Hydrolysis of t-butyl halides

The color of the solution with indicator changes from blue to yellow after different time intervals

Scientific name: Alkaline hydrolysis of haloalkanes leads to a change in the reaction medium from an alkaline to acid due to the formation of HBr


Hydrolysis of t-butyl halides

by Hegelrast

hydrolysis of t-butyl chloride

by LaFFle


by chemistvip

Hydrolysis of t-Butyl Chloride

by wickee007


by chemistvip

Sn1 reaction tert butyl chloride with hydroxide in acetone and water

by Scott Milam

Hydrolysis of t-ButylChloride. Kinetics. Experiment #5. SN1 Reaction.

by uofgchem2700


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Reaction formula

(CH3)3CBr + H2O → (CH3)3COH + HBr

(CH3)3CCl + H2O → (CH3)3COH + HCl

NaOH + HBr → NaBr + H2O

Step-by-step instruction

  1. Prepare the solvent. Mix 200 ml of water and 30 mL of acetone in a 300-ml beaker.
  2. Add 7.5 ml of 1M sodium hydroxide solution and a small amount of bromothymol blue.
  3. Increase the volume of the resulting solution to 300 ml with water and mix.
  4. Divide the solution into 2 portions of 150 ml, pour each into a glass jar.
  5. Prepare solutions of tert-butyl halides. Dissolve 920 mg of t-butyl chloride in 10 ml of acetone. Dissolve 1370 mg of t-butyl bromide in 10 ml of acetone.
  6. Transfer the solution of tert-butyl chloride into the first jar and the solution of t-butyl bromide into the second jar.
  7. Close the jars and shake them.
  8. After some time there will be a color change from blue to yellow in the jar with t-butyl bromide. Much later, it will happen in the jar with a tert-butyl chloride.

Scientific background

Tert-butyl halide is suspect to alkaline hydrolysis like all haloalkanes.

Hydrolysis of the t-butyl halide proceeds via a mechanism forming a carbocation (SN1).

R-X --> R+ → R-OH

The reaction rate doesn't depend on the concentration of the nucleophile, but depends on the nature of the substrate. Bromine is a better leaving group than chloro, so the reaction with t-butyl bromide proceeds much faster. The color change of the indicator is due to changes in the reaction medium from alkaline to acid due to the formation of hydrogen bromide.


Published on 15 May 2015

  • Fire
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