Solving SN1 Reaction: t-Butyl Bromide & HOH

  • Thread starter Thread starter daniel6874
  • Start date Start date
  • Tags Tags
    Reaction
Click For Summary
SUMMARY

The discussion centers on the reaction of tert-butyl bromide with water (HOH), resulting in the formation of HBr and tert-butyl alcohol. It highlights that tert-butyl alcohol reacts with hydrochloric acid (HCl) to yield tert-butyl chloride. The strength of HBr as a stronger acid compared to HCl is identified as a key factor influencing these different reactions. The discussion concludes that using concentrated HX is essential to obtain tBuX (where X is Cl or Br) from the corresponding alcohol, as high water concentration leads to hydrolysis and an equilibrium favoring the alcohol.

PREREQUISITES
  • Understanding of SN1 reaction mechanisms
  • Knowledge of acid strength and its effects on reaction outcomes
  • Familiarity with equilibrium concepts in chemical reactions
  • Experience with organic compounds, specifically tert-butyl derivatives
NEXT STEPS
  • Research the mechanism of SN1 reactions in detail
  • Study the properties and reactions of strong acids like HBr and HCl
  • Explore equilibrium dynamics in hydrolysis reactions
  • Investigate the synthesis and applications of tert-butyl derivatives
USEFUL FOR

Chemistry students, organic chemists, and professionals involved in synthetic organic chemistry who are interested in reaction mechanisms and the behavior of alkyl halides.

daniel6874
Messages
64
Reaction score
0
tert-butyl bromide reacts with HOH to give HBr and the corresponding alcohol ,
C
C-C-C
OH

But tert-butyl alcohol reacts with HCl to give tert-butyl chloride.

HBr is a "stronger" acid than HCl. Is this part of the explanation of the different reactions?
 
Chemistry news on Phys.org
In order to get tBuX [X=Cl, Br] from the corresponding alcohol, you need to use conc. HX. If the proportion of water is too high (i.e. the concentration of X- is low] you will mostly have the alcohol in the equilibrium mixture. This is why when you treat tBuX [X=Cl, Br] with water you get hydrolysis - water is in vast excess compared to Br- at equilibrium.
 

Similar threads

  • · Replies 1 ·
Replies
1
Views
6K
  • · Replies 2 ·
Replies
2
Views
3K
  • · Replies 3 ·
Replies
3
Views
6K
  • · Replies 1 ·
Replies
1
Views
6K
  • · Replies 1 ·
Replies
1
Views
5K
  • · Replies 5 ·
Replies
5
Views
8K
  • · Replies 1 ·
Replies
1
Views
5K
Replies
5
Views
3K
  • · Replies 10 ·
Replies
10
Views
13K
Replies
4
Views
6K