Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 14, Problem 38P
We noted in Section
that an NMR spectrum is an average spectrum of the
conformations populated by a molecule. From the following data, estimate the percentages
of axial and equatorial bromine present in bromocyclohexane.
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Compounds X and Y both have the formula C7H₁4.
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Sn [F
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Chapter 14 Solutions
Organic Chemistry - Standalone book
Ch. 14.3 - Prob. 1PCh. 14.3 - Prob. 2PCh. 14.4 - The 1H NMR signal for bromoform (CHBr3) appears at...Ch. 14.5 - identify the most shielded and least shielded...Ch. 14.5 - (a) Assign the chemical shifts 1.6, 2.2, and 4.8...Ch. 14.5 - Assign the chemical shifts 1.1, 1.7, 2.0, and 2.3...Ch. 14.5 - Assign the chemical shifts 1.6, 4.0, 7.5, 8.2, and...Ch. 14.6 - The 300-MHz 1H NMR spectrum of 1,4-dimethylbenzene...Ch. 14.6 - Prob. 9PCh. 14.6 - How many signals would you expect to find in the...
Ch. 14.7 - Describe the appearance of the 1H NMR spectrum of...Ch. 14.8 - Describe the appearance of the 1H NMR spectrum of...Ch. 14.11 - Prob. 13PCh. 14.11 - Prob. 14PCh. 14.12 - Hydrogen bonding between the oxygen of dimethyl...Ch. 14.14 - Prob. 16PCh. 14.15 - The 13C NMR spectrum of 1-bromo-3-chloropropane...Ch. 14.15 - Consider carbons x, y, and z in p-methylanisole....Ch. 14.15 - Prob. 19PCh. 14.16 - To which of the compounds of Problem 14.16 does...Ch. 14.18 - DEPT spectra for a compound with the formula...Ch. 14.20 - Vibrational frequencies are sensitive to isotopic...Ch. 14.21 - Prob. 23PCh. 14.22 - Prob. 24PCh. 14.23 - Prob. 25PCh. 14.23 - Which one of the C5H8 isomers shown has its max at...Ch. 14.24 - Knowing what to look for with respect to isotopic...Ch. 14.24 - The base peak appears at m/z105 for one of the...Ch. 14.24 - Mass spectra of 1-bromo-4-propylbenzene and...Ch. 14.25 - Prob. 30PCh. 14 - Each of the following compounds is characterized...Ch. 14 - Deduce the structure of each of the following...Ch. 14 - From among the isomeric compounds of molecular...Ch. 14 - The H1NMR spectrum of fluorene has signals at 3.8...Ch. 14 - Prob. 35PCh. 14 - H1NMR spectra of four isomeric alcohols with...Ch. 14 - Prob. 37PCh. 14 - We noted in Section 14.13 that an NMR spectrum is...Ch. 14 - Identify each of the C4H10O isomers on the basis...Ch. 14 - A compound (C3H7ClO2) exhibited three peaks in its...Ch. 14 - Label nonequivalent carbons in the following...Ch. 14 - Compounds A and B are isomers of molecular formula...Ch. 14 - C13 NMR spectra for four isomeric alkyl bromides...Ch. 14 - Prob. 44PCh. 14 - Prob. 45PCh. 14 - Identify the C3H5Br isomers on the basis of the...Ch. 14 - Prob. 47PCh. 14 - A compound (C8H10O) has the IR and H1NMR spectra...Ch. 14 - Deduce the structure of a compound having the...Ch. 14 - Figure 14.53 presents IR, H1NMR, C13NMR and mass...Ch. 14 - H1NMR, C13NMR, IR, and mass spectra are shown for...Ch. 14 - 1H NMR and IR spectra for a compound with the...Ch. 14 - FriedelCraftsalkylation of benzene with...Ch. 14 - Prob. 54DSPCh. 14 - Prob. 55DSPCh. 14 - Prob. 56DSPCh. 14 - Prob. 57DSPCh. 14 - Prob. 58DSP
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- When bromine is added to two beakers, one containing phenyl isopropyl ether and the other containing cyclohexene, the bromine color in both beakers disappears. What observation could you make while performing this test that would allow you to distinguish the alkene from the aryl ether?arrow_forwardExplain why the following compounds have the indicated boiling points. All three are polar, have rounded molecular weights, and are not the basis for justification. Describe the specific structural characteristic to justify the difference between the highest boiling point and the lowest boiling point.arrow_forwardIdentify which of the following functional groups appear in the molecule daumone. (Note that some of the functional groups in daumone will not be listed as an answer option) Daumone has been isolated and is found to extend life in worms. When Caenorhabditis elegans worms find their environment crowded and inhospitable, they hibernate until food becomes available, effectively extending their life span. Daumone is the compound that has been found to be responsible for this hibernation. HO но. OH Daumone O Esterarrow_forward
- Rank the following compound in terms of increasing predicted boiling points. Explain your answer. Compounds: Benzene Ring, phenol, dichlorobenzene, Phenylarrow_forwardAccount for the fact that 2-phenylpropanal is formed rather than its constitutional isomer, 1-phenyl-1-propanone.arrow_forwardIn addition to more highly fluorinated products, fluorination of 2-methylbutane yields a mixture of compounds with the formula C5H10F2. Draw the structures of all the isomers with the formula C5H10F2 that would be produced and label with a star all the chiral centers present in their structures.arrow_forward
- Acrolein and 1,3-cyclohexadiene react in a one-step concerted manner to yield a single product. Give the structure of the product. What kind of reaction is this an example of? In terms of this reaction, how would you classify acrolein? How would you classify 1,3-cyclohexadiene? Hint: acrolein is not a systematic name so you may need to look up its structure if you are not already familiar with it.arrow_forwardCyclopropenones are described as having aromatic character. How would you account for this, given that the ring contains three π-electrons?arrow_forwardCarbons 1 and 4 of 1,3-cyclohexadiene are equivalent (they form the same carbocation upon protonation.) Likewise, carbons 2 and 3 are also equivalent. Draw the bond-line formula (or skeletal structure) of the carbocation formed by protonation of C-2 or C-3 to verify that it is not allylic and therefore not a stable as the one formed by protonation of C-1 or C-4.arrow_forward
- The structure of the molecule cyclohexene is Does the absorption of ultraviolet light by cyclohexene occur at longer or at shorter wavelengths than the absorption by benzene? Explain.arrow_forwardHow process of ring-flipping also affects the orientation of cyclohexane's hydrogen atoms ?arrow_forwardCompounds B and C are isomers with molecular formula C5H9BrO2. The 1H NMR spectrum of compounds B and C are shown below. The IR spectrum corresponding to compound B showed strong absorption bands at 1739, 1225, and 1158 cm-1, while the spectrum corresponding to compound C have strong bands at 1735, 1237, and 1182 cm-1. 1.Based on the information provided, determine the structure of compounds B and C. 2.Assign all peaks in 1H NMR spectrum of compounds B and C.arrow_forward
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