EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 9780100591318
Author: McMurry
Publisher: YUZU
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Chapter 15.SE, Problem 35AP
Calicene, like azulene (Problem 15-17), has an unusually large dipole moment for a hydrocarbon. Explain, using resonance structures.
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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".
Draw the Lewis structure for the polyatomic trisulfide
anion. Be sure to include all resonance structures that satisfy the octet rule.
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1. 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…
Chapter 15 Solutions
EBK ORGANIC CHEMISTRY
Ch. 15.1 - Prob. 1PCh. 15.1 - Give IUPAC names for the following compounds:Ch. 15.1 - Prob. 3PCh. 15.2 - Pyridine is a flat, hexagonal molecule with bond...Ch. 15.3 - Prob. 5PCh. 15.4 - Draw the five resonance structures of the...Ch. 15.4 - Prob. 7PCh. 15.4 - Prob. 8PCh. 15.5 - Prob. 9PCh. 15.5 - Prob. 10P
Ch. 15.6 - Prob. 11PCh. 15.6 - How many electrons does each of the four nitrogen...Ch. 15.SE - Give IUPAC names for the following substances (red...Ch. 15.SE - All-cis cyclodecapentaene is a stable molecule...Ch. 15.SE - 1, 6-Methanonaphthalene has an interesting 1H NMR...Ch. 15.SE - Prob. 16VCCh. 15.SE - Azulene, an isomer of naphthalene, has a...Ch. 15.SE - Give IUPAC names for the following compounds:Ch. 15.SE - Draw structures corresponding to the following...Ch. 15.SE - Prob. 20APCh. 15.SE - Prob. 21APCh. 15.SE - Draw and name all possible aromatic compounds with...Ch. 15.SE - Propose structures for aromatic hydrocarbons that...Ch. 15.SE - Look at the three resonance structures of...Ch. 15.SE - Prob. 25APCh. 15.SE - Prob. 26APCh. 15.SE - Look at the five resonance structures for...Ch. 15.SE - Prob. 28APCh. 15.SE - 3-Chlorocyclopropene, on treatment with AgBF4,...Ch. 15.SE - Prob. 30APCh. 15.SE - Prob. 31APCh. 15.SE - Prob. 32APCh. 15.SE - Which would you expect to be most stable,...Ch. 15.SE - How might you convert 1, 3, 5, 7-cyclononatetraene...Ch. 15.SE - Calicene, like azulene (Problem 15-17), has an...Ch. 15.SE - Pentalene is a most elusive molecule that has been...Ch. 15.SE - Prob. 37APCh. 15.SE - Prob. 38APCh. 15.SE - Compound A, C8H10, yields three substitution...Ch. 15.SE - Prob. 40APCh. 15.SE - Propose structures for compounds that fit the...Ch. 15.SE - Prob. 42APCh. 15.SE - Prob. 43APCh. 15.SE - N-Phenylsydnone, so-named because it was first...Ch. 15.SE - Prob. 45APCh. 15.SE - Prob. 46APCh. 15.SE - Prob. 47APCh. 15.SE - Propose a structure for a molecule C14H12 that has...Ch. 15.SE - The proton NMR spectrum for a compound with...Ch. 15.SE - The proton NMR spectrum of a compound with formula...Ch. 15.SE - Aromatic substitution reactions occur by addition...Ch. 15.SE - Prob. 52APCh. 15.SE - Consider the aromatic anions below and their...Ch. 15.SE - After the reaction below, the chemical shift of Ha...Ch. 15.SE - Prob. 55APCh. 15.SE - Azo dyes are the major source of artificial color...
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- 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
- For the structure below, draw the resonance structure that is indicated by the curved arrow(s). Be sure to include formal charges. :ÖH Modify the second structure given to draw the new resonance structure. Include lone pairs and charges in your structure. Use the + and - tools to add/remove charges to an atom, and use the single bond tool to add/remove double bonds.arrow_forwardUsing the table of Reactants and Products provided in the Hints section, provide the major product (with the correct stereochemistry when applicable) for questions below by selecting the letter that corresponds to the exact chemical structures for the possible product. OH conc Hydrochloric acid 40°C Temp A/arrow_forwardUsing arrows to designate the flow of electrons, complete the reaction below and provide a detailed mechanism for the formation of the product OH conc Hydrochloric acid 40°C Temp All chemical structures should be hand drawn on a piece of paper Paragraph BI UAE +varrow_forward
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