Experiment #21 Nucleophilie Aromatic Substitution: Synthesis of 1-Ethoxy-4-Nitro

Question

Experiment #21 Nucleophilie Aromatic Substitution: Synthesis of 1-Ethoxy-4-Nitrobenzene Nucleophilic aromatic substitution (SyAr) can occur with aromatic halides when one (or more) strong O electron-withdrawing groups, such as nitro groups, are in the ortho or para position(s) relative to the halogen atom. The group) heips stabilize the carbanion intermediate more than the other halogen atoms In groups activate the aromatic ring atom. The use of aryl fluorides works best, because the fluorine atom (being a strong, electron- rawing group) helps stabilize dra wing contrast to electrophilic aromatic substitution, toward nucleophilic aromatic substitution. The nitro group in the para position activates the aromatic ring toward nucleophilic substitution. In the present experiment, an ethoxide anion (the nucleophile) replaces the fluorine atom (the leaving group) of 1-fluoro-4-nitrobenzene to form 1-ethoxy4 Infrared Infrared sene ralso known as 4-nitrophenetole). Recrystallization will be usod to purify your product spectroscopy and melting point will be used to characterize the product. CH NO2 NO1 Substance p-Fluoronitrobenzene 141. 21% Sodium ethoxide MW ds/mL) M.PCG B.PCG Refractive Inde 1330 1.5316 in ethanol 1-Ethoxy-4-nitrobenzene 1672 1.118 60 Anhydrous ethanol SAFETY PRECAUTIONS Safety goggles are required for performing this lab exercise. Minimize the breathing of any vapors and skin contact of chemical reagents Sodium ethoxide is strongly basic. Wash any skin exposed to sodium ethoxide. Handle hot lab items with proper protection. Dispose chemical waste according to your instructor's directions. Wash your hands thoroughly when the lab exercise has been completed. enz 1. Place 2 mL of anhydrous alcohol in a 5-mL vial containing a spin vane and green cap with e 2. Add 1 mL of 21% sodium ethoxide in ethanol into the 5-mL vial. 3. Cap vial and stir for 15 seconds. orange septum. (More sodium ethoxide may cause the formation of a dark gummy substance) Revised July 2013

Explanation / Answer

If for starting weight you mean the weight of the initial p-fluronitrobenzene is 0.205g

If not, the weights that can be calculated are:

The weight of the product before the oven

13.2418g(before oven)-13.0971g (empy beaker)=0.1447g

The final weight of the product is:

13.2309g (after oven)- 13.0971g (empty beaker)=0.1338g<--- this is the weight of the product

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