Introductory Chemistry: Foundation - Text (Looseleaf)
9th Edition
ISBN: 9781337399623
Author: ZUMDAHL
Publisher: Cengage
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Chapter 3, Problem 48AP
A(n) always has the same composition.
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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
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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 3 Solutions
Introductory Chemistry: Foundation - Text (Looseleaf)
Ch. 3.2 - Exercise 3.1 Which of the following are physical...Ch. 3.2 - Prob. 3.2SCCh. 3.4 - Exercise 3.3 Classify each of the following as a...Ch. 3.5 - The scanning tunneling microscope allows us to...Ch. 3 - When water boils, you can see bubbles rising to...Ch. 3 - If you place a glass rod over a burning candle,...Ch. 3 - The boiling of water is a physical change because...Ch. 3 - Is there a difference between a homogeneous...Ch. 3 - Sketch a magnified view (showing atoms and/or...Ch. 3 - Are all physical changes accompanied by chemical...
Ch. 3 - Why would a chemist find fault with the phrase...Ch. 3 - Are separations of mixtures physical or chemical...Ch. 3 - Explain the termselement, afoul, and compound....Ch. 3 - Mixtures can be classified as either homogeneous...Ch. 3 - Prob. 11ALQCh. 3 - Look at Table 2.8 in your text. How do the...Ch. 3 - Label of the following as an atomic element, a...Ch. 3 - Match each description below with the following...Ch. 3 - Prob. 1QAPCh. 3 - What is the chief factor that determines...Ch. 3 - Of the three stales of matter, and are not very...Ch. 3 - has a definite volume hut takes the shape of its...Ch. 3 - Compare and contrast the ease with which molecules...Ch. 3 - Matter in the __________ state has no shape and...Ch. 3 - What similarities are there between the solid and...Ch. 3 - A sample of matter that is “rigid” has...Ch. 3 - Consider three 10-g samples of water: one as ice,...Ch. 3 - ¡n a sample of a gaseous substance, more than 99%...Ch. 3 - Elemental bromine is a dense, dark-red,...Ch. 3 - Is the process represented below a physical or...Ch. 3 - From the information given above, indicate...Ch. 3 - Prob. 14QAPCh. 3 - You want to cook some raw noodles to make a pasta...Ch. 3 - Which of the following is/are examples of a...Ch. 3 - Classify each of the following as a physical or...Ch. 3 - Classify each of the following as aphysical or...Ch. 3 - Prob. 19QAPCh. 3 - What is acompound? What are compounds composed of?...Ch. 3 - Certain elements have special affinities for other...Ch. 3 - _________ can he broken down into the component...Ch. 3 - The composition of a given pure compound is always...Ch. 3 - Which of the following are considered compounds...Ch. 3 - If iron filings are placed with excess powdered...Ch. 3 - If the combination of iron filings and sulfur in...Ch. 3 - Prob. 27QAPCh. 3 - Which of the following substances is(are)...Ch. 3 - Classify the following asmixturesorpure...Ch. 3 - Classify the following asmixturesorpure...Ch. 3 - Classify the following mixtures...Ch. 3 - Read the “Chemistry in Focus” segmentConcrete—An...Ch. 3 - Prob. 33QAPCh. 3 - Describe how the process offiltrationcould be used...Ch. 3 - In a common laboratory experiment in general...Ch. 3 - During a filtration or distillation experiment, we...Ch. 3 - Prob. 37APCh. 3 - Classify each of the following as a(n) element,...Ch. 3 - 1f a piece of hard, white blackboard chalk is...Ch. 3 - During a very cold winter, the temperature may...Ch. 3 - Prob. 41APCh. 3 - True or false? Salad dressing (such as oil and...Ch. 3 - Prob. 43APCh. 3 - Which of (he following are true? P4 is considered...Ch. 3 - (For Exercises 4546) Solutions containing...Ch. 3 - (For Exercises 4546) Solutions containing...Ch. 3 - The processes of melting and evaporation involve...Ch. 3 - A(n) always has the same composition.Ch. 3 - Classify each of the following as...Ch. 3 - Which of the following contains an element, a...Ch. 3 - Classify the following mixtures...Ch. 3 - Which of the following best describes the air...Ch. 3 - Give three examples each ofheterogeneousmixtures...Ch. 3 - True or false? Mixtures always result in a...Ch. 3 - Choose an element or compound with which you are...Ch. 3 - Prob. 56APCh. 3 - Give an example of each of the following: a...Ch. 3 - Prob. 58APCh. 3 - Sketch the apparatus commonly used for simple...Ch. 3 - Prob. 60APCh. 3 - Which of the following best describes the...Ch. 3 - Prob. 62CPCh. 3 - Which of the following describes a chemical...Ch. 3 - Prob. 64CPCh. 3 - Prob. 1CRCh. 3 - Prob. 2CRCh. 3 - You have learned the basic way in which scientists...Ch. 3 - Many college students would not choose to take a...Ch. 3 - Prob. 5CRCh. 3 - Prob. 6CRCh. 3 - Prob. 7CRCh. 3 - Prob. 8CRCh. 3 - Prob. 9CRCh. 3 - What ismatter? What is matter composed of? What...Ch. 3 - Prob. 11CRCh. 3 - Prob. 12CRCh. 3 - Prob. 13CRCh. 3 - Prob. 14CRCh. 3 - Prob. 15CRCh. 3 - Prob. 16CRCh. 3 - Prob. 17CRCh. 3 - a. Given that 1100. mL of ethyl alcohol weighs...Ch. 3 - Which of the following represent physical...
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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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