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Concept explainers
(a)
Interpretation:
The reason as to why
Concept introduction:
Many nuclei and electrons have spin; due to this spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an
(b)
Interpretation:
The assignment of the given data to the compound is to be validated. The resonances in the
Concept introduction:
Many nuclei and electrons have spin, due to this spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.
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Chapter 13 Solutions
EBK ORGANIC CHEMISTRY
- 10.23 Suggest conditions for carrying out each of the following conversions to yield a product that is as free of isomers as possible. (а) НО, Br, Br HO CH3 ČH3 (b) (CH;),CH(CH,),OH (CH,),CH(CH,),CI > (c) CH3 H;C, Br -CHCH, -CH3 ОН OH Brarrow_forwardGive logical fragmentation reactions to account for the following ions observed in these mass spectra.(a) n-octane: 114, 85, 71, 57 (b) methylcyclohexane: 98, 83 (c) 2-methylpent-2-ene: 84, 69(d) pentan-1-ol: 70, 55, 41, 31 (e) N-ethylaniline (PhNHCH2CH3): 121, 106, 77*(f) 1-bromo-2-methylbutane: 152, 150, 123, 121, 71 (base)arrow_forwardQ4. The following is the 13C NMR spectrum of a highly concentrated solution of dicyclopentadiene obtained in chloroform-d. Despite the high purity of the compound based on ¹H NMR, there is a massive peak observed at 77.2 ppm in this 13C spectrum, which doesn't correspond to any resonances expected for dicyclopentadiene. What is this peak, and why do you not see a corresponding peak for this compound in your ¹H NMR spectrum? 79-751 <-136.22 -132.62 132.27 132.23 135 130 125 120 115 110 105 100 95 90 85 80 75 70 65 60 55 50 45 40 35 30arrow_forward
- 07) A chemist plans to carry out the sequence of reactions shown below. (a) List, for each step, the changes that the chemist should expect to find when comparing the infrared spectrum of the starting material with that of the product. (b) Decide, for each step, whether or not it is possible to “know” (in the sense of having reasonable certainty, or at least a good indication) whether the desired transformation has occurred using only infrared spectroscopyarrow_forward14. Please write the major product for each following Diels-Alder reaction. Explain why they are formed by using Frontier Molecular Orbital theory. (a) 1-(diethylamino)-1,3-butadiene + acrylate (b) 2-ethoxy-1,3-butadiene + acrylate Moreover, draw Molecular Orbitals of 1-(diethylamino)-1,3-butadiene, 2-ethoxy-1,3-butadiene & acrylate. In addition, mark energy levels and predict the products by using FMO theory.arrow_forward16) The partial chemical structure and ¹H NMR spectrum of 1-bromopropane (C3H/Br) are shown below. Draw in the hydrogen atoms and label them with a subscript that corresponds to the labeled peaks in the ¹H NMR spectrum. Provide a brief rationale for your structural assignments. 11 10 NSP-00-184 T 9 8 7 6 Peak 1: 3.39 ppm 2H Triplet 5 4 3 Peak 3: 1.03 ppm 3H Triplet Peak 2: 1.87 ppm 2H Sextet ppm Rationale for peak assignments in structure: I 2 1 0 Draw in labeled hydrogen atoms (H₂, H₂, H₂) and assign them to peaks 1-3 CI- 14. : I figner that % H. H₂ HS - H² Structure of 1-bromopropanearrow_forward
- Alkylbenzenes such as toluene (methylbenzene) react with NBS to give products in which bromine substitution has occurred at the position next to the aromatic ring (the benzylic position). Explain, based on the bond dissociation energies in Table 6-3 on page 170.arrow_forward(b) Predict the suitable solvent (H2O or CH3COCH3) to increase the reaction of bromopropane (CH3CH2CH2B1) with sodium hydroxide (NaOH). Two reactions are shown below: NaOH, 55 °C CH;CH,CH,Br CH;CH,CH,OH + NaBr H,O (i) NaOH, 55 °C CH;CH,CH,Br CH;CH,CH,OH NaBr H,C CH (ii)arrow_forward(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) Ph THF A Ph Ph B H₂SO4 100 °C 3 OH (iii) In analysing both these methods, are there other possible alkene products other than methylenecyclohexane 2? Use mechanistic details to support your answer.arrow_forward
- For each of the molecules below: (a) Provide the bond line structures (b) Indicate the number of peaks that would be seen in their ¹H-NMR spectra. Number each unique type of hydrogen peaks as shown in the example on the right. (c) Label the diasterotopic and enantiotopic atoms and/or groups. 1. (1R,4S) 4-secbutyl-2,3-diethyl-6,6-dimethylcyclohex-2-enol 2. (2R,6S) 2,6-dibromo-4,4-dimethylcyclohexanol 3. (5S,7R) -7-bromo-3,9-diethyl-6,6-dimethylundec-3,8-dien-5-ol Example: 1 2 1Η 2arrow_forward4.) HX is used as a reagent in the reaction below. „NH2 + HX + NEN: + A. What functional-group transformation occurs in this reaction? B. What is the likely identity of HX? Verify your decision with the table of K, values in the back of your textbook. Consider the following thermodynamic data for the reaction shown above. „NH2 HX + NEN: + AH°¡ (kJ/mol) -386 260.1 30.00 -393.5 S° (J/mol K) 166 146.0 191.3 191.5 213.8 C. Does the reaction absorb or release heat? Justify with a calculation. 0==0arrow_forward(b) Predict the suitable solvent (H2O or CH3COCH:) to increase the reaction of bromopropane (CH3CH2CH2B1) with sodium hydroxide (NaOH). Two reactions are shown below: NaOH, 55 °C CH;CH,CH,Br CH;CH,CH,OH + + NaBr H,O (i) NaOH, 55 °C CH;CH,CH,Br CH;CH,CH,OH + NaBr (ii) H,C- CH3arrow_forward
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