(a)
Interpretation: For the IR spectral data of 4-methyl-2-pentanol, in the functional group region the absorptions associated with alcohol function need to be specified.
Concept Introduction : The analysis of interaction of infrared light with a molecule is termed as infrared spectroscopy. The main use of infrared spectroscopy is identification of
(b)
Interpretation: The various resonances to the hydrogen nuclei need to be assigned in the
Concept Introduction : Nuclear magnetic resonance (NMR) is a spectroscopy technique that works on the basis that the nucleus of the atom absorbs
(c)
Interpretation: Various resonances to carbon nuclei responsible for the
Concept Introduction : Carbon-13 NMR has several advantages over proton NMR in terms of its power to elucidate organic and biochemical structures. First Carbon-13 NMR provides information about the backbone of molecules rather than about the periphery. In addition, the chemical shift range for
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Experimental Organic Chemistry: A Miniscale & Microscale Approach (Cengage Learning Laboratory Series for Organic Chemistry)
- 4. Suggest two different chemical tests and a major IR frequency that would help distinguish between the following pairs of compounds a. Benzaldehyde and benzyl alcohol b. 2-pentanone and 3-pentanone c. Propanol and diethyl ether d. Propanol and propanoic acidarrow_forwardThe infrared spectrum shown is consistent with which compound? 500 Benzaldehyde a. Ethyl benzoate b. 2-Hexanone C. 4-Hydroxy-4-methyl-2-pentanone d. 1-Hexen-5-one е.arrow_forwardAn oxygen-containing compound shows an absorption band at 1700 cm', and no absorption at 3300 cm', 2700 cm', or 1100 cm1. Which class of compounds is suggested in the given information? A. Carboxylic Acid B. Ester C. Ketone D. Aldehyde E. Alcoholarrow_forward
- 8. One stereoregular form of polystyrene (A) has a 'H NMR spectrum containing a triplet centered at about 1.4 ppm and a quintet at about 1.9 ppm. Another stereoregular form (B) has an octet at about 1.6 ppm and a quintet at about 2.3 ppm. (Both spectra also exhibit phenyl proton resonances further downfield.) Interpret the spectra and determine which corresponds to isotactic and which to syndiotactic. (Syndiotactic polystyrene was first reported by N. Ishihara and co-workers in a 1986 paper. You may wish to locate the paper and check your answer.)arrow_forwardWrite the reaction involved in Ferrox Test. a. What is the species responsible? b. Why is phenol negative in Ferrox Test? Based on the theoretical result, what is the order of reactivity of primary, secondary, and tertiary alcohols in the Lucas Test? a. Lucas Reagent contains ZnCl2 in HCl. What is the role of ZnCl2?arrow_forward3. 'H-NMR interpretation When dissolved in CDC13, phenacetin shows 6 signals. All of the peaks are sharp, except for the signal f not below. Draw the chemical structure of phenacetin, labeling each hydrogen with an alphabetical letter. Make a larger version of the chart below (half or full page), and complete it with the missing information. Explanation of splitting patter 8 (ppm) Letter # H (integration Splitting pattern value) 7.94 f 1 Broad singlet 7.36 e 6.80 d 3.98 с 2.09 b 1.38 a Extra Credit Question 4. Describe/predict how the 'H-NMR spectrum differs for acetaminophen.arrow_forward
- Write the reaction involved in Ferrox Test. a. What is the species responsible? b. Why is phenol negative in Ferrox Test? Based on the theoretical result, what is the order of reactivity of primary, secondary, and tertiary alcohols in the Lucas Test? a. Lucas Reagent contains ZnCl2 in HCl. What is the role of ZnCl2? What reagents are used in the esterification of Alcohols and Phenols? a. Write the reaction involved in Primary Alcohol (Ethanol) and Acetyl Chloride b. Write the reaction involved in Phenol and Acetyl Chloride What is the purpose of the Chromic acid test? a. What are the reagents used? b. Write oxidation reaction of Primary Alcohols and Secondary Alcoholsarrow_forwardUsing the attached infrared spectroscopy spectrum for the compound Heptanoic Acid, identify the functional group and any observed characteristic absorbtions in cm-1. Compare with the attached roadmap for interpreting IR spectra.arrow_forwardWhat accounts for the geometry (pyramidalization) of the NH2 group in aniline? 1. Resonance between the NH2 group and the benzene ring. 2. The electronic withdrawing nature of the sp2 carbons in the phenyl group. 3. Participation of the nitrogen lone pair to make the system aromatic. 4. Both 1 and 3.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_forwardAnalyze both IR and NMR spectra ,Identify the unknown (solid sample )? Note: the same unknown is used in the experiment to get both IR and NMR. The list of all the possible organic compounds are as follows: Cumene, 3-Methy-2-butanone, Phenethyl alcohol, Isopropyl Acetate, Ethel benzoate, 3-phenylpropionaldehyde, isobutyl cinnamate, cyclamen aldehyde, Styrallyl acetate, Butyl butyrate, propiophenon, phenylacetylene, Cis-Hexenyl-3-Acetate, Benzyl propionate, 3-(p-ethyl-phenyl)-2,2-dimethyl propionaldehyde, 2-methoxy-4-ethyl-phenol, P-ethylphenol, diphenyl amine, 4-phenyl-3-buten-2-one, Diethyl Terphthalate, glutaric acid, cinnamic acid, P- ethylbenzoic acid, Coumarin, vanillin, (2,2,2-trichloro-1-phenylethyl)acetate, 4-(p-hydroxyphenyl)-2-butanone, 2-ethoxy-5-prop-1-enylphenol, t-butyl-phenol, Thymol, Calone, Syringol, Syringaldehyde. Borderline MP unknowns: Styrallyl alcohol, 1,1-dimethyl-2-phenethyl acetate, 1,1-dimethyl-2-phenyl ethanol.arrow_forwardII. Give one test to differentiate the following pairs of compounds. Encircle the name of the compound which will yield a positive result. Test phenylacetaldehyde cyclohexanone 2-pentanone 2-pentanone Compounds benzyl alcohol cyclohexyl methyl ether 3-pentanone 2-pentanol Choices (different tests) a. Lucas' test b. Oxidation test c. Ferric Chloride Test d. 2,4-dinitrophenylhydrazine test e. Tollen's test f. Benedicts' test g. Iodoform's testarrow_forward
- Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole