Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 18.SE, Problem 25MP
Predict the product(s) and provide the mechanism for each two-step process below.
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36. The emission spectrum below for a one-electron (hydrogen-like) species in the gas
phase shows all the lines, before they merge together, resulting from transitions to the
first excited state from higher energy states. Line A has a wavelength of 434 nm.
BA
Increasing wavelength, λ
(a) What are the upper and lower principal quantum numbers corresponding to the lines
labeled A and B? (b) Identify the one-electron species that exhibits the spectrum.
f) The unusual molecule [2.2.2] propellane is pictured.
1) Given the bond length and bond angles in the image, what hybridization scheme
best describes the carbons marked by the askerisks?
2) What types of orbitals are used in the bond between the two carbons marked by
the askerisks?
3) How does this bond compare to an ordinary carbon-carbon bond (which is usually
1.54 Å long)?
H₂C
H₂C
CH2 1.60Å
ハ
C.
*
CH₂
H₂C
*
C
H₂
120°
Question
Resonance Forms a) Draw all resonance forms of the molecules. Include curved arrow notation. Label major resonance contributor
Resonance Forms a) Draw all resonance forms of the molecules. Include curved arrow notation. Label major resonance contributor
Chapter 18 Solutions
Organic Chemistry
Ch. 18.1 - Name the following ethers:Ch. 18.2 - Why do you suppose only symmetrical ethers are...Ch. 18.2 - How would you prepare the following ethers using a...Ch. 18.2 - Review the mechanism of oxymercuration shown in...Ch. 18.2 - How would you prepare the following ethers? Use...Ch. 18.2 - Prob. 6PCh. 18.3 - Prob. 7PCh. 18.3 - Write the mechanism of the acid-induced cleavage...Ch. 18.3 - Why are HI and HBr more effective than HCl in...Ch. 18.4 - What product would you expect from Claisen...
Ch. 18.5 - Prob. 11PCh. 18.6 - Predict the major product of each of the following...Ch. 18.6 - Prob. 13PCh. 18.6 - Predict the major product of the following...Ch. 18.7 - 15-Crown-5 and 12-crown-4 ethers complex Na+ and...Ch. 18.8 - Prob. 16PCh. 18.8 - 2-Butene-l-thiol is one component of skunk spray....Ch. 18.9 - The 1H NMR spectrum shown is that of a cyclic...Ch. 18.SE - Give IUPAC names for the following compounds...Ch. 18.SE - Show the product, including stereochemistry, that...Ch. 18.SE - Prob. 21VCCh. 18.SE - Treatment of the following alkene with a...Ch. 18.SE - Prob. 23MPCh. 18.SE - Prob. 24MPCh. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - The alkoxymercuration of alkenes involves the...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - Prob. 29MPCh. 18.SE - Ethers undergo an acid-catalyzed cleavage reaction...Ch. 18.SE - Treatment of 1, 1-diphenyl-l, 2-epoxyethane with...Ch. 18.SE - Fluoxetine, a heavily prescribed antidepressant...Ch. 18.SE - When 2-methyl-2, 5-pentanediol is treated with...Ch. 18.SE - Prob. 34MPCh. 18.SE - Prob. 35MPCh. 18.SE - Aldehydes and ketones undergo acid-catalyzed...Ch. 18.SE - Propose a mechanism to account for the following...Ch. 18.SE - Prob. 38APCh. 18.SE - Prob. 39APCh. 18.SE - How would you prepare the following ethers?Ch. 18.SE - Prob. 41APCh. 18.SE - tert-Butyl ethers can be prepared by the reaction...Ch. 18.SE - Treatment of trans-2-chlorocyclohexanol with NaOH...Ch. 18.SE - Predict the products of the following ether...Ch. 18.SE - Prob. 45APCh. 18.SE - Prob. 46APCh. 18.SE - Write the mechanism of the hydrolysis of cis-5,...Ch. 18.SE - Prob. 48APCh. 18.SE - Acid-catalyzed hydrolysis of a 1,...Ch. 18.SE - Prob. 50APCh. 18.SE - Epoxides are reduced by treatment with lithium...Ch. 18.SE - Prob. 52APCh. 18.SE - The red fox (Vulpes vulpes) uses a chemical...Ch. 18.SE - Anethole, C10H12O, a major constituent of the oil...Ch. 18.SE - Propose structures for compounds that have the...Ch. 18.SE - Prob. 56GPCh. 18.SE - How would you synthesize anethole (Problem 18-54)...Ch. 18.SE - How could you prepare benzyl phenyl ether from...Ch. 18.SE - Meerwein's reagent, triethyloxonium...Ch. 18.SE - Prob. 60GPCh. 18.SE - Prob. 61GPCh. 18.SE - The Zeisel method is an old analytical procedure...Ch. 18.SE - Prob. 63GPCh. 18.SE - Prob. 64GPCh. 18.SE - Prob. 65GPCh. 18.SE - Identify the reagents a-e in the following scheme:Ch. 18.SE - Propose structures for compounds that have the...Ch. 18.SE - Prob. 68GPCh. 18.SE - Prob. 69GPCh. 18.SE - Predict the product(s) if the starting materials...
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- Can you show me or determine the longest carbon chain, which is octane? Potentially highlight it in different sections to show me, plz, or individually?arrow_forwardPLEASE ANSWER ALL PARTS!!arrow_forwardd) Determine the formal charge on the nitrogen atom in each of the structures. NH3 NH2 N C бобкат : N N H H Н H2N-OH A B C D E F Garrow_forward
- Lewis Structure, Hybridization & Molecular Geometry a) Draw the Lewis Structure of the molecules; Label the hybridization of each carbon atom; Predict the approximate molecular geometry around each carbon atom. CH3CHO CH3CN b) Draw the Lewis Structure of Nitromethane; Predict the approximate molecular geometry around the nitrogen atom. CH3NO2 c) Draw the Lewis Structure; Label the hybridization of the boron atom; Predict the approximate molecular geometry. BF3 BF4arrow_forwarda. The structure of the bicarbonate (hydrogen carbonate) ion, HCO3-, HCO3 " is best described as a hybrid of several contributing resonance forms, two of which are shown here. HO :0: HO + :Ö: Bicarbonate is crucial for the control of body pH (for example, blood pH 7.4). A more self-indulgent use is in baking soda, where it serves as a source of CO2 CO2 gas, which gives bread and pastry their fluffy constituency. (i) Draw at least one additional resonance form. = (ii) Using curved "electron-pushing" arrows, show how these Lewis structures may be interconverted by movement of electron pairs. (iii) Determine which form or forms will be the major contributor(s) to the real structure of bicarbonate, explaining your answer on the basis of the criteria in Section 1-5.arrow_forwardCalibri 11 + BIL NAME: Jaylena M A student is investigating the ctect of volume on pressure during a lab activity. The student uses the following volumes (mL). 12, 13, 14, 16, 17, 18, 19, 20, 21, 22, 23, 24, 26, 28, 30, 33, 34, 35, 38, 40, 42, 44. 46, and 50. As the volume changed they measured the following pressures (atm) 11.0, 10.5, 10.0, 9.2. 8.5, 78, 75, 7.0, 6.8, 6.5, 6.0, 5.9, 5.5, 5.0, 4.8, 4.5, 4.2, 3.9, 3.8, 3.5, 3.3, 3.2, 3.0, 2.9. What is the independent variable? Volume Imla What is the dependent variable? Pressure Jatm Use the data and make a PROPER data table. Volume 1mL) Pressure latm 110arrow_forward
- Draw all resonance forms of the molecules. Include curved arrow notation. Label major resonance contributor.arrow_forward: Resonance Forms a) Draw all resonance forms of the molecules. Include curved arrow notation. Label major resonance contributor. SO₂ NO3arrow_forward1d. Use Le Chatelier's principle to describe the effect of the following changes on the position of the Haber-Bosch equilibrium: N2(g) + 3H2(g)= 2NH3(9) AH = -92kJ Choose one of the following answers: shift to reactant side, shift to product side or no change and draw the resulting graph. I. Increase the [N2(g)] Effect: H₂ N₂ NH3 II. Decrease the volume of the container. Effect: H₂ N₂2 NH3arrow_forward
- f) The unusual molecule [2.2.2] propellane is pictured. 1) Given the bond length and bond angles in the image, what hybridization scheme best describes the carbons marked by the askerisks? 2) What types of orbitals are used in the bond between the two carbons marked by the askerisks? 3) How does this bond compare to an ordinary carbon-carbon bond (which is usually 1.54 Å long)? CH2 1.60Å H₂C * H₂C CH2 C H2C * C Of H₂ 120°arrow_forwarde) Determine the hybridization and geometry around the indicated carbon atoms. H3C CH3 B HC CH2 A C C C CH3arrow_forwardDon't used Ai solution and hand raitingarrow_forward
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