12. Alcohols, Ethers, Epoxides and Thiols
Williamson Ether Synthesis
12. Alcohols, Ethers, Epoxides and Thiols
Williamson Ether Synthesis - Video Tutorials & Practice Problems
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Get a 10 bullets summary of the topicThere are 4 major methods to create ethers. Most of these should look familiar in some way since they are variations of reactions we have used before.
Williamson Ether Synthesis
The name given for the SN2 substitution of an oxide with an alkyl halide.
- Only works with 0°, 1° alkyl halides since 2° and 3° alkyl halides will favor E2.
1
concept
The Mechanism of Williamson Ether Synthesis.
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PRACTICE PROBLEMS AND ACTIVITIES (49)
- c. Give two sets of reactants (each set including an alkyl halide and a nucleophile) that could be used to syn...
- What is the best way to prepare the following ethers using an alkyl halide and an alkoxide ion? a. b.
- Which of following ethers cannot be made by a Williamson ether synthesis?
- a. Propose a mechanism for the following reaction:
- (a) Show how ethanol and cyclohexanol may be used to synthesize cyclohexyl ethyl ether (tosylation followed ...
- A good Williamson synthesis of ethyl methyl ether would be < of reaction> What is wrong with the followi...
- Phenols (pKa ≈ 10) are more acidic than other alcohols, so they are easily deprotonated by sodium hydroxide o...
- (••) Identify the two possible combinations of haloalkane and alkoxide that can be used to make the following ...
- (•••) The reaction of alkoxides with haloalkanes is not a viable way to form ethers. (a) Why? (b) Why can thi...
- How could the reaction in Figure 13.67(b) be modified to produce the following ether?<IMAGE>
- Show how the following ethers might be synthesized using (1) alkoxymercuration– demercuration and (2) the Wi...
- There are two different ways of making 2-ethoxyoctane from octan-2-ol using the Williamson ether synthesis. W...
- Propose a Williamson synthesis of 3-butoxy-1,1-dimethylcyclohexane from 3,3-dimethyl-cyclohexanol and butan-...
- Propose a mechanism for each of the following reactions: b.
- Fluoxetine hydrochloride (Prozac®) is a widely used antidepressant. How might you stereoselectively install th...
- Predict the product when the dihydroxybenzene shown is treated with a single equivalent of both base and haloa...
- What is the product of the following reaction?<IMAGE>
- Predict the product of the following substitution/addition reactions involving phenoxides. [Because this probl...
- Predict the product of the following reactions. [Two of them are Williamson ether syntheses. Why isn't the oth...
- Identify the alkene and alcohol partners that could be used to make the following ethers.(a) <IMAGE>
- Predict the product of the following reactions. [Two of them are Williamson ether syntheses. Why isn't the oth...
- Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.(b) <IMAGE>
- Two different Williamson ether syntheses can be used to make the compound in (a). Show them. The compound in (...
- (••) In contrast to Assessment 13.102, only one combination of haloalkane and alkoxide can be used in the Will...
- Predict the product of the following reactions. [Two of them are Williamson ether syntheses. Why isn't the oth...
- (••••) LOOKING BACK In Chapter 12, we learned that crown ethers were used to increase the rate of S_N2 reacti...
- Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.(a) <IMAGE>
- (••••) Provide the reagents necessary to carry out the following synthesis. What is the purpose of steps (a) a...
- How could you synthesize isopropyl propyl ether, using isopropyl alcohol as the only carbon-containing reagent...
- a. Draw the product of each of the following reactions:2. CH3CH2CH2OH→2. CH3Br1. NaH
- What is the best way to prepare the following ethers using an alkyl halide and an alkoxide ion?c. <IMAGE>...
- A chemist wanted to synthesize the anesthetic 2-ethoxy-2-methylpropane. He used ethoxide ion and 2-chloro-2-me...
- Design a synthesis for each of the following, using an intramolecular reaction:e. <IMAGE>
- The compound shown below has three different types of OH groups, all with different acidities. Show the struct...
- Show how you would use the Williamson ether synthesis to prepare the following ethers. You may use any alcohol...
- Show how you would accomplish the following transformations. Some of these examples require more than one step...
- Show how you would accomplish the following transformations. Some of these examples require more than one step...
- A student wanted to use the Williamson ether synthesis to make (R)-2-ethoxybutane. He remembered that the Will...
- The Williamson ether synthesis involves the displacement of an alkyl halide or tosylate by an alkoxide ion. Wo...
- Both LiAlH4 and Grignard reagents react with carbonyl compounds to give alkoxide ion intermediates (that becom...
- Show how you would synthesize the following ethers in good yield from the indicated starting materials and any...
- Show how the following ethers might be synthesized using(1) alkoxymercuration– demercuration and(2) the Willia...
- Show how the following ethers might be synthesized using(1) alkoxymercuration– demercuration and(2) the Willia...
- Show how the following ethers might be synthesized using(1) alkoxymercuration– demercuration and(2) the Willia...
- Show how you would synthesize the following ethers in good yield from the indicated starting materials and any...
- Both LiAlH4 and Grignard reagents react with carbonyl compounds to give alkoxide ion intermediates (that becom...
- Both LiAlH4 and Grignard reagents react with carbonyl compounds to give alkoxide ion intermediates (that becom...
- In Chapter 14, we saw that Agent Orange contains (2,4,5-trichlorophenoxy) acetic acid, called 2,4,5-T. This co...
- Design a synthesis for each of the following, using an intramolecular reaction: a.