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

Question 1

Multiple Choice

A sample of 1-chloro-1-phenylethane with an [α]25D 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]25D 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 sample of 1-chloro-1-phenylethane with an [α]<sup>25</sup><sub>D</sub> of -94.8° is reacted with NH<sub>3</sub> in methanol/water solvent. The major substitution product of the reaction is 1-phenyl-1-ethylamine with an [α]<sup>25</sup><sub>D</sub> 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<sub>N</sub>1 mechanism B) Net inversion 12% with 88% racemization - S<sub>N</sub>1 mechanism C) Net inversion 75% with 25% racemization - S<sub>N</sub>2 mechanism D) Net inversion 12% with 88% racemization - S<sub>N</sub>2 mechanism E) Net inversion 88% with 12% racemization - S<sub>N</sub>2 mechanism


A) Net inversion 25% with 75% racemization - SN1 mechanism
B) Net inversion 12% with 88% racemization - SN1 mechanism
C) Net inversion 75% with 25% racemization - SN2 mechanism
D) Net inversion 12% with 88% racemization - SN2 mechanism
E) Net inversion 88% with 12% racemization - SN2 mechanism

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