Concept explainers
(a)
Interpretation:The triplet centered near 1.0 and 1.1 and the doublet centered near 1.6 to the hydrogen nuclei of the three different isomers from which they arise is to be assigned.
Concept Introduction : Nuclear Magnetic Resonance (NMR) spectroscopy is a logical chemistry method used in quality control.
It studies for defining the material and purity of a sample and their molecular structure. It explains magnetic energy levels undergoing the resonance transition when the atomic nuclei are exposed to an external magnetic field and an
(b)
Interpretation:The integrated area of the selected multiplets in the spectrum are as given, the approximate percentage of each isomer present in the mixture is to be calculated.
Concept Introduction : Nuclear Magnetic Resonance (NMR) spectroscopy is a logical chemistry method used in quality control.
It studies for defining the material and purity of a sample and their molecular structure. It explains magnetic energy levels undergoing the resonance transition when the atomic nuclei are exposed to an external magnetic field and an electromagnetic radiation is applied with the specific frequency. The NMR spectrum is obtained by detecting the absorption signals.
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Chapter 9 Solutions
EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
- 4. A student has prepared 0.05 M solution of CH3-C=CH and has added to it 0.05 M solution of potassium tert-butoxide (K" O-C(CH3)3). (iv) Calculate the percentage of deprotonated methyl acetylene taking into account that pKa of the conjugate acid of potassium tert-butoxide equals 18 and pKa of methyl acetylene equals 24.arrow_forward1) The ¹H NMR spectra of carvone and the epoxidation product(s) are extremely complicated, so we've only given you partial spectra (from 8 3.0 -7.0 ppm), showing the double bond regions. There are three peaks in this region in the carvone spectrum, corresponding to Ha, H, and H. Based on chemical shift or coupling considerations, assign the peaks for H₂ and Hb/c (you can't distinguish between H, and Hc, so just label both peaks Hbic). H₂C 80 Transmittance [%] 30 40 50 60 70 80 6.8 6.6 ****** ¹H spectrum (partial) of (D)-(+)-carvone ¹H spectrum (partial) of unknown epoxidation product 6.8 6.6 6.4 6.2 6.0 5.8 5.6 5.4 6.2 6.0 5.8 5.6 5.4 ✓ Carvone IR.jpg BRUKER 3500 8895 *** He 3000 H₂₂ (D)-(+)-carvone 5.2 5.2 5.0 4.8 f1 (ppm) 2500 5.0 f1 (ppm) Ha -CH3 Ⓒ 4.6 2000 Wavenumber cm-1 4.6 4.4 4.2 4.0 4.2 4.0 3.8 1645.58- 1500 r 3.8 3.6 3.6 1000 3.4 S 3.4 3.2 3.0 3.2 3.0 500arrow_forwardEthers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide. Draw the structure of the expected organic product of the reaction of 1-iodo-2-methylpropane with the following alkoxide ic + O Na You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Do not include counter-ions, e.g., Na", I", in your answer. C opy astearrow_forward
- Tertiary hydrogen atoms react with Cl # about 5.5 times as fast as primary ones. Predict the product ratios for chlorination of isobutane.arrow_forward11. One doctor allowed 2-methylbutane to undergo chlorination at 300°C and obtained as products 36% 1-chloro-2-methylbutane, 18% 2-chloro-2-methylbutane, 28% 2-chloro-3-methylbutane, and 18% 1-chloro-3-methylbutane. Calculate the relative ease of removal of a hydrogen atom from a tertiary, secondary, and primary carbocation? (8%)arrow_forwardElimination of HBr from 2-bromobutane affords a mixture of 1-butene and 2-butene. With sodium ethoxide as base, 2-butene constitutes 81% of the alkene products, but with potassium tert-butoxide, 2-butene constitutes only 67% of the alkene products. Offer an explanation for this difference.arrow_forward
- 1. What is the function of CH2Cl2 in the bromination reactions? Why can it fulfill this role?2. In not more than three (3) sentences, explain why terminal alkynes are acidic.3. What impurities are removed when acetylene gas is made to pass through an acidified solution of CuSO4?4. Explain the difference in the rate of free-radical bromination reactions of toluene and cyclohexane.5. Give the reagent or chemical test that would differentiate the following pairs o fcompounds. Provide only the reagents or chemical tests discussed in the module. Write chemical equations for the reactions involved. a. benzene and ethylbenzeneb. 1-butyne and 2-butynec. 2-methylpentane and 2-methyl-2-pentened. toluene and 1-methylcyclohexenearrow_forwardS.10. Describe the product formed as a result of the reaction between cyclohexanone and 3-butene-2-one by also writing the mechanism of the reaction. 1'CH,ON H;C, 2 HO CH,arrow_forward1) Show the steps for the free radical chlorination of toluene using Cl2 and light to give benzyl chloride. 2) Demonstrate resonance forms for the benzyl radical that is the principal intermediate, showing how the benzene ring stabilizes this radical.arrow_forward
- Diels Alder Reaction of Tetraphenylcyclopentadienone Purpose of the Experiment: To successfully synthesize dimethyltetraphenylphthalate via a Diels Alder reaction. The melting point of the product is 258oC. Why should we not do a melting point of the product? The intermediate in brackets loses CO to form the product at 180oC. If the C=O were replaced by CH2, do you think the same type of reaction would happen with loss of :CH2?arrow_forward12:53 ul 4G O 2. Show a reaction scheme with all the reactants and reagents of the nitration reaction of bromobenzene and show the major products(s), with valid reasons motivate why the positioning of the two constituents' favour ortho, para and/or meta positioning Add a caption... > Status (Custom) +arrow_forwardAlkenyl halides such as vinyl bromide, CH2=CHBr, undergo neither SN1 nor SN2 reactions. What factors account for this lack of reactivity?arrow_forward