Williamsons ether synthesis (rate)

In summary, the conversation discusses which option, A or B, will undergo faster Williamson ether synthesis and the factors that determine the mechanism of the reaction. Option B is chosen as the correct answer due to the SN2 mechanism being more favorable for ether synthesis. The factors involved include steric hindrance and bond strength.
  • #1
Suraj M
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Homework Statement


Which will undergo faster Williamson ether syntehsis
It was either faster or better, I'm not sure

A)3-Chlorobutan-1-ene
B)1-Bromobutane

Homework Equations

The Attempt at a Solution


I thought option A because of its alylic position it will form a stable carbocation (and through SN1)
Is it correct? Or is it B because bromine is more weakly bound to the primary carbon

Thank you :-)
 
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  • #2
What mechanism is involved in Williamson ether synthesis, SN1 or SN2? What factors are most important for reactions of that type?
 
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  • #3
The mechanism depends on the reactants right?
What factors? I'd say driving force of the stabilized carbocation if it's SN1 else steric factor and strength of the CX bond for SN2?
Is that right?
 
  • #4
Suraj M said:
The mechanism depends on the reactants right?
You should double check what your text says about the mechanism of Williamson ether synthesis.
 
Last edited:
  • #5
Oh always SN2?
Then in that case it's option B right?
 
  • #6
Yes. If you were to try to form an ether via an SN1 reaction, you would probably have too much competition from the E1 product.
 
  • #7
Ah okay
Thanks Ygggrasil ! :-)
 

1. What is Williamsons ether synthesis?

Williamsons ether synthesis is a chemical reaction used to synthesize ethers from alcohols and alkyl halides in the presence of a strong base.

2. How does the rate of Williamsons ether synthesis compare to other reactions?

The rate of Williamsons ether synthesis is generally slower than other reactions due to the low reactivity of the alkyl halide and the need for a strong base.

3. What factors can affect the rate of Williamsons ether synthesis?

The rate of Williamsons ether synthesis can be affected by the strength of the base used, the steric hindrance of the alkyl halide, and the solvent used.

4. How can the rate of Williamsons ether synthesis be increased?

The rate of Williamsons ether synthesis can be increased by using a more reactive alkyl halide, a stronger base, or by heating the reaction mixture.

5. What is the mechanism behind Williamsons ether synthesis?

The mechanism of Williamsons ether synthesis involves an SN2 reaction between the alkoxide ion generated from the alcohol and the alkyl halide, followed by elimination of the halide ion to form the ether product.

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