(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
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Organic Chemistry (9th Edition)
- 1. Provide the mechanism of the reaction shown in the picture. 2. Explain why it cannot be done in basic conditions. 3. Why is the enol tautomer favored over the keto tautomer? Ph H3C OH H H3O+/H₂O HO H3C Pharrow_forwardDraw the missing organic structures in this short synthetic sequence. Assume an appropriate workup is performed after each reaction. Convert carbonyls to thioacetals, then treat with Raney Ni/H2 Compound B + Compound Aarrow_forwardAlkylation 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_forward
- Synthesize the following compounds from the given starting material. You can add on any alkyl/ alkyl halide under or equal to 4 carbons or any necessary inorganic reagent needed (this includes triphenyl phosphine (Ph3P). Please draw all intermediates and reagents necessary to get to the product. b. sobarrow_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_forward3. Show how the following compound can be synthesized using an Aldol Condensation reaction.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_forwardA different way of synthesising the product 4,4- diphenylbut-3-en-2-one is via an aldol condensation. What starting materials would you use and what reaction conditions would you employ? Draw the full reactionarrow_forwardThe reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, doesnot work with primary alcohols. a. Propose a mechanism for the Ritter reaction.b. Why does the Ritter reaction not work with primary alcohols?c. How does the Ritter reaction differ from the acid-catalyzed hydrolysis of a nitrile to form an amide?arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning