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ADVANCED LEVEL

1. There are six different alkenes (A), (B), (C), (D), (E) and (F). Each on addition of one mole of
hydrogen gives (G) which is the lowest molecular weight hydrocarbon containing only one
asymmetric carbon atom. None of the above alkenes gives acetone as a product on ozonolysis.
Give the structures of (A), (B), (C), (D), (E) and (F). Identify the alkene which is likely to give a
ketone containing more than five carbon atoms on treatment with a warm concentrated solution of
alkaline KMnO4.

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2. An organic compound (A) of molecular formula C5H8 when treated with sodium in liquid ammonia
followed by reaction with n-propyl iodide yields (B), C 8H14. (A) gives a ketone (C), C 5H10O, when
treated with dilute H2SO4 and HgSO4. (B) on oxidation with alkaline KMnO 4 gives two isomeric acids
(D) and (E), C4H8O2. Give structure of compounds (A) to (E) with proper reasoning.

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3.

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4.

Identify A to F.

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5. An organic compound A of m.f. C2H4 was treated with an acid in presence of liquid benzene to give a
compound B. Cl2 gas was bubbled through a solution of B and was irradiated. This yielded C.
Elemental analysis of C confirmed the presence of only one halogen atom. C was dissolved in
C2H5OH and a few NaOH pellets were added. This reaction gave a compound D. D when treated
with Br2/CCl4 gave a colourless liquid and the colourless liquid on treatment with NaNH 2/liq. NH3
gave E. Identify A to E.

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6. Write the structures of the compounds from the following data.

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7. Arrange the following in decreasing order of reactivity towards ring nitration.

a) benzene, mesitylene (1,3,5, -C6H3(CH3)3), toluene, m-xylene, p-xylene.
b) benzene, bromobenzene, nitrobenzene, toluene.
c) acetanilide, acetophenone, aniline, benzene.
d) terephthalic acid, toluene, p-toluic acid, p-xylene.

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8. Outline the separation by chemical methods of a mixture of p-cresol, p-toluic acid, p-toluidine and p-
nitrotoluene. Show with the help of a chart.

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9. A compound A, C14H10N2O, when heated with dilute sulphuric acid gave ammonium sulphate, a
compound B, C8H6O4, and a compound C, C6H7N (as its sulphate). Compounds B and C behaved
as follows:

Suggest a formula for A and account for the above reactions.

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10. An unknown compound (A) contained chlorine and nitrogen. It dissolved readily in water to give a
solution that turned litmus red. Titration of (A) with standard base gave a neutralization equivalent of
131+2. When a sample of (A) was treated with aqueous NaOH a liquid separated; it contained
nitrogen but no chlorine. Treatment of the liquid with nitrous acid followed by alkaline b-naphthol
gave a red precipitate. What is A?

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11. An unsaturated hydrocarbon (A) C5H10 reacts with HBr to yield a compound (B) containing 53% of
bromine. (B) on treatment with alcoholic KOH gives (C); a compound isomeric with (A). On oxidation
of (C) by ozone and followed by hydrolysis gives acetone and acetaldehyde. Identify (A) to (C).

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12. A certain hydrocarbon (A) was found to contain 85.7% carbon, 14.3% hydrogen. This compound
consumes one molar equivalent of hydrogen to give a saturated hydrocarbon (B). 1gm of
hydrocarbon (A) just decolourised 38.05gm of 5% solution (by weight) of Br 2 in CCl4. Compound (A)
on oxidation with concentrated KMnO4 gave compound (C) molecular formula C4H8O and acetic
acid. Compound (C) could easily be prepared by the action of acidic aqueous mercuric sulphate on
2-butyne. Determine the molecular formula of (A) and deduce the structure of (A), (B) and (C).

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13. An organic compound (X) on analysis gives 24.24% carbon and 4.04% hydrogen. Further sodium
extract of 1.0gm of (X) gives 2.90gm of AgCl with acidified AgNO 3 solution. The compound (X) may
be presented by two isomeric structures of (Y) and (Z), (Y) on treatment with aqueous potassium
hydroxide gives a dihydroxy compound; while (Z) on similar treatment gives ethanal. Find the
molecular formulae of (X) and give the structure of (Y) and (Z).

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14. One mole hydrocarbon (A) reacts with one mole of bromine giving a dibromo compound C5H10Br2.
Substance (A) on treatment with cold dilute KMnO4 solution in alkaline medium forms a compound
C5H12O2. On ozonalysis (A) gives equimolar quantities of ethanal and propanone. Deduce the
structural formula of (A).

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15. A pure hydro-carbon of formula C3H6 decolourises bromine water and yields propane on
hydrogenation. On ozonalysis it gives formaldehyde and acetaldehyde. What is its structure?

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16. Silver salt of unknown alkyne contain 67.08% of silver. Assuming no other functional group present.
What is the structure of alkyne?

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17. An alkene (A) on ozonalysis yields acetone and aldehyde. The aldehyde is easily oxidised to an acid
(B). When (B) is treated with Br2 in presence of phosphorus it yields compound (C), which on
hydrolysis gives a hydroxyl acid (D). This acid can also be obtained from acetone by the reaction
with hydrogen cyanide followed by hydrolysis. Identify the compounds (A), (B), (C) and (D).

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18. (A) organic compound having molecular formula C5H10 on treatment with hydrobromic acid in
absence of peroxide gives a compound C5H11Br (B). (B) on alkali treatment gives a tertiary alcohol
(C). (A) on ozonalysis give acetone, acetaldehyde and acetic acid. Identify (A), (B) and (C), give
reactions.

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19. A chloro compound (A) showed the following properties:

(i) Decolourised Br2 is CCl4
(ii) Absorbed hydrogen catalytically
(iii) Gave a precipitate with ammonical cuprous chloride
(iv) when vapourised, 1.49gm of (A) gave 448 ml of vapour at STP.
Identify (A) and write down the equation of reaction at step (iii).

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20. An unsaturated hydrocarbon (A), C6H10 readily gives (B) on treatment with NaNH 2 in liquid NH3.
When (B) is allowed to react with 1-chloropropane a compound (C) is obtained. On partial,
hydrogenation in the presence of Lindlar catalyst (C) gives (D) C 9H18. On ozonalysis, (D) gives 2,2–
dimethyl propanal and 1–butanal. With proper reasoning give the structures of (A), (B), (C) and (D).

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21. A white precipitate was formed slowly when silver nitrate was added to a compound (A) with
molecular formula C6H13Cl. Compound (A) on treatment with hot alcoholic KOH gave a mixture of
two isomeric alkenes (B) and (C) having formula C6H12. The mixture of (B) and (C) on ozonalysis
furnished four compounds:
(i) CH3CHO (ii) C2H5CHO
(iii) CH3 – CO – CH3 and (iv) (CH3)2CHCHO
Identify the compounds (A),(B) and (C).

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22. Two compounds (A) and (B) on combustion analysis gave C = 88.82%, H = 11.18%. Both
decolourises Br2 in CCl4 solution. Compound (A) gives a precipitate with ammonical AgNO 3 and
oxidises to CO2 and propionic acid. Compound (B) does not give a ppt. with ammonical AgNO 3 and
oxidises to CO2 and oxalic acid. Write down the structural formula of (A) and (B).

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23. An unsaturated hydrocarbon (A) on hydration gave alcohol (B). Oxidation of (B) gave a ketone (C)
when the hydrocarbon (A) was submitted to ozonolysis it gave formaldehyde and propionaldehyde.
What formula would you assign to A, B and C. Give the reactions involved.

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24. A volatile organic compound contains 10% carbon; 0.84% hydrogen and 89.21% chlorine. In Victor
Mayer and method 0.6gm of the substance displaces 112cc of air at NTP. Find out the molecular
formula and name of the compound.

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25. An organic compound (A) having carbon and hydrogen, adds on mole of hydrogen in the presence
of platinum catalyst to form n–hexane. On vigorous oxidation with KMnO 4 it gives a single carboxylic
acid containing three carbon atoms. Assign structure to the compound (A).

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26. An organic compound of formula C6H12 absorbs one molecule of Br2 to give C6H12Br2. On reduction it
gives 2-methyl pentane, while on oxidation it yields a mixture of acetic and isobutyric acid. Derive the
structural formula of the compound and give its IUPAC name.

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27. Deduce the structural formula of a compound of molecular formula C6H10 which (i) adds 2 moles of H
to form 2-methyl pentane (ii) forms carbonyl compound in aqueous H2SO4 + HgSO4 solution and (iii)
does not react with ammonical AgNO3 solution.

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28. A hydrocarbon of the formula C8H12 adds 2 moles of H2 per mole of the hydrocarbon. It undergoes
reductive ozonalysis give 2 moles of butan-l, 4-dial. Deduce the structure of the hydrocarbon.

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29. In the study of chlorination of propane, four products (A. B, C, and D) of the formula C 3H6Cl2 were
isolated. Each was further chlorinated to provide trichloro products C 3H5Cl3. It was found that (A)
provided one trichloro products, (B) gave two and (C), (D) gave three trichloro products. What are
the structural formulae of (A), (B), (C) and (D)?

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30. A dihalogen derivative (A) of a hydrocarbon having two carbon atoms react with alcoholic potash
and forms another hydrocarbon which gives red precipitate with ammonical cuprous chloride.
Compound (A) gives an aldehyde when treated with aqueous KOH. Give the structure of the organic
compound.

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