Interpretation:
To prove that a tetrahedral intermediate is formed in the given reaction.
Concept introduction:
The nucleophilic acyl substitution reaction in esters is an
For the formation of the tetrahedral intermediate, the nucleophilic acyl substitution reaction takes place on the carbonyl carbon in the first step of the reaction.
For the collapse of the tetrahedral intermediate, the group attached to the substituent attached to the acyl group leaves leading to the formation of carbonyl compound and a weaker base.
Want to see the full answer?
Check out a sample textbook solutionChapter 15 Solutions
Organic Chemistry; Organic Chemistry Study Guide A Format: Kit/package/shrinkwrap
- The trimethylsilyl protecting group is easily removed in aqueous solution containing a trace of acid. Propose a mechanism for this reaction. (Note that a TBDMS protecting group is stable under these conditions because of the greater steric crowding around silicon created by the t-butyl group.)arrow_forwardAn elimination step is involved in the synthesis of aromatic amino acids. We can also envision this occurring in a laboratory setting with a strong base. Provide a 1 step mechanism for this decarboxylation reaction. Note: under strongly basic conditions, hydroxide is a reasonable leavinggroup.arrow_forwardStrong support for the mechanism of the nucleophilic aromatic substitutionreaction that proceeds through a benzyne intermediate comes from the reaction shown here, in which bromobenzene is treated with KNH2 in the presence of cyclopentadiene. A product that is isolated has the formula C11H10. Draw the structure of that product and explain how it validates the production of a benzyne intermediate.arrow_forward
- 10.2 Complete the following reactions: Show the step-by-step process. Do not use shortcut methods. Make it as detailed as it can be. Encode (not hand-written)!arrow_forwardThe reaction that occurs when the benzaldehyde you have is reacted in a basic environment is called the Cannizzaro reaction, and when it is reacted with cyanide, it is called benzoin production. Write down the reaction mechanisms of these reactions and explain why.arrow_forwardLike other strong nucleophiles, triphenylphosphine attacks and opens epoxides. The initial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses to an alkene and triphenylphosphine oxide. Show how this sequence might be used to convert cis-cyclooctene to trans-cyclooctene.arrow_forward
- if this molecule underwent a SN2 reaction what would the product bearrow_forwardProvide the mechanism of the protecting group using the following reagents below.arrow_forwardDraw structures and propose mechanistic steps that clearly show how your postulated reaction product formed from the N,Oacetal.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning