The ester was pently ethanoate. Spectroscopy. Obtain an infrared spectrum and a

Question

The ester was pently ethanoate.

Spectroscopy. Obtain an infrared spectrum and a 3C NMR spectrum of your product Interpret both spectra in your report to the instructor. Questions: 1. Why is the mixture extracted with aqueous sodium bicarbonate solution? Give an 2. Using your alcohol, determine which starting material is the limiting reagent in this 3. Tertiary alcohols do not work well in the procedure outline for this experiment, they give equation and explain its relevance. procedure. Which reagent is used in excess? a different product than you might expect. Explain this and draw the expected product from t-butyl alcohol. 4. Why is glacial acetic acid designated as "glacial"?

Explanation / Answer

1. In order to remove an acidic compound from a mixture, a base like NaOH or NaHCO3 is used. The carboxylic (or mineral) acid and the base react to form a sodium salt, which is usually exhibits a higher solubility in aqueous solutions due to its negative charge and higher polarity.

RCOOH+ NaHCO3= RCOONa + CO2 + H2O

2. This answer is related to the initial conc. of the alcohol taken.

3. The t-butyl alcohol readily will form the carbocation which is highly stable due to the +I effect of the methyl groups. THus the electrophilicity of the OH group of the alcohol is lost and the esterification would not work. Note that the mechanism of the esterification reaction the carboxylic acid O group is first protonated and the Oh attcks the carbonyl center of the carboxylic acid.

4. Acetic acid that contains a very low amount of water is called anhydrous (water-free) acetic acid or glacial acetic acid. It's called glacial is because it solidifies into solid acetic acid crystals just cooler than room temperature.

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