T-Butyl Chlor

t-Pentyl Chloride

Purpose: To get an end product of t-pentyl chloride using an SN1 reaction.

Table of Chemicals:



Theory:

The tertiary alkyl halide can be prepared by allowing t-pentyl alcohol to react with concentrated hydrochloric acid, which in this case it is HCL. The reaction is accomplished simply by shaking the two reagents in a separatory funnel. The mixture is allowed to react at room temp to form the product. As the reaction proceeds, the insoluble alkyl halide products forms an upper phase. The reaction of the tertiary substrate occurs through Sn1 mechanism. It takes three washes of the organic layer to separate. First wash using D.I. water is to remove the unreacted t-pentyl alcohol. The second is with 5% NaHCO3 to remove the hydrogen ions. The third rinse is using another 10mL of D.I. water to remove the remaining Na and HCO3 Ions. A small amount of alkene, 2-methyl-2-butene, is produced as a by-product in this reaction. We use distillation to separate the product from the by product since their b.p. are far apart we use simple distillation.

Procedure:

Obtain a 3 inch ring holder and a ring stand,

clamp the ring holder on the ring stand.

Obtain a 125-mL separatory funnel, check for leaks with acetone.

Dispense 10.0-mL of t-pentyl alcohol (2-methyl-2-butanol) in the 125-mL separator funnel

next dispense 25-mL of concentrated HCl(12 M) into the 125-mL separatory funnel. **Do not stopper and swirl gently for 1 minute**

Next stopper the top and invert, immediately open the stopcock. Close stopcock shake once and immediately open stopcock. Repeat until no more pressure is release.

Next shake the inverted 125-mL separatory funnel for about 3 minutes with occasional venting.

Place the 125-mLseparatory funnel in the ring holder and remove the glass stopper.

Allow the two layers to separate. Organic layer should be on top.

Drain the bottom aqueous layer, check the aqueous with a drop of water. If the drop of water dissolves...