EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 9780100591318
Author: McMurry
Publisher: YUZU
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Chapter 22.SE, Problem 41AP
Interpretation Introduction
Interpretation:
The observation that 1-phenyl-2-propenone when treated with a strong base such as LDA does not yield an anion, though it contains a H atom on the carbon atom next to carbonyl group is to be explained.
Concept introduction:
Hydrogen atom on a carbon adjacent to carbonyl group is acidic as the carbanion is stabilized by electron delocalization over the carbonyl group.
To explain:
The observation that 1-phenyl-2-propenone when treated with a strong base such as LDA does not yield an anion, though it contains a H atom on the carbon atom next to carbonyl group.
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The following equations represent the formation of compound MX. What is the AH for the
electron affinity of X (g)?
X₂ (g) → 2X (g)
M (s) → M (g)
M (g)
M (g) + e-
AH = 60 kJ/mol
AH = 22 kJ/mol
X (g) + e-X (g)
M* (g) +X (g) → MX (s)
AH = 118 kJ/mol
AH = ?
AH = -190 kJ/mol
AH = -100 kJ/mol
a)
-80 kJ
b)
-30 kJ
c)
-20 kJ
d)
20 kJ
e)
156 kJ
A covalent bond is the result of the
a)
b)
c)
d)
e)
overlap of two half-filled s orbitals
overlap of a half-filled s orbital and a half-filled p orbital
overlap of two half-filled p orbitals along their axes
parallel overlap of two half-filled parallel p orbitals
all of the above
Can the target compound at right be efficiently synthesized in good yield from the unsubstituted benzene at left?
starting
material
target
If so, draw a synthesis below. If no synthesis using reagents ALEKS recognizes is possible, check the box under the drawing area.
Be sure you follow the standard ALEKS rules for submitting syntheses.
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Note for advanced students: you may assume that you are using a large excess of benzene as your starting material.
C
T
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X
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Chapter 22 Solutions
EBK ORGANIC CHEMISTRY
Ch. 22.1 - Prob. 1PCh. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3PCh. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5PCh. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7PCh. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P
Ch. 22.7 - Draw a resonance structure of the acetonitrile...Ch. 22.7 - Why do you suppose ketone halogenations in acidic...Ch. 22.7 - Prob. 13PCh. 22.7 - Prob. 14PCh. 22.7 - Prob. 15PCh. 22.7 - Prob. 16PCh. 22.SE - Prob. 17VCCh. 22.SE - Prob. 18VCCh. 22.SE - Prob. 19VCCh. 22.SE - Prob. 20MPCh. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Prob. 23MPCh. 22.SE - In the Hell–Volhard–Zelinskii reaction, only a...Ch. 22.SE - Prob. 25MPCh. 22.SE - Nonconjugated , -unsaturated ketones, such as...Ch. 22.SE - Prob. 27MPCh. 22.SE - Using curved arrows, propose a mechanism for the...Ch. 22.SE - Prob. 29MPCh. 22.SE - One of the later steps in glucose biosynthesis is...Ch. 22.SE - The Favorskii reaction involves treatment of an...Ch. 22.SE - Treatment of a cyclic ketone with diazomethane is...Ch. 22.SE - Prob. 33MPCh. 22.SE - Amino acids can be prepared by reaction of alkyl...Ch. 22.SE - Amino acids can also be prepared by a two-step...Ch. 22.SE - Heating carvone with aqueous sulfuric acid...Ch. 22.SE - Identify all the acidic hydrogens (pKa 25) in the...Ch. 22.SE - Rank the following compounds in order of...Ch. 22.SE - Prob. 39APCh. 22.SE - Base treatment of the following , -unsaturated...Ch. 22.SE - Prob. 41APCh. 22.SE - Prob. 42APCh. 22.SE - Prob. 43APCh. 22.SE - Which, if any, of the following compounds can be...Ch. 22.SE - Prob. 45APCh. 22.SE - Prob. 46APCh. 22.SE - Prob. 47APCh. 22.SE - How might you convert geraniol into either ethyl...Ch. 22.SE - Prob. 49APCh. 22.SE - One way to determine the number of acidic...Ch. 22.SE - Prob. 51APCh. 22.SE - Prob. 52APCh. 22.SE - Prob. 53APCh. 22.SE - Prob. 54APCh. 22.SE - Prob. 55APCh. 22.SE - Prob. 56APCh. 22.SE - All attempts to isolate primary and secondary...Ch. 22.SE - How would you synthesize the following compounds...Ch. 22.SE - Prob. 59APCh. 22.SE - Prob. 60APCh. 22.SE - Prob. 61APCh. 22.SE - Prob. 62APCh. 22.SE - As far back as the 16th century, South American...Ch. 22.SE - The key step in a reported laboratory synthesis of...Ch. 22.SE - Prob. 65AP
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