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

question 69

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

---

Definitions:

Wife-battering

A form of domestic violence characterized by the physical abuse of a wife by her husband.

Lower-income Families

Families whose income is significantly below the median income level of a society, often facing financial struggles and limited access to resources.

Blaming Oneself

The act of attributing fault or responsibility for something, often negative, to oneself.

Being Raped

The act of being subjected to rape, which is a form of sexual assault usually involving sexual intercourse without the consent of the victim.