Concept explainers
Treatment of benzaldehyde
Want to see the full answer?
Check out a sample textbook solutionChapter 13 Solutions
Organic Chemistry
Additional Science Textbook Solutions
Chemistry & Chemical Reactivity
General Chemistry: Principles and Modern Applications (11th Edition)
Introductory Chemistry (5th Edition) (Standalone Book)
General, Organic, and Biological Chemistry (3rd Edition)
General Chemistry: Atoms First
- Ketones undergo a reduction when treated with sodium borohydride, NaBH4. What is the structure of the compound produced by reaction of 2-butanone with NaBH4 if it has an IR absorption at 3400 cm-1 and M+=74 in the mass spectrum?arrow_forwardReaction of iodoethane with CN- yields a small amount of isonitrile, CH3CH2N≡C, along with the nitrile CH3CH2N≡N, as the major product. Write electron-dot structures for both products, assign formal charges as necessary, and propose mechanisms to account for their formation.arrow_forwardC9H10O2: IR absorption at 1718 cm–1. Propose a structure with data given.arrow_forward
- A hydrocarbon, compound B, has molecular formula C6H6, and gave an NMR spectrum with two signals: delta 6.55 pm and delta 3.84 pm with peak ratio of 2:1. When warmed in pyridine for three hr, compound B quantitatively converts to benzene. Mild hydrogenation of B yielded another compound C with mass spectrum of m/z 82. Infrared spectrum showed no double bonds; NMR spectrum showed one broad peak at delta 2.34 ppm. With this information, address the following questions. a) How many rings are in compound C? b) How many rings are probably in B? How many double bonds are in B? c) Can you suggest a structure for compounds B and C? d) In the NMR spectrum of B, the up-field signal was a quintet, and the down field signal was a triplet. How must you account for these splitting patterns?arrow_forwardThe mass, IR, and 1H-NMR spectra of a compound are shown below. Suggest a possible structure for the compound, explaining how you reach your decision.arrow_forwardFrom the following 1H-NMR and 13C-NMR spectra, assign a structure for a compound with a formula of C4H9Br. Give reasons (explanations) for the choosen structure.arrow_forward
- A compound has the molecular formula C5H1002. Its IR spectrum shows a strong absorption band near 1740 cm1. Its 'H NMR spectrum consists of two singlets at Õ 1.2 and o 3.6. Which is the most likely structure of the compound?arrow_forwardAs reaction of (CH3)2CO with LIC≡CH followed by H2O affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600−3200, 3303, 2938, and 2120 cm−1. D shows the following 1H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?arrow_forwardTreatment of ketone A with ethynyllithium (HC≡CLi) followed by D3O+ afforded a compound B of molecular formula C12H13DO3, which gave an IR absorption at approximately 1715 cm−1. What is the structure of B and how is it formed?arrow_forward
- There are several isomeric alkanes of molecular formula C6H14. Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers. Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm Isomer B: δ = 0.84 (t, 3 H), 0.86 (t, 9H), 1.22 (q, 2H) ppmarrow_forwardWhat's structure for a compound that meets the following description: C4H8O with IR absorption at 1715 cm-1. O i Y OH ➡ =Oarrow_forwardCompound X has molecular formula C5H10. In the presence of a metal catalyst, compound X reacts with one equivalent of molecular hydrogen to yield 2-methylbutane. (1) Suggest three possible structures for compound X. (2) Hydroboration-oxidation of compound X yields a product with no chirality centers. Identify the structure of compound X.arrow_forward