A Sample of 1-Chloro-1-Phenylethane with an [α]²⁵_D of -94

question 1

Multiple Choice

A sample of 1-chloro-1-phenylethane with an [α]²⁵_D of -94.8° is reacted with NH₃ in methanol/water solvent. The major substitution product of the reaction is 1-phenyl-1-ethylamine with an [α]²⁵_D of -8.6°. Given that optically pure (R) 1-chloro-1-phenylethane has a specific rotation of -109.0° and that optically pure (R) 1-phenyl-1-ethylamine has a specific rotation of +39.3°, which of the following statements best describes this reaction?

• A) Net inversion 25% with 75% racemization - S_N1 mechanism
• B) Net inversion 12% with 88% racemization - S_N1 mechanism
• C) Net inversion 75% with 25% racemization - S_N2 mechanism
• D) Net inversion 12% with 88% racemization - S_N2 mechanism
• E) Net inversion 88% with 12% racemization - S_N2 mechanism

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