Reaction Mechanisms: Substitution, Addition, Elimination - Higher Difficulty Problems

Q. In a nucleophilic substitution reaction, what is the role of the solvent?
  • A. To stabilize the nucleophile
  • B. To stabilize the leaving group
  • C. To provide a medium for the reaction
  • D. To increase the reaction rate
Q. In an E2 elimination reaction, which of the following is a requirement for the reaction to occur?
  • A. A strong nucleophile
  • B. A good leaving group
  • C. A polar protic solvent
  • D. A tertiary substrate
Q. In the reaction of 2-bromobutane with KOH in ethanol, what type of mechanism is primarily involved?
  • A. SN1
  • B. SN2
  • C. E1
  • D. E2
Q. What is the IUPAC name of the compound with the formula CH3-CH2-CH(CH3)-CH2-CH3?
  • A. 2-pentyl
  • B. 3-methylpentane
  • C. 2-methylpentane
  • D. 3-pentyl
Q. What is the IUPAC name of the compound with the structure CH3-CH(CH3)-C(=O)-OH?
  • A. 2-methylbutanoic acid
  • B. 3-methylbutanoic acid
  • C. 2-methylpropanoic acid
  • D. 3-methylpropanoic acid
Q. What is the major product of the following reaction: CH3Br + NaOH (ethanol)?
  • A. CH3OH
  • B. CH3O-Na+
  • C. CH3-NaBr
  • D. CH3-CH2-OH
Q. What is the major product of the reaction of 2-methyl-2-bromopropane with KOH?
  • A. 2-methylpropene
  • B. 2-bromopropene
  • C. 2-methyl-2-propanol
  • D. No reaction
Q. What is the product of the elimination reaction of 2-bromobutane with KOH in ethanol?
  • A. But-1-ene
  • B. But-2-ene
  • C. But-3-ene
  • D. Butane
Q. What is the product of the reaction between 1-pentene and HBr?
  • A. 1-bromopentane
  • B. 2-bromopentane
  • C. 3-bromopentane
  • D. 4-bromopentane
Q. What is the stereochemical outcome of the reaction of (R)-2-bromobutane with NaOH in a polar aprotic solvent?
  • A. Retention of configuration
  • B. Inversion of configuration
  • C. Racemization
  • D. No reaction
Q. What type of reaction occurs when 1-hexene reacts with HBr?
  • A. Addition
  • B. Substitution
  • C. Elimination
  • D. Oxidation
Q. Which of the following compounds undergoes an SN1 reaction mechanism?
  • A. 1-bromopropane
  • B. 2-bromopropane
  • C. 3-bromopropane
  • D. Bromobenzene
Q. Which of the following is a characteristic of an SN2 reaction?
  • A. Involves a carbocation intermediate
  • B. Bimolecular reaction rate
  • C. Involves a strong base
  • D. Occurs with tertiary substrates
Q. Which of the following reactions is an example of an SN1 mechanism?
  • A. Tertiary alkyl halide with water
  • B. Primary alkyl halide with NaOH
  • C. Secondary alkyl halide with KCN
  • D. Tertiary alkyl halide with NaOEt
Q. Which of the following statements about stereochemistry is true for the reaction of 2-bromobutane with NaOH?
  • A. Only R isomer is formed
  • B. Only S isomer is formed
  • C. Both R and S isomers are formed
  • D. No stereoisomers are formed
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