Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
5th Edition
ISBN: 9781260170405
Author: SMITH
Publisher: MCG
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Chapter 23, Problem 23.55P
What reaction conditions—base, solvent, and temperature—are needed to convert
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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 23 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
Ch. 23 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 23 - Prob. 23.2PCh. 23 - Problem 23.3 When phenylacetaldehyde is dissolved...Ch. 23 - Prob. 23.4PCh. 23 - Problem 23.5 Which bonds in the following...Ch. 23 - Prob. 23.6PCh. 23 - Prob. 23.7PCh. 23 - Prob. 23.8PCh. 23 - Prob. 23.9PCh. 23 - Prob. 23.10P
Ch. 23 - Problem 23.11 Draw the products of each...Ch. 23 - Problem 23.12 Draw the products of each reaction....Ch. 23 - Prob. 23.13PCh. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Problem 23.18 How can pentan-2-one be converted...Ch. 23 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 23 - Problem 23.20 Which of the following compounds...Ch. 23 - Problem 23.21 Draw the products of each...Ch. 23 - Prob. 23.22PCh. 23 - Prob. 23.23PCh. 23 - Prob. 23.24PCh. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - 23.29 Draw enol tautomer(s) for each compound....Ch. 23 - 22.30 The cis ketone A is isomerized to a trans...Ch. 23 - 23.31 Draw enol tautomer(s) for each compound.
...Ch. 23 - Prob. 23.32PCh. 23 - Prob. 23.33PCh. 23 - Prob. 23.34PCh. 23 - 23.35 Rank the labeled protons in each compound in...Ch. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - 23.38 Acyclovir is an effective antiviral agent...Ch. 23 - 23.39 Explain why forms two different alkylation...Ch. 23 - Prob. 23.40PCh. 23 - 23.41 Acid-catalyzed bromination of pentanone ...Ch. 23 - 23.42 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.43PCh. 23 - Prob. 23.44PCh. 23 - 23.45 Devise a synthesis of valproic acid , a...Ch. 23 - 23.46 Synthesize each compound from diethyl...Ch. 23 - Prob. 23.47PCh. 23 - Prob. 23.48PCh. 23 - Prob. 23.49PCh. 23 - 23.50 Draw the organic products formed in each...Ch. 23 - 23.51 Draw the products formed (including...Ch. 23 - Prob. 23.52PCh. 23 - Prob. 23.53PCh. 23 - 23.54 Clopidogrel is the generic name for Plavix,...Ch. 23 - 23.55 What reaction conditions—base, solvent, and...Ch. 23 - Prob. 23.56PCh. 23 - 23.57 Draw a stepwise mechanism showing how two...Ch. 23 - 23.58 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.59PCh. 23 - 23.60 Draw stepwise mechanisms illustrating how...Ch. 23 - Prob. 23.61PCh. 23 - Prob. 23.62PCh. 23 - 23.63 Synthesize each compound from cyclohexanone...Ch. 23 - Prob. 23.64PCh. 23 - Prob. 23.65PCh. 23 - 23.66 Synthesize (Z)-hept-5-en-2-one from ethyl...Ch. 23 - Prob. 23.67PCh. 23 - 23.68 Capsaicin, the spicy component of hot...Ch. 23 - 23.69 Treatment of W with , followed by , affords...Ch. 23 - Prob. 23.70PCh. 23 - Prob. 23.71PCh. 23 - Prob. 23.72PCh. 23 - Prob. 23.73PCh. 23 - Prob. 23.74P
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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
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- 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
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