ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
10th Edition
ISBN: 9781259972348
Author: Carey
Publisher: MCG CUSTOM
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Question
Chapter 26, Problem 43P
Interpretation Introduction
Interpretation:
The mechanisms for the rearrangement and coupling steps are to be written in NCL for the given reaction.
Concept Introduction:
The sulfur atom in the side chain of cysteine acts as a nucleophile and can attack the carbonyl carbon of the thioester of an amino acid.
The non-native thioester linkage in the product undergoes a rearrangement in order to form a more stable amide linkage.
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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 26 Solutions
ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
Ch. 26.1 - Prob. 1PCh. 26.2 - Prob. 2PCh. 26.2 - Prob. 3PCh. 26.3 - Prob. 4PCh. 26.3 - Prob. 5PCh. 26.4 - Prob. 6PCh. 26.4 - Prob. 7PCh. 26.4 - Prob. 8PCh. 26.5 - Prob. 9PCh. 26.6 - Prob. 10P
Ch. 26.6 - Prob. 11PCh. 26.6 - Prob. 12PCh. 26.7 - Prob. 13PCh. 26.7 - Prob. 14PCh. 26.7 - Prob. 15PCh. 26.7 - Prob. 16PCh. 26.7 - Prob. 17PCh. 26.9 - Prob. 18PCh. 26.10 - Digestion of the tetrapeptide of Problem 26.18...Ch. 26.12 - Prob. 20PCh. 26.12 - Prob. 21PCh. 26.15 - Prob. 22PCh. 26.15 - Prob. 23PCh. 26.16 - Prob. 24PCh. 26.17 - Prob. 25PCh. 26.18 - Prob. 26PCh. 26 - Prob. 27PCh. 26 - Prob. 28PCh. 26 - Prob. 29PCh. 26 - Prob. 30PCh. 26 - Prob. 31PCh. 26 - Prob. 32PCh. 26 - Prob. 33PCh. 26 - Prob. 34PCh. 26 - Prob. 35PCh. 26 - Prob. 36PCh. 26 - Prob. 37PCh. 26 - Prob. 38PCh. 26 - Prob. 39PCh. 26 - Prob. 40PCh. 26 - If you synthesized the tripeptide Leu-Phe-Ser from...Ch. 26 - Prob. 42PCh. 26 - Prob. 43PCh. 26 - Prob. 44PCh. 26 - Prob. 45DSPCh. 26 - Prob. 46DSPCh. 26 - Prob. 47DSPCh. 26 - Prob. 48DSPCh. 26 - Prob. 49DSPCh. 26 - Prob. 50DSP
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