EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 8220100591310
Author: McMurry
Publisher: CENGAGE L
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Textbook Question
Chapter 25.SE, Problem 64AP
D-Mannose reacts with acetone to give a diisopropylidene derivative (Problem 25-33) that is still reducing toward Tollens' reagent. Propose a likely structure for this derivative.
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each pair of substrates below, choose the one that will react faster in a substitution reaction, assuming that:
1. the rate of substitution doesn't depend on nucleophile concentration and
2. the products are a roughly 50/50 mixture of enantiomers.
Substrate A
Substrate B
Faster Rate
X
Ś
CI
(Choose one)
(Choose one)
CI
Br
Explanation
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Br
(Choose one)
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NMR spectrum of ethyl acetate has signals whose chemical shifts are indicated below. Which hydrogen or set of hydrogens corresponds to the signal at
4.1 ppm? Select the single best answer.
The
H
O
HỌC—C—0—CH, CH,
2
A
ethyl acetate
H NMR: 1.3 ppm, 2.0 ppm, 4.1 ppm
Check
OA
B
OC
ch
B
C
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How many signals do you expect in the H NMR spectrum for this molecule?
Br Br
Write the answer below.
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.
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.
Check
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.
O
✓
No additional Hs to color in top
molecule
ง
No additional Hs to color in bottom…
Chapter 25 Solutions
EBK ORGANIC CHEMISTRY
Ch. 25.1 - Prob. 1PCh. 25.2 - Prob. 2PCh. 25.2 - Prob. 3PCh. 25.2 - Prob. 4PCh. 25.2 - Prob. 5PCh. 25.3 - Prob. 6PCh. 25.3 - Prob. 7PCh. 25.4 - Prob. 8PCh. 25.4 - Prob. 9PCh. 25.4 - Prob. 10P
Ch. 25.5 - Prob. 11PCh. 25.5 - Prob. 12PCh. 25.5 - Prob. 13PCh. 25.5 - Prob. 14PCh. 25.5 - Prob. 15PCh. 25.6 - Prob. 16PCh. 25.6 - Prob. 17PCh. 25.6 - Prob. 18PCh. 25.6 - Prob. 19PCh. 25.6 - Prob. 20PCh. 25.6 - Prob. 21PCh. 25.6 - Prob. 22PCh. 25.6 - Prob. 23PCh. 25.7 - Prob. 24PCh. 25.8 - Show the product you would obtain from the...Ch. 25.SE - Prob. 26VCCh. 25.SE - Prob. 27VCCh. 25.SE - Prob. 28VCCh. 25.SE - Prob. 29VCCh. 25.SE - Prob. 30MPCh. 25.SE - Prob. 31MPCh. 25.SE - Glucosamine, one of the eight essential...Ch. 25.SE - D-Glicose reacts with acetone in the presence of...Ch. 25.SE - Prob. 34MPCh. 25.SE - Prob. 35MPCh. 25.SE - Prob. 36APCh. 25.SE - Prob. 37APCh. 25.SE - Prob. 38APCh. 25.SE - Prob. 39APCh. 25.SE - Prob. 40APCh. 25.SE - Assign R or S configuration to each chirality...Ch. 25.SE - Prob. 42APCh. 25.SE - Prob. 43APCh. 25.SE - Prob. 44APCh. 25.SE - Prob. 45APCh. 25.SE - Prob. 46APCh. 25.SE - Prob. 47APCh. 25.SE - Prob. 48APCh. 25.SE - Prob. 49APCh. 25.SE - Prob. 50APCh. 25.SE - Prob. 51APCh. 25.SE - Prob. 52APCh. 25.SE - Prob. 53APCh. 25.SE - Prob. 54APCh. 25.SE - Prob. 55APCh. 25.SE - Prob. 56APCh. 25.SE - Prob. 57APCh. 25.SE - Prob. 58APCh. 25.SE - Prob. 59APCh. 25.SE - Prob. 60APCh. 25.SE - Prob. 61APCh. 25.SE - Prob. 62APCh. 25.SE - Prob. 63APCh. 25.SE - D-Mannose reacts with acetone to give a...Ch. 25.SE - Prob. 65APCh. 25.SE - Prob. 66APCh. 25.SE - Prob. 67APCh. 25.SE - Prob. 68APCh. 25.SE - Prob. 69APCh. 25.SE - Prob. 70APCh. 25.SE - Prob. 71AP
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