Concept explainers
(a)
Interpretation:
The products of the elimination reaction of two stereoisomers of bromodecalin with
Concept introduction:
The
The bimolecular elimination reaction that favours the removal of an
(b)
Interpretation:
The compound that undergoes faster elimination reaction with
Concept introduction:
The chemical reaction that consists of an alkyl halide, a good leaving group which reacts with Lewis base to form an alkene is termed as elimination reaction. In this reaction there is complete removal of the leaving group takes place without any substitution.
The bimolecular elimination reaction that favours the removal of a
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Organic Chemistry (9th Edition)
- 1. For the following reaction step, indicate which pattern of arrow pushing it represents. a. proton transferb. rearrangementc. loss of a leaving group2. Melphalan, a drug used in chemotherapy, reacts with itself in the body before binding with its target, as illustrated in the mechanism below. What is the first pattern of arrow pushing seen in this reaction? a. rearrangementb. loss of a leaving groupc. nucleophilic attackarrow_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_forward2. When the following pair of reactants are combined in the presence of a basic catalyst, a number of aldol addition products are possible (since both of the reactants possess an acidic alpha proton). a. b. C. CH3 + H₂C H NaOH/H₂O Draw the structures for the two possible enolate ions. Draw the structures for all possible aldol addition products (also show the enolate ion and electrophilic carbonyl compound responsible for each product). For each of the aldol addition products predicted in part b, draw the structures for all of the corresponding aldol condensation products after loss of water (if E/Z isomers are possible, show both isomers)arrow_forward
- 1. 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_forwardPropose a mechanism for the following reaction. a. Explain why two products are formed. b. Explain why methanol substitutes for only one of the brominesarrow_forwarda. What reagent(s) are needed to synthesize the enamine below. Also, draw the resonance structure(s) for the enamine. b. Predict the product of the reaction between the enamine from part a and ethyl iodide. Also explain why it forms, including any selectivities. Hint: Consider the type of reaction alkyl halides take part in and the resonance structure(s) in part a. Etlarrow_forward
- Which nucleophile would prefer simple addition over conjugate addition? CH3MgBr NaCN CH3CH2NH2 (CH3CH2)2CuLiarrow_forwarda. Draw the structures of all the elimination products. b. The reaction occurs through an E2 mechanism. Using one of your products writethe mechanism of the reaction using curved arrows. c. Is this reaction regioselective? Explain your answer. d. Explain why the reaction is stereoselective.arrow_forwardWhich solvents favor SN1 reactions and which favor SN2 reactions?arrow_forward
- When trichloride J is treated with CH3OH, nucleophilic substitution forms the dihalide K. Draw a mechanism for this reaction and explain why one Cl is much more reactive than the other two Cl’s so that a single substitution product is formed.arrow_forwarda. Which of the following reactions does not give the carbonyl product shown?b. Which of the reactions that do not occur can be made to occur if an acid catalyst is added to the reaction mixture?arrow_forward1. From the two synthetic routes shown below which one would be the best route for the desired product. Explain your reasoning and draw the stepwise reaction mechanism for both pathways to support your answer. 1. NaBH, 2. H,o* 1. NaH 2. H,оarrow_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