
CHEMISTRY >CUSTOM<
8th Edition
ISBN: 9781309097182
Author: SILBERBERG
Publisher: MCG/CREATE
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Question
Chapter 19, Problem 19.95P
Interpretation Introduction
Interpretation:
When adding aqueous
Concept Introduction:
Le Chatelier’s principle:
When a
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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 19 Solutions
CHEMISTRY >CUSTOM<
Ch. 19.1 - Calculate the pH of a buffer consisting of 0.50 M...Ch. 19.1 - Prob. 19.1BFPCh. 19.1 - Prob. 19.2AFPCh. 19.1 - The molecular scenes below show three samples of a...Ch. 19.1 - Prob. 19.3AFPCh. 19.1 - What is the component concentration ratio, [NH3]/...Ch. 19.2 - A chemist titrates 20.00 mL of 0.2000 M HBrO (Ka =...Ch. 19.2 - For the titration of 30.00 mL of 0.1000 M benzoic...Ch. 19.3 - Write the ion-product expression at equilibrium...Ch. 19.3 - Prob. 19.5BFP
Ch. 19.3 - Prob. 19.6AFPCh. 19.3 - Prob. 19.6BFPCh. 19.3 - Prob. 19.7AFPCh. 19.3 - Prob. 19.7BFPCh. 19.3 - Prob. 19.8AFPCh. 19.3 - Prob. 19.8BFPCh. 19.3 - Prob. 19.9AFPCh. 19.3 - Prob. 19.9BFPCh. 19.3 - Prob. 19.10AFPCh. 19.3 - Prob. 19.10BFPCh. 19.3 - Prob. 19.11AFPCh. 19.3 - Prob. 19.11BFPCh. 19.3 - Prob. 19.12AFPCh. 19.3 - Prob. 19.12BFPCh. 19.3 - An environmental technician collects a sample of...Ch. 19.3 - A lake that has a surface area of 10.0 acres (1...Ch. 19.4 - Cyanide ion is toxic because it forms stable...Ch. 19.4 - Prob. 19.13BFPCh. 19.4 - Prob. 19.14AFPCh. 19.4 - Calculate the solubility of PbCl2 in 0.75 M NaOH....Ch. 19 - Prob. 19.1PCh. 19 - Prob. 19.2PCh. 19 - Prob. 19.3PCh. 19 - Prob. 19.4PCh. 19 - Prob. 19.5PCh. 19 - Prob. 19.6PCh. 19 - Prob. 19.7PCh. 19 - Prob. 19.8PCh. 19 - Does the pH increase or decrease with each of the...Ch. 19 - The scenes below depict solutions of the same...Ch. 19 - The scenes below show three samples of a buffer...Ch. 19 - What are the [H3O+] and the pH of a propanoic...Ch. 19 - What are the [H3O+] and the pH of a benzoic...Ch. 19 - Prob. 19.14PCh. 19 - Prob. 19.15PCh. 19 - Prob. 19.16PCh. 19 - Find the pH of a buffer that consists of 0.95 M...Ch. 19 - Prob. 19.18PCh. 19 - Prob. 19.19PCh. 19 - Prob. 19.20PCh. 19 - Find the pH of a buffer that consists of 0.50 M...Ch. 19 - A buffer consists of 0.22 M KHCO3 and 0.37 M...Ch. 19 - A buffer consists of 0.50 M NaH2PO4 and 0.40 M...Ch. 19 - What is the component concentration ratio,...Ch. 19 - Prob. 19.25PCh. 19 - Prob. 19.26PCh. 19 - Prob. 19.27PCh. 19 - Prob. 19.28PCh. 19 - A buffer that contains 0.40 M of a base, B, and...Ch. 19 - A buffer that contains 0.110 M HY and 0.220 M Y−...Ch. 19 - A buffer that contains 1.05 M B and 0.750 M BH+...Ch. 19 - A buffer is prepared by mixing 204 mL of 0.452 M...Ch. 19 - A buffer is prepared by mixing 50.0 mL of 0.050 M...Ch. 19 - Prob. 19.34PCh. 19 - Prob. 19.35PCh. 19 - Prob. 19.36PCh. 19 - Choose specific acid-base conjugate pairs to make...Ch. 19 - An industrial chemist studying bleaching and...Ch. 19 - Oxoanions of phosphorus are buffer components in...Ch. 19 - The scenes below depict the relative...Ch. 19 - Prob. 19.41PCh. 19 - What species are in the buffer region of a weak...Ch. 19 - Prob. 19.43PCh. 19 - Prob. 19.44PCh. 19 - Prob. 19.45PCh. 19 - Prob. 19.46PCh. 19 - Prob. 19.47PCh. 19 - Prob. 19.48PCh. 19 - Prob. 19.49PCh. 19 - Prob. 19.50PCh. 19 - Prob. 19.51PCh. 19 - Prob. 19.52PCh. 19 - Prob. 19.53PCh. 19 - Prob. 19.54PCh. 19 - Prob. 19.55PCh. 19 - Prob. 19.56PCh. 19 - Prob. 19.57PCh. 19 - Prob. 19.58PCh. 19 - Prob. 19.59PCh. 19 - Prob. 19.60PCh. 19 - Prob. 19.61PCh. 19 - Use figure 19.9 to find an indicator for these...Ch. 19 - Prob. 19.63PCh. 19 - Prob. 19.64PCh. 19 - Prob. 19.65PCh. 19 - Prob. 19.66PCh. 19 - Write the ion-product expressions for (a) silver...Ch. 19 - Write the ion-product expressions for (a)...Ch. 19 - Write the ion-product expressions for (a) calcium...Ch. 19 - Prob. 19.70PCh. 19 - The solubility of silver carbonate is 0.032 M at...Ch. 19 - Prob. 19.72PCh. 19 - Prob. 19.73PCh. 19 - The solubility of calcium sulfate at 30°C is 0.209...Ch. 19 - Prob. 19.75PCh. 19 - Prob. 19.76PCh. 19 - Prob. 19.77PCh. 19 - Calculate the molar solubility of Ag2SO4 in (a)...Ch. 19 - Prob. 19.79PCh. 19 - Prob. 19.80PCh. 19 - Prob. 19.81PCh. 19 - Prob. 19.82PCh. 19 - Prob. 19.83PCh. 19 - Write equations to show whether the solubility of...Ch. 19 - Prob. 19.85PCh. 19 - Prob. 19.86PCh. 19 - Prob. 19.87PCh. 19 - Does any solid PbCl2 form when 3.5 mg of NaCl is...Ch. 19 - Prob. 19.89PCh. 19 - Prob. 19.90PCh. 19 - Prob. 19.91PCh. 19 - A 50.0-mL volume of 0.50 M Fe(NO3)3 is mixed with...Ch. 19 - Prob. 19.93PCh. 19 - Prob. 19.94PCh. 19 - Prob. 19.95PCh. 19 - Write a balanced equation for the reaction of in...Ch. 19 - Prob. 19.97PCh. 19 - Prob. 19.98PCh. 19 - Prob. 19.99PCh. 19 - What is [Ag+] when 25.0 mL each of 0.044 M AgNO3...Ch. 19 - Prob. 19.101PCh. 19 - Prob. 19.102PCh. 19 - Prob. 19.103PCh. 19 - When 0.84 g of ZnCl2 is dissolved in 245 mL of...Ch. 19 - When 2.4 g of Co(NO3)2 is dissolved in 0.350 L of...Ch. 19 - Prob. 19.106PCh. 19 - A microbiologist is preparing a medium on which to...Ch. 19 - As an FDA physiologist, you need 0.700 L of formic...Ch. 19 - Tris(hydroxymethyl)aminomethane [(HOCH2)3CNH2],...Ch. 19 - Water flowing through pipes of carbon steel must...Ch. 19 - Gout is caused by an error in metabolism that...Ch. 19 - In the process of cave formation (Section 19.3),...Ch. 19 - Phosphate systems form essential buffers in...Ch. 19 - The solubility of KCl is 3.7 M at 20°C. Two...Ch. 19 - It is possible to detect NH3 gas over 10−2 M NH3....Ch. 19 - Manganese(II) sulfide is one of the compounds...Ch. 19 - The normal pH of blood is 7.40 ± 0.05 and is...Ch. 19 - A bioengineer preparing cells for cloning bathes a...Ch. 19 - Sketch a qualitative curve for the titration of...Ch. 19 - Prob. 19.120PCh. 19 - The scene at right depicts a saturated solution of...Ch. 19 - Prob. 19.122PCh. 19 - The acid-base indicator ethyl orange turns from...Ch. 19 - Prob. 19.124PCh. 19 - Prob. 19.125PCh. 19 - Prob. 19.126PCh. 19 - Prob. 19.127PCh. 19 - Prob. 19.128PCh. 19 - Prob. 19.129PCh. 19 - Calcium ion present in water supplies is easily...Ch. 19 - Calculate the molar solubility of Hg2C2O4 (Ksp =...Ch. 19 - Environmental engineers use alkalinity as a...Ch. 19 - Human blood contains one buffer system based on...Ch. 19 - Quantitative analysis of Cl− ion is often...Ch. 19 - An ecobotanist separates the components of a...Ch. 19 - Some kidney stones form by the precipitation of...Ch. 19 - Prob. 19.137PCh. 19 - Prob. 19.138PCh. 19 - Because of the toxicity of mercury compounds,...Ch. 19 - A 35.0-mL solution of 0.075 M CaCl2 is mixed with...Ch. 19 - Rainwater is slightly acidic due to dissolved CO2....Ch. 19 - Prob. 19.142PCh. 19 - Ethylenediaminetetraacetic acid (abbreviated...Ch. 19 - Buffers that are based on...Ch. 19 - NaCl is purified by adding HCl to a saturated...Ch. 19 - Scenes A to D represent tiny portions of 0.10 M...Ch. 19 - Prob. 19.147PCh. 19 - Prob. 19.148PCh. 19 - Prob. 19.149P
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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
- In a reaction of A + B to give C, another compound other than A, B or C may appear in the kinetic equation.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_forwardGiven the reaction R + Q → P, indicate the rate law with respect to R, with respect to P and with respect to P.arrow_forward
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