How is Ether Formed from an Alkyl Halide?

  • Thread starter alingy1
  • Start date
  • Tags
    Ether
In summary, the process of forming ether from alkyl halide is known as Williamson ether synthesis, which involves the reaction of an alkyl halide with a deprotonated alcohol. The reagents required for this reaction include an alkyl halide, a deprotonated alcohol, a strong base, and a polar aprotic solvent. This method has various applications, such as synthesizing ethers and using them as solvents or intermediates. However, not all alkyl halides can be used in this synthesis, and there may be limitations and drawbacks, such as difficulty with tertiary alcohols and the formation of side products.
  • #1
alingy1
325
0
Please look at attachments.
The book's answer seems way off. Where is there starting halide!? I posted my solution (I made a typo there. It is not EtO- but CH3O-).
 

Attachments

  • Screen Shot 2014-08-07 at 2.09.31 PM.png
    Screen Shot 2014-08-07 at 2.09.31 PM.png
    18 KB · Views: 513
  • Screen Shot 2014-08-07 at 2.02.00 PM.png
    Screen Shot 2014-08-07 at 2.02.00 PM.png
    2.6 KB · Views: 558
  • My reaction.png
    My reaction.png
    811 bytes · Views: 470
Physics news on Phys.org
  • #2
They use CH3I in the second reaction, that's the halide, isn't it?
 
  • #3
alingy1 said:
The book's answer seems way off. Where is [STRIKE]there[/STRIKE] their starting halide!?
It appears in the second step: CH3I

[Edit: Borek, you're always too quick for me!]
 
  • #4
Perfect! I had an eureka moment a few seconds ago!
 
  • #5


I would like to address the content and response regarding the formation of ether from alkyl halide. The book's answer does not provide enough information to fully understand the process of forming ether. It is important to note that the starting material in this reaction is an alkyl halide, which is a compound containing a halogen atom (such as chlorine, bromine, or iodine) attached to an alkyl group.

The reaction described in the attachment involves the use of a strong base, such as sodium hydroxide (NaOH), to deprotonate the alcohol, converting it into an alkoxide ion (CH3O-). This alkoxide ion then acts as a nucleophile, attacking the carbon atom of the alkyl halide and displacing the halogen atom. This results in the formation of the desired ether product, along with a byproduct of a halide ion (Cl-, Br-, or I-).

It is important to note that the specific starting alkyl halide used in this reaction is not mentioned in the attachment, but it is necessary for the reaction to take place. Additionally, the use of a strong base is crucial for this reaction to occur as it helps to facilitate the deprotonation step and promote the nucleophilic attack.

In summary, the formation of ether from alkyl halide involves the use of a strong base and a specific starting alkyl halide. It is important to fully understand the mechanism and reagents involved in this reaction to accurately predict the products. Thank you for bringing attention to this topic and offering your own solution.
 

FAQ: How is Ether Formed from an Alkyl Halide?

1. What is the process of forming ether from alkyl halide?

The process of forming ether from alkyl halide is known as Williamson ether synthesis. It involves the reaction of an alkyl halide with a deprotonated alcohol to form an ether.

2. What are the reagents and conditions required for forming ether from alkyl halide?

The reagents required for Williamson ether synthesis are an alkyl halide and a deprotonated alcohol. The conditions usually involve the use of a strong base, such as sodium hydride or potassium hydroxide, and a polar aprotic solvent, such as dimethyl sulfoxide (DMSO) or tetrahydrofuran (THF).

3. What are the main applications of forming ether from alkyl halide?

Forming ether from alkyl halide is a common method for synthesizing ethers, which are important functional groups in many organic compounds. Ethers can also be used as solvents or as intermediates in the synthesis of other compounds.

4. Can any alkyl halide be used in Williamson ether synthesis?

No, not all alkyl halides are suitable for Williamson ether synthesis. Alkyl halides that are primary or secondary and have a good leaving group, such as iodide or bromide, are most commonly used. Tertiary alkyl halides may also be used, but they can undergo competing elimination reactions.

5. Are there any limitations or drawbacks to forming ether from alkyl halide?

One limitation of Williamson ether synthesis is that it cannot be used to form ethers with tertiary alcohols, as they do not easily deprotonate. Additionally, this method may result in the formation of side products or byproducts, such as elimination products or rearranged products, which can reduce the overall yield of the desired ether.

Similar threads

Which Acetylide Anion and Alkyl Halide Can Form CH3C≡CCH2CH2CH2CH3?
Replies
2
Views
2K
Chemistry Elimination question on alkyl halide
Replies
0
Views
604
Chemistry How do I form the product with alkylation and condensation?
Replies
1
Views
2K
What will be the product of this organic reaction?
Replies
28
Views
4K
Selectivity of free radicals in halogenation.
Replies
4
Views
3K
Reactivity with Water: Arrange 1-6 (Allyl Halide to Tertiary Alkyl Halide)
Replies
9
Views
3K
Why E2 Favors Secondary Halides: Exploring 2-Chlorobutane Reactivity in Ethoxide
Replies
5
Views
3K
Organic Chemistry: Sn1/E1/Sn2/E2/Alchol/Ether Transformations
Replies
4
Views
8K
Alkyl halides left in an open container what happens?
Replies
2
Views
7K
Physical Properties Dimethyl ether vs ethanol
Replies
1
Views
21K

Hot Threads

Recent Insights

Back
Top