Medical University Entrance Examination (Bulgaria) · Organic Chemistry and Biomolecules

Oxygen and Nitrogen Containing Compounds

35 practice questions, each with the answer and an explanation.

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All 35 questions

  1. What product is formed by the controlled oxidation of a secondary alcohol (such as propan-2-ol) with acidified potassium dichromate?
  2. Which reagent distinguishes primary, secondary, and tertiary alcohols based on the rate of turbidity formation?
  3. Why is phenol significantly more acidic than cyclohexanol (pKa ~ 10 vs ~ 16)?
  4. What test distinguishes aldehydes from ketones by forming a bright silver mirror on the inner glass surface of the test tube?
  5. What reddish precipitate is formed when an aliphatic aldehyde is heated with Fehling's solution?
  6. Which structural feature is required for a compound to give a positive yellow precipitate in the iodoform (triiodomethane) test?
  7. What is the nucleophilic addition-elimination product formed when ethanal (acetaldehyde) reacts with hydroxylamine (NH2OH)?
  8. What reagents are employed in the Fischer esterification of ethanoic acid with ethanol to produce ethyl ethanoate?
  9. What is the order of acid strength among ethanoic acid, chloroethanoic acid, and trichloroethanoic acid?
  10. Which carboxylic acid derivative exhibits the greatest reactivity toward nucleophilic acyl substitution?
  11. What process converts animal fats (triglycerides) into glycerol and soap (fatty acid sodium salts) using aqueous sodium hydroxide?
  12. Why is ethylamine a stronger base than aniline in aqueous solution?
  13. What salt is formed when primary aromatic amines such as aniline react with nitrous acid (NaNO2 + HCl) at 0 to 5 degrees Celsius?
  14. What is the product formed when ethanal reacts with hydrogen cyanide (HCN) in the presence of a trace base catalyst?
  15. What reaction occurs when benzaldehyde is heated with concentrated sodium hydroxide in the absence of alpha-hydrogens?
  16. What type of product is formed by self-condensation of ethanal in dilute aqueous sodium hydroxide followed by heating?
  17. Which reagent selectively reduces ketones to secondary alcohols without reducing carbon-carbon double bonds?
  18. What type of chemical bond connects the two acetyl groups in acetic anhydride?
  19. What is the IUPAC name for the carboxylic acid with formula CH3-CH(OH)-COOH?
  20. Which compound reacts with neutral iron(III) chloride solution to produce an intense violet coloration?
  21. What is formed when diethyl ether is heated with excess concentrated hydroiodic acid (HI)?
  22. What product is obtained by the reaction of benzoyl chloride with anhydrous ammonia?
  23. Which functional group is characterized by the presence of a carbon atom triply bonded to a nitrogen atom (-C#N)?
  24. Why does methanoic acid (formic acid, HCOOH) reduce Tollens' reagent and Fehling's solution, unlike all other carboxylic acids?
  25. What is the common name of the aromatic dicarboxylic acid with carboxyl groups on adjacent ring carbons (1,2-benzenedicarboxylic acid)?
  26. What type of amine is trimethylamine ((CH3)3N)?
  27. What is the product formed when an aldehyde reacts with one equivalent of an alcohol in the presence of an acid catalyst?
  28. What type of chemical reaction converts an amide into an amine with one less carbon atom using bromine and sodium hydroxide?
  29. What chemical compound is produced when salicylic acid (2-hydroxybenzoic acid) is acetylated with acetic anhydride?
  30. What is the IUPAC name for the simplest ketone, commonly known as acetone?
  31. Why do carboxylic acids have higher boiling points than alcohols of comparable molar mass?
  32. Which reaction reduces a nitro group (-NO2) on an aromatic ring to a primary amine (-NH2)?
  33. What is the product of the catalytic hydration of ethyne (acetylene) in dilute sulfuric acid with mercury(II) sulfate at 60 degrees Celsius?
  34. What type of bond is formed when the amino group of one molecule reacts with the carboxyl group of another with loss of water?
  35. What reagent converts a carboxylic acid directly into an acyl chloride (acid chloride)?

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