
Concept explainers
(a)
Interpretation: The different types of protons present in given compound are to be predicted.
Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and

Answer to Problem 14.36P
In the given compound, two different types of protons are present.
Explanation of Solution
In the given compound, one carbon atom is bonded to three other carbon atoms on which three hydrogen atoms are present. The central carbon atom will give multiplet whereas the other three carbon atoms will give doublet in NMR spectroscopy. The splitting of peaks takes place according to
In the given compound, two different types of protons are present.
(b)
Interpretation: The different types of protons present in given compound are to be predicted.
Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Answer to Problem 14.36P
In the given compound, seven different types of protons are present.
Explanation of Solution
The given compound contains seven different types of protons each labeled as
Figure 1
Each proton will give different chemical shift value in NMR spectroscopy.
In the given compound, seven different types of protons are present.
(c)
Interpretation: The different types of protons present in given compound are to be predicted.
Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Answer to Problem 14.36P
In the given compound, five different types of protons are present.
Explanation of Solution
The given compound contains five different types of protons each labeled as
Figure 2
Each proton will give different chemical shift value in NMR spectroscopy.
In the given compound, five different types of protons are present.
(d)
Interpretation: The different types of protons present in given compound are to be predicted.
Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Answer to Problem 14.36P
In the given compound, three different types of protons are present.
Explanation of Solution
The given compound contains three different types of protons each labeled as
Figure 3
Each proton will give different chemical shift value in NMR spectroscopy.
In the given compound, three different types of protons are present.
(e)
Interpretation: The different types of protons present in given compound are to be predicted.
Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Answer to Problem 14.36P
In the given compound three different types of protons are present.
Explanation of Solution
The given compound contains three different types of protons each labeled as
Figure 4
Each proton will give different chemical shift value in NMR spectroscopy.
In the given compound, three different types of protons are present.
(f)
Interpretation: The different types of protons present in given compound are to be predicted.
Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Answer to Problem 14.36P
In the given compound four different types of protons are present.
Explanation of Solution
The given compound contains four different types of protons each labeled as
Figure 5
Each proton will give different chemical shift value in NMR spectroscopy.
In the given compound four different types of protons are present.
(g)
Interpretation: The different types of protons present in given compound are to be predicted.
Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Answer to Problem 14.36P
In the given compound, six different types of protons are present.
Explanation of Solution
In the given compound, a chiral carbon atom is bonded to another carbon atom on which two protons and an methyl group is present. Hence, these protons are termed as diasterotropic protons. Each diasterotropic protons gives different chemical shift value.
Therefore, the given compound contains six different types of protons each labeled as
Figure 6
Each proton will give different chemical shift value in NMR spectroscopy.
In the given compound, six different types of protons are present.
(h)
Interpretation: The different types of protons present in given compound are to be predicted.
Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Answer to Problem 14.36P
In the given compound four different types of protons are present.
Explanation of Solution
The given compound contains four different types of protons each labeled as
Figure 7
Each proton will give different chemical shift value in NMR spectroscopy.
In the given compound four different types of protons are present.
(i)
Interpretation: The different types of protons present in given compound are to be predicted.
Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Answer to Problem 14.36P
In the given compound, three different types of protons are present.
Explanation of Solution
The given compound contains three different types of protons each labeled as
Figure 8
Each proton will give different chemical shift value in NMR spectroscopy.
In the given compound, three different types of protons are present.
(j)
Interpretation: The different types of protons present in given compound are to be predicted.
Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Answer to Problem 14.36P
In the given compound four different types of protons are present.
Explanation of Solution
In the given compound, diastereotropic protons are present on two carbon atoms. However, due to symmetry of the molecule, one peak is observed.
Therefore, the given compound contains four different types of protons each labeled as
Figure 9
Each proton will give different chemical shift value in NMR spectroscopy.
In the given compound four different types of protons are present.
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Chapter 14 Solutions
ORGANIC CHEMISTRY
- Decide whether these proposed Lewis structures are reasonable. proposed Lewis structure Is the proposed Lewis structure reasonable? Yes. :0: Cl C C1: 0=0: : 0 : : 0 : H C N No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* ☐ Yes. No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* Yes. ☐ No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* | * If two or more atoms of the same element don't satisfy the octet rule, just enter the chemical symbol as many times as necessary. For example, if two oxygen atoms don't satisfy the octet rule, enter "0,0".arrow_forwardDraw the Lewis structure for the polyatomic trisulfide anion. Be sure to include all resonance structures that satisfy the octet rule. с [ ] - Garrow_forward1. Calculate the accurate monoisotopic mass (using all 1H, 12C, 14N, 160 and 35CI) for your product using the table in your lab manual. Don't include the Cl, since you should only have [M+H]*. Compare this to the value you see on the LC-MS printout. How much different are they? 2. There are four isotopic peaks for the [M+H]* ion at m/z 240, 241, 242 and 243. For one point of extra credit, explain what each of these is and why they are present. 3. There is a fragment ion at m/z 184. For one point of extra credit, identify this fragment and confirm by calculating the accurate monoisotopic mass. 4. The UV spectrum is also at the bottom of your printout. For one point of extra credit, look up the UV spectrum of bupropion on Google Images and compare to your spectrum. Do they match? Cite your source. 5. For most of you, there will be a second chromatographic peak whose m/z is 74 (to a round number). For one point of extra credit, see if you can identify this molecule as well and confirm by…arrow_forward
- Please draw, not just describe!arrow_forwardcan you draw each step on a piece of a paper please this is very confusing to mearrow_forward> Can the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants, in one step, by moderately heating the reactants? esc ? A O O •If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in any arrangement you like. • If your answer is no, check the box under the drawing area instead. olo 18 Ar Explanation Check BB Click and drag to start drawing a structure. 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center Accessibilityarrow_forward
- Name the structurearrow_forward> For each pair of substrates below, choose the one that will react faster in a substitution reaction, assuming that: 1. the rate of substitution doesn't depend on nucleophile concentration and 2. the products are a roughly 50/50 mixture of enantiomers. Substrate A Substrate B Faster Rate X CI (Choose one) (Choose one) CI Br Explanation Check Br (Choose one) C 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy A F10arrow_forwardHow to draw this mechanism for the foloowing reaction in the foto. thank youarrow_forward
- Predict the major products of the following organic reaction: Some important notes: CN A? • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. • Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. No reaction. Explanation Check Click and drag to start drawing a structure. 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use Privacy Centerarrow_forwardDraw the major product of the following reaction. Do not draw inorganic byproducts. H3PO4 OHarrow_forwardPredict the major products of this organic reaction: HBr (1 equiv) Δ ? Some important notes: • Draw the major product, or products, of this reaction in the drawing area below. • You can draw the products in any arrangement you like. • Pay careful attention to the reaction conditions, and only include the major products. • Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. • Note that there is only 1 equivalent of HBr reactant, so you need not consider the case of multiple additions. Explanation Check X ©2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacyarrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning

