A chemist needs an ether to use as a solvent for a reaction and wants to synthesize it in one step from two of the following available reagents: sodium ethoxide, bromomethane, potassium tert-butoxide, and 2-bromo-2-methylpropane. i) Which combination(s) will give a good yield of an ether? Illustrate, showing the mechanism of the reaction. ii) Illustrate with a mechanism the reaction of one of the combinations that will not yield an ether?

A chemist needs an ether to use as a solvent for a reaction and wants to synthesize it in one step from two of the following available reagents: sodium ethoxide, bromomethane, potassium tert-butoxide, and 2-bromo-2-methylpropane. i) Which combination(s) will give a good yield of an ether? Illustrate, showing the mechanism of the reaction. ii) Illustrate with a mechanism the reaction of one of the combinations that will not yield an ether?

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.45P: Draw a structural formula for the major organic product of each reaction and specify the most likely...

See similar textbooks

Similar questions

Draw a structural formula for the major organic product of each reaction and specify the most likely mechanism by which each is formed. (g) CH3CH2ONa++CH2=CHCH2Clethanol
Reaction of 2° alcohol A with HCl forms three alkyl chlorides, all of which result from rearrangement of the 2° carbocation initially formed. Draw the structures of these products and a mechanism that illustrates how each is formed.
Several reagents and several organic structures are shown below. Construct a multistep synthetic route from the reactant 2-methyl-1-butene to the product 3-bromo-2-methyl-2-butanol by dragging the appropriate pieces into the bins. Note that each bin will hold only one item, and not every given reagent or structure will be used.
In the following reaction Series, write down the appropriate reagents that can be used where there are question marks
Draw a structural formula for the major organic product of each reaction and specify the most likely mechanism by which each is formed.
Choose the best reagents from the list provided below for carrying out the following conversion. Match the reagent with the step number. HCl (aq), Zn(Hg) KMnO4, H3O+ CH3Cl, AlCl3 HNO3, H2SO4 Cl2, FeCl3 fuming sulfuric acid
The reaction of tert-butyl cyclopentyl ether with trifluoroacetic acid is shown below. Explain what kind of reaction this is (SN1, SN2, E1, E2...) and show the mechanism for this transformation.
Give a detailed reaction mechanism for the reaction expected to occur when 2-bromo-2-methylpentane is heated with sodium methoxide. Draw clear structural formulas of all relevant species and use curved arrows to represent electron flow. Also indicate which step is likely to be rate-determining. The answer you sent before will be used for this question.
When 1,2-cyclohexanediol is dehydrated in the presence of concentrated sulfuric acid, the major product is not an alkene. Instead, you get cyclohexanone. Write a reasonable and detailed mechanism for the dehydration of 1,2-cyclohexanediol to form cyclohexanone. Use curved arrows to show the flow of electrons and draw the structures of all intermediates and byproducts formed in the course of this reaction as well as any alternative resonance structures that will help you to account for the formation of the major product observed in this reaction.
Fill in the appropriate reagents for the following reaction:
On acid-catalyzed dehydration, 1-butanol (CH3CH2CH2CH2OH) can be converted to 1-butene. Write out an equation for the reaction Assign each the appropriate symbol for the mechanism of the reaction (E1 or E2) Draw a suitable mechanism for the reaction
Propose a mechanism for this reaction. Account for both its regioselectivity and stereoselectivity.