Chemistry: Structure and Properties Plus MasteringChemistry with eText -- Access Card Package
1st Edition
ISBN: 9780321729736
Author: Nivaldo J. Tro
Publisher: PEARSON
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Chapter 11, Problem 13E
Interpretation Introduction
To explain: The simple
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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
B-Alkylated carbonyl
species or amines
Cyclic B-Ketoester
R₁₁
HOB
R
R₁B
R
R₁₂
B-Hydroxy carbonyl
R
diester
R2 R3
R₁
RB
OR
R₂ 0
aB-Unsaturated carbonyl
NaOR
Aldol
HOR
reaction
1) LDA
2) R-X
3) H₂O/H₂O
ketone,
aldehyde
1) 2°-amine
2) acid chloride
3) H₂O'/H₂O
0
O
R₁
R₁
R
R₁
R₁₂
Alkylated a-carbon
R₁
H.C
R₁
H.C
Alkylated methyl ketone
acetoacetic
ester
B-Ketoester
ester
R₁
HO
R₂ R
B-Dicarbonyl
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 11 Solutions
Chemistry: Structure and Properties Plus MasteringChemistry with eText -- Access Card Package
Ch. 11 - Prob. 1SAQCh. 11 - Prob. 2SAQCh. 11 - Prob. 3SAQCh. 11 - Prob. 4SAQCh. 11 - Prob. 5SAQCh. 11 - Prob. 6SAQCh. 11 - Prob. 7SAQCh. 11 - A gas mixture is a 1.55-L container at 298 K...Ch. 11 - Prob. 9SAQCh. 11 - Prob. 10SAQ
Ch. 11 - Prob. 11SAQCh. 11 - Prob. 12SAQCh. 11 - Prob. 13SAQCh. 11 - Prob. 14SAQCh. 11 - Prob. 15SAQCh. 11 - Prob. 1ECh. 11 - Prob. 2ECh. 11 - Prob. 3ECh. 11 - Prob. 4ECh. 11 - Prob. 5ECh. 11 - Prob. 6ECh. 11 - Prob. 7ECh. 11 - Prob. 8ECh. 11 - Prob. 9ECh. 11 - Prob. 10ECh. 11 - Prob. 11ECh. 11 - Prob. 12ECh. 11 - Prob. 13ECh. 11 - Prob. 14ECh. 11 - Prob. 15ECh. 11 - Prob. 16ECh. 11 - Prob. 17ECh. 11 - Prob. 18ECh. 11 - Prob. 19ECh. 11 - Prob. 20ECh. 11 - Prob. 21ECh. 11 - Prob. 22ECh. 11 - If a reaction occurs in the gas phase at STP, the...Ch. 11 - Prob. 24ECh. 11 - Prob. 25ECh. 11 - Prob. 26ECh. 11 - Prob. 27ECh. 11 - Prob. 28ECh. 11 - Prob. 29ECh. 11 - Prob. 30ECh. 11 - Prob. 31ECh. 11 - Prob. 32ECh. 11 - A 48.3-mL sample of gas in a cylinder is warmed...Ch. 11 - A syringe containing 1.55 mL of oxygen gas is...Ch. 11 - A balloon contains 0.158 mol of gas and has a...Ch. 11 - Prob. 36ECh. 11 - Prob. 37ECh. 11 - Prob. 38ECh. 11 - Prob. 39ECh. 11 - Prob. 40ECh. 11 - Prob. 41ECh. 11 - Prob. 42ECh. 11 - Prob. 43ECh. 11 - Prob. 44ECh. 11 - Prob. 45ECh. 11 - Prob. 46ECh. 11 - A wine-dispensing system uses argon canisters to...Ch. 11 - Prob. 48ECh. 11 - Prob. 49ECh. 11 - Prob. 50ECh. 11 - Aerosol cans carry clear warnings against...Ch. 11 - Prob. 52ECh. 11 - Prob. 53ECh. 11 - Use the molar volume of a gas at STP to calculate...Ch. 11 - What is the density (in g/L) of hydrogen gas at...Ch. 11 - Prob. 56ECh. 11 - Prob. 57ECh. 11 - A 113-mL gas sample has a mass of 0.171 g at a...Ch. 11 - A sample of gas has a mass of 38.8 mg. Its volume...Ch. 11 - Prob. 60ECh. 11 - A gas mixture contains each of these gases at the...Ch. 11 - A gas mixture with a total pressure of 745 mmHg...Ch. 11 - We add a 1.20-g sample of dry ice to a 755-mL...Ch. 11 - A 275-mL flask contains pure helium at a pressure...Ch. 11 - A gas mixture contains 1.25 g N2 and 0.85 g O2 in...Ch. 11 - Prob. 66ECh. 11 - The hydrogen gas formed in a chemical reaction is...Ch. 11 - Prob. 68ECh. 11 - Prob. 69ECh. 11 - Prob. 70ECh. 11 - Prob. 71ECh. 11 - Prob. 72ECh. 11 - Prob. 73ECh. 11 - Prob. 74ECh. 11 - Prob. 75ECh. 11 - Prob. 76ECh. 11 - Prob. 77ECh. 11 - Prob. 78ECh. 11 - Prob. 79ECh. 11 - Prob. 80ECh. 11 - Prob. 81ECh. 11 - Prob. 82ECh. 11 - CH3OH can be synthesized by the reaction:...Ch. 11 - Oxygen gas reacts with powered aluminum according...Ch. 11 - Automobile airbags inflate following serious...Ch. 11 - Lithium reacts with nitrogen gas according to the...Ch. 11 - Prob. 87ECh. 11 - Prob. 88ECh. 11 - Prob. 89ECh. 11 - Carbon monoxide gas reacts with hydrogen gas to...Ch. 11 - Prob. 91ECh. 11 - Prob. 92ECh. 11 - Prob. 93ECh. 11 - Use the vander Waals equation and the ideal gas...Ch. 11 - Pennies that are currently being minted are...Ch. 11 - A 2.85 g sample of an unknown chlorofluorocarbon...Ch. 11 - Prob. 97ECh. 11 - A 118 mL flask is evacuated and found to have a...Ch. 11 - Prob. 99ECh. 11 - A gaseous hydrogen- and carbon-containing compound...Ch. 11 - Prob. 101ECh. 11 - Consider the reaction: 2Ag2O(s)4Ag(s)+O2(g) If...Ch. 11 - When hydrochloric acid is poured over potassium...Ch. 11 - Consider the reaction: 2SO2(g)+O2(g)2SO(g)3 If...Ch. 11 - Ammonium carbonate decomposes upon heating...Ch. 11 - Ammonium nitrate decomposes explosively upon...Ch. 11 - Prob. 107ECh. 11 - Prob. 108ECh. 11 - Gaseous ammonia is injected into the exhaust...Ch. 11 - Prob. 110ECh. 11 - Prob. 111ECh. 11 - Prob. 112ECh. 11 - Prob. 113ECh. 11 - Prob. 114ECh. 11 - Prob. 115ECh. 11 - Prob. 116ECh. 11 - Prob. 117ECh. 11 - Prob. 118ECh. 11 - Prob. 119ECh. 11 - Prob. 120ECh. 11 - Prob. 121ECh. 11 - Prob. 122ECh. 11 - Prob. 123ECh. 11 - Prob. 124ECh. 11 - Prob. 125ECh. 11 - Prob. 126ECh. 11 - When 0.583 g of neon is added to an 800-cm3bulb...Ch. 11 - A gas mixture composed of helium and argon has a...Ch. 11 - Prob. 129ECh. 11 - Prob. 130ECh. 11 - Prob. 131ECh. 11 - Prob. 132ECh. 11 - Prob. 133ECh. 11 - Prob. 134ECh. 11 - The atmosphere slowly oxidizes hydrocarbons in a...Ch. 11 - Prob. 136ECh. 11 - Prob. 137ECh. 11 - Prob. 138ECh. 11 - Prob. 139ECh. 11 - Prob. 140ECh. 11 - Prob. 141ECh. 11 - Prob. 142ECh. 11 - Prob. 143ECh. 11 - Which gas would you expect to deviate most from...Ch. 11 - Prob. 145ECh. 11 - Prob. 146ECh. 11 - Prob. 147E
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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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