ECAT — Engineering College Admission Test (UET)

ECAT Chemistry — Organic Chemistry: Hydrocarbons to Carbonyls (Set 2)

Take the ECAT Chemistry — Organic Chemistry: Hydrocarbons to Carbonyls (Set 2): 30 multiple-choice questions (40 minutes) with instant scoring and a full…

What this test covers

Sample questions with answers

The first 5 questions of this test, with the correct answer and explanation.

  1. Q1. The IUPAC name of CH₃–CH=C(CH₃)–CH₃ is:

    • A. pent-2-ene
    • B. 2-methylbut-3-ene
    • C. 3-methylbut-2-ene
    • D. 2-methylbut-2-ene ✓

    Answer: D. 2-methylbut-2-ene

    Explanation: Number the 4-carbon chain from the end nearer the double bond: the C=C starts at C-2 and the methyl group is on C-2.

  2. Q2. How many structural isomers of C₄H₁₀O are alcohols?

    • A. 4 ✓
    • B. 2
    • C. 3
    • D. 7

    Answer: A. 4

    Explanation: Butan-1-ol, butan-2-ol, 2-methylpropan-1-ol and 2-methylpropan-2-ol. (The other three C₄H₁₀O isomers are ethers.)

  3. Q3. Cis-but-2-ene and trans-but-2-ene do not interconvert at room temperature because:

    • A. They are optical isomers
    • B. The C–C single bonds cannot rotate
    • C. Rotation about the C=C bond would require breaking the π bond ✓
    • D. They have different molecular formulae

    Answer: C. Rotation about the C=C bond would require breaking the π bond

    Explanation: The π bond is formed by sideways overlap of parallel p orbitals; twisting the molecule would destroy this overlap, which needs about 250 kJ mol⁻¹.

  4. Q4. How many structural isomers are possible for dichlorobenzene, C₆H₄Cl₂?

    • A. 3 ✓
    • B. 6
    • C. 2
    • D. 4

    Answer: A. 3

    Explanation: The two Cl atoms can be 1,2 (ortho), 1,3 (meta) or 1,4 (para).

  5. Q5. What volume of oxygen is needed for the complete combustion of 2 dm³ of propane, measured at the same temperature and pressure?

    • A. 7 dm³
    • B. 10 dm³ ✓
    • C. 5 dm³
    • D. 6 dm³

    Answer: B. 10 dm³

    Explanation: C₃H₈ + 5O₂ → 3CO₂ + 4H₂O; by Gay-Lussac's law 2 dm³ propane needs 2 × 5 = 10 dm³ O₂.

The other 25 questions

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  1. Q6. A mixture of CH₃Br and C₂H₅Br is treated with sodium in dry ether (Wurtz reaction). The alkanes formed are:

    • A. Ethane, propane and butane
    • B. Ethane and butane only
    • C. Methane and ethane
    • D. Propane only
  2. Q7. Heating sodium propanoate (CH₃CH₂COONa) with soda lime gives:

    • A. Ethane
    • B. Methane
    • C. Ethene
    • D. Propane
  3. Q8. 2-Bromobutane is heated with alcoholic KOH. According to Saytzeff's rule, the major product is:

    • A. But-2-ene
    • B. Butane
    • C. But-1-ene
    • D. Butan-2-ol
  4. Q9. Ethanol heated with excess concentrated H₂SO₄ at about 170°C gives mainly:

    • A. Ethyl hydrogen sulphate only
    • B. Ethene
    • C. Ethanal
    • D. Diethyl ether
  5. Q10. Alkenes are converted to alkanes by hydrogen gas in the presence of finely divided nickel at about 250°C. This is called:

    • A. Friedel–Crafts reaction
    • B. Sabatier–Senderens reaction
    • C. Kolbe's reaction
    • D. Wurtz reaction
  6. Q11. What mass of bromine adds completely to 14 g of ethene (C₂H₄ + Br₂ → C₂H₄Br₂; Br = 80)?

    • A. 40 g
    • B. 160 g
    • C. 80 g
    • D. 28 g
  7. Q12. Ethyne is prepared in the laboratory by the action of water on:

    • A. Aluminium carbide
    • B. Sodium ethanoate
    • C. Calcium carbonate
    • D. Calcium carbide
  8. Q13. Ethyne is more acidic than ethene and ethane because:

    • A. Its carbon atoms are sp hybridized with 50% s-character, holding the C–H electrons closer
    • B. It has more hydrogen atoms
    • C. It contains no π bonds
    • D. It is a polar molecule
  9. Q14. When ethyne is passed through a red-hot iron tube, three molecules combine to give:

    • A. Vinylacetylene
    • B. Cyclohexane
    • C. Benzene
    • D. Hexane
  10. Q15. When benzene is treated with chlorine in bright sunlight in the absence of a catalyst, the product is:

    • A. Benzyl chloride
    • B. 1,4-dichlorobenzene
    • C. Chlorobenzene
    • D. Benzene hexachloride, C₆H₆Cl₆
  11. Q16. In the nitration of benzene with a mixture of concentrated HNO₃ and H₂SO₄, the electrophile is:

    • A. NO₃⁻
    • B. NO₂⁺
    • C. NO₂⁻
    • D. H₂SO₄
  12. Q17. Toluene is heated with alkaline KMnO₄ and then acidified. The organic product is:

    • A. Benzaldehyde
    • B. Benzoic acid
    • C. Phenol
    • D. Benzyl alcohol
  13. Q18. Chlorine is passed into boiling toluene in sunlight without a catalyst. The main product is:

    • A. Chlorobenzene
    • B. o-Chlorotoluene
    • C. Benzyl chloride, C₆H₅CH₂Cl
    • D. p-Chlorotoluene
  14. Q19. The reactivity of alkyl halides towards nucleophilic substitution is in the order R–I > R–Br > R–Cl > R–F because:

    • A. The C–X bond strength increases from C–I to C–F
    • B. Polarity of the C–X bond increases from I to F
    • C. Iodides are the most polar
    • D. Fluorine is the largest halogen
  15. Q20. Ethyl bromide reacts with aqueous KOH and with alcoholic KOH. The main products are respectively:

    • A. Ethanol and ethene
    • B. Ethane and ethene
    • C. Ethanol in both cases
    • D. Ethene and ethanol
  16. Q21. Which alkyl halide undergoes SN1 reaction most rapidly?

    • A. CH₃CH₂Br
    • B. (CH₃)₂CHBr
    • C. (CH₃)₃CBr
    • D. CH₃Br
  17. Q22. To prepare propan-1-ol using a Grignard reagent, ethylmagnesium bromide should be treated with ______ followed by acid hydrolysis.

    • A. Propanone
    • B. Ethanal
    • C. Carbon dioxide
    • D. Methanal
  18. Q23. In the fermentation of glucose to ethanol, the enzyme that converts glucose into ethanol and CO₂ is:

    • A. Invertase
    • B. Zymase
    • C. Maltase
    • D. Diastase
  19. Q24. Phenol dissolves in aqueous NaOH but does not liberate CO₂ from aqueous NaHCO₃. This shows that phenol is:

    • A. A base
    • B. A stronger acid than carbonic acid
    • C. A weaker acid than carbonic acid but acidic enough to react with a strong base
    • D. Neutral
  20. Q25. Which reagent can be used to distinguish phenol from ethanol?

    • A. Concentrated H₂SO₄
    • B. Sodium metal
    • C. Neutral FeCl₃ solution, which gives a violet colour with phenol
    • D. Water
  21. Q26. An aldehyde, but not a ketone, reduces Fehling's solution on warming to give a red precipitate of:

    • A. Cu(OH)₂
    • B. Cu
    • C. Cu₂O
    • D. CuO
  22. Q27. Which carbonyl compound is the most reactive towards nucleophilic addition?

    • A. Ethanal
    • B. Butanone
    • C. Methanal
    • D. Propanone
  23. Q28. Reduction of propanone with NaBH₄ (or H₂/Ni) gives:

    • A. Propan-2-ol
    • B. Propan-1-ol
    • C. Propane
    • D. Propanal
  24. Q29. Ketones are generally prepared in the laboratory by the oxidation of:

    • A. Alkanes with KMnO₄
    • B. Tertiary alcohols
    • C. Secondary alcohols
    • D. Primary alcohols
  25. Q30. A hydrocarbon of molar mass 42 g mol⁻¹ decolourizes bromine water. Its molecular formula is:

    • A. C₃H₄
    • B. C₂H₆
    • C. C₃H₆
    • D. C₃H₈