Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 14, Problem 14.1YT
Interpretation Introduction
Interpretation:
The resonance structure corresponding to the given VB picture is to be drawn.
Concept introduction:
Chemical and structural features of molecules are unaccounted for by VB theory, most notably electron delocalization or resonance over three or more nuclei. The VB theory picture of a species that has resonance is inaccurate because it represents a single resonance structure, not the hybrid.
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Problem Set #5
III) Acid/Base Reaction - Answer the next few questions about Molecule B, shown below.
a) Circle the terms that correctly describe the molecule.
H-bond acceptor
dextrorotatory
contains ketone
racemic
has enantiomer
H-bond donor
Molecule B
optically active
contains aldehyde
levorotatory
[a] = -27.8°
b) Molecule B can react with another molecule in an acid/base reaction (shown below).
+
H
In the spaces provided, please do the following:
i) Draw the structure of the missing molecule in the space provided.
ii) Circle ONE: The missing molecule is a:
conjugate acid
conjugate base
iii) Clearly draw curved arrows to show the forward mechanism.
iv) Without referring to pKa values, predict whether the equilibrium will favor
reactants or products, and give an explanation why.
Circle ONE:
reactants
products
Explanation:
7. Draw curved arrows indicating the movements of electrons between the following pair of
resonance structures. Name the pattern of resonance shown. What is the hybridization of the
carbon atoms?
8. Draw the remaining three resonance structures for the molecule in problem 7 above.
9. There are several possible forms of a trisubstituted cyclohexane with the formula C10H200. I
have drawn four of them. From these, which one do you think is most commonly naturally
occurring, and why? Which is least commonly occurring and why?
HO
HO"
HO
HO
What is the most polar/functionality for this compound?
Chapter 14 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 14 - Prob. 14.1PCh. 14 - Prob. 14.2PCh. 14 - Prob. 14.3PCh. 14 - Prob. 14.4PCh. 14 - Prob. 14.5PCh. 14 - Prob. 14.6PCh. 14 - Prob. 14.7PCh. 14 - Prob. 14.8PCh. 14 - Prob. 14.9PCh. 14 - Prob. 14.10P
Ch. 14 - Prob. 14.11PCh. 14 - Prob. 14.12PCh. 14 - Prob. 14.13PCh. 14 - Prob. 14.14PCh. 14 - Prob. 14.15PCh. 14 - Prob. 14.16PCh. 14 - Prob. 14.17PCh. 14 - Prob. 14.18PCh. 14 - Prob. 14.19PCh. 14 - Prob. 14.20PCh. 14 - Prob. 14.21PCh. 14 - Prob. 14.22PCh. 14 - Prob. 14.23PCh. 14 - Prob. 14.24PCh. 14 - Prob. 14.25PCh. 14 - Prob. 14.26PCh. 14 - Prob. 14.27PCh. 14 - Prob. 14.28PCh. 14 - Prob. 14.29PCh. 14 - Prob. 14.30PCh. 14 - Prob. 14.31PCh. 14 - Prob. 14.32PCh. 14 - Prob. 14.33PCh. 14 - Prob. 14.34PCh. 14 - Prob. 14.35PCh. 14 - Prob. 14.36PCh. 14 - Prob. 14.37PCh. 14 - Prob. 14.38PCh. 14 - Prob. 14.39PCh. 14 - Prob. 14.40PCh. 14 - Prob. 14.41PCh. 14 - Prob. 14.42PCh. 14 - Prob. 14.43PCh. 14 - Prob. 14.44PCh. 14 - Prob. 14.45PCh. 14 - Prob. 14.46PCh. 14 - Prob. 14.47PCh. 14 - Prob. 14.48PCh. 14 - Prob. 14.49PCh. 14 - Prob. 14.50PCh. 14 - Prob. 14.51PCh. 14 - Prob. 14.52PCh. 14 - Prob. 14.53PCh. 14 - Prob. 14.54PCh. 14 - Prob. 14.55PCh. 14 - Prob. 14.56PCh. 14 - Prob. 14.57PCh. 14 - Prob. 14.58PCh. 14 - Prob. 14.59PCh. 14 - Prob. 14.60PCh. 14 - Prob. 14.61PCh. 14 - Prob. 14.62PCh. 14 - Prob. 14.63PCh. 14 - Prob. 14.64PCh. 14 - Prob. 14.65PCh. 14 - Prob. 14.66PCh. 14 - Prob. 14.1YTCh. 14 - Prob. 14.2YTCh. 14 - Prob. 14.3YTCh. 14 - Prob. 14.4YTCh. 14 - Prob. 14.5YTCh. 14 - Prob. 14.6YTCh. 14 - Prob. 14.7YTCh. 14 - Prob. 14.8YTCh. 14 - Prob. 14.9YTCh. 14 - Prob. 14.10YTCh. 14 - Prob. 14.11YTCh. 14 - Prob. 14.12YTCh. 14 - Prob. 14.13YT
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