Reaction Mechanisms: Substitution, Addition, Elimination - Problem Set

Q. In a nucleophilic substitution reaction, what is the role of the nucleophile?
  • A. To donate a proton
  • B. To accept electrons
  • C. To attack the electrophile
  • D. To stabilize the leaving group
Q. In an S_N2 reaction, what is the stereochemical outcome when the substrate is a chiral center?
  • A. Retention of configuration
  • B. Inversion of configuration
  • C. Racemization
  • D. No stereochemical change
Q. In the context of reaction mechanisms, what does the term 'rate-determining step' refer to?
  • A. The fastest step in a reaction
  • B. The step with the highest energy barrier
  • C. The step that produces the final product
  • D. The step that involves the most reactants
Q. What is the major product of the addition of HBr to 2-pentene?
  • A. 1-bromopentane
  • B. 2-bromopentane
  • C. 3-bromopentane
  • D. No reaction
Q. What is the stereochemical configuration of the product formed from the reaction of (R)-2-bromobutane with a strong nucleophile in an S_N2 reaction?
  • A. R
  • B. S
  • C. R and S
  • D. No stereochemical change
Q. What type of reaction mechanism is involved when an alkyl halide reacts with a nucleophile to form an alcohol?
  • A. Elimination
  • B. Substitution
  • C. Addition
  • D. Rearrangement
Q. Which functional group is formed when an alcohol undergoes dehydration?
  • A. Ether
  • B. Alkene
  • C. Alkyne
  • D. Aldehyde
Q. Which of the following compounds can undergo an E2 elimination reaction?
  • A. Tertiary alkyl halides
  • B. Primary alkyl halides
  • C. Vinyl halides
  • D. All of the above
Q. Which of the following compounds undergoes an S_N1 reaction mechanism?
  • A. 1-bromopropane
  • B. 2-bromopropane
  • C. 3-bromopropane
  • D. Bromobenzene
Q. Which of the following is a characteristic of an S_N2 reaction?
  • A. Involves a carbocation intermediate
  • B. Bimolecular reaction rate
  • C. Involves a strong base
  • D. Occurs in a polar protic solvent
Q. Which of the following is a characteristic of E2 elimination reactions?
  • A. Requires a strong nucleophile
  • B. Involves a carbocation intermediate
  • C. Occurs in a single concerted step
  • D. Produces a racemic mixture
Q. Which of the following statements about stereochemistry is true for E2 reactions?
  • A. They require a strong nucleophile
  • B. They can lead to both E and Z isomers
  • C. They require anti-periplanar geometry
  • D. They always produce a racemic mixture
Q. Which of the following statements is true regarding E1 elimination reactions?
  • A. They require a strong base
  • B. They proceed through a carbocation intermediate
  • C. They are stereospecific
  • D. They occur in a single step
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