(a)
Interpretation: To assign the various resonances to the hydrogen nuclei of 2-bromo-2-methylbutane in
Concept Introduction: Nuclear magnetic resonance (NMR) is a spectroscopy technique that works on the basis that the nucleus of the atoms absorbs
(b)
Interpretation: To assign the various resonances to the carbon nuclei of 2-bromo-2-methylbutane in
Concept Introduction: Carbon-13 NMR has several merits over proton NMR in terms of its power to explain biochemical and organic structures. Carbon-13 NMR provides information related to the backbone of molecules instead of the periphery. In addition, the chemical shift range for Carbon-13 for most organic compounds is around 200 ppm related with 10 to 15 ppm for the proton.
Want to see the full answer?
Check out a sample textbook solutionChapter 10 Solutions
EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
- II. Mechanisms The reaction of 2-methyl-1,3-butadiene (isoprene) with Br2 yields this product mixture. Br Br Br Br Br Br 3% 21% 76% a. Write the mechanism for the formation of the three products. b. Write a plausible reason for the given product mixture percentages.arrow_forwarda. Write the mechanism for thebromination of pyridine and draw the products. b.There are three (3) possible structures for the products of this electrophilic substitution reaction. Which one is the major product? c. Explain your answer in (b)by providing the resonance contributing structures of intermediates formed by attack of pyridine to Br+.arrow_forwardthis is the spectral data for 4-cyclohexene-cis-1,2-dicarboxylic acid - Write the 1H NMR spectral information in ACS formatarrow_forward
- Mechanism. Consider the following reaction... HNO, (1 eq.) HSO, 0°C "NO: NO2 MA JOR MINOR a. Draw the mechanism for the formation of the EAS electrophile for this reaction. What is the role of sulfuric acid in this process? b. Draw all of the possible resonance forms for this reaction's sigma complex, as well as the resonance hybrid structure. c. Using both pictures and words, explain the regioselectivity of this reaction, or why the nitro group was added to the designated carbon.arrow_forwardWrite a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction. A. Write the mechanism for step one of this reaction. Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. B. Write the mechanism for step two of this reaction (where the product of step one reacts with the solvent, ethanol). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. C.Write the mechanism for the last step of this reaction (formation of ethyl isopropyl ether). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Cl- will act as the base in this reaction.arrow_forward15. a. Label the reactive features of the following reactants, select the most reactive feature, then write and highlight what it needs. Also, state if a carbocation, carbon radical, or carbanion will start to develop, and/or if aromatic character will be lost as a result of a reaction between these molecules. p-fluorotoluene + Cl2 and FeCls b. Use mechanism arrows to illustrate the reaction that occurs. If applicable, use stabilization resources to deal with the carbocation, carbon radical, or carbanion that starts to develop during the reaction, and draw the structure of any resonance- stabilized intermediate. Continue labelling and diagramming the reaction until you find the major stable product(s). Finally, state the stereochemistry of the major product(s) and use either Fisher projection or perspective formula representations to illustrate that stereochemistry.arrow_forward
- Except for one, all of the following statements concerning anthracene are correct which is:a. In Baeyer's test, it returns a negative result.b. A yellow, smoky, sooty flame is produced.c. In cold H2SO4, it is insoluble.d. Under dark conditions, it reacts with bromine. EXCEPT for one 2,3-dimethylheptane and 2,3-dimethylhepta-1,5-diene, the following tests or reagents could distinguish them.a. Under gloomy conditions, Br2 in waterb. Alkylation Friedel-Crafts Testc. Combustionarrow_forward1. Summarize the main characteristics of nucleophilic acyl substitution. 2. Choose one carboxylic acid that has applications in diagnostic tests, nutrition, or pharmacology. Explain how the molecular property contributes to the bulk property of the carboxylic acid.arrow_forwardNitration of furan with acetylnitrate leads to 2,5-dinitrofuran. Mononitration can be done by A. carrying out the reaction at higher temperature. B. using nitric acid instead of acetyl nitrate. C. carrying out the nitration in the presence of pyridine D. using concentrated nitric acid/sulfuric acid instead of acetyl nitrate.arrow_forward
- Which of the statement is INCORRECT? a. The increase in stability of 2,4-hexadiene over 1,3-hexadiene is due to the increased double bond substitution of the former. b. The stabilization of dienes by conjugation is less pronounced than the aromatic stabilization of benzene. c. Resonance description in alkenes usually involves charge separation. d. Higher energy pi-orbitals often have decreasing number of nodes.arrow_forwardPlease answer both parts to the questions completely. I will rate the answer afterwards. For a diels-alder reaction between anthracene and maleic anhydride, are the exo and endo forms of product 9,10-dihydroanthracene-9,10-ɑ,β-succinic acid anhydride different stereoisomers or are they the same molecule? Explain your answer by drawing the molecule. Would it be favorable to get a 1,4-adduct of anthracene and maleic anhydride? Why or why not? If the 1,4-adduct of anthracene and maleic anhydride had formed, would it have different exo and endo isomers? Yes or no and why?arrow_forwardD. Halogen-sp³ carbon bonds are often used as electron pair acceptors, known as electrophiles, in organic reactions. Electrophiles typically use their LUMO to an accept an electron pair from a donor known as a nucleophile. Given your knowledge of M.O. theory please predict what would happen if the nucleophile HS-would donate a lone pair of electrons to the LUMO of chloromethane. Please explain your prediction.arrow_forward