acid, D gives C4H8O2(E) of
which C is the sodium salt. B may be converted to an alcohol (F) then to a halide. The Grignard reagent from the latter
reacts with carbon dioxide to give E. On oxidation F gives successively C3H6O(G) and C3H6O2(H). Identify the
compounds A to H.
7. 0.4 g of a sample of impure urea on treatment with alkaline sodium hypobromite gave 112.0 cm3 of nitrogen at STP.
Calculate the per cent purity of the sample off urea.
8. An organic compound A(C3H6Cl2) gives with alkali B(C3H6O) or C(C3H4). The compound B gives D (C5H12O) with
ethyl magnesium iodide. The compound D forms an iodide E. Thee compound C reacts with dilute sulphuric acid
containing mercuric sulphate to give F(C3H6O) which gives the salt G(C2H4O2) with bromine in alkali. The Grignard
reagent from E reacts with F to give H(C8H18O). Identify the compounds A to H giving the reactions involved.
9. An organic compound X contains 68.97% carbon, 14.94% hydrogen, the remaining being nitrogen. It reacts with
nitrous acid, producing a substance Y which does not contain nitrogen. Y on oxidation yields an acid Z whose ethyl
ester has the vapour density 65. X, Y and Z are optically active. Deduce the structures of X, Y and Z with adequate
interpretation.
10. An organic compound A of the formula C2H6O on treatment with concentrated H2SO4 gives a neutral compound B
(C4H10O). The latter on treatment with PCl5 gives a product which on subsequent treatment with KCN yields a
compound C(C3H5N). The compound C on hydrolysis gives an acid (C3H6O2) and on reduction with sodium amalgam
gives a base C3H9N. What are the compounds A, B and C? Also give the reactions involved.
11. The compound C8H9Cl(A) on treatment with KCN followed by hydrolysis gives C9H10O2(B). Ammonium slat of B
on dry distillation yields C which reacts with alkaline solution of bromine to give C8H11 N(D). Another compound
E(C8H10O)is obtained by the action of nitrous acid on D or by the action of aqueous potash on A. E on oxidation
gives F(C8H6O4) which gives the inner anhydride G on heating. Deduce the structures of A to G giving the reactions
involved.
12. An organic compound A(C7H6O2) forms a crystalline derivative with sodium bisulphite. When A is treated with cold
sodium hydroxide solution, two substances, the sodium salt of an acid B and C, a primary alcohol, are obtained, B
contains 60.9% carbon and 4.35% hydrogen and may also be obtained by oxidation of A. B when distilled with soda
lime gives phenol. C contains 67.75% carbon and 6.45% hydrogen and may be obtained by reducing A. Deduce the
structures A, B and C giving involved reactions.
13. A substance A shows the following composition : 70.6% carbon, 5.87% hydrogen and 23.5% oxygen. Its vapour
density is 68. A when treated with PCl5 and subsequently with NH3 gives a substance B. When reacted with Br2 and
KOH, B forms a base C which on diazotization and boiling with water gives o-cresol. What are A, B and C?
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