Solving SN1 Reaction: t-Butyl Bromide & HOH

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In summary, when tert-butyl bromide is reacted with HOH, it produces HBr and the corresponding alcohol, tert-butyl alcohol. On the other hand, when tert-butyl alcohol is reacted with HCl, it produces tert-butyl chloride. This difference in reactions is due to the fact that HBr is a stronger acid than HCl. Furthermore, in order to obtain tert-butyl halides (X= Cl, Br) from the corresponding alcohol, concentrated HX must be used. If the proportion of water is too high, the equilibrium mixture will mostly contain the alcohol, explaining why hydrolysis occurs when treating tert-butyl halides with water.
  • #1
daniel6874
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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?
 
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  • #2
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.
 

1. What is an SN1 reaction?

An SN1 reaction is a type of nucleophilic substitution reaction where the rate-determining step involves the formation of a carbocation intermediate from a leaving group, followed by the attack of a nucleophile to form a new bond.

2. How does t-butyl bromide participate in an SN1 reaction?

t-Butyl bromide, also known as 2-bromopropane, is a primary alkyl halide that can participate in an SN1 reaction by undergoing nucleophilic substitution at the carbon attached to the bromine atom. The leaving group (bromine) is replaced by a nucleophile, resulting in the formation of a new compound.

3. What is the role of HOH in an SN1 reaction?

HOH, or water, is a common nucleophile that can participate in an SN1 reaction. It attacks the carbocation intermediate formed by the leaving group, leading to the formation of an alcohol product.

4. What factors affect the rate of an SN1 reaction?

The rate of an SN1 reaction is affected by the stability of the carbocation intermediate, the strength of the leaving group, and the strength of the nucleophile. Additionally, the solvent used can also impact the rate of the reaction.

5. How can the yield of an SN1 reaction be optimized?

The yield of an SN1 reaction can be optimized by using a good leaving group, a strong nucleophile, and a polar solvent. Additionally, controlling the reaction temperature and carefully monitoring the reaction progress can also help improve the yield.

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