Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Question
Chapter 28, Problem 28.21P
Interpretation Introduction
Interpretation:
The transition state for [3, 3] sigma tropic reaction is to be analyzed as the interaction of two allylic radicals, and that the same stereochemical outcome is to be predicted.
Concept introduction:
Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.
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Arrange the solutions in order of increasing acidity. (Note that K (HF) = 6.8 x 10 and K (NH3) = 1.8 × 10-5)
Rank solutions from least acidity to greatest acidity. To rank items as equivalent, overlap them.
▸ View Available Hint(s)
Least acidity
NH&F NaBr NaOH
NH,Br NaCIO
Reset
Greatest acidity
1. Consider the following molecular-level diagrams of a titration.
O-HA molecule
-Aion
°°
о
°
(a)
о
(b)
(c)
(d)
a. Which diagram best illustrates the microscopic representation for the
EQUIVALENCE POINT in a titration of a weak acid (HA) with sodium.
hydroxide?
(e)
Answers to the remaining 6 questions will be hand-drawn on paper and submitted as a single
file upload below:
Review of this week's reaction:
H₂NCN (cyanamide) + CH3NHCH2COOH (sarcosine) + NaCl, NH4OH, H₂O --->
H₂NC(=NH)N(CH3)CH2COOH (creatine)
Q7. Draw by hand the reaction of creatine synthesis listed above using line structures without showing
the Cs and some of the Hs, but include the lone pairs of electrons wherever they apply. (4 pts)
Q8. Considering the Zwitterion form of an amino acid, draw the Zwitterion form of Creatine. (2 pts)
Q9. Explain with drawing why the C-N bond shown in creatine structure below can or cannot rotate. (3
pts)
NH2(C=NH)-N(CH)CH2COOH
This bond
Q10. Draw two tautomers of creatine using line structures. (Note: this question is valid because problem
Q9 is valid). (4 pts)
Q11. Mechanism. After seeing and understanding the mechanism of creatine synthesis, students should
be ready to understand the first half of one of the Grignard reactions presented in a past…
Chapter 28 Solutions
Organic Chemistry
Ch. 28 - Prob. 28.1PCh. 28 - Prob. 28.2PCh. 28 - Prob. 28.3PCh. 28 - Prob. 28.4PCh. 28 - Prob. 28.5PCh. 28 - Prob. 28.6PCh. 28 - Prob. 28.7PCh. 28 - Prob. 28.8PCh. 28 - Prob. 28.9PCh. 28 - Prob. 28.10P
Ch. 28 - Prob. 28.11PCh. 28 - Prob. 28.12PCh. 28 - Prob. 28.13PCh. 28 - Prob. 28.14PCh. 28 - Prob. 28.15PCh. 28 - Prob. 28.16PCh. 28 - Prob. 28.17PCh. 28 - Prob. 28.18PCh. 28 - Prob. 28.19PCh. 28 - Prob. 28.20PCh. 28 - Prob. 28.21PCh. 28 - Prob. 28.22PCh. 28 - Prob. 28.23PCh. 28 - Prob. 28.24PCh. 28 - Prob. 28.25PCh. 28 - Prob. 28.26PCh. 28 - Prob. 28.27PCh. 28 - Prob. 28.28PCh. 28 - Prob. 28.29APCh. 28 - Prob. 28.30APCh. 28 - Prob. 28.31APCh. 28 - Prob. 28.32APCh. 28 - Prob. 28.33APCh. 28 - Prob. 28.34APCh. 28 - Prob. 28.35APCh. 28 - Prob. 28.36APCh. 28 - Prob. 28.37APCh. 28 - Prob. 28.38APCh. 28 - Prob. 28.39APCh. 28 - Prob. 28.40APCh. 28 - Prob. 28.41APCh. 28 - Prob. 28.42APCh. 28 - Prob. 28.43APCh. 28 - Prob. 28.44APCh. 28 - Prob. 28.45APCh. 28 - Prob. 28.46APCh. 28 - Prob. 28.47APCh. 28 - Prob. 28.48APCh. 28 - Prob. 28.49APCh. 28 - Prob. 28.50APCh. 28 - Prob. 28.51APCh. 28 - Prob. 28.52APCh. 28 - Prob. 28.53APCh. 28 - Prob. 28.54APCh. 28 - Prob. 28.55AP
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