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

Hydrocarbons and Functional Groups

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

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  1. What is the IUPAC name of the branched alkane with structural formula (CH3)2CH-CH2-CH(CH3)2?
  2. What type of isomerism is demonstrated by butane and 2-methylpropane (isobutane)?
  3. What is the most stable conformation of cyclohexane at room temperature due to minimized torsional and steric strain?
  4. Which step in the free-radical chlorination of methane generates chlorine radicals by homolytic cleavage of Cl2?
  5. According to Markovnikov's rule, what major product is formed when propene reacts with hydrogen bromide (HBr)?
  6. Why does addition of hydrogen bromide to propene in the presence of benzoyl peroxide yield 1-bromopropane as the major product?
  7. What type of reaction converts an alkene to a vicinal diol using cold dilute alkaline potassium permanganate (Baeyer's reagent)?
  8. What is the molecular geometry and hybridization of the two carbons in ethyne (acetylene, C2H2)?
  9. Why is the hydrogen atom in terminal alkynes (such as propyne) significantly more acidic than in alkenes or alkanes?
  10. According to Huckel's rule, what criteria must a monocyclic planar conjugated ring meet to be aromatic?
  11. Why does benzene undergo electrophilic aromatic substitution rather than electrophilic addition across its double bonds?
  12. What electrophile is generated in the nitration of benzene by a mixture of concentrated nitric and sulfuric acids?
  13. How does a hydroxyl substituent (-OH) on a benzene ring influence further electrophilic aromatic substitution?
  14. Which substituent on a benzene ring is strongly deactivating and directs incoming electrophiles exclusively to the meta position?
  15. Which mechanism describes the nucleophilic substitution of primary bromoethane with aqueous sodium hydroxide?
  16. Why do tertiary alkyl halides such as 2-bromo-2-methylpropane undergo substitution primarily via the SN1 mechanism?
  17. What is the stereochemical outcome of an SN1 reaction occurring at a single chiral center?
  18. According to Zaitsev's rule, what is the major alkene formed during the base-induced E2 elimination of 2-bromobutane?
  19. What is the relationship between two stereoisomers that are non-superimposable mirror images of each other?
  20. What is the term for a molecule that contains chiral carbon centers but is achiral overall due to an internal plane of symmetry?
  21. How many stereoisomers can exist for a molecule containing three non-identical chiral stereocenters according to the 2^n rule?
  22. What reagent is used to distinguish terminal alkynes (containing a -C#C-H group) from non-terminal alkynes via formation of a reddish-brown precipitate?
  23. What product is formed by catalytic hydrogenation of 2-butyne over Lindlar's palladium catalyst?
  24. Which compound is classified as a six-membered aromatic heterocycle containing a tertiary ring nitrogen whose lone pair resides in an sp2 hybrid orbital outside the aromatic pi system?
  25. What is the Cahn-Ingold-Prelog (CIP) priority order for the following substituents: -OH, -CH3, -H, -COOH?
  26. What type of constitutional isomerism exists between propan-1-ol and propan-2-ol?
  27. What is the functional group present in an organic molecule with the general structure R-O-R'?
  28. Which organic reaction mechanism converts benzene into bromobenzene in the presence of iron(III) bromide catalyst?
  29. What gas is evolved when calcium carbide (CaC2) reacts with water at room temperature?
  30. Which compound is antiaromatic because it is planar, fully conjugated, and contains 4n pi electrons (n = 1)?
  31. What product is obtained when an alkene is treated with ozone followed by reductive workup with dimethyl sulfide (Zn/H2O)?
  32. Why is trans-1,2-dimethylcyclohexane more thermodynamically stable than cis-1,2-dimethylcyclohexane in its chair conformation?
  33. What is the IUPAC name for the compound CH3-C(CH3)=CH-CH3?
  34. What type of reagent is a Grignard reagent (R-Mg-X) in organic synthesis?
  35. Which reaction produces an alkane by coupling two molecules of alkyl halide using metallic sodium in dry ether?

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