Experiment 23B – Synthesis of t-Pentyl Chloride – Name _____________________
OH
Cl
HCl
1. Data Table: Fill in the appropriate spaces in the data table below. Under the Amount
column, use g for solids, mL for liquids. The abbreviation na stands for not applicable. A
mmol is 1/1000th of a mole.
Reagent
Amount
(g or mL)
mmol
bp (oC) observed
2-methyl-2-butanol
na
hydrochloric acid
na
2-chloro-2-methyl
butane
2. Percent Yield (show calculations on a separate sheet and attach to this page)
Percent yield of distilled product
%
3. Mechanism. On a separate sheet (attach to this report), write a step-by-step
mechanism for the reaction of 2-methyl-2-butanol with HCl to form 2-chloro-2methylbutane.
4. Questions. On a separate sheet (attach to this report) provide answers to the
following questions.
A.) A by-product, 2-methyl-2-butene, may be formed in fairly small amounts (E1). Give a
stepwise mechanism which would account for the formation of this by-product.
B.) Why did you use aqueous sodium bicarbonate (a weak base, baking soda) to wash
the crude t-pentyl chloride?
C.) Why did you not wash the crude t-pentyl chloride with aqueous sodium hydroxide (a
strong base)? Hint: see question D).
D.) Propose a mechanism for the formation of 2-methyl-2-butene from the reaction of tpentyl chloride with aqueous sodium hydroxide.