
Modified Mastering Chemistry with Pearson eText -- Standalone Access Card -- for Chemistry: A Molecular Approach (4th Edition)
4th Edition
ISBN: 9780134162430
Author: Nivaldo J. Tro
Publisher: PEARSON
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Question
Chapter 9, Problem 84E
Interpretation Introduction
To explain: Why the given reaction is improbable.
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(racemic)
19.84 Using your reaction roadmaps as a guide, show how to convert 2-oxepanone and ethanol
into 1-cyclopentenecarbaldehyde. You must use 2-oxepanone as the source of all carbon
atoms in the target molecule. Show all reagents and all molecules synthesized along
the way.
&
+ EtOH
H
2-Oxepanone
1-Cyclopentenecarbaldehyde
R₂
R₁
R₁
a
R
Rg
Nu
R₂
Rg
R₁
R
R₁₂
R3
R
R
Nu enolate forming
R₁ R
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species or amines
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R₁₁
HOB
R
R₁B
R
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B-Hydroxy carbonyl
R
diester
R2 R3
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RB
OR
R₂ 0
aB-Unsaturated carbonyl
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HOR
reaction
1) LDA
2) R-X
3) H₂O/H₂O
ketone,
aldehyde
1) 2°-amine
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3) H₂O'/H₂O
0
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R₁
R₁
R
R₁
R₁₂
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R₁
H.C
R₁
H.C
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ester
R₁
HO
R₂ R
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HO
Alkylated carboxylic acid
malonic ester
Write the reagents required to bring about each reaction next to the arrows shown.
Next, record any regiochemistry or stereochemistry considerations relevant to the
reaction. You should also record any key aspects of the mechanism, such as forma-
tion of an important intermediate, as a helpful reminder. You may want to keep
track of all reactions that make carbon-carbon bonds, because these help you build
large molecules from smaller fragments. This especially applies to the reactions in…
Provide the reasonable steps to achieve the following synthesis.
Chapter 9 Solutions
Modified Mastering Chemistry with Pearson eText -- Standalone Access Card -- for Chemistry: A Molecular Approach (4th Edition)
Ch. 9 - Prob. 1SAQCh. 9 - Q2. Which set of elements is arranged in order of...Ch. 9 - Q3. Which is the correct Lewis structure for...Ch. 9 - Q4. Which compound is likely to have an incomplete...Ch. 9 - Prob. 5SAQCh. 9 - Prob. 6SAQCh. 9 - Prob. 7SAQCh. 9 - Prob. 8SAQCh. 9 - Prob. 9SAQCh. 9 - Prob. 10SAQ
Ch. 9 - Q11. Determine the formal charge of nitrogen in...Ch. 9 - Prob. 12SAQCh. 9 - Q13. Use formal charge to choose the best Lewis...Ch. 9 - Prob. 14SAQCh. 9 - Prob. 15SAQCh. 9 - Prob. 1ECh. 9 - Prob. 2ECh. 9 - Prob. 3ECh. 9 - Prob. 4ECh. 9 - 5. Describe the octet rule in the Lewis model.
Ch. 9 - 6. According to the Lewis model, what is a...Ch. 9 - 7. How do you draw an ionic Lewis structure?
Ch. 9 - 8. How can Lewis structures be used to determine...Ch. 9 - Prob. 9ECh. 9 - Prob. 10ECh. 9 - Prob. 11ECh. 9 - Prob. 12ECh. 9 - Prob. 13ECh. 9 - Prob. 14ECh. 9 - 15. In a covalent Lewis structure, what is the...Ch. 9 - Prob. 16ECh. 9 - 17. How does the Lewis model for covalent bonding...Ch. 9 - 18. How does the Lewis model for covalent bonding...Ch. 9 - 19. What is electronegativity? What are the...Ch. 9 - Prob. 20ECh. 9 - 21. Explain percent ionic character of a bond. Do...Ch. 9 - 22. What is a dipole moment?
Ch. 9 - Prob. 23ECh. 9 - Prob. 24ECh. 9 - Prob. 25ECh. 9 - 26. What are resonance structures? What is a...Ch. 9 - 27. Do resonance structures always contribute...Ch. 9 - 28. What is formal charge? How is formal charge...Ch. 9 - 29. Why does the octet rule have exceptions? List...Ch. 9 - 30. Which elements can have expanded octets? Which...Ch. 9 - Prob. 31ECh. 9 - Prob. 32ECh. 9 - 33. What is the electron sea model for bonding in...Ch. 9 - Prob. 34ECh. 9 - 35. Write the electron configuration for N. Then...Ch. 9 - 36. Write the electron configuration for Ne. Then...Ch. 9 - 37. Write the Lewis symbol for each atom or...Ch. 9 - 38. Write the Lewis symbol for each atom or...Ch. 9 - 39. Write the Lewis symbols for the ions in each...Ch. 9 - 40. Write the Lewis symbols for the ions in each...Ch. 9 - 41. Use Lewis symbols to determine the formula for...Ch. 9 - 42. Use Lewis symbols to determine the formula for...Ch. 9 - 43. Explain the trend in the lattice energies of...Ch. 9 - 44. Rubidium iodide has a lattice energy of –617...Ch. 9 - 45. The lattice energy of CsF is –744 kJ/mol,...Ch. 9 - 46. Arrange these compounds in order of increasing...Ch. 9 - 47. Use the Born–Haber cycle and data from...Ch. 9 - 48. Use the Born–Haber cycle and data from...Ch. 9 - 49. Use covalent Lewis structures to explain why...Ch. 9 - 50. Use covalent Lewis structures to explain why...Ch. 9 - 51. Write the Lewis structure for each...Ch. 9 - 52. Write the Lewis structure for each...Ch. 9 - 53. Write the Lewis structure for each...Ch. 9 - 54. Write the Lewis structure for each...Ch. 9 - 55. Determine if a bond between each pair of atoms...Ch. 9 - 56. Determine if a bond between each pair of atoms...Ch. 9 - 57. Draw the Lewis structure for CO with an arrow...Ch. 9 - 58. Draw the Lewis structure for BrF with an arrow...Ch. 9 - 59. Write the Lewis structure for each molecule or...Ch. 9 - 60. Write the Lewis structure for each molecule or...Ch. 9 - 61. Write the Lewis structure for each molecule or...Ch. 9 - 62. Write the Lewis structure for each molecule or...Ch. 9 - 63. Write a Lewis structure that obeys the octet...Ch. 9 - 64. Write a Lewis structure that obeys the octet...Ch. 9 - 65. Use formal charge to identify the better Lewis...Ch. 9 - 66. Use formal charges to identify the better...Ch. 9 - 67. How important is the resonance structure shown...Ch. 9 - 68. In N2O, nitrogen is the central atom and the...Ch. 9 - 69. Draw the Lewis structure (including resonance...Ch. 9 - 70. Draw the Lewis structure (including resonance...Ch. 9 - 71. What are the formal charges of the atoms shown...Ch. 9 - 72. What are the formal charges of the atoms shown...Ch. 9 - 73. Write the Lewis structure for each molecule...Ch. 9 - 74. Write the Lewis structure for each molecule...Ch. 9 - 75. Write the Lewis structure for each ion....Ch. 9 - 76. Write Lewis structures for each molecule or...Ch. 9 - 77. Write Lewis structures for each molecule or...Ch. 9 - 78. Write Lewis structures for each molecule or...Ch. 9 - 79. Order these compounds in order of increasing...Ch. 9 - 80. Which compound shown here has the stronger...Ch. 9 - 81. Hydrogenation reactions are used to add...Ch. 9 - 82. Ethanol is a possible fuel. Use average bond...Ch. 9 - 83. Hydrogen, a potential future fuel, can be...Ch. 9 - Prob. 84ECh. 9 - 85. Write an appropriate Lewis structure for each...Ch. 9 - 86. Write an appropriate Lewis structure for each...Ch. 9 - 87. Each compound contains both ionic and covalent...Ch. 9 - 88. Each compound contains both ionic and covalent...Ch. 9 - 89. Carbon ring structures are common in organic...Ch. 9 - 90. Amino acids are the building blocks of...Ch. 9 - 91. Formic acid is responsible for the sting of...Ch. 9 - 92. Diazomethane is a highly poisonous, explosive...Ch. 9 - 93. The reaction of Fe2O3(s) with Al(s) to form...Ch. 9 - 94. NaCl has a lattice energy of –787 kJ/mol....Ch. 9 - 95. Draw the Lewis structure for nitric acid (the...Ch. 9 - 96. Phosgene (Cl2CO) is a poisonous gas used as a...Ch. 9 - 97. The cyanate ion (OCN–) and the fulminate ion...Ch. 9 - Prob. 98ECh. 9 - Prob. 99ECh. 9 - 100. Use Lewis structures to explain why Br3– and...Ch. 9 - 101. Draw the Lewis structure for HCSNH2. (The...Ch. 9 - 102. Draw the Lewis structure for urea, H2NCONH2,...Ch. 9 - 103. Some theories of aging suggest that free...Ch. 9 - 104. Free radicals are important in many...Ch. 9 - Prob. 105ECh. 9 - 106. Calculate ΔHrxn for the combustion of octane...Ch. 9 - 107. Draw the Lewis structure for each...Ch. 9 - Prob. 108ECh. 9 - Prob. 109ECh. 9 - 110. Calculate for the reaction using the bond...Ch. 9 - Prob. 111ECh. 9 - Prob. 112ECh. 9 - 113. A compound composed of only carbon and...Ch. 9 - Prob. 114ECh. 9 - 115. The main component of acid rain (H2SO4) forms...Ch. 9 - 116. A 0.167-g sample of an unknown acid requires...Ch. 9 - Prob. 117ECh. 9 - Prob. 118ECh. 9 - Prob. 119ECh. 9 - 120. The standard heat of formation of CaBr2 is...Ch. 9 - Prob. 121ECh. 9 - Prob. 122ECh. 9 - Prob. 123ECh. 9 - Prob. 124ECh. 9 - Prob. 125ECh. 9 - 126. Which statement is true of an endothermic...Ch. 9 - Prob. 127ECh. 9 - Prob. 128ECh. 9 - Prob. 129ECh. 9 - Prob. 130QGWCh. 9 - Prob. 131QGWCh. 9 - Prob. 132QGWCh. 9 - 133. Draft a list of step-by-step instructions for...Ch. 9 - Prob. 134QGWCh. 9 - 135. Evidence for the additional stabilization of...
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- (a) Draw the structures of A and B in the following reaction. (i) NaNH2, NH3(1) A + B (ii) H3O+arrow_forwardFor the reaction 2 N2O5(g) → 4 NO2(g) + O2(g), the following mechanism has been proposed: N2O5 →> NO₂+ NO3_(K1) NO2 + NO3 → N2O5 (k-1) NO2 + NO3 → → NO2 + O2 + NO (K2) NO + N2O5- NO2 + NO2 + NO2 (K3) d[N₂O5] __2k‚k₂[N2O5] Indicate whether the following rate expression is acceptable: dt k₁₁+ k₂arrow_forwardConsider the following decomposition reaction of N2O5(g): For the reaction 2 N2O5(g) → 4 NO2(g) + O2(g), the following mechanism has been proposed: N2O5 → NO2 + NO3 (K1) NO2 + NO3 → N2O5 (k-1) NO2 + NO3 → NO2 + O2 + NO (K2) NO + N2O5 → NO2 + NO2 + NO2 (K3) Indicate whether the following rate expression is acceptable: d[N2O5] = -k₁[N₂O₂] + K¸₁[NO₂][NO3] - K¸[NO₂]³ dtarrow_forward
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