Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 15.17, Problem 36P
Explain why the chemical shift of the OH proton of a
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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.
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Least acidity
NH&F NaBr NaOH
NH,Br NaCIO
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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 15 Solutions
Organic Chemistry
Ch. 15.1 - Prob. 1PCh. 15.1 - Prob. 2PCh. 15.4 - How many signals would you expect to see in the 1H...Ch. 15.4 - Prob. 4PCh. 15.4 - How could you distinguish the 1H NMR spectra of...Ch. 15.4 - Draw an isomer of dichlorocyclopropane that gives...Ch. 15.5 - Prob. 7PCh. 15.5 - Prob. 8PCh. 15.5 - Prob. 9PCh. 15.5 - Where would you expect to find the 1H NMR signal...
Ch. 15.6 - Prob. 11PCh. 15.7 - Prob. 12PCh. 15.7 - Prob. 13PCh. 15.7 - Without referring to Table 14.1, label the proton...Ch. 15.8 - [18]-Annulene shows two signals in its 1H NMR...Ch. 15.9 - How would integration distinguish the 1H NMR...Ch. 15.9 - Which of the following compounds is responsible...Ch. 15.10 - Prob. 19PCh. 15.10 - Explain how the following compounds, each with the...Ch. 15.10 - The 1H NMR spectra of two carboxylic acids with...Ch. 15.11 - Draw a diagram like the one shown in Figure 14.12...Ch. 15.12 - Indicate the number of signals and the...Ch. 15.12 - How can their 1H NMR spectra distinguish the...Ch. 15.12 - Identify each compound from its molecular formula...Ch. 15.12 - Prob. 27PCh. 15.12 - Propose structures that are consistent with the...Ch. 15.12 - Describe the 1H NMR spectrum you would expect for...Ch. 15.13 - Prob. 30PCh. 15.13 - Identify the compound with molecular formula...Ch. 15.14 - Prob. 32PCh. 15.15 - a. For the following compounds, which pairs of...Ch. 15.17 - Explain why the chemical shift of the OH proton of...Ch. 15.17 - Prob. 37PCh. 15.17 - Prob. 38PCh. 15.17 - Prob. 39PCh. 15.20 - Answer the following questions for each compound:...Ch. 15.20 - Prob. 41PCh. 15.20 - How can 1,2-, 1,3-, and 1,4-dinitrobenzene be...Ch. 15.20 - Identify each compound below from its molecular...Ch. 15.22 - Prob. 44PCh. 15.22 - What does cross peak X in Figure 14.34 tell you?Ch. 15 - Prob. 46PCh. 15 - Draw a spitting diagram for the Hb proton and give...Ch. 15 - Label each set of chemically equivalent protons,...Ch. 15 - Match each of the 1H NMR spectra with one of the...Ch. 15 - Determine the ratios of the chemically...Ch. 15 - How can 1H NMR distinguish between the compounds...Ch. 15 - Prob. 52PCh. 15 - The 1H NMR spectra of three isomers with molecular...Ch. 15 - Prob. 54PCh. 15 - Prob. 55PCh. 15 - Prob. 56PCh. 15 - Compound A, with molecular formula C4H9Cl, shows...Ch. 15 - The 1H NMR spectra of three isomers with molecular...Ch. 15 - Would it be better to use 1H NMR or 13C NMR...Ch. 15 - There are four esters with molecular formula...Ch. 15 - An alkyl halide reacts with an alkoxide ion to...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Prob. 64PCh. 15 - How can the signals in the 6.5 to 8.1 ppm region...Ch. 15 - The 1H NMR spectra of two compounds, each with...Ch. 15 - Draw a splitting diagram for the Hb proton if Jbc...Ch. 15 - Sketch the following spectra that would be...Ch. 15 - How can 1H NMR be used to prove that the addition...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Dr. N. M. Arr was called in to help analyze the 1H...Ch. 15 - Calculate the amount of energy (in calories)...Ch. 15 - The following 1H NMR spectra are four compounds,...Ch. 15 - When compound A (C5H12O) is treated with HBr, it...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Identify each of the following compounds from its...Ch. 15 - Identity the compound with molecular formula...Ch. 15 - Identify the compound with molecular formula C6H14...
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