CAUTION: Wear gloves to do the reaction and extraction. 1. Place 10.0 mL of t-pentyl alcohol and 25 mL of concentrated hydrochloric acid (d - 1.18 g/mL) in a 125 mL separatory funnel. Do not stopper the funnel. (Why?)
2. Gently swirl the mixture in the separatory funnel for about 1 minute. Stopper the separatory funnel and carefully invert it.
3. Without shaking the separatory funnel, immediately open the stopcock to release the pressure.
4. Close the stopcock, shake the funnel several times, and again release the pressure through the stopcock. Shake the funnel for 2-3 minutes, with occasional venting.
5. Let the mixture stand in the separatory funnel until the two layers have completely separated.
6. The t-pentyl chloride should be the top layer. Drain the lower layer, add a few drops of water to verify it is aqueous, and then discard it.
EXTRACTION The steps here should be done as rapidly as possible since the t-pentyl chloride can hydrolyze back to alcohol in water and sodium bicarbonate. In all the following steps, the organic layer should be on top; you can add a few drops of water to
7. Wash the organic layer by shaking with 10 mL of water. Separate the layers and discard the aqueous phase after making certain that the proper layer has been saved.
8. Add 10 mL of 5% aqueous sodium bicarbonate to the separatory funnel. Gently swirl the fun- nel (unstoppered) until the contents are thoroughly mixed. Stopper the funnel and carefully invert it and release the excess pressure through the stopcock. Shake
9. Wash the organic layer by shaking it with 10 mL of water. Discard the lower aqueous layer.
10. Pour the organic layer, from the top of the separatory funnel, into a dry Erlenmeyer flask.
11. Dry the t-pentyl chloride with about 1.0 g of anhydrous calcium chloride. Stopper it lightly with a rubber stopper and leave it for 5-10 minutes. The product will be clear when dry.
12. Transfer the product to a pre-weighed, labeled vial and determine the weight of product to calculate the percent yield of the product.
Analysis: Perform infrared spectroscopy on your sample and compare it to the IR of authentic sample shown on next page.
S,1 reactions are carried out by a carbocation mechanism. The leaving group of the substrate leaves the substrate creating a carbocation as the transition state. The nucleophile then attacks the carbocation to give the product. This mechanism involves a t
In this reaction you will treat t-pentyl alcohol (2-methyl-2-butanol) with hydrochloric acid to produce the product, t-pentyl chloride (2-chloro-2-methylbutane). The purpose of hydrochloric acid is two-fold: first is to protonate the alcohol to make it a