Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 13.9, Problem 16P
How could you use 1H NMR to determine the regiochemistry of electrophilic addition to
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Hydrohalic acids (i.e., HCl, HBr, HI) add to the double bond of alkenes to yield alkyl halides. Shown below is the carbon NMR spectrum of an alkene of formula C5H10. What is the structure of this alkene?
6- In a 1H-NMR spectra on a scale of 0 – 10 ppm, Show the exact locations in ppm of 1-the saturated hydrocarbons, 2- the unsaturated hydrocarbons, 3- the halogenatedhydrocarbons and 4- the aromatic hydrocarbons.
Ethers 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 iodomethane with the following alkoxide ion:
CH3
H3C
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.
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Chapter 13 Solutions
Organic Chemistry
Ch. 13.1 - Prob. 1PCh. 13.1 - Prob. 2PCh. 13.2 - Prob. 3PCh. 13.3 - The following 1H NMR peaks were recorded on a...Ch. 13.3 - When the 1Η NMR spectrum of acetone, CH3COCH3, is...Ch. 13.4 - Each of the following compounds has a single 1H...Ch. 13.4 - Identify the different types of protons in the...Ch. 13.5 - How many peaks would you expect in the 1H NMR...Ch. 13.6 - Predict the splitting patterns you would expect...Ch. 13.6 - Draw structures for compounds that meet the...
Ch. 13.6 - The integrated 1H NMR spectrum of a compound of...Ch. 13.7 - Identify the indicated sets of protons as...Ch. 13.7 - How many kinds of electronically nonequivalent...Ch. 13.7 - How many absorptions would you expect (S)-malate,...Ch. 13.8 - 3-Bromo-1-phenyl-1-propene shows a complex NMR...Ch. 13.9 - How could you use 1H NMR to determine the...Ch. 13.11 - Prob. 17PCh. 13.11 - Propose structures for compounds that fit the...Ch. 13.11 - Prob. 19PCh. 13.12 - Prob. 20PCh. 13.12 - Prob. 21PCh. 13.12 - Prob. 22PCh. 13.13 - Prob. 23PCh. 13.SE - Into how many peaks would you expect the 1H NMR...Ch. 13.SE - How many absorptions would you expect the...Ch. 13.SE - Sketch what you might expect the 1H and 13C NMR...Ch. 13.SE - How many electronically nonequivalent kinds of...Ch. 13.SE - Identify the indicated protons in the following...Ch. 13.SE - Prob. 29APCh. 13.SE - Prob. 30APCh. 13.SE - When measured on a spectrometer operating at 200...Ch. 13.SE - Prob. 32APCh. 13.SE - Prob. 33APCh. 13.SE - How many types of nonequivalent protons are...Ch. 13.SE - The following compounds all show a single line in...Ch. 13.SE - Prob. 36APCh. 13.SE - Propose structures for compounds with the...Ch. 13.SE - Predict the splitting pattern for each kind of...Ch. 13.SE - Predict the splitting pattern for each kind of...Ch. 13.SE - Identify the indicated sets of protons as...Ch. 13.SE - Identify the indicated sets of protons as...Ch. 13.SE - The acid-catalyzed dehydration of...Ch. 13.SE - How could you use 1H NMR to distinguish between...Ch. 13.SE - Propose structures for compounds that fit the...Ch. 13.SE - Propose structures for the two compounds whose 1H...Ch. 13.SE - Prob. 46APCh. 13.SE - How many absorptions would you expect to observe...Ch. 13.SE - Prob. 48APCh. 13.SE - How could you use 1H and 13C NMR to help...Ch. 13.SE - How could you use 1H NMR, 13C NMR, and IR...Ch. 13.SE - Assign as many resonances as you can to specific...Ch. 13.SE - Assume that you have a compound with the formula...Ch. 13.SE - The compound whose 1H NMR spectrum is shown has...Ch. 13.SE - The compound whose 1H NMR spectrum is shown has...Ch. 13.SE - Propose structures for compounds that fit the...Ch. 13.SE - Long-range coupling between protons more than two...Ch. 13.SE - The 1H and 13C NMR spectra of compound A, C8H9Br,...Ch. 13.SE - Propose structures for the three compounds whose...Ch. 13.SE - The mass spectrum and 13C NMR spectrum of a...Ch. 13.SE - Compound A, a hydrocarbon with M+=96 in its mass...Ch. 13.SE - Propose a structure for compound C, which has...Ch. 13.SE - Prob. 62GPCh. 13.SE - Propose a structure for compound E, C7H12O2, which...Ch. 13.SE - Compound F, a hydrocarbon with M+=96 in its mass...Ch. 13.SE - 3-Methyl-2-butanol has five signals in its 13C NMR...Ch. 13.SE - A 13C NMR spectrum of commercially available...Ch. 13.SE - Carboxylic acids (RCO2H) react with alcohols (ROH)...Ch. 13.SE - Prob. 68GPCh. 13.SE - The proton NMR spectrum is shown for a compound...Ch. 13.SE - The proton NMR spectrum of a compound with the...Ch. 13.SE - The proton NMR spectrum is shown for a compound...
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- Following is a balanced equation for the allylic bromination of propene. CH2==CHCH3 + Br2 h CH2==CHCH2Br + HBr (a) Calculate the heat of reaction, H 0, for this conversion. (b) Propose a pair of chain propagation steps and show that they add up to the observed stoichiometry. (c) Calculate the H 0 for each chain propagation step and show that they add up to the observed H 0 for the overall reaction.arrow_forward09:28 Is the following compound aromatic or not? choose the correct answer (with motive) from the options given O A. It has 8 TT electrons and satisfy Huckel's rule therefore it is aromatic O B. It is aromatic with electrons 10 TT electrons and satisfy Huckel's rule OC It is not aromatic because the total number of electrons and does not satisfy Huckel's rule O D. It has 6 TI electrons, therefore it does not satisfiy Huckel's rule Add a caption... > Status (Custom)arrow_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 iodoethane with the following alkoxide ion: H3C CH3 + 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. P opy aste [*arrow_forward
- Are the following two reactions valid methods of synthesizing the same organic compound?arrow_forwardNitration of an aromatic ring involves an electrophilic substitution reaction. Draw the structure of the electrophile that is attacked by the aromatic ring and the intermediate formed after attachment of the electrophile to the ring. Be sure to show formal charges.arrow_forwardDetermine reagents C and D from the reaction scheme below. Choose two (2) answers. Select one or more: H2O, Δ Cl2, CCl4 HCl H2SO4, Δ Cl2, H2Oarrow_forward
- Explain why the bond dissociation enthalpy of a C-H bond in benzene is significantly greater than that in alkanesarrow_forwardFor following substituted benzenes: [1] C6H5Br; [2] C6H5CN; [3] C6H5OCOCH3: Does the substituent activate or deactivate the benzene ring inelectrophilic aromatic substitution?arrow_forwardSuppose you have two bottles, labeled ketone A and ketone B. You know that one bottle contains CH3CO(CH2)5CH3 and one contains CH3CH2CO(CH2)4CH3, but you do not know which ketone is in which bottle. Ketone A gives a fragment at m/z = 99 and ketone B gives a fragment at m/z = 113. What are the likely structures of ketones A and B from these fragmentation data?arrow_forward
- 16-17 Propylamine (bp 48°C), ethylmethylamine (bp 37°C), and trimethylamine (bp 3°C) are constitutional isomers with the molecular formula C3HgN. Account for the fact that trimethylamine has the lowest boiling point of the three and propylamine has the highest.arrow_forwardNitriles, R–=C≡N, undergo a hydrolysis reaction when heated with aqueous acid. What is the structure of the compound produced by hydrolysis of propanenitrile, CH3CH2C≡N, if it has IR absorptions from 2500–3100 cm-1 and at 1710 cm-1, and has M+=74?arrow_forwardTreatment of a hydrocarbon A (molecular formula C9H18) with Br2 in the presence of light forms alkyl halides B and C, both having molecular formula C9H17Br. Reaction of either B or C with KOC(CH3)3 forms compound D (C9H16) as the major product. Ozonolysis of D forms cyclohexanone and acetone. Identify the structures of A–D.arrow_forward
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