Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 21.SE, Problem 68AP
When a
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Here are the energies (in kcal/mol) for staggered and eclipsed interactions
for CH, CC, and CBr bonds
eclipsed (0°) staggered (60°)
bonds
CH/CH
1.0
0.0
CH/CC
1.3
0.0
Br:
CC/CC
3.0
0.9
Br
CH/CBr
1.8
0.0
CC / CBr
3.3
1.0
CBr / CBr
3.7
1.2
a) I've drawn the Newman projection for one of the staggered conformations of the molecule
above, looking down the C2-C3 bond. Draw Newman projections for the other two staggered
and the three eclipsed conformations (in order).
CH₂
H3C.
H'
H
Br
b) Calculate the relative energies for each of the conformations and write them below each
conformation.
90. Draw the stereoisomers obtained from each of the following reactions:
a.
H₂
b.
H₂
C.
H₂
Pd/C
Pd/C
Pd/C
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.
Chapter 21 Solutions
Organic Chemistry
Ch. 21.1 - Give IUPAC names for the following substances:Ch. 21.1 - Draw structures corresponding to the following...Ch. 21.2 - Prob. 3PCh. 21.2 - Rank the compounds in each of the following sets...Ch. 21.2 - Predict the products of the following nucleophilic...Ch. 21.2 - Prob. 6PCh. 21.3 - Prob. 7PCh. 21.3 - If the following molecule is treated with acid...Ch. 21.4 - How might you prepare the following esters using a...Ch. 21.4 - Prob. 10P
Ch. 21.4 - Prob. 11PCh. 21.4 - Prob. 12PCh. 21.4 - Prob. 13PCh. 21.5 - Prob. 14PCh. 21.5 - What product would you expect from reaction of one...Ch. 21.6 - Prob. 16PCh. 21.6 - Prob. 17PCh. 21.6 - Show the products you would obtain by reduction of...Ch. 21.6 - What ester and what Grignard reagent might you...Ch. 21.7 - Prob. 20PCh. 21.7 - How would you use the reaction of an amide with...Ch. 21.8 - Write the mechanism of the reaction shown in...Ch. 21.9 - Prob. 23PCh. 21.9 - Prob. 24PCh. 21.10 - Prob. 25PCh. 21.10 - Prob. 26PCh. 21.SE - Name the following compounds:Ch. 21.SE - Prob. 28VCCh. 21.SE - Prob. 29VCCh. 21.SE - Prob. 30VCCh. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the complete...Ch. 21.SE - Prob. 35MPCh. 21.SE - When 4-dimethylaminopyridine (DMAP) is added in...Ch. 21.SE - Prob. 37MPCh. 21.SE - Prob. 38MPCh. 21.SE - Prob. 39MPCh. 21.SE - The hydrolysis of a biological thioester to the...Ch. 21.SE - Prob. 41MPCh. 21.SE - Prob. 42MPCh. 21.SE - Prob. 43MPCh. 21.SE - In the iodoform reaction, a triiodomethyl ketone...Ch. 21.SE - Give IUPAC names for the following compounds:Ch. 21.SE - Prob. 46APCh. 21.SE - Draw and name compounds that meet the following...Ch. 21.SE - Predict the product, if any, of reaction between...Ch. 21.SE - Prob. 49APCh. 21.SE - Prob. 50APCh. 21.SE - What product would you expect to obtain from...Ch. 21.SE - Prob. 52APCh. 21.SE - Prob. 53APCh. 21.SE - The following reactivity order has been found for...Ch. 21.SE - Prob. 55APCh. 21.SE - Outline methods for the preparation of...Ch. 21.SE - Prob. 57APCh. 21.SE - When ethyl benzoate is heated in methanol...Ch. 21.SE - tert-Butoxycarbonyl azide, a reagent used in...Ch. 21.SE - Prob. 60APCh. 21.SE - Prob. 61APCh. 21.SE - What is the structure of the polymer produced by...Ch. 21.SE - Polyimides with the structure shown are used as...Ch. 21.SE - Prob. 64APCh. 21.SE - Propose a structure for a compound, C4H7ClO2, that...Ch. 21.SE - Assign structures to compounds with the following...Ch. 21.SE - Prob. 67APCh. 21.SE - When a carboxylic acid is dissolved in...Ch. 21.SE - Prob. 69APCh. 21.SE - Prob. 70APCh. 21.SE - Prob. 71APCh. 21.SE - Phenyl 4-aminosalicylate is a drug used in the...Ch. 21.SE - N,N-Diethyl-m-toluamide (DEET) is the active...Ch. 21.SE - Tranexamic acid, a drug useful against blood...Ch. 21.SE - One frequently used method for preparing methyl...Ch. 21.SE - Prob. 76APCh. 21.SE - Assign structures to compounds with the following...Ch. 21.SE - Propose structures for compounds with the...Ch. 21.SE - Propose a structure for the compound with the...Ch. 21.SE - Draw the structure of the compound that produced...Ch. 21.SE - Prob. 81APCh. 21.SE - Epoxy adhesives are prepared in two steps. SN2...
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- 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°arrow_forwardQuestion 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 contributorarrow_forwardCan 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_forward
- PLEASE 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_forwardLewis 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_forward
- a. 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_forwardDraw 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_forwardf) 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_forward
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