Question

Instructions:

1. Write a balanced chemical reaction in Marvin Sketch.

2. In your Marvin Sketch OR neatly draw, identify and label (or name) the base/nucleophile, the electrophile, and the leaving group.

3. Decide whether the reaction is a substitution or an elimination, and in Marvin Sketch, label the reaction as E or S.

4. Write all the names of the group members who contributed or approve of this answer in the Marvin Sketch page.

Tert-butyl chloride (20.0 mmol) was heated to 45 °C in ethanol (50.0 mL) for 1 hour. The mixture was then cooled to room temperature and neutralized with saturated aqueous sodium bicarbonate (a weak base). Tert-butoxyethane was separated by isolated by fractional distillation (Tvapor = 70-74 °C). MC, RD, CF, CS

Answer 1

The reaction would proceed through S_N¹ (Substitution Nucleophilic unimolecular) mechanism because tert-butyl cation obtained from tert-butyl chloride is stabilized by the electron donating nature of three methyl groups present on the carbo cation. The most likely mechanism is as follows:

cha che & ce- slow H₂C - ca ch to burst chlonde cha 2) Calls + Hace che che the 3 cache си-

t-butory elhane at ht والے

Step 1 is the slowest step and is the rate determining step. As this reaction is a Nucleophilic substitution reaction (substituting Cl by the nucleophile C₂H₅OH) and involves only one molecule in the slowest step, it is a S_N¹ reaction