Boron tribromide (BBr3) cleaves ethers to give alkyl halides and alcohols. ROR' + BBr3 R-O-BBr2 + R'Br R-O-BBr2 + 3 H₂O ROH+B(OH)3 + 2 HBr The reaction is thought to involve attack by a bromide ion on the Lewis acid-base adduct of the ether with BBr3 (a strong Lewis acid). ▼ Part A Propose a mechanism for the reaction of butyl methyl ether with BBr3 to give (after hydrolysis) butan-1-ol and bromomethane Draw all missing reactants and/or products in the appropriate boxes by placing atoms on the canvas and connecting them with bonds. Add charges where needed. Electron flow arrows should start on the electron(s) of an atom or a bond and should end on an atom, bond, or location where a new bond should be created.
Boron tribromide (BBr3) cleaves ethers to give alkyl halides and alcohols. ROR' + BBr3 R-O-BBr2 + R'Br R-O-BBr2 + 3 H₂O ROH+B(OH)3 + 2 HBr The reaction is thought to involve attack by a bromide ion on the Lewis acid-base adduct of the ether with BBr3 (a strong Lewis acid). ▼ Part A Propose a mechanism for the reaction of butyl methyl ether with BBr3 to give (after hydrolysis) butan-1-ol and bromomethane Draw all missing reactants and/or products in the appropriate boxes by placing atoms on the canvas and connecting them with bonds. Add charges where needed. Electron flow arrows should start on the electron(s) of an atom or a bond and should end on an atom, bond, or location where a new bond should be created.
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Reactions of Ethers
Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.
Epoxides
Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.
Williamson Ether Synthesis
An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.
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Transcribed Image Text:Boron tribromide (BBr3) cleaves ethers to give alkyl halides and alcohols.
R-OR' + BBr3 →R-O-BBr2 + R'Br
R-O-BBr2 + 3 H₂O → ROH+B(OH)3 + 2 HBr
The reaction is thought to involve attack by a bromide ion on the Lewis acid-base adduct of the ether with BBr3 (a strong Lewis acid).
Part A
Propose a mechanism for the reaction of butyl methyl ether with BBr3 to give (after hydrolysis) butan-1-ol and bromomethane.
Draw all missing reactants and/or products in the appropriate boxes by placing atoms on the canvas and connecting them with bonds. Add charges where needed. Electron flow
arrows should start on the electron(s) of an atom or a bond and should end on an atom, bond, or location where a new bond should be created.
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