
Pearson eText Organic Chemistry -- Instant Access (Pearson+)
8th Edition
ISBN: 9780135213711
Author: Paula Bruice
Publisher: PEARSON+
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Textbook Question
Chapter 19.5, Problem 7P
Explain why cyclopentadiene (pKa = 15) is more acidic than pyrrole (pKa - 17), even though nitrogen is more electronegative than carbon.
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How many signals do you expect in the H NMR spectrum for this molecule?
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Also, in each of the drawing areas below is a copy of the molecule, with Hs shown. In each copy, one of the H atoms is colored red. Highlight in red all other H
atoms that would contribute to the same signal as the H already highlighted red.
Note for advanced students: In this question, any multiplet is counted as one signal.
Number of signals in the 'H NMR spectrum.
For the molecule in the top drawing area, highlight in red any other H atoms that will contribute to
the same signal as the H atom already highlighted red.
If no other H atoms will contribute, check the box at right.
No additional Hs to color in top
molecule
For the molecule in the bottom drawing area, highlight in red any other H atoms that will contribute.
to the same signal as the H atom already highlighted red.
If no other H atoms will contribute, check the box at right.
No additional Hs to color in bottom
molecule
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Row 2: Your answer is incorrect.
Consider this molecule:
How many H atoms are in this molecule?
22
How many different signals could be found in its 'H NMR spectrum?
12
Note: A multiplet is considered one signal.
13
How many signals would you expect to see in the
Check
O
signal(s)
X
§
'C NMR spectrum for the following compound?
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Chapter 19 Solutions
Pearson eText Organic Chemistry -- Instant Access (Pearson+)
Ch. 19.1 - Name the following:Ch. 19.2 - Prob. 3PCh. 19.2 - Prob. 4PCh. 19.3 - Draw the product of each of the following...Ch. 19.5 - Prob. 6PCh. 19.5 - Explain why cyclopentadiene (pKa = 15) is more...Ch. 19.5 - When pyrrole is added to a dilute solution of...Ch. 19.6 - Prob. 10PCh. 19.6 - How to the mechanisms of the following reactions...Ch. 19.6 - Prob. 12P
Ch. 19.6 - Rank the following compounds from easiest to...Ch. 19.7 - Prob. 14PCh. 19.7 - Prob. 15PCh. 19.7 - Prob. 16PCh. 19.7 - Prob. 17PCh. 19.7 - Prob. 18PCh. 19.7 - Prob. 19PCh. 19.7 - Prob. 20PCh. 19 - Name the following:Ch. 19 - Prob. 22PCh. 19 - Rank the following compounds from strongest acid...Ch. 19 - Which of the following compounds is easier to...Ch. 19 - Rank the following compounds from most reactive to...Ch. 19 - One of the following compounds undergoes...Ch. 19 - Benzene undergoes electrophilic aromatic...Ch. 19 - Pyrrole reacts with excess...Ch. 19 - The dipole moments of furan and tetrahydrofuran...Ch. 19 - Name the following:Ch. 19 - Prob. 31PCh. 19 - Prob. 32PCh. 19 - a. Draw resonance contributors to show why...Ch. 19 - The chemical shifts of the C-2 hydrogen in the...Ch. 19 - Explain why protonating aniline has a dramatic...Ch. 19 - Prob. 36PCh. 19 - Propose a mechanism for the following reaction:Ch. 19 - Prob. 38PCh. 19 - Propose a mechanism for the following reactions:Ch. 19 - Prob. 40PCh. 19 - Prob. 41PCh. 19 - Prob. 42PCh. 19 - Organic chemists work with tetraphenylporphyrins...Ch. 19 - Show how the following compounds can be prepared...
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- 13 Consider the "C NMR spectrum below. 140 120 100 80 60 40 20 20 PPM 0 The spectrum belongs to which one of the following constitutional isomers of the compound C,H12? Select the single best answer. Check ✓ G Save For Later 2025 McGraw Hill LLC. All Rights Reserved. Terms of Usearrow_forwardThe structure of compound 1,3,5-trimethylbenzene (mesitylene) is given below. How many signals would you expect to find in the 'H NMR spectrum of 1,3,5-trimethylbenzene (mesitylene)? Check ×arrow_forward1 How many signals do you expect in the 'H NMR spectrum for this molecule? CI CI Cl Write the answer in the table below. Also, in each of the drawing areas below is a copy of the molecule, with H atoms shown. In each copy, one of the H atoms is highlighted red. Highlight in red all other H atoms that would contribute to the same signal as the H already highlighted red. Note for advanced students: Remember, a multiplet is considered one signal in the 'H NMR spectrum. 1 Number of signals in the 'H NMR spectrum. ☐ For the molecule in the top drawing area, highlight in red any other H atoms that will contribute to the same signal as the H atom already highlighted red. If no other H atoms will contribute, check the box at right. No additional H atoms to highlight in top molecule For the molecule in the bottom drawing area, highlight in red any other H atoms that will contribute to the same signal as the H atom already highlighted red. If no other H atoms will contribute, check the box at…arrow_forward
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