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<sup>∘</sup> 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<sup>∘</sup>. Given that optically pure (R) 1-chloro-1-phenylethane has a specific rotation of -109.0<sup>∘</sup> and that optically pure (R) 1-phenyl-1-ethylamine has a specific rotation of +39.3<sup>∘</sup>, 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](https://d2lvgg3v3hfg70.cloudfront.net/TB6198/11eab45f_cd76_a940_acdb_2b79ef3dd03c_TB6198_00.jpg)
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