(a)
Interpretation:
The structure of a diketone that would cyclize to form the given compound is to be drawn.
Concept introduction:
When a basic or acidic mixture of an aldol product is heated, dehydration of an alcohol
(b)
Interpretation:
A mechanism for the cyclization of diketone for the formation of given compound is to be proposed.
Concept introduction:
When a basic or acidic mixture of an aldol product is heated, dehydration of an alcohol functional group takes place. The product formed is a conjugated
Want to see the full answer?
Check out a sample textbook solutionChapter 22 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
- Alkylation of the following compound with methyl iodide under two different conditions forms two different ketoesters (A and B). Each ketoester forms a cyclic diketone (C and D) when treated with methoxide ion in methanol. a. Draw the structures of A and B, and indicate the conditions used in the alkylation reaction that cause that ketoester to be formed. b. Draw the mechanism for the conversion of A to C.arrow_forward1. The molecule below is ascorbic acid, also known as vitamin C. a. As drawn below, ascorbic acid is shown as a diketone. An enol tautomer of ascorbic acid exists and is how the molecule is usually drawn. Draw the enol tautomer of ascorbic acid. b. Show the mechanism for tautomerization under basic conditions from the ketone to the enol. c. Ascorbic acid has a pK₂ of 4.6 which is more similar to that of a carboxylic acid than an alcohol. Which H is most acidic in ascorbic acid? d. Explain why Vitamin C is so acidic. OH OH ascorbic acid OHarrow_forwardAlkylation of the following compound with methyl iodide under two different conditions forms two different ketoesters (A and B). Each ketoester formsa cyclic diketone (C and D) when treated with methoxide ion in methanol. a. Draw the structures of A and B, and indicate the conditions used in the alkylation reaction that cause that ketoester to be formed.b. Draw the mechanism for the conversion of A to C.arrow_forward
- Vanillin has an acidic OH and an electrophilic aldehyde group that could conceivably react with sodiumhydroxide. However, in the aldol reaction, you added the NaOH directly to the solution of vanillin andacetone, rather than pre-treating acetone with base. Why could you do this successfully? a) NaOH is a weak base and a weak nucleophile.b) The reaction of NaOH with phenol OH groups and aromatic aldehydes is reversible, and thereaction is driven to the most stable product.c) The aldehyde in vanillin is unreactive towards nucleophiles.d) The NaOH is not soluble in the reactionarrow_forwardShow how you will carry out the following substance from benzaldehyde and any other reagents needed.arrow_forwardSynthesisarrow_forward
- Does it matter whether acetone is added first to the eq. NaOH solution then the benzaldehyde, or if the benzaldehyde is added first to the aq. NaOH solution, then the acetone in an aldol synthesis of dibenzalacetonearrow_forwardWhich combination of reagent is appropriate for the following transformation? Ph OMe Ph HO.arrow_forwardShow what reagents you would use to synthesize this ether by each of the following methods, show mechanism for method A and C. A. Acid-catalyzed ether formation from alcohols B. Alkoxymercuration-demercuration (do not show mechanism) C. Williamson ether synthesisarrow_forward
- I. Propose a one-step synthetic route to get the following compound using only SN2. Explain. H3C- CH3 H3C II. Propose a reasonable mechanism to explain the following reaction. Explain. Br etanol calorarrow_forward4. Provide a synthetic route to the following molecule using benzene and cyclohexane. Reagents cannot contain more than one carbon. Provide a mechanism for the last step of your synthetic route.arrow_forwardShow how to synthesize the following compound from an alkyl halide and a ketone oraldehyde. Hint: use a Wittig reaction.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