Reaction Mechanisms: Substitution, Addition, Elimination - Numerical Applications

Q. In an SN2 reaction, which of the following substrates would react the fastest with a nucleophile?
  • A. tert-butyl chloride
  • B. isopropyl bromide
  • C. ethyl chloride
  • D. methyl iodide
Q. In the reaction of benzene with bromine in the presence of FeBr3, what type of reaction occurs?
  • A. Electrophilic substitution
  • B. Nucleophilic substitution
  • C. Addition
  • D. Elimination
Q. What is the expected product when 2-bromo-2-methylpropane reacts with a strong base in a bimolecular elimination reaction?
  • A. 2-methylpropene
  • B. 2-bromopropane
  • C. 2-methyl-2-bromopropane
  • D. Propane
Q. What is the IUPAC name for the compound with the formula CH3-CH2-CH(Cl)-CH3?
  • A. 1-chlorobutane
  • B. 2-chlorobutane
  • C. 3-chlorobutane
  • D. butyl chloride
Q. What is the IUPAC name of the compound with the formula C4H9Br?
  • A. 1-bromobutane
  • B. 2-bromobutane
  • C. 1-bromo-2-methylpropane
  • D. 2-bromo-2-methylpropane
Q. What is the major product of the reaction of 1-pentene with H2 in the presence of a palladium catalyst?
  • A. Pentane
  • B. 1-pentanol
  • C. 2-pentanol
  • D. Cyclopentane
Q. What is the product of the reaction between ethene and HBr?
  • A. Bromoethane
  • B. Ethyl bromide
  • C. 1-bromopropane
  • D. 2-bromopropane
Q. What is the product of the reaction of 1-chloropropane with potassium thiocyanate?
  • A. propyl thiocyanate
  • B. propyl isothiocyanate
  • C. 1-thiocyanatopropane
  • D. no reaction
Q. What is the stereochemical outcome of the SN2 reaction of (R)-2-bromobutane with sodium iodide?
  • A. (R)-2-iodobutane
  • B. (S)-2-iodobutane
  • C. (R)-2-bromobutane
  • D. (S)-2-bromobutane
Q. What type of reaction occurs when 2-bromobutane reacts with sodium ethoxide?
  • A. SN1
  • B. SN2
  • C. E1
  • D. E2
Q. Which mechanism is likely to occur when 2-bromo-2-methylpropane reacts with a strong nucleophile?
  • A. SN1
  • B. SN2
  • C. E1
  • D. E2
Q. Which of the following compounds is most likely to undergo an E1 reaction?
  • A. 1-bromobutane
  • B. 2-bromobutane
  • C. 3-bromobutane
  • D. 1-bromo-2-methylpropane
Q. Which of the following compounds undergoes elimination more readily?
  • A. 1-bromopropane
  • B. 2-bromobutane
  • C. 3-bromopentane
  • D. 1-bromo-2-methylpropane
Q. Which of the following compounds undergoes elimination to form an alkene when treated with a strong base?
  • A. 1-bromobutane
  • B. 2-bromobutane
  • C. 1-bromo-2-methylpropane
  • D. 2-bromo-2-methylpropane
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